Planning the perfect vacation can be a daunting task. But what if there was a secret to having an incredible trip every single time? Today, we're diving into the art of trip planning with an expert who's organized thousands of incredible vacations. We'll uncover whether you're actually choosing your trip or if your trip is choosing you, essential organization tips, and how to create an itinerary that guarantees an unforgettable experience.

I'm Chris Hutchins, this is All The Hacks, and whether you're a meticulous planner or love spontaneous adventures, you will leave this episode ready to make your next vacation your best one yet. And big favor before we jump in is to give us a quick thumbs up to help others find this channel.

And if you're new here and you want to keep upgrading your life, money, and travel, consider subscribing. What is the secret to having an incredible vacation? Look, I've planned thousands of vacations for hundreds of people, and I'll tell you that it all boils down to one thing. Is this trip choosing you or are you choosing this trip?

And what do you mean by that? What I mean by that is how organized are you for the trip that you want to have? Is this something you've been dreaming about for years you've thought about? Or is this a spontaneous pop-up that maybe you didn't have planned for, but you're going to go on it anyway because the flight's worked out, or there's a great hotel, or you're going to stay with friends or whatever, and you're just going along for the ride?

Are you in control? And have you planned this thing and you've been meticulous about it? Or are you deciding, "Oh, hey, this sounds fun. Let's go do this." When people set out to do something and they go accomplish that trip that they've been thinking about, dreaming about for years, whether it's a honeymoon or a bucket list trip or whatever, then it's incredible.

But there's also this openness for spontaneity and the opportunity that comes with, "Oh, yeah, this sounds like this could be pretty cool. Let's do this too." And that can be an incredible pathway too. Now, look, both can be fraught with danger, and we'll talk today about some classic examples of where people fail in both those cases.

But as long as your mindset is open to, "Yeah, let's go plan and do this thing we've been dreaming about for years," or, "Oh, hey, this popped up. This looks cool. Let's go do this, and let's be open to it," you'll have a great time. And so you have to know which one you're going into.

Exactly. And know how to handle both scenarios, because there's obviously very different levels of planning involved with both. Okay. So I think let's start with someone who's trying to plan the trip, trying to be in control, but doesn't actually know what the trip is. Because the goal today is to walk people through, I don't know, like a masterclass on how to plan a trip all the way from the beginning of, "Where do I want to go?" to booking things, to planning things, and actually what you do when you're there and what you need to know before.

So that's what I want to accomplish. Well, first, let's start with how are you organizing yourself? Because if you have that openness mindset to, "The world's my oyster. There's a blue sky out there. I can go see anything," you have to start with organization to make sure that all the things you do want to do are captured in the right place.

So for a lot of our clients that are the online folks, they're working with a Google Sheet, or they're working with a spreadsheet of some sort where their travel inspiration lives. They're sending themselves emails, they're tagging it in their inbox. Maybe they're saving things on Instagram or Pinterest or somewhere digitally that they can go back and reference and say, "Hey, this looks like a cool destination," or, "Hey, let's add this to our list." What we do with our clients is we check in with them on a quarterly basis.

We say, "Hey, every 90 days, what else is on that list that we should be aware of?" Or, "What's popped up that's been inspiring to you?" Maybe your friends have been. Maybe you've seen it in a magazine that you're really excited about. For the analog people, people who are not so online, maybe they're a little older or older school, or maybe they just love to journal, we actually have a written list that folks will keep and keep prizing us of and letting us know, "Yeah, this is now on my list," or, "This is something exciting." So it first starts with organization.

Writing down and keeping your inspirations in one place that you can reference, super important. Later on, we're chatting about something that I think is very important around organization, which is checking in with your organizational list, making sure that you're doing the things you want to do, that you've set out to do, and cross-referencing them, and then keeping notes on what you've done.

So I think if you can be digitally inclined and do things in Google Spreadsheets and set up your right digital organization to capture all of your inspiration and all of your notes, you're going to be great. Okay. But what if that organization expands so much? So I imagine there are people listening.

They're like, "Okay. I saw a cool Instagram video about Japan. I want to go there. The Olympics are happening in Paris. I want to go there." And then all of a sudden, they've got a thousand things on their list. How do they start to think about, "Where should I take this next trip?" Or, "I've got some vacation this year.

Where should I go now?" Yeah. Great questions. So first, check in with yourself. What is that really inspiring, exciting trip for you and why? And write down the qualities of it, right? Olympics. I've always wanted to go to a major sporting event. I want to be where the people are.

I want to do something really exciting. Those characteristics of that trip, where the people are, exciting, sporting, those things are valuable and important to you. And maybe you look at Japan and you say, "Oh, I've always wanted to go to a cultural place with history and a deep connection to self," right?

You circle those words and you say, "Okay. For this trip, I'm looking for more activity. So maybe I won't go to Japan now because I don't want to have the introspective, quiet, slower trip. I want to have the fast-paced, loud Paris trip for the Olympics." And so that's what decides you on this one.

It doesn't mean you have to get rid of Japan altogether or say that any destination that would be introspective or slow isn't exciting for you. Instead, it's that, "Okay, this trip, this time is this experience. And I know I can come back to this list and look for inspiration and the qualities I want for my next trip." Also, it's interesting to see as you gather all these destinations and you get all this inspiration, what is it that really does motivate you to travel and why, right?

It's a nice check-in and this is why I recommend people do this on a 90-day, on a quarterly basis. But why do these destinations matter to you, right? What are the things you're seeing online, whether it's an Instagram or Pinterest or wherever your inspiration is, that's motivating you to say, "Hey, I want to go to this destination." And what does that mean for you?

What's alive in you, right? When we plan trips for people, there are so many different levers or so many different reasons people are going to different destinations. And it could be the same destination but three different trips because they're going with different people, they're taking their kids, they're taking their parents, they're traveling to eat this time, next time they're going on a spa relaxation time where they don't want to eat at all.

Who knows? So, it's interesting to see how those themes pop up for people. So, let's say someone's done some thinking about what kind of trip they want. They say, "I want a little bit of culture, but I want to do it a little bit slower. I need a relaxation.

I want to get away from work. So, I don't want it to be too high-paced." Lots of places out there, maybe they haven't set up this inspiration for years. Where can they go to start to get inspiration and how do they narrow the list down? Great question. So, the first thing is, talk to your friends.

Talk to your social circle and see who's been places that might match those characteristics you're looking for. Get their feedback. What do they love? What do they not love? How do they do it? How do they plan it? Get an understanding of what has worked for other people that you know because you've got a great filter in knowing them.

That's going to work for you. Second is, look at places like magazines, blogs, articles recently, and local papers, whatever it is that fit your style and see where the inspiration lies for you with them. Again, I love reading Rod Report or Travel and Leisure. Not all those destinations, not all those experiences they talk about match my style.

So, I have a filter when I look at those media outlets to know that, okay, I'm learning here, but I'm not also applying every bit of knowledge to my own life. With those two filters and with friends, with media, and with online inspiration as well, and do be careful online because there's so much out there that you can learn about from blogs, from newsletters, from ChatGPT, which we'll talk about, that we have to take all that with a grain of salt.

If you've been reading a blog for years and you know the style and the preferences of that traveler, then great. Apply that filter as well. But if not, maybe you want to be a little bit wary because you might be reading someone's experience, maybe they were paid to go there, maybe there's something else happening on the back end that you don't know about, and it might be tainting your kind of perspective trip.

So, I say when you're reading media that you're not comfortable with or not familiar with, take it with a grain of salt because it's good for inspiration, good for fact-checking, but maybe not good for being the sole source of inspiration for you. So, with those filters, take a look back at your lists and the qualities that you're looking for for this trip and come up with a couple of concentric circles, right?

This destination has the qualities I'm looking for, people I know, media I've read, talked about why this would work well for me. Great. Now I've got a destination, let me start planning. Let me start building some scaffolding around this trip and test it and see, is this the trip that I want to have?

A couple of things you didn't mention that I'll flag that we've done. So, one, I really like the New York Times 52 places list. It's great. There's a couple publications that do an annual kind of inspiration gathering thing. If you're going to go somewhere this year, here are some great places.

I like that for inspiration. If you have a region in mind, I think the first 20 pages of any Lonely Planet guide, they have the top 20 experiences or 30 experiences or 15 experiences. And so, sometimes if you're like, "Oh, I'm thinking of going to Southeast Asia," go get the Lonely Planet Southeast Asia.

And by the way, you don't have to buy it. Oftentimes, those pages are in the preview on Amazon before you buy it. A lot of libraries let you have access to downloadable eBooks for free. So, that's one way I've gathered inspiration that we didn't mention. And the other is thinking about seasonality.

So, you mentioned what kind of trip do you want, the intersection of where might be fun. So, maybe you decide that a Caribbean vacation is for you, but the only time you have off is in August. Right. North American summer in the Caribbean. Sounds like a dream. Yeah. So, how do you think about weather and seasonality when it comes to some of these things and going during the time when it's best or going during the time where it's maybe on the shoulder season?

Yeah. Well, that comes back to the idea of, is this vacation choosing you or are you choosing it? Seasonality really plays very heavily into this. Sometimes we're time-bound by school years and other vacations where we really can't take off in that season that would be ideal to go in.

And sometimes, actually, we want to be traveling in shoulder seasons because pricing is lower, experiences might be more accessible, there might be just fewer people, and it might be better. So, two things that I will chat about. One is those 52 lists, the top list, top 20 this year, whatever, are great lists to help you discover a destination to reinforce questions or ideas you might have around an inspiration.

They're also very good at driving people this year and next year. So, if you find something that's really good on that list, maybe you might want to put it on your list for three years down the road. Let people come in, kind of cycle through, and then you can go check it out because it might be a little quieter seasonally to go two years later than it is to go this year or go next.

When it comes to seasonality, I tend to think that shoulder seasons are the best times to go places because A, fewer people, B, lower pricing, and C, you get sometimes even better weather or better experiences without having to deal with all the madness. Case in point, the Amalfi Coast.

As you've probably heard me say on this podcast before, I love Italy, I've been there so many times. I love the Amalfi Coast. It's truly incredible, but in July and August, it's a zoo. It's crazy. In fact, it's so busy and nuts that many local Amalfitani leave the coast and go elsewhere and come back in September because it's just so overwhelming.

So, you should do that too. You should come back in September. Now, granted, if you've got a school schedule where you've got to be back in school August 20th and you have to be in Amalfi that summer, well, maybe you go in May. Another great shoulder season when crowds are a little slower and a little quieter, still busy, but great time to go.

But September, October, perfect. Perfecto. Same thing in Rwanda. We were just in Rwanda in March. Traditionally, it's not a space or time of year to go because it's a lot rainier than the rest of the year, but for us, it was perfect. We were one of very few people out on the gorilla tracks those days and we had the gorillas all to ourselves.

It just felt so magical to be in those misty mountains. Yes, there was rain, no doubt, but it was just us and the gorillas and the experience was much different than people I know who had been three weeks prior in February when they had hot, bright, sunny days and it was a zoo.

Also, pricing was a lot cheaper. Just going into March, we were actually able to save about half of the money we would have spent on permits for February just because of a seasonality program that the Rwandan government has. So, as you research these destinations and you look at seasonality and timing, think about where am I flexible and could I go a month later, a month earlier?

Maybe I change the weather a little bit. I change the logistics a little bit, but I get a little bit better of an experience, maybe a lower price, maybe fewer people. I like it. So, I put together a notion table where we put all the destinations that we wanted to go.

So, I filled them out. My wife, Amy, filled them out and we had a bunch of columns and I went in and I actually, with the help of Chat GPT, was kind of like, "Here's 20 places. Help me figure out when the prime season is for weather." Love it.

"Figure out the shoulder season." And we tagged, "Here are the seasons that are good for this place." And then she and I each ranked the destinations one to five. Love your organization. I hope you'll share this in the notes here today. Yeah. And then we had an average. So, now when we wanted to take a trip, we're like, "Oh, we're going to think about where to go in the summer." Well, we already looked at the 30 or 40 places we want to go.

Let's look at those places, filter by summer, sort by average rating for Amy and I. Love it. And we have some sense of some inspiration. So, that's where we're collecting our inspiration. And people always ask on the show like, "Oh, you talk about notion a lot. How do you use it?" That's one example of building a table that we can add to.

And then each item in a table, this is where I think Google Sheets lets down and a database wins, is that each item in that table might be called Italy or might be called the Amalfi Coast or Sweden. And then each item is a page. So, you can open that Sweden page.

And go in-depth there. And start clipping things to it and clipping things. Totally. And if you use... There's a couple of notion bookmarklet tools or browser extensions. "Oh, here's a cool article. Send it there. Here's something. Send it here." And you start to gather all your ideas on an Italy page or a Sweden page, but that page is actually just part of a database of inspiration.

I love that. And let me add a couple other bits to that too, right? You can add additional filters on top of that because Amalfi might be great for you and Amy just by yourselves. But when you add in a couple of young toddlers or you add in older people, it may not be the great multi-generational destination you want it to be, right?

So, you could say, "Here's a filter for kids. Here's a filter for my parents. Here's a filter for all of us together." Again, taking that same idea and other filters, what about how crowded you want things to be, right? If everybody else finds that it's a 4.5 to go to Amalfi in October, maybe you guys go in February and you're not going to the beach, you're not going on the water, but you're getting the true essence and the character of those towns because that's what you're looking for, right?

So, those filters are really, really important. One other item that I would call out is that you guys have gotten way advanced at this, which I love, but check in with yourselves on that list. Right now, Japan might be super hot for you because everybody else has been there and all of your friends have been talking about it, and maybe you're really hunkering to go back, but maybe in a year Japan's lost its luster and Malaysia's the new thing for you.

I don't know. Check in on it every quarter and see, "Is this rating still true to me and do I really want to do this?" It takes five minutes, but it just helps you guys check in with, "Okay, should a pop-up trip become available and now I can go here, do we actually want to do this?" Right?

The last thing we'll say is chat GPT. Big fan of accessible information at our fingertips. Double-check the validity of that information as often as possible. Maybe they said that March was a great season to go to Rwanda because the weather's not that bad. Yeah, the weather wasn't that bad, but the weather definitely was not as good as February or as good as June.

You really want to double-check that what data you're getting out is actually valid for the purposes you want. We were looking at it a couple of weeks ago and said, "What are the best things people should do in Paris this summer for the Olympics?" They said, "Go inside Notre Dame." I was like, "Whoa, I'd love to do that too, but it's still under construction from the fire." Why are we getting this hallucination kind of data?

Can you really validate everything you're getting from chat GPT? Or whatever AI tool you want to use. A couple of tips there. One, I tried to get specific data instead of opinion. Instead of saying, "Where should we go with good weather?" I said, "Can you give me the average highs and lows for these cities in this month?" Or, "What is the percent chance of rain in this month?" But still, we have this trip to Europe planned in the summer and we have no actual agenda.

We just have flights. We'll get to that right after this about when the trip finds you. I said, "Where could we go that doesn't get warmer than 85?" We don't want to go somewhere where it's 90s in the summer. Humid and you're suffering. Yeah. It might be fun for kids.

And they came up with all these destinations. And then I was like, "What about Portugal?" And they're like, "Oh, that would be a great idea." But it's not a human. So I'm like, "Why did you put it on the list?" And they're like, "Oh, sorry. I'll add it now." And so sometimes I've found myself just asking after every response, "Are there any places you forgot about?" And unfortunately, 90% of the time, it's like, "Well, yeah, here are three more." So you're right.

You can't trust it. However, I go back to people I know that don't fall into this optimizer's curse, which I do, and maybe you do a little bit less, which is they're like, "Oh, we want to take a trip. Let's just go to Italy." They don't try to pick the best trip.

And so I like timeboxing this, and it's something that we're working on. And I won't say we do a perfect job at it, but the idea being, "Okay, we're going to take a trip. And this week, we're going to figure out where we're going." And you know what? We have a lot of years and a lot of trips ahead of us.

But this one doesn't have to be the only one. And a friend of mine actually took a trip to, I think, Australia. And they'd always said, "We can't go to Australia because we need two weeks. We need two weeks." And then finally, they're like, "Well, we have one week." They found a deal.

They went. And they're like, "Yo, we can always go back if we need two weeks." Yeah. Totally. And so every trip will be great if you aren't too stressed out planning it. Agreed. And I think sometimes we fall into that boat. In many cases, this trip is that because I think kids add this X factor where one day, your kids are super well-behaved, and you're like, "You know what?

We should take them on this trip." And then the next day, you're like, "The kids are monsters." And you're like, "Are we biting off too much?" So if the trip found you, and you know where you're going because you've got these great flight deals, or if you've used one of these flight discovery tools we talked about to find this amazing idea, that's one case.

The other case is you've decided where you're going, and you need to book the flight. And at the end of both of those scenarios, we're ready to start planning. So any quick tips on the, "I know where I want to go. I'm being intentional. I've got to book the flights that maybe we haven't covered before." Flights for my trip that I've decided is in Italy or is somewhere.

Yeah. Or sometimes there's a connection where maybe they'll have... In your connecting flight, they'll change the flight times. And now you have too short or too long of a connection or schedule change of any other sort, keep monitoring them. And what you can do is sign up for alerts from the airline to make sure that they notify you for every change that happens to your flight.

But also you can use monitoring tools that are out there. TripIt has some of them. Other tools have these automatic monitoring to make sure that you're getting the right flights and that changes don't occur. In terms of how else to book, I would always keep an eye on optimizing your flights to see if maybe the price you've paid does drop.

With points and miles in particular, you can usually get a rebate back of whatever the flight difference is. You were very lucky this summer. I think you've booked flights for 45,000 miles per person. That's incredible. You're probably not going to optimize around that. But if you'd booked them for 120,000 and maybe flights on the same day had dropped to 45, you'd be getting that huge chunk of miles back.

So you do want to keep searching or keep monitoring automatically with tools to see if there's an advantage to take there. Yeah. And sometimes the same thing's true with fares. So TripIt's great as a monitoring tool. It'll say, "Hey, the flight you booked has gone down in price. You should go rebook it." And then you can.

Exactly. And yes, now I might get a credit on whatever airline that was. And who knows how easy that credit will be to use. But it was free to get the credit. So might as well keep track. And we'll talk a little bit about organizing everything on a trip as we go.

Any advice? This is a question from a listener who said, "When I'm planning these big trips, how do I think about layovers? And do I think about them differently than if I'm flying domestically and I have a sense of how travel works?" Yeah, that's a great question. So generally speaking, when you're flying from the States to Europe or to Asia, you're flying on the first segment on a very long-haul flight to a hub in that continent.

And then from there, you're going to connect onwards. So what's nice about landing in a hub is that if, God forbid, you did miss your connection because your inbound flight was delayed, generally speaking, from hub to endpoint, there are other flights that are out there. Awesome. What you may want to do when you've booked your flight is just double-check, okay, what would be the next flight if, for some reason, we were delayed by an hour and a half, we miss our two-hour connection, right?

What's the next flight from Frankfurt onwards to Vienna, right? And then you can kind of have a sense for how many more flights there are that day or if you're going to end up sleeping in the Frankfurt airport that night. Now, what I always like to do whenever I go into Europe or Asia, for this matter, is I like to have at least a two-hour layover.

Why two hours? Because you're going to end up most likely having a clear immigration and you'll have probably to go through security again. Most European airports, a lot of Asian ones too, require another layer of security. And that's security without pre, without clear, whatever you're used to in an American security system, out the window.

Out the window. So get used to that. And also, you're going to be groggy. You may not have slept the last 10 hours. Your kids might be super grumpy. It's a bit of an experience. So don't make it too rushed for yourself. On the flip side, maybe you do want to pack in a really long layover.

Maybe you want to spend eight hours in the Frankfurt area, not necessarily airport. What I would do in that case is leave my bags at the airport. There's a left luggage sort of compartment desk. When you do pass through customs, you can leave your luggage there, your carry-on luggage, and then you can go explore the city and come back.

And so last summer, our family flew to Europe and we actually did just that. We left our bags at the sort of checked baggage area in the Frankfurt airport, took the train, the U-Bahn into town, hung out, had a great little tour by ourselves of different districts of Frankfurt, had a wonderful meal, came back to the airport in time, got on our next flight.

And so I would highly recommend that if you do have longer than let's say a four or five hour layover, take a look at what's in that area. Can you get into that town? Can you go explore before coming back to the airport and connecting onwards? The other thing you can do too if you have the budget for it and it's of interest is get a greeter.

Oftentimes there are connection greeters. Amsterdam Schiphol airport, great example of this, it's only like 160 bucks to get a greeter. I think it goes up per person from there, not too much though. And that greeter will take you from your origination gate to your departing gate through all the formalities, security, whatever.

There's a lounge, they'll give you access to that lounge as well. And it's a great way of taking what would be normally a stressful time and making it as stress-free as possible. So whatever you can do to make those layovers count, I would do it, but I wouldn't just disregard them.

When you book your ticket, be intentional, check your backups, take a look at if you can extend your layover and make an experience out of it. Oftentimes, by the way, airlines will let you extend a layover up to about 24 hours without actually repricing your ticket. And some airlines, if you're flying through their hub, like if you're flying Emirates through Dubai or flying Iceland air through Reykjavik.

Or Turkish through Istanbul. They'll let you stay for days at a time without any extra fees. Might only be 24 hours, but it could be two or three days. Absolutely. And in those cases, by the way, it is useful to see, do I need a visa to enter the country even temporarily?

In the case of Turkey, yes, but you'll go and experience something that you weren't counting on doing. If you're using Turkish to get from the States down to North Africa, well, all of a sudden now you have a great time spending 12 hours in Turkey. It's pretty awesome. It's a bonus.

Let's say the layover is pretty short and you don't see any other flights the rest of the day on the airline that you're flying or any of their partners, but you do see some cheap flights on other airlines that maybe are cheap now, three months out, six months out, but are probably not going to be cheap day of.

Do you factor that in at all? Or are you only looking for other flights that day on the carrier you're flying? That's a great question. The unfortunate part is carriers who would then be responsible for rebooking you should there be a big delay. If they don't work with the other carriers, they don't care that there's other flights.

Even though there are flights from Istanbul to wherever you might be going on other airlines that are not Turkish, if you flew Turkish into Istanbul and they were responsible for your delay, you're spending the night on Turkish time till the next day. You could, if you're just carrying on, you could risk buying your own last minute ticket and flying outbound and then maybe working with your credit card company later on to see if they'll reimburse for some of that, but Turkish won't.

Turkish would not do that at all, actually. Unfortunately, if it's a different carrier, they may not care. You may be able to get somebody at the Istanbul airline counter, the transfer desk, who would look upon you humanely and say, "Oh, you were just carrying on a bag and you're missing a wedding.

We'll get you there," but I wouldn't always count on it. It is helpful to look at that research ahead of time and know that you might be risking it a little bit. Maybe build in an extra bit of time if you can, a day on either side so that it's not like you're taking the last flight in and the first flight out.

Yeah. One other option. If you're looking at these flights and there's three Lufthansa flights from Frankfurt to Amsterdam, wherever you're going, maybe you're fine. If there's not, maybe you add a little more buffer. If you can't add a little more buffer, maybe that's where a greeter comes in to help make sure that goes smoothly.

Absolutely. If there are flights on another airline and it's not a discount airline that's not part of some airline alliance you can use points with, it's surprising that in some regions, the short regional flights can be very, very inexpensive. Yeah. If you book those through a program with free cancellation, even better if it's a program you already have points on.

Maybe if there is a really important thing and you're flying on Air France and you're flying through Paris and you're worried you're going to miss that connection to, let's say, Frankfurt or Munich, you could see if you can use United Points to book that flight later in the day knowing that you could cancel before, but it's really important to understand the cancellation rules.

I will link to a post that someone else, not me, has written about all these cancellation rules because some airlines you can cancel 10 minutes before and some you cancel 24 hours before, but I think that's a decent option. Yeah. The little hack here, though, is obviously if you're too late and you miss both those flights in air and you can't cancel it, that's a problem.

I would say find someone on the ground. Who can help you out. Give them your record, locator, itinerary number and say, "Hey, if you haven't heard from me before this plane takes off, just cancel it for me so I get my points back." Right. Well, the one other thing I'll call out there, too, is make sure you don't double book yourself on the same airline because if you have an Air France connecting flight from Paris and you book yourself a later flight from Paris on Air France or on KLM, they will cancel that flight for you because they see you as double booked and they don't want to do that.

They don't want to have a double booked passenger. So be creative, but not too creative. Yes. Although I currently am double booked on a United flight, but one is booked through United and one is booked through Air Canada. And I did not put the same frequent flyer number in, but I did put the same birthday and they have not canceled either.

So... Fingers crossed. I'm not... I knew there would be a risk doing this. So if I do get canceled, no one should feel... It's on you. It's on me, but that sometimes works. Okay. So, all right. We've got some flight tips. We figured out where we're going. For all intents and purposes, we now have a plan to where we're going for this trip.

Let's talk a little bit about the itinerary because before you could go to book hotels, let's say you decided it is a summer vacation in France, you need to figure out where to go. Do you have a general rule of thumb on how many days to think about spending in a place?

If you have two weeks, is that one destination, two, three, four? Is there a minimum? Well, Chris, I appreciate you asking that because so many people have this idea that they're going to go on a two-week holiday in Europe and they're going to see 16 things. And this has been their mindset, their vision for so long.

They're going to go see all of Europe in two weeks. And I'm like, "Guys, you're going to be day three exhausted and you're going to hate yourself for having done this. So please don't do that." So I think it's really important to temper your expectations with the realism of what feels great.

What is too much? What is just enough? Taking that and applying it to an actual real trip, we like to build a scaffolding for people. They have their flight in, their flight out. We know what their big purpose of going on this trip is. It's relaxation, it's seeing the sights, it's eating these meals, it's going to a Taylor Swift concert.

And then we put that centerpiece, that capstone somewhere in that trip. Everything else around that, we ask a few questions. How much activity and motion do you want to have? How many different things each day do you want to be doing? If you had to cut all of this out and just focus on one thing, what's the thing that matters the most?

So as you look at this trip scaffolding and you figure out the amount of activity and the motion that you want to have, you then can start to slot in, "Okay, well, maybe I've been to Paris before. I've spent five days there in the past. Maybe I just need three days this time.

And I'm okay splitting it up to do two days upon arrival and one day before departure so that I can get my bearings set when I land and I can feel back into Paris. But then as soon as I'm set, I can scoot off and go somewhere else, do the thing I want to do, come back to Paris the night before my flight to make sure that I'm not going to be freaking out about a 9 a.m.

departure from Paris when I'm still two hours outside of town on the last day." So maybe that's the way that you feel like the motion and the movement could be right. But I like to have people draw this out on a piece of paper. "These are the days I'm in town.

These are what I'm doing. This is the amount of motion. Does this feel right?" And ask themselves those questions. "Hey, I'm going to be spending three hours on the train this day. Do I really want to have a museum the moment I arrive and then go to a nice three Michelin star dinner?" That's a lot in one day.

Maybe we chunk that out and now instead of spending two days in town, you're spending three because the next day you'll go to the museum and the final night you're there, you'll do the big Michelin star meal. So when people can see things visually, I think it really helps them.

Adding things to a digital calendar, very important. Putting it on a spreadsheet, day by day, breakfast, lunch, dinner, what are my activities, where am I going, super helpful. But scaffolding it out so that people know how much motion and activity, that matters the most. Yeah, when we look at itineraries, we do something similar.

And I think you often forget how much packing and traveling adds to the day. So you might be thinking, "Oh, we're just going from Paris to London. It's a short train ride." But that whole day is probably pretty close to written off because you wake up and you're like, "Well, now I want to make sure I'm all packed." And maybe this is different if you're a solo traveler and you just have a backpack.

But when we have two kids, that day's gone. And so I try to make sure we're in each place for at least three nights. Because otherwise, as soon as you get there, you're starting to think about, "Now we got to go to this next place." And depending on the density of a destination, or how easy transportation is, might dictate whether you're taking on too much or not.

In a place like Japan, where you could hop on a train and be somewhere. Or Europe, within a country, that's often true. Great. In a place where you've got to drive an hour to get to an airport, and then land, and then drive another. It could just feel like two destinations in two weeks is the max.

Yeah. And honestly, if you're in Paris, it doesn't mean you can't take a day trip up to Normandy while you're there, right? Or you can't go out to Champagne for the afternoon. It's a long day, a long afternoon, but you can do those things, right? And still return back to Paris and have a base there.

You don't need to pick up and move every two days or three days. And I think that's a common misconception for a lot of, especially North American travelers, is that if they have their two week vacation every year, and this is it, they got to pack it all in, they got to see everything.

Scaffold your trip out, put it all out there and say, "What does seeing everything actually look like?" And then come back to me and we'll talk. Yeah. And I've never actually been someone that's tried this, but let's say you rent an Airbnb in Paris for a week, or in Tokyo.

You could choose anywhere in the world, it doesn't matter. And you've got this place for a week, or even two weeks. The savings you probably get booking something for that long probably would afford you the ability to even do a little overnight someplace. Totally. So you could leave all the bags for your two week vacation in that place, pack a little overnight bag.

Maybe more work with kids than not, but it could be a way to see a place that's maybe a little too far for a day trip, but not feel like you're having to pack it all up and move. And I know people have done this, we have not done this, but it's something that I think might be in the future, especially when kids are out of diapers, able to carry their own bags, not sleeping in cribs.

Yeah. We do this all the time ourselves, and we do it for our clients obviously too, where you have a home base and then you explore for that night or two nights even. I'm going to be in Europe later this summer and we're going to take a 48 hour trip from our rented apartment up to Switzerland and then we'll come back.

And it's great to be able to literally take a backpack with us and that's it. You have everything you need contained for the next 48 hours in that backpack. And you don't have to worry about schlepping everything, unpacking, repacking, ah, it's just simple, right? So highly recommend it. Yes.

Are we paying for two hotel rooms for the same night? In essence, we are, right? Because we've got our hotel in Switzerland and we've got our rented apartment in Europe or in Italy, but it's worth it. It's great. Once you've figured out where you want to go and you're starting to book things, in the U.S.

it might be more straightforward sometimes where it's like, well, you just go look online. There's lots of sites that have hotels. Does that apply everywhere else in the world? Or are there places where looking for a place to stay isn't as simple as going to booking.com, Google hotel search?

Sure. I think when you look at the big booking engines like booking.com, Expedia, Airbnb, others, hotels.com, they've done a great job of trying to gobble up most of the available inventory that's out there for rent in private homes, apartments, etc. throughout these cities. So when you're looking online on those sites, you're probably going to find most of what's out there.

I think the question and sort of hack angle here is, are you getting the best deal by looking on those sites? Oftentimes, I've found that if I actually find a suitable accommodation and I either Google the name of that accommodation and do a reverse image search to find if they have got their own website for that villa or that apartment, or if they're managed by an apartment rental company, if I can find that rental company, or even find sometimes that the hotels themselves are directly bookable and they're cheaper.

If I just book on their website, I can save some bucks. And so I definitely do that and highly recommend that for our clients. What you're also asking about is, are there like hyper-regional Paris apartment rentals in the 14th that you can just find a website dedicated to that?

And the answer is yes, there are. There's rental agencies that specialize in certain areas, certain neighborhoods, and those guys usually will have a website that will catalog what's available for them, but they may not be in English or they may not be consumer friendly to a North American audience.

So it's worth doing your diligence and understanding, am I getting the best deal? Am I in the right area? Is there a specialist who just focuses in on this area? Where we go in Northern Italy often, there's a little real estate agency, basically, that has summer rentals for Italians.

And so we negotiate directly with them on what apartments are available through them. And they send us Airbnb-like listings for their apartments. It's all in Italian and we sort of negotiate it and figure it out. And would those have shown up on Booking.com if you've looked? They might have.

In fact, that agency is listed on Booking.com. The pricing is a lot higher and the terms and conditions are very different. So I wouldn't recommend booking there unless that was the sort of safest and easiest thing for you. We're fine navigating and negotiating in Italian. Not everybody can do that or not everybody wants to do that.

So Booking.com is a great avenue for that. But if you're willing to sort of noodle around, especially in Paris, especially in some other European cities where neighborhoods really, really matter, Madrid is one of them, there's local real estate agencies that can help with this. That are going to be a better deal going direct.

Yeah. And again, I wouldn't do it for a three-night stay or maybe even a week-long stay, but a multi-week, month-long, etc. stay, absolutely. Okay. And then we've also covered, just like on flights, hotel points, deals. Similarly, lots of alerting tools, lots of search tools that we've covered in past episodes.

And like flights, keep an eye on it. A lot of hotels and flights have pretty flexible cancellation policies. I know it can give a little bit of anxiety when you think, "Okay, we haven't fully committed." So I'd encourage people to say, "No, we're committed to this." Right. And turn off the alerts for things that you're not so excited about that it would be an easy switch.

Right. Because what you don't want is here are three okay hotels. You picked the one that was available or the best deal. And then the other one's a similar deal. And now you're like looking at the nuance of, "Oh, what kind of soap do they use in the shower?" Or like, "What hours is the breakfast open?" And you're kind of reviews of the breakfast and like, "Oh, the croissants were stale this morning." Yeah.

Now you're back at the optimizer's curse. But if you're looking for points in a city and you've booked a standard double tree hotel, and you've got your eye on an amazing deal using your Hilton free nights at a Waldorf, and that pops up, no brainer. Scoop it. Yeah. Take it.

Well, one of the things they'll say that's a pitfall around this optimizer's curse and holding options is that people often forget to cancel the things they've booked as a hedge or sort of as a backup. And so I would do whatever you can in your scaffolding, in your remindering of yourself, in your calendaring to make sure that you know that, "Okay, if July 30th is the last date, you can cancel this." Like cancel on the 28th just to be safest, right?

You've got time zone differences, all that. Because the last thing you want is to have to beg your way out of a hotel booking or to have it be non-refundable and you're in trouble. So set yourself alerts and reminders for that. You joined me for episode one and we talked about this email path.

For anyone who hasn't been here for all the years, what do you like to do every time you have a hotel book? Well, I want to introduce myself. I want to let the hotel know who I am and why I'm staying there, how long I intend to come in.

Maybe I'm checking in the first thing in the morning once my flight lands and I booked for the, of course, afternoon. They're not expecting me at 9.30 AM, but I'd love to get in there, right? So I want to let them know, "Hey, I'm Chris, traveling with my wife, Amy.

Here are our kids. We're coming in from a red-eye. We're going to hopefully sleep on the plane, but we'll be exhausted by the time we get there. We know we will. Any chance you could let us in? By the way, yes, there are four of us and here's how we normally do bedding in our rooms.

Would it be possible if we need to adjust the reservation, if there's a $50 a night rollaway fee, whatever, please let me know." Explain more about your family, who you are, what are you doing in town, right? "Well, the day we arrive, we're going to be exhausted. We're going to take a nap.

We want to take a shower. We'd love to have a 5 PM dinner, even though they don't do dinner in 5 PM in Europe, but we'll be exhausted. Is there any way you can help us out with a reservation at the bar or at the downstairs restaurant? The next day we're going to Montmartre.

We'll be up at 7.00. Is breakfast served at 7.30?" Whatever the questions are you want to ask, ask them there. Give that hotel all that information they need to know about you to make your stay there special. Why does that matter? Because this is their shot to shine, right?

They want to really make your stay dazzle. And if they do, they know that you're going to come back, you're going to go home and tell friends. So that's their whole goal for while you're there. So the more information you can give them, the more responsive they can be to that information and take better care of you.

So I would highly recommend emailing them ahead of time. Then I'd recommend a couple of days prior to your arrival, re-emailing them in case anything's changed. Plans do change, right? "Hey, our youngest has been a little snotty lately. So we might need a local pharmacy." Just alerting your concierge just in case, right?

Or, "Hey, we really love... Our five-year-old's into giraffes. Can you put a giraffe balloon in the room when we get there? I've seen it all." Whatever. But let the hotel know who you are and how they can make your stay special. And you'll see it's night and day what happens.

Yeah. I would say of the listeners that have written in, 50-plus percent at something happening. Someone's gone and said, "Oh, it's my daughter's birthday." And there was a massive birthday celebration. "Oh, we're celebrating this thing. There was an upgrade." Someone had their initials monogrammed on pillows. Right. Thought that was a bit strange.

But they do it. They do it sometimes. And it's memorable and they share that experience. And that's what the hotel wants you to do. So empower them to help you. Great. And you talked about the concierge. Let's talk about what you do when you're in a place. Yeah. You're now decided, "OK, we've got our hotel.

We've got our scaffolding. We know we're going to spend four days, Tokyo, Paris, Cartagena, wherever it is in the world." How do you start to fill out the day and make sure you're doing the most but not overwhelming yourself? Yeah. So I think it goes back to that mindset.

Right. And using that as the ultimate filter of what is it that we want to accomplish on this trip in this place. By the way, your stay in Paris may be very different from your stay out on the beach. Right. And so noting that ahead of time and optimizing for that is really important.

Then I'd go back to that concierge if you're staying at a hotel. Right. And go back to that concierge and say, "Hey, you know, we're in Paris for three nights. We want to have an action-packed three days here. What do you recommend? Here's our family profile, as you know.

What do you recommend we do? Can you give me some sample itineraries that other families have done that you've helped them with? We will review that itinerary and we'll come back to you with the areas that we want you to help us reserve, whether it's museums or car services or whatever.

Right. So that's one avenue to do it. Second is to take a look at literally Googling child-friendly activities Paris. Right. Or like, is the Musée d'Orsay the best for a five-year-old? Like those kinds of questions, Google and chat GPT. Of course, your friends can help inform that as well.

But I think when you start with the mindset, you apply it to the scaffolding of your trip and you say, "These are the amounts of activity each day that I want to have. And these are the key capstones in each day that I want to have." I like to look at it as one key activity per day, one museum visit, one meal, one whatever it is that you're trying to accomplish for that day.

And then build kind of the day around that. So maybe you've got Musée d'Orsay tickets at 11 a.m. Maybe your hotel is an hour walk away from the museum or a 15-minute metro ride. Take the hour walk, right? Enjoy walking through town and make that hour walk an hour and a half.

So now you know you have to leave at 9.15 because you want to beat the museum 15 minutes early to make sure you're in there on time, in case of security lines, whatever. So that's now your morning activity leading up into the museum. Or maybe you know that your kids are terrible getting out the house in the morning and you need to budget some extra time.

So what you want to do is optimize for metro there, walking back. And maybe along the walking path on the way back, you'll stop for lunch and you'll enjoy yourselves. So we apply a little different version of this to whenever we plan Japan because people who go to Japan always want to go to the Toyosu fish market and they want to be up at 5 in the morning to go see the 4 in the morning to go see the auction activity.

When you fly from the U.S. to Japan, you end up having the first night that you're in town. You usually go to bed right as you get there and you wake up at the crack of dawn because your body is still all jet lagged. One of the things we do is we book that Toyosu fish market for either the first or the second day you're in Japan.

And we make sure that that's built into your itinerary as your capstone that day. And that kind of the rest of the day is at leisure or chill because you'll come home, you'll want to have a little nap, you'll have a nice lunch. Maybe you'll go to a park in the afternoon and that'll be your day.

Right. So we try to use logistics and that scaffolding intelligently for what that traveler experience is going to be. And again, not packing too much into one day. You don't want to go to Toyosu and then, you know, a shrine right after that, and then a big market tour in the afternoon, and then go to a giant three mission star meal that evening.

You'll be exhausted. Right. Dorset with kids. That's your activity for the day. You're walking around parks, walking around neighborhoods, you're doing some shopping, some eating. That's your day. And where do you go to find some of these things that aren't as obvious as, you know, a museum, you could just book tickets online.

But whether it's an experience, a tour, how do you think about sites like Airbnb Experiences, Viator, and any other ones as avenues to find things to do? Yeah, I love them. I mean, look, I think Airbnb Experiences is a really interesting marketplace. Sort of currently they've paused it. It's still active.

You can book things, but they're not adding a lot of inventory to that space just yet. But I think that will be a very big arena for them to play in. Viator is great because if you can think of a tour, Viator probably has it in that city. And so you can know, okay, this is a thing to do, or maybe not to do.

You can also read great reviews on the tour guide or that experience from other people. If you're totally blue sky and new to a city and you're trying to plan it out, I like to look at context tours. They're an amazingly sort of higher range, both private as well as small group tour.

And they tend to have the sort of more specialist tours in each town. And they give you a really good sense of how much time I'll need in this town, right? So they might have the same experience sort of across seven or eight different of their tours. So you kind of know, okay, this is one thing I have to experience while I'm there.

Or it might be not that exciting to you and you're like, well, I want to do everything that doesn't include that piece, right? And you don't have to book a context tour. At all. But use them as a good curated tour site. Correct. Correct. And I would say on the whole, we've never had a client book a context tour and be like, "Oh, this is terrible." People are really appreciative of the experience, the knowledge of those guides, et cetera.

So it's actually a great resource to use to study, but also if you did want to splurge for one, it's great to do as well. Yeah. We've definitely booked some, I can't remember all the sites. There was one that was like show around. There was one where it was like individual tour marketplaces.

I remember we went to Greece and we went to the Acropolis and we went on this tour and we thought, "Oh, it'd be cool to get a little history." But this was like the driest, most boring history tour ever. That's tough. And it's hot. And I think there are some people who would really want that.

That wasn't us. And I think just trying to figure out what it is you're looking for in the tour versus it being the highest rated might apply the same lessons you said. Make sure you know what you want out of this. But I do love the experience of booking a local...

If you find marketplaces for things like that, you remove the middleman, maybe get a better deal, but a little bit of a mixed bag sometimes. Well, I think for the key things that are the most important ones for your trip, those capstone events each day, if you don't have a confident feeling that this is the place I want to go, I want to go to Context or I want to go to Viator, go to your hotel concierge if you have one and ask them and say, "Look, I'm looking for a young person who will guide me through the local markets as a local person.

I don't want to go to a tourist market. I want to go to the vintage market and I want to have somebody who knows the vintage market walk me through." Who do you know? And just ask them for a bio on that tour guide. Confirm the availability of that person.

But understand who would it be who'd be walking me through this experience and am I willing to pay for that? And if you are, then scoop it up through whichever channel you can get. The last thing you want is to go on a generic, boring, dry, tasteless tour where that's your capstone of the day and that's the thing you came to do in that town.

So I pay keen attention to that. When we fill out the scaffolding for people, we highlight and circle what's the most important thing they're doing that day and how do we make sure it's a success and then everything else from there flows. I wouldn't recommend this for children or at least young children.

But the free walking tours in almost every city are so good. I don't think we've ever been on one we didn't enjoy. They are all free. And then, of course, work for tips. So you really have to be good in order to make money doing it. Otherwise, you wouldn't be doing it.

And so I love that they are not usually private. So the challenge there is if you bring kids and they want to slow down or take a break, you're kind of you're kind of lost. But I highly recommend free walking tours. I imagine almost any city in the world, you type city name, free walking tour, and you will find it.

And they run almost every day, multiple times a day in some cases. I love doing that on the first day. Yeah, because you often get a good sense of what is this city? What is a local like what's going on? You know that it's a pretty low key activity.

Yeah. So that's something we do a lot. Well, and also, if you know that you connect with that vibe of that tour guide, then you can ask them at the end of that tour. Hey, listen, we're looking for like these things these next couple of days. What would you recommend?

What's the best park for kids? What's the best place for us to go buy X, Y and Z? Hey, we want to really mellow restaurant tonight. What do you recommend? And they have the answers to that. Right. What's also great is that you can then amplify that to your friends and family and your social crowd.

So as you post a selfie with them on Instagram tag, you know, Stanislaus touring me around Warsaw today was the most amazing guy X, Y, Z. Here's his Instagram handle. Right. And now when people are knowing in the future, they're going to put that in their travel inspiration folder.

They're going to read it to Stanislaus to be like, when are you touring? I want to tour with you. Right. Happens all the time. Love that. I also think one thing that has been interesting is. Short form video on the Internet for long form activities can be a little deceptive, and so it's interesting because we're planning this trip to Iceland for listeners, and I remember planning the entire thing with Brandon, who's the tour guide and who I interviewed on an episode about Iceland.

And I would find these videos. I'm like, well, this looks really cool. Like we get to go inside a volcano. Like, why are we doing this? And he's like, you just watched the like 30 second video of it. He's like, why don't you go look on YouTube and find someone who painstakingly took a GoPro on like this long version of the entire adventure?

And you'll be like, that wasn't actually that exciting. And so as much as some of the content can be boring, there seems to be no shortage of people who have recorded every second of almost every activity in every city. It's true. And you will find that some activities might have made your inspiration list in a one minute clip.

And then when you watch the 10 minute, 20 minute, 45 minute, 90 minute version, you're like, that's not how I want to spend my day. So when it comes to inspiration for activities, YouTube has a lot of good options that cover a little bit longer form. Sometimes people share their highlights, and I found it really easy to quickly be like, actually, I don't want to do that.

Yeah, I do want to do that. Totally. And that's important in this sort of like mood board for your trip. Put a negative space in there where you're like, I would really like to avoid these things. I don't want to go to St. Mark's Square in the middle of the day when 50,000 people are there, and it's a zoo, and I'm just claustrophobic and agoraphobic at the same time, and it's too much.

But I do want to go at 11 o'clock at night when there's a tango musician playing, and there's somebody dancing, and it's quiet, and there's pigeons, and me, and the sea. By the way, you may want the exact opposite of that. You may want to go see All Colors of Life showing up to check out midday St.

Mark's. Who knows? But put that out there. Circle what you do and don't want to do, and make sure you come back to that as you finalize your trip plans. And you said this, though not explicitly, the wandering and getting lost in a city is so incredible. Yeah. Even in a small little village, right?

That's where you see the true essence of life in that. Look, I love St. Mark's Square in Venice, but the best parts of Venice are little canals and bridges into the smallest neighborhoods where you hear a woman singing as she's cooking sofrito in her kitchen, right? And you see a guy who's fixing part of his boat in a little canal, and that's what he's been doing all morning.

And it's not like the tourist hubba-bubba. It's just life, right? And that's, for me, why I travel. I love to get lost and explore, but you got to build time in to do that. And if you're hoping to find the right spot, and maybe you're lost along the way, and maybe you're running late to your activity or otherwise, it might be hard for you to take in the moment and appreciate that this is a gift that you're getting to experience, right?

But I would highly recommend that anytime you can purposely build in getting lost, you do. Yeah. I did an episode with Rolf Potts, who wrote this book, Vagabonding, and we talked about flaneuring, which is basically a term for just kind of getting lost and being. And I would encourage you, when you see that person tinkering on that boat, go ask them what they're doing.

Maybe they speak English, maybe they don't, but it never hurts to ask. And I've had some really interesting conversations just talking to people on random streets. I remember in India, someone invited us into their workshop. That was so great. So lots of tips there. You mentioned concierge a lot.

And for someone not staying at a hotel, they might be thinking, "Oh, well, my credit card comes with a concierge." Is that a concierge you can trust for a lot of these kind of local activities? No. So I would trust a local for those local activities. I would not trust somebody who's a generalist, right?

And so I'll tell you very honestly, when we work in a market that we don't know so well, we work through a destination management company, a destination expert, right? Who really knows that little village, that little town, and how to make things happen. And the reason for that is that the internet and chat GPT now can kind of answer generic questions for you on a very high level about something.

But when you want to know what is the best bakery in a certain town and why, you need to go to a local. You need to go to somebody who has on-the-ground experience. And so if you're staying at an Airbnb or a Verbo, I've all the time reached out to those hosts and said, "Hey, hi.

This is who I am. This is my family. This is what we're coming to do. What do you recommend for X, Y, and Z, right? We want to wake up in the morning and go to do this. Is this a good idea?" We're staying in Monaco at the end of the month just for one night.

And I'm like, "We've got five hours basically to see all of the highlights of Monaco from a local's perspective. I don't want to go to the casino only. I want to do what a local would do, what a Monegasque person would really enjoy. How do you do that?" I have an awesome itinerary back 24 hours later, right?

So you ask a local for what their experience is. Take it with a grain of salt. It may not be you, right? He might've said, "Oh, but watch shopping and not into watches." That's fine. Filter it. But definitely start with somebody who is on-the-ground or close to. And nowadays, there are travel content people who are beyond just kind of like Instagram video stuff.

And so when I did an episode on London with Jess Dante, she runs this Love in London blog. And she actually has these neighborhood-specific guides where she's reviewed everything that she sells for reasonable prices. I don't know the directory of all of those people, but I imagine in almost every city in the world, major cities at least, there's someone who has some content that you could book.

And I imagine if you booked that through their site and you emailed them with some questions, they would probably answer them. Oh, in a heartbeat. If you don't have a hotel concierge or you booked an Airbnb, but it's really through a property management company run in another city, I would look for that or I would go on the free walking tour, ask the local there or walk into a restaurant or a bar on the first day and ask someone working there.

One thing Amy and I realized was we just don't love going to art and history museums. And if we do, it's like one in a trip. And so there are cities that we've been to where we ask people what to do. And we look at the guidebooks and they would say, "If you're there for a week, spend three or four days going to museums.

Or if you're in Cambodia, go to Angkor Wat, but go for four days. Get the four-day pass." And we loved going to Angkor Wat for a day. But at the end of the day, I was sure that we didn't wanna go for three more. It just wasn't our type of travel.

We'd much rather go get lost and eat food in some local village. And so don't let the guidebook, the recommendations influence you to do something that you know isn't what you want. So those notes you like to take after a trip, keep those in mind. Well, to add to that, Chris, if you go, you build three days in your itinerary of museums each day.

And on day one, you're like, "I'm pretty museumed out." Great. You don't have to go to day two and three if you don't want to. You can have that flexibility built into your itinerary that you can just take a left turn here and decide to do something totally different and be okay with that.

Again, it's all about mindset. It's all about the flexibility of building your trip the way you want it to be, but also not feeling like you're stuck in that trip that you have to check every single box on that itinerary. If after day one, you're over museums, write down on your itinerary, "Pretty done with museums." And then now what you know in the future, when you come back to look at that trip review, "Okay, I'm going to book way fewer museums in the future because this was enough for me." Yeah.

Love that. So I think we've covered a lot of the things that you need to do. We talked about itinerary management. So now you've got this whole trip put together. We talked about TripIt. Anything else you think about when you're organizing all of this in advance? Well, look, we keep coming back to the word "scaffolding," but it's so important because you want to visually look at your entire trip to understand what are the elements that go into it, what are the key things you need to know, key times, et cetera.

I love to copy that and make sure it's on my calendar. One key note here is that if you're using a Google Gmail address and you're using Google Calendar, you may get these automatic updates to your calendar where Google's like, "Oh, we noticed you've got a train ticket," and they'll plop it into your calendar.

Sweet. Just double check that those times are actually correct. Oftentimes, I've seen that trains, sometimes even flights, will end up at the wrong time zone, which is mind-blowing, on my Google Calendar. So it might be 9 or 10 or 12 hours off, which is like no bueno, right? So you can just edit the event in your Google Calendar and bring it to the right time.

That's great. But definitely put things on the spreadsheet, put things on the calendar, and then go back and take a look at what are you referencing from your original trip planning, ideation, dreaming, visioning, to what is actually happening, and are you living the trip of your dreams? Is this trip something that you wanted to do when you thought of it originally and it's evolved, or are you sort of like shoehorning yourself into a trip?

And just be present with that for a minute, right? Nothing's wrong, but it's interesting to look at what you're dreaming of and what actually you've planned. And then post-trip, I like to go back and kind of figure out, "Okay, well, what worked and what didn't and why?" And use that same organization, make notes on, "Okay, this transfer time was too short.

I needed longer here. I need to have a longer layover. I didn't like this hotel because it was in a crappy location, and I thought it was better because of the research I did online, and next time I'll do different research," right? So kind of have like a post-trip notes that you can take that you can then use every time you're future planning all your other travels.

A lot of my clients like to have this in TripIt, right? Because TripIt for them is their sort of single source of truth. I think it's a great tool. As you said, it monitors for changes and delays, and that's awesome. TripIt can be a little clunky sometimes for some people.

They don't like it. They'd rather have it in Google Sheets or a printable PDF, which we do a lot for people. But whatever system works for you, make sure you do and make sure you file that somewhere so you can go back and reference it later or share it with friends later.

One thing that I was surprised about was when I first started traveling years ago is that, for example, if you've never been abroad, when you go through customs, they're like, "Where are you staying? What's the address? What's the phone number for the hotel?" And you can be caught off guard.

"Well, I don't know all these things." And so having some place where you're like, "This is the hotel we're staying at. This is the address and the phone number." That's where TripIt can become a lot of handy. It comes back to another point, which is being able to access all of this.

You need data. Now, I think nowadays, it's a lot easier to find a free Wi-Fi or just have data that travels with you if you're on T-Mobile or Google Fi. It just works internationally. If you're on carriers like Mint Mobile, you can actually now buy international plans or you could buy eSIMs from sites like AirAllo where you can just get local SIM cards for data.

And you could do it electronically so you don't even need the physical SIM card anymore. But just make sure you have that information and make sure you can access it because you'll always be surprised when you might need to know where you're going, what the address is, what the phone number is, or something like that.

Totally. And I will call out that it's very important to send your itinerary to somebody who's not traveling with you just to be safe. You never know what might happen, God forbid, overseas or what might be going on in your life. And you might need somebody else's eyes on your safety or your security at certain points.

So, definitely share that around. Does that mean you need to tell everyone where you are or make sure that everybody has your confirmation numbers? No, don't post it online. Just share it with friends or family. And if you do come into problems, we've had multiple people send the advice in that you would be surprised at how helpful your local embassy can be abroad.

100%. And similarly, you can be very surprised at how unhelpful local police stations can be. Yes. You hopefully don't have to visit either of those places. But if you do lose a phone, for instance, and your phone's your single source of truth that has all of your data on it, you need to go to your local police office, talk to them, make sure that they have a filed police report so you can claim insurance later on.

The downside is there's crookedness sometimes and there's bureaucracy and red tape and that could take you a whole day just to file that police report, but it's very important to do. But if God forbid there's a real issue, go to your embassy or consulate and there are the people who can really help you.

And make sure that the people at home who know where you're traveling know that you've gone to the embassy or consulate to be helpful as well. They may be called upon to provide backup data or whatever that you might need. Yeah. But for things like I'm having a medical emergency, obviously go to a hospital, but I'm having a medical situation that I'm not sure what to deal with, or we lost our passport.

Yeah. Embassy is a great place to go. We've planned our trip. We've mapped it out. We know where we're going, what we're doing. We're going to have a great time. What are other little details of things to figure out? One that comes to mind for me is accessing money.

I think a long time ago, people would try to exchange money at home. Now, I think the only thing that you should be doing is taking money out of an ATM, unless you've learned that ATMs don't work in this country. And then in which case you'll probably be better off bringing larger denomination US dollars.

Correct. Clean. Yeah. Clean, not ripped. In the US, everyone takes every dollar. Overseas, some places don't take $1 bills. Some places don't take old crumply dollar bills, but there are a handful of banks, Fidelity, Schwab that reimburse overseas international ATM fees. I talked about a whole episode on bank, the best banks and listed a lot of these, but ATM is where I get currency.

At the airport right away, no problem. Don't care about the whatever fee to take it out because I have a bank that's going to reimburse that fee anyway. Exactly. In addition to banking is travel insurance when it makes sense for their needs. And I would say that for most people, they're okay risking it, but you have to take a look at what is refundable, what is non-refundable, what are the costs that if you were to cancel last minute, you would basically have to eat, right?

So those are museum tickets. Sometimes they're non-refundable hotels, but like airfare, if you booked on points and miles and you can cancel last minute, great, good for you. You're getting your refunds back. If you've booked with cash, are you able to use that same airline in the future and use the credit you have as a canceled ticket on that airline?

Ask yourself these questions, understand what's the right amount that you should be insuring for in the event that something were to spur you to cancel, and then take a look at the ways you bought those tickets, paid for those airline tickets or hotels or experiences. If it's on a credit card that carries some travel insurance benefit, great, but understand what the limitations of those benefits are so that you know if insurance really makes sense or not.

Yeah. And I was surprised it's not actually as expensive as I had thought. No. And in many cases, it covers medical related things that you might not know about even though your insurance might cover it. I don't know whether Cigna is going to cover my health insurance situation abroad, but I know that even if they are, it's going to be a pain in the ass.

A giant pain in the ass. So God forbid you got to go to a hospital, at least you're covered to start and you can go from there. Yeah. And so there's probably plenty of companies out there. We've used Trawick before and we've used World Nomads before. I'm not going to say that there aren't better ones.

Maybe there's ones you've used, but those are two I've looked at. We tend to look at a dozen different insurance options depending on who the travelers are and what their needs are and where they're going, obviously. I wouldn't highlight one over the other. I would say that do your diligence and spend a few minutes.

If you're insuring $1,000 of value, that's one thing. If you're insuring $15,000 or $20,000, it's a little different. I would do a different level of diligence on those kinds of companies. But it's very important to understand what you can expect to get back out of insurance and why you're buying it to begin with before you start.

So highlight what does medical coverage look like and why does that matter to me? Is it first payer or second? That's important. And then also take a look at what are the eventualities that I want to be covered for? If I lose my $1,000 iPhone while I'm over there, okay, well, does that get replaced?

Is it a check? Do I buy it and then they reimburse me? How does all that work? It's helpful to know so that you can be prepared if God forbid you have to face that eventuality. So another thing that I recommend to people is about a week before each trip, I sit down with my spouse and we go through each of the trip elements that we have coming up.

We make sure that obviously all of our passports haven't changed from what we thought. They have the right expiration dates and we have the right visas if we need them. Sometimes when you're doing a visa on arrival, by the way, they're either going to be requiring you paying local currency, which can be tricky if you haven't exchanged money ahead of time, or they're going to give you a usurious rate at the airport to exchange to be able to do that.

So that's one good callout. Another is sometimes those visa fees are required to be paid in US dollars. Again, crisp, clean, newer US dollars. They don't have writings or markings on them. But I would highly recommend doing that trip review ahead of time and kind of walking through scenarios like, "Hey, do we know where our ATM card is?

Do we know where our credit card is? Do we have a backup credit card somewhere in a different spot in case our wallet gets stolen?" Right? "Have you called your bank in case you need to, if you're going to a destination that might be a little bit dodgy or might not be so easy to be banking in?" Right?

Make sure that somebody else is aware of your itinerary. And then the final thing that I always like to do is double check for the things that are flexible in our itinerary. Kind of highlight them, recircle them and say, "We know that we could trade this out if we needed to." Right?

"We know that we can cancel this if we had to because it doesn't matter to us or it's not locking us in." So if we look at an itinerary a week out and we're like, "Whoa, this is a lot and this isn't matching the vision we set nine months ago when we had this idea," kind of circle and create some space for you to be flexible with this trip because you never know what might happen.

Friends of ours were just in Lisbon and Morocco and the moment they got to Lisbon, their four-year-old developed an ear infection. And so the next three days of the Lisbon plans were out the door. Doctor was on the phone, local house call doctor, all of that. You can't plan for that.

So circle those things that don't really matter in the end and know that you have some flexibility going into your trip and then go have amazing, amazing times. Document the hell out of it. Live in the moment. Don't be on your phone looking at what everybody else is doing on Instagram.

Be present. Eat that thing. Eat another one of them and have a great time. I love it. That was a great way to wrap. I hope anyone planning a vacation at least got a handful of tips here so that they can make their next trip awesome. Amy's not here or otherwise we probably would have had a real-time breakdown of the trip and we would have figured out everything we're doing.

But I now have a plan for how we're going to finalize our trip. Lee, thanks for being here. Thank you, Chris. It's always a pleasure. It's great to see you in this beautiful space. Congratulations to you and thank