(upbeat music) - Hello, and welcome to another episode of All The Hacks, a show about upgrading your life, money, and travel. If you're new here, I'm your host, Chris Hutchins, and I love to travel. And even more, I love optimizing that travel to have the best experience at the lowest cost.

And one country that's at the top of my list, and many of yours who've emailed in, is Italy. Now, technically I've been to Italy before, but Amy and I did Rome and Venice for two days each back in college almost 20 years ago. So at this point, it almost feels like I've never been.

And I couldn't think of anyone better to join me for this episode than my good friend and guest from episode one, Lee Rowan, who runs a travel company called Savanti, and has been to Italy 40 to 50 times. So many, he actually lost track of the count. We're gonna talk about the places to go, the spectacular cuisine, the gorgeous coastlines, ancient ruins, and some of Italy's rich history.

We'll also get to some of Lee's favorite off the beaten path locations for an authentically local experience, and hear why he thinks life is just that much better in Italy. Finally, we're gonna dive into some of the best ways you can use your points and miles for your trip to Italy, including a quick overview of a new site I've been using to help you get the best hotel deals with points.

So let's get into it right after this. Lee, thank you for being here. Round three, you get to take the title as most visited guest. You already had it, but now you get it again. Thank you for having me here in this new setup you have. I'm looking around, it's really quite impressive.

Beautiful job you've done. - Yeah, I took this course, DreamStudioCourse.com that this guy Kevin Chen created, and you'll get a better view if you're watching this on YouTube than listening, 'cause you can't really see it. You'll get an even better view when I start to actually record in a couple days with a virtual thing, because that was what I optimized for.

But there is now an in-studio option for all the hacks, which we have here. - It's very cool, very cool. Thank you for inviting me in here to chat about one of my favorite places in the entire world. - Yeah, so I am excited because we started with London because I was going on a trip and I wanted to figure it out.

And then we dove into Japan, which actually now that I think about it, Brandon Presser made his second appearance. And now we're talking to Italy, which I'm really excited about because I was about to go to London. I had been to Japan a lot. And Italy, I went on the few days after our college whirlwind trip, but it's a trip that we wanna take.

And it's not gonna happen this year, but it's gonna happen in the future. And I'm really excited to dive in. I don't know a lot, so I'm glad we have the expert here. - Yeah, well, I appreciate you inviting me, of course, and giving me this chance to chat about something that is truly one of my favorite places for people, for food, for culture, for beauty, for sights.

I mean, we could chat for much longer than this podcast will go about everything that's great in Italy. So I'm excited to dive into your questions and share some of my own passion. - So why do you keep going back? What is it? I mean, you just listed a bunch of things, but what makes Italy such a unique travel place?

- Yeah, well, I've been to 70 countries. I've been very fortunate to go all seven continents around the world. And the thing that makes me feel most at home in Italy is just that the Italians know how to live. They know how to live life. Great food, great wine, great coffee.

But more than all of that, it's just this continual enjoyment of life. There's the evening passeggiata, where people walk. Everywhere you can go, you walk, which is incredible. Big cities, small cities, everyone walks. But they're out and about, and they're walking from cafe to cafe. They're seeing friends, they're being social.

But no one's in a hurry, no one's in a rush. No one's off to catch the next thing. They're just there living in the moment, being. And if you look at that as a narrative example of how you can live, right? These people have been doing this for thousands of years, 3000 years of civilization in Italy, where they're just being.

There's no greater thing to do, or to-do list, or all these things that keep us busy here at home. It's just being. And that, for me, is so refreshing. So I feel like I have to go back and back to get another taste of that every chance I get.

And of course, the food. When I'm there, I'm tasting that too. And it's incredible, the diversity and the ability of the Italian cuisine to take these wonderful things from their natural, abundant resources, the sea, the mountains, their fields, and turn them into these masterpieces on the table. - Okay, so I think one of the things I'm just gonna preface everyone to consider, which is a lot of times people travel and they say, "I gotta go do this." It sounds like a big attraction in Italy is learning to kind of relax and enjoy what you're doing.

So maybe that's a theme that we'll just kind of keep here, which is as much as we might talk about lots of cool things to see and don't feel like need to spend every single moment of every single day doing. - That is 100%. The biggest takeaway I think people can take from this podcast is the discussion of be here now in the moment, the place that you are in Italy, knowing that you're, yeah, you're not gonna see all the rest of it.

Like I've been to Italy 40 or 50 times. I forgot the count. And what's crazy is that out of all of the 20 Italian regions that there are, I'm still missing a few of them after having been there 40 times. And so I, an Italophile, somebody who loves going to Italy, speaking Italian, eating Italian food, seeing Italian culture, I still haven't seen it all.

And I will never see it all because there's such a diversity in that country. 60 plus million people, you know, it's the fifth most visited country in the world, but there is still so much to see that people don't scratch beyond the surface and see when they do their Rome, Florence, Venice trip and they think they've seen Italy.

You've seen three cities in Italy, come back and see everything, come see a lot more. - Well, I think most people listening probably won't in their lifetime make 40 trips to Italy. So it sounds wonderful, but let's just talk high level. Someone wants to go to Italy and it's impossible to see it all, but nobody or most people don't have 10 weeks a year to go spend in Italy, which I'm sure if they did, you would highly recommend, but maybe they've got a week or two and they're like, I wanna go see Italy.

I wanna experience what you're talking about. How would you suggest they start to approach it? Or what are a few different approaches? - Yeah, great question. So I think the first thing to realize and understand is that no approach is the right approach. There are so many different ways of seeing Italy.

If you look at it as like a matrix, right? All the different cities, all the different sites, all the different reasons for visiting, and you could go just see museums and be busy for 10 days in Rome alone, or you could do the Rome, Venice, Florence tour, Milan tour of all the museums or all the churches and historical sites and still not see all of the highlights that you could see in 10 days.

So I think knowing that you're going into it, leaving a lot on the table, leaving things to come back and visit in the future is great. The second idea is knowing that it's really easy to burn out on too much eating, too much museuming, too much churching as you go to Italy.

And so building a nice mix in an itinerary is a really important thing to do. So where do I find inspiration? There's a lot of really great media right now that focuses on an aspect of Italian culture or life. You know, Stanley Tucci has been doing for the past two years his sort of Tour d'Italia, and he's going to all 20 regions, and he's eating his way through.

And if you look at the way that he's approached his episodes, these hour-long sort of opus, these hour-long bits of love to Lazio, where Rome is, or Campania, where they grow the tomatoes that become your pizza tomatoes here in the States, you look at him really getting to know a people and a culture and a place, something that he's very familiar with already, but through the lens of food and culture.

And that's a wonderful approach for people to take, is they find some angle that they love, whether it's in a book or a TV series, and they say, "Hey, I want to go recreate an element of that on my trip. So I want to go to the place where Stanley Tucci finds the tomato in the field of San Marzano and says, "Okay, I found the real tomato.

Now I know what it's supposed to taste like." That's a centerpiece for their trip. But there are so many blogs that are out there. There's so many travel advisors willing to help. There's so many books you can read about everything to eat, see, and do in Italy. My biggest takeaway for people, again, is take your time and know that you're not going to see it all.

You're not going to do it all. And you're going to have an amazing time in the process of whatever you do, see, and do. - So I feel like I'm both more excited to go to Italy, and I have no idea what I should do with a week and a trip.

Maybe give some options. I'm thinking one to two weeks, maybe let's throw out two or three things that you might send someone to. Is Rome a must include on any first trip to Italy? - In my opinion, yes. All roads lead to Rome for good reason, right? Look, it's the third most visited city in all of Europe.

To me, it is a place that is happy and fun and lively and young and still so very old, full of incredible cuisine, full of some of the best historical sites in the world. Look, to me, the fact that they could build the Pantheon, this concrete domed roof with an open hole in the oculus in the center, 2,000 years ago, and it's still standing.

It's still standing, it's like mind blowing. Like we can't build a road here. They can build a, 2,000 years ago, a dome that is in the center of town that is remarkable. And so when you see that, you have a sense of awe that returns to you, whether you've been there 40 times or this is the first.

So I think Rome is absolutely an incredible place to go. Go see the sites, go see the touristy sites that are overcrowded, the Colosseum, Vatican, because they really are monuments to humanity and to an incredible society that has built and upkept these buildings for 2,000 years. But also get lost, go off the beaten path in Rome and don't just go to the fancy gelateria across from the Trevi Fountain.

It's beautiful, it's great for Instagram, but go wind through the streets of Trastevere, across the river where the Romans live and the Romans go eat, and explore that little village and see what it's like to be in a little borgo, a little village inside of a big metropolitan city.

Have a meal on a piazza where maybe you're the only person who doesn't speak fluent Italian, that's okay. You're gonna be welcomed in, you're gonna eat an incredible meal, and you're gonna see the way that the sweetness of doing nothing passes by in front of you on passeggiata as people are walking from the cafe to the restaurant to their home and beyond.

- Okay, so that's Rome. So let's say I wanna do Rome and something else. What are a few options? - Well, from Rome within, if you draw like a big circle, you say I wanna take a two-hour train ride from Rome, you've got a ton of options, north and south.

Traditionally, people would go south to the Amalfi Coast. It's incredible, it's iconic, it's beautiful. It's been made famous since the movies in the '50s, right, where you're driving along these mountainside roads and there's a sheer cliff 500 feet down and beautiful beaches and incredible food and wine. That's amazing, it really is.

The downside to it is that everyone wants to be there. So that coast between, let's say, June and early September is a zoo. What is normally a 20-minute ride in a car or a bus could be an hour and a half stuck in traffic on a one lane. That's a bummer when you're on a limited vacation time.

So what I would recommend is go to Amalfi, but maybe go in May or go in late September or October. The weather is still amazing, you can experience it and that's wonderful. So another piece to take away from the conversation is seasonality. You can always go to Rome, Rome is happening year round.

Harder to go to a beach in November. (laughs) But the Amalfi Coast in October is still really lovely and you'll have a third of the crowds that are there throughout the year. Nearby Amalfi, you've got Naples, you've got Pompeii or Ercanuleo, which is the nearby town that's like a mini Pompeii that has incredible ruins that are really not visited.

You can go walk amongst 2,000 year old homes that were damaged in the ash from Vesuvius in 79 AD and you can just walk around and there's no one around you. Whereas in Pompeii, it can be pretty busy. So there's little alternatives to each place along the way that you should try to explore.

But if you don't wanna go south, you can always go north. Florence is only an hour and 20 minute train ride from Rome. There's trains that leave every 15 minutes. It's an incredible town. It's like a medieval village that still comes alive today. And I actually studied abroad there and did culinary school there in 2003, a little while ago.

And it was just an incredible place to be young, to be alive and to be living in a medieval city of today. So great sights and sounds, amazing food. If you like pork, that is your city. If you like red wine, that is your region. And there's a ton to do.

But let's say you've done Rome and you've done Florence. What do you do on your second or third trip back to Italy? Most of your flights are gonna fly either into Rome or into Milan in the north. That's where most of the flights from North America tend to land.

So what I like to do is get off the beaten path and explore other areas that are maybe less popular with North American tourists, but still to me pack authenticity, incredible food, and great experiences into a small area. So something to consider might be Umbria, the green heart of Italy that's right next to Tuscany.

You have 2000 year old villages there, in fact, sometimes even older to the Etruscan age. You've got incredible food and wine, and you've got a third of the tourists that are in Tuscany. And you're probably paying half to three quarters of the price as well. So that's a wonderful place if you feel confident and you're okay to get off the beaten path by yourself.

Even if you don't speak Italian, you can get by in Umbria, eat, drink, and see well, and go see some incredible sights and sounds that are unlike anywhere else in the world. The last plug I'll make for Umbria, by the way, May 15th. Every year, my favorite festival in the whole world takes place.

It's called the Corsa di Ceri. What that means is the running of the candles. You think running of the candles, how does that candle blows out when you run? How does that work? These crazy people in this town of Gubbio, they take these huge wooden slats. They're like 30 feet long.

And a bunch of husky men hold onto them. And on top of the slats are these big tall columns with a saint on top. And they run these candles through the town, through the medieval town. And the walls of the buildings next to you are like encroaching upon these candles as you run through the streets.

And they sing songs and they play trumpets and music. And it's insane. It's a party and no one outside of Italy goes there. It's like, not like it's a running of the bulls or the Tomatera in Spain. It's like this true Italian festival in the heart of Umbria. I've only been twice.

I would love to go back again. 'Cause it's, to me, it's the most exciting element of seeing people in their thing, doing their thing, living their lives, celebrating their history and culture and having a blast doing it. - You said a couple times, even if you don't speak Italian, should anyone be nervous going to Italy if they speak no Italian?

- No, because the Italians are the kindest, nicest people. And I say that as a overarching stereotype. You're gonna have your bad apples for sure. But the people who work in trades that tourists are going to be engaging with, restaurateurs, cafe owners, cafe workers, transportation people, et cetera, are really excited that a big lifeblood of the Italian economy, tourism, is back.

During COVID, Italy was one of the places that locked down the hardest in Europe. And it was tough for Italians to even leave their homes. Now that you can leave your home, the Italians are so excited to have work again, to have an influx of tourists again, and to see people.

Look, in 2019, there were 65 million tourists that came to Italy, okay? 2022, that number was down by about a third. And 2022 was the busiest year for tourism since COVID, obviously. So that's quite a difference, going from 65 million to about 40 million in terms of tourists. The tourism is huge for a country of 60 million that really relies on tourist dollars and tourist euros, I guess.

So getting by without Italian is totally fine. You may end up in these off-the-beaten-path hill towns where they get fewer tourists. You may end up doing the whole pointing thing, the shrugging your shoulders thing when you don't know a word, and that's totally okay. The Italians roll with the punches, and they love that.

So I would not feel worried at all about not speaking the language. Instead, I would, maybe if you have a few hours before you go, study up on Duolingo, or brush up on learning some Italian phrases online. A little bit of Italian will go a long way, and you'll never have to worry about feeling like you have no idea what you're saying.

- Any other kind of cultural norms worth calling out so people kind of fit in and don't stand out like American tourists sometimes can? - Yeah, don't try to make a 6 p.m. dinner reservation. (laughs) The Italians, they're not the Spaniards, where they're eating at 11 o'clock at night, but they're not far off.

They do eat on a different schedule than North Americans typically do. So breakfast is lighter. It's a cappuccino, coffee of some sort, and a croissant, or a piece of bread. Lunch is a big affair, and it can go on sometimes for two or even three hours. But dinner will take place usually very late.

Seven o'clock is the absolute earliest people eat in the winter. In the summer, it's even pushed to eight or sometimes nine. So if you're walking around and you see the restaurant and it says they open up at 2100, don't think that it's like a nightclub. It's actually just their standard business hours for dinner.

And when we were there with even young kids this summer, we would eat at like 8.30, nine o'clock, and we'd be finishing our meal at 10.30 or 11, and there'd be families with our kids' ages sitting down for dinner at 11 o'clock, which is really crazy. - Do people sleep in, or how do they make this work?

- They do. They sleep in and they take a pausa pranzo. They take a big gap for lunch. So if you're working in an office, let's say, from about 12.30 or one, oh, about three o'clock, maybe a little later, you're kind of out of the office. People are either eating a long lunch, they're napping, they're just not working.

They're going for that pasta giatta, whatever they're doing. But people do tend to take a gap in the middle of the day. - And so when you went with young kids, did you just kind of change the time schedule so that they were just up later and sleep in later?

- You have to, yeah. And we mandated a family nap, not just kidnap, but a family nap every afternoon. 'Cause in the summer in particular, depending on where you are, it can be very hot. So having a midday nap was a nice thing. But, you know, it would be amazing.

We'd see kids out at 11 o'clock, 12 o'clock at night. And then those same kids would be up at like, you know, 9.30 in the morning. And I'm like, how do you do it? (laughs) - Easy to meet local Italians. What's the vibe like between tourists and locals when it comes to meeting each other, trying to make friends with locals and kind of get a true authentic local experience?

- Yeah. So I would say the more of an authentic and local place you're in, the more likely you are to meet Italians. And what I mean by that is Piazza Navona in Rome. One of the most incredible piazzas that there is. Beautiful fountains in the middle and benches all around that and restaurants circling the entire piazza.

And it's an incredible place, but it's not built for Romans, it's built for tourists. Romans go there, but if you wanted to meet Romans, you're gonna meet them in the piazza around Santa Maria in Trassevere, the place I mentioned earlier, Trassevere. You're gonna meet tourists in tourist places. You're gonna meet Europeans or Italians in particular in their neighborhood, where they are.

So what I would recommend is choose the opportunities to meet with people and seek them out and go find them because you will find them and people will want to meet you. They'll wanna hear your story. Where are you from? Why are you here? They're so proud to show off their neighborhood or their city or their country.

And so when they hear, "Oh, wow, you're Californian, amazing. I've always dreamed of going to California," is the thing that they'll say. And then they'll be so proud to show you their piazza and they'll be so happy that you're there. So find the Romans in their neighborhoods. Find the Italians in their cities, not necessarily at the tourist traps.

- And how are you getting around Italy? Are you flying into one city and renting a car? You mentioned the train. I know you could probably even fly between cities. - The trains run pretty well. I mean, Mussolini did that whole thing, I guess, and electrified and brought trains everywhere.

And there was some dilapidation after that. And the trains nowadays don't run perfectly, but they're fairly reliable. So I would say to take a train as much as you can. You definitely don't need to drive a car if you're going from city to city to city. When you get into the country, the trains don't run.

And so buses run or private car transfers are very simple and easy to set up. If you're gonna be staying in Tuscany or Umbria and you're gonna want to explore from your hotel or your villa, absolutely rent a car. Driving in Italy is interesting, it's easy, but I would take caution as you drive because Italian drivers can be a little aggressive, nothing to be scared about or worried about.

There's no road rage. They're just gonna pass you by because you're going too slow. (laughs) That's fine. Italian towns tend to be very small and roadways even smaller. So when you drive from town to town, it may be hard for you to find parking inside the town walls. Just park outside and walk in, it's easy.

Better than trying to navigate your rental car through medieval streets that were really meant for cows and sheep, not for humans and not for cars. You don't want to have that on your car insurance bill. But as a general rule, it's easier to get around in Italy when you plan ahead and you know the train schedules from city to city and then from there, if you need to take a taxi or a car rental.

- Getting the crew together isn't as easy as it used to be. I get it, life comes at you fast, but trust me, your friends are probably desperate for a good hang. So kick 2024 off right by finally hosting that event. Just make sure you do it the easy way and let our sponsor Drizly, the go-to app for drink delivery, take care of the supplies.

All you need to come up with is the excuse to get together. It doesn't even have to be a good one. It could be your dog's birthday, that the sun finally came out, or maybe you just want to celebrate that you got through another week. With Drizly, you can make hosting easy by taking the drink run off your to-do list, which means you can entice your friends to leave their houses without ever leaving yours.

And since I know you like a good deal, Drizly compares prices on their massive selection of beer, wine, and spirits across multiple stores. So when I really wanted to make a few cocktails while we were hosting family last week, not only could I get an Italian Amaro delivered in less than an hour, but I found it for $15 less than my local liquor store.

So whatever the occasion, download the Drizly app or go to drizly.com. That's D-R-I-Z-L-Y.com today. Must be 21 plus, not available in all locations. I love helping you answer all the toughest questions about life, money, and so much more, but sometimes it's helpful to talk to other people in your situation, which actually gets harder as you build your wealth.

So I want to introduce you to today's sponsor, Long Angle. Long Angle is a community of high net worth individuals with backgrounds in everything from technology, finance, medicine, to real estate, law, manufacturing, and more. I'm a member of Long Angle. I've loved being a part of the community, and I've even had one of the founders, Tad Fallows, join me on all the hacks in episode 87 to talk about alternative investments.

Now, the majority of Long Angle members are first generation wealth, young, highly successful individuals who join the community to share knowledge and learn from each other in a confidential, unbiased setting. On top of that, members also get access to some unique private market investment opportunities. Like I said, I'm a member, and I've gotten so much value from the community because you're getting advice and feedback from people in a similar situation to you on everything from your investment portfolio, to your children's education, to finding a concierge doctor.

So many of these conversations aren't happening anywhere else online. So if you have more than 2.2 million in investable assets, which is their minimum for membership, I encourage you to check out Long Angle, and it's totally free to join. Just go to longangle.com to learn more, and if you choose to apply, be sure to let them know you heard about it here.

Again, that's longangle, A-N-G-L-E, .com. - So you said plan ahead. You and I both like saving money. Let's say you're planning a trip. You've kind of figured out your itinerary. What are you thinking you should do ahead of time? Any way to get a deal, whether it's transportation, flights, lodging, what are you thinking about?

- Yeah, so it definitely goes to say that the places you know you wanna go, book in advance. So that goes for hotels. It's obviously a lot cheaper to book in advance for most of these hotels. You can book a nonrefundable rate with a lot of them, and it'll save 10 to 20%.

You can also call a hotel ahead of time and say, "Hey, listen, I see you've got a nonrefundable thing online. "What if I went even further and said, "I don't need breakfast?" They might even do a bigger deal with you for that, if you're interested. But booking ahead is very important for hotel trains, in particular.

Your trains will be allowable to book between 30 and 60 days out in Italy, depending on the train line you're on. And typically, the cheapest rates are 30 to 60 days out, but highly recommend that. Also recommend restaurant reservations. At places you must go, book them in advance. But don't book every night.

Give yourself some flexibility on what spontaneously might happen, what you wanna pop into, where you wanna go, et cetera. The places that you have to go, like the Pier Luigi in Rome or Osteria Francescana, if you can get in, and Modena, book those. Build your trip around them if you need to.

But when you're in a place, don't have every single meal booked, because you may wanna have that spontaneity to just eat a bunch of prosciutto on the side of the road, 'cause it's really good and it's there. - So we talked a little bit about restaurants. Broadly speaking, when someone's doing research, is there a reliable site for Italy to figure out where to go, what's good, or what do you recommend?

- Yeah, so I use a couple sites as a travel advisor myself, when I'm trying to figure out new and upcoming places to check out or to send people. The first is that the Italians have their own Michelin guide. It's called the Gambero Rosso, the red shrimp. And Gambero Rosso is like the Bible for food and wine in Italy.

They have a fork rating. So if you get forks, it's a legit place, right? You should go. Up to three, I believe, or maybe it's four. I have to double check. But anyway, the more forks, the merrier, obviously. So check out Gambero Rosso. It oftentimes isn't only in Italian, so you might have to use Google Translate to figure out what's going on.

But that's a great place to find off-the-beaten-path restaurants. Look, in a big city like Rome or Milan, any international, whether it's the New York Times or the Michelin guide or even food blogs you've read, they're all gonna have the same general information. But when you're going off the beaten path, a Gambero Rosso is incredible.

And actually, I find the most joy in smaller Italian towns. And I find that if you just go a little outside of the tourist envelope, you can have these incredible culinary experiences that are half the price sometimes of the tourist bubbles, but they're so much richer and more meaningful and more connected to the area.

An example, I love the Cinque Terre. It's one of the top spots to see in the north of Italy on the Italian Riviera in the Liguria state that borders basically, goes from almost Pisa all the way over to the French border. And it's this little horseshoe on the Italian coast.

It's stunningly gorgeous. You've got the five towns of the Cinque Terre, you've got Genoa, you've got Portofino, these really iconic and incredible places, but they're very, very, very touristy. And so for me, instead of eating in Portofino and spending 15 euro for a panino that I could get three euro elsewhere, I rather go elsewhere and explore and see what else I could find and eat.

So a great example is a town right next to Portofino called Rapallo. I actually have lived in Rapallo on and off a couple of times during the summers, because every time we have a child, we decide that we're gonna go to Rapallo and spend our parental leave there. It's just an incredibly magnetic place.

But Rapallo is a town with kind of nothing to do, but everywhere to go easily from. And the eating there is exceptional. There's a little prosciutto place right on the harbor called Parla Come Mangi, Speak Like You Eat, that's the name of it. And they highlight local prosciutto and salami and cheese makers from around the region and from actually around Northern Italy.

And that's all they sell, is prosciutto, cheese, salumi, and some sauces. It's like this amazing delicatessen experience. Again, you don't need to speak English going in there. You don't need to know what you want. You just kind of go in and say, hey, I like this, and they'll guide you through the whole experience.

So you could go spend 15 euro for a panino made in Portofino, that's just fine. Or you can go spend 15 euro and get three different tastes of things from Parla Come Mangi, and life is good. You'll see it in Gambarorosso. You'll see it on maybe some food blogs 'cause it's now gained popularity.

But that's an incredible spot. And the same idea, by the way, when I lived in Rapallo, we'd go down to the Cinque Terre for the day. We'd go see the five towns, but we didn't have to be there, immersed in them and all of the tourists' sort of onslaught that was there.

And that, to me, was a great way of seeing and experiencing the culture, but not having to like be enveloped in it. We could choose we wanted to see the tourist experience, but we could also live like Italian local. So my recommendation is if you're going to some places like Como, Cinque Terre, really popular tourist sites, maybe even Venice, take a look at the nearby areas and say, does it make better sense for me to stay in those nearby areas?

And then maybe pop in to the tourist spot for a day or two, as opposed to basing myself in the tourist bubble, only experiencing that. - And where are you staying when you're leaving a city center? I know in a lot of countries, it's like there's not a hotel there.

Are you booking Airbnbs? Is there a different site in Italy that it's for finding houses or apartments? - Great question. So Italy has all ranges of accommodation. The most expensive hotel in Northern Italy outside of Venice is actually in Portofino. It's the Belmond there. And it's an incredible property.

Right outside of Portofino, you have Santa Margherita, you have got Rapallo, you've got other towns. And in those towns, there are four and five star hotels that are not the Belmond, but they're lovely. And they're a third or a quarter of the price for an interestingly similar level of luxury.

Not the same, but close. You, of course, can go much down market from there and you can find lots of wonderful things. The Italians are huge on camping. They love camping in the summer. So there's actually campsites within towns that have like motorhome or camper van style campers that you can rent sometimes.

And that's a really fun way of getting local and immersed. Airbnb is huge there, VRBO more in the outskirts when you're getting into villas and homes outside of town. So you can definitely do that. But honestly, what I like to do is look around on booking.com, hotels.com, get a feel for some of the hotels that are selling through those channels that I may not recognize internationally.

And then I go right to their websites and I find what are their specials, what are their deals. I reach out to them through their contact form or through their booking form and say, "Hey, this is when we're coming. "We don't need this. "We don't need a breakfast. "We don't need a suite.

"We're barely gonna be in the room. "What do you got?" And they'll absolutely do a deal with it. The best part about some of these Italian hotels too is that they won't take a deposit. They'll just take your credit card. And when you get there, you pay. So some of them have very flexible cancellation policies as well if you go that route.

Or if you prepay and you make it non-refundable, you can even get a better deal sometime. - And what about the kind of typical chain hotels? Are they worth considering? Are there Hyatt's, Marriott's, Hilton's kind of thing? - All over the place. All over the map, yeah. Actually, the funniest thing I think is that the best Western brand here in North America, not exactly the nicest hotels.

If you go to Italy, they're actually not that bad in some places. And surprisingly, the best Westerns in off-the-beaten-path cities are actually okay. And now granted, not my preference always, but it's a good economical way of staying when maybe the competition nearby is another 100 euro more. But yes, if you've got Hyatt points or Marriott points and you want to use them in the big cities, there's definitely opportunities to do so.

In Italy in particular, you should look out for small luxury hotels that are often part of the Hyatt, sort of world of Hyatt program. Those oftentimes will allow for outsized value where you can use your Hyatt points to save on these boutique hotels that would otherwise be very, very expensive.

Personally for me, when I'm in big cities, Italy has some of the most incredible hotels that are not parts of big brands. So it's really fun to experience some of those hotels. There's one in particular, it is part of the Relais Chateau Marketing Partnership, but in Rome, it's called Palazzo Manfredi and it is at the Colosseum.

And when I say at the Colosseum, I mean there are suites that if you open up your sliding door, the Colosseum is in front of you. There is an unobstructed view, nothing between you and the Colosseum. That's incredible. And where else in the world do you get that? And so sure, you could stay at the St.

Regis, which is an incredible property in Rome, beautiful, but you can also stay at the Colosseum. So to me, it's like when you're in Rome, when in Rome, when you're in Italy, you should, you know, Il San Pietro on the Amalfi Coast, that family that's been running that hotel for 40 years now, they've built by hand every single room into a rock on the side of a cliff overlooking Positano.

There's nothing like that in the world. - Which hotel is this? - Il San Pietro, and they are incredible hoteliers. They've mastered the art of luxury hotel. Food is remarkable. It's got a Michelin star and it's in Gambarodo. So it's just an incredible experience, but you know, you could choose to stay at like a whatever hotel nearby, or you could stay in this icon, this place that is truly incredible.

There's nothing like it in the world. So when I look at the big bucket list trip to Italy, I look at staying in some places like that. If they're available, if they're affordable, if not, absolutely use your points at the St. Regis. It's an incredible place. - But it sounds like if you're gonna take three or four trips and you've got points for not all of them, maybe Italy's one where you're not gonna use your points for hotels or lodging.

- That's correct. And I would prepare to find then the boutiques, the other cool places, the three, four, five star hotels, the B&Bs, honestly, that are a good fit for what you want in that city. And don't be afraid to look around and comparison shop all over the place, and then reach out directly to the hotelier and say, "Hey, these are my dates, what can we do?" - What about when you're in the city and you wanna do things?

Do you need to set up tours? Do you need to set up guides? Do you get lost on your own? How do you find them? What about booking activities, booking thing? - Yeah, all of the above. (laughs) So look, there are some bucket list things that you're gonna wanna see in Rome, right?

You're gonna wanna go to the Vatican. You're gonna wanna maybe go to the Coliseum if you're into that. And so you're gonna wanna pre-book those as much as you can. Vatican in particular, the thing I like to do is the Vatican Museum sells this on their website, so you don't need to buy a special tour for it.

But Breakfast at the Vatican, it's called. You actually go to the Sistine Chapel pre-opening, and you're part of a very small group of people that can do that. And then you will have breakfast after the fact at the Vatican in their cafeteria. That's an incredible way of seeing one of the most amazing sites in all of the world.

It's usually very crowded throughout the day. So getting in a little early is worth the extra dollars or euros. Now, if you wanted to completely privatize that experience too, find other people. We can do that. But that's a lot more money and a lot more consideration than just buying a ticket online.

But the dates you know you're gonna be in Rome, especially those dates that may be like you've just arrived the day before, and you know you're gonna be all jet lagged the day later, like buy the early morning tickets. Make sure that you get in to have that experience as privately as you can.

But do leave space for spontaneity and what you might find. And do feel free to sort of throw your afternoon plans away 'cause you're just into the vibe of this cafe or this piazza and you just wanna sit there and watch for a little bit, right? So I like to have structured and semi unstructured time in all the itineraries I put together.

Now, on a city by city basis, there's so much to do. I definitely recommend looking around on various guide websites to see who can do what according to what style of tour or experience you want. You know, there's a Jewish ghetto in Rome and there's a great historical food tour that we often combo.

And that again, leads into then sitting at a cafe or at someone's restaurant and parlando un po, chatting a little bit for the next three hours after that tour. Or we do a sidecar tour of a couple of these different cities where you actually hop in a motorcycle sidecar and drive around and get to see the historical sites.

And you never know where you might end up or where you might stop on that tour. So some of those kinds of fun experiences, pre-planned with flexibility in the end, works really, really well. - If you don't have plans, I always like taking free walking tours. I feel like they're always led by young, excited people who wanna show off their town.

They're working for tips. So that's something you can do in any city I imagine. I've found them almost everywhere. So I've said that a lot, but I think it's a great thing to do if you don't have anything planned and you decide you wanna do something and you haven't booked it in advance.

- Absolutely. And I would say like, take inspiration from websites that actually have lists of tours that they offer. Whether you use those tours or not yourself, take inspiration. Understand what they're showing you because that's clearly a good guide for what you should see in that town. And so what I like to do is go look at Context Travel.

They're great tours. We do a lot of them, a lot of work with them. Or even like Airbnb Experiences. And just see what people are offering in that area so you know what you should focus on or not focus on while you're there. But don't feel like you need to buy the expensive private tour all of the places.

You know, in the height of summer in Rome, in Florence, in Venice, in Milan, it's gonna be busy and there's gonna be a lot of people there. So maybe you do wanna take a private tour somewhere. But outside of those times or those places, maybe you can be okay dealing with some crowds.

The exceptions to those rules are places that have timed entry tickets. The Accademia in Florence, where you see the David. Or the Uffizi, where you see Botticelli's work and a lot of the Renaissance paintings. Or in Milan, when you wanna go see The Last Supper. Those things are very time controlled.

You need to have a ticket. And you'll see as you research your tours, it'll say, "Hey, this includes a timed entry to blank." But what I would say is some of the best parts of Italy are just getting lost and wandering on your own. And maybe you don't know what's in front of you, but that's okay.

It's beautiful nonetheless. And you're there. And so just be there and enjoy it. - I know we hit a lot of places, but I'm curious if there are any that we left off that you wanna talk about. - So I think it's important as we record this, it's 2023 and the White Lotus is like the thing in the media right now.

And it's their season two, which was filmed in Sicily. And it was filmed at the Four Seasons in Taormina at the San Domenico Palace. It's beautiful. Stunning property that they put a bunch of money into, redeveloped and it's gorgeous. And it's amazing to see the impact of that show and what has happened to travel desire around Sicily.

Sicily is always a constant for North Americans. We wanna go there. A lot of people with Italian roots came from Sicily or had family in Sicily. And so people wanna go see their genealogy and they wanna go see the sights and sounds of Sicily. So it's always busy, but this year it's exceptionally busy.

So I would say, A, book now. There's a lot of interest. But B, know that Sicily is a place where you could easily spend two weeks and not see a fraction of it. The area around Taormina, which is where they filmed White Lotus is incredible. You've got the Etna volcano, you've got Catania, Ragusa, Siracusa, all these amazing towns that are on the East side of Sicily.

Full of history and culture and art and food and food and food and food. So you could just spend two weeks there bouncing around from town to town with your own car and you'd be happier than you know what to do with. But I would also recommend heading a little further West in Sicily.

The town of Agrigento has some of the best Greek temples, better preserved, in fact, than some of those you'd find in Greece. And then there's Palermo, which is incredible. Right North of Sicily, you've got the Aeolian Islands. The word volcano comes from an island in that little island chain because there's a giant volcano on it.

It's called Volcano. So I'd go there or Stromboli or some of these amazing places in the summer that have lava and mud baths and beautiful beaches and it's just you and the volcano. So Sicily is incredibly in demand. Puglia on the heel of Italy, another place incredibly in demand.

Hotels, especially luxury hotels, are popping up left and right down there. And if you like the orecchiette pasta, the kind of ear shaped pasta, that's its home. If you like sausage and peppers, that's their home. If you like beautiful white sand beaches with no one on them for a kilometer, that's your home.

And it's an incredible place where you can go and explore, spend a week, 10 days, not see the same thing twice, and eat the best meals of your life. And it's not as expensive as Tuscany or Umbria or elsewhere in the North. So in the South, those are my winners.

Sicily, Puglia, and they make for great vacations. Do keep in mind if you go in the very heart of summer in July and August, it's hot. Talking could be easily over 100 degrees Fahrenheit each day. That's pretty toasty down there, but it's beautiful. And the sea is warm and refreshing.

Another area that I would also recommend as a side trip from the Amalfi Coast, everyone always goes to Capri. The island of Capri is incredible and beautiful and it's stunning. It's a sight to see, but it's also very expensive and it's very crowded. And you get the sense when you're there that there aren't really any caprese.

That's people who live in Capri. You don't find the locals. You find people serving tourists. So my recommendation would be go to a neighboring island right across the Gulf called Ischia, I-S-C-H-I-A. There you'll find true Italians. It's a place that is volcanic in origin. So you have mud baths and hot springs and crazy stuff all over the place.

You have people who are so happy and so proud to show you their island, 'cause it's less touristed. And you have the ability to get around in, whether it's a rental car or a Vespa, or actually they drive these little things called apes, little, called bees. They're a little like farm equipment, like a lawnmower with a couple of seats, but they're stylish and they drive you around the island in those.

And you can really get to know the culture and the people and the restaurants that way. And at a third of the price of Capri. - So I think we hit everything. Anything in the north, we moving up the coast, any? Let's talk about the north. - In the north, you have Venice.

And the Venice is an incredible place to go for a night or two. If you're gonna stay in Venice and you've never been before, I absolutely recommend you stay overnight, at least one night, probably no more than two. The reason is that there's a lot of day trippers that come in and out of Venice.

And you'll want to see the city at night when most of the tourists leave. It's a magical place. But if you've been to Venice before and you haven't been to the area around Venice, and that could be anywhere from Trieste, which is all the way to the east, close to Slovenia, or even the Dolomites about an hour or two north of Venice, then you need to go back to that eight region and go see those places.

The true heart for me of the Veneto, which is the area around Venice, is not necessarily in Venice proper, but it's the area around it. It's the rich farmland, the Palladian villas, the beautiful mountains and the other cities, especially canal cities that make that area so rich. So I would say, make sure you see Venice.

It's incredible. St. Mark's Square, nothing like it in the world. And then get out of town. Go see something nearby. - I feel like we hit a lot. I think someone listening to this maybe has some inspiration for their next trip. - Or they're totally overwhelmed. - Or they're totally overwhelmed.

Maybe listen to it twice. You mentioned a few places that you love. Are there any other things that when you think of, if you were going on a tour through a lot of these places that are like, you gotta eat here, you gotta have a drink here, you gotta have a coffee here, are there anything like standouts that maybe aren't the obvious ones that someone searching blogs are gonna find?

- For sure. As a general rule, as I said earlier, I love looking at Gambaroro. So I love looking at the Michelin guide. I love to understand what, it doesn't need to be three or even two starred. What's Bib Gourmand? What is a good place to go check out that's local and legit?

And I start there. And then I look at actually TripAdvisor in Italian reviews. Again, if you don't speak Italian, take the TripAdvisor reviews in Italy from Italian people and Google translate them into English. You'll get a real sense of what something is from an Italian's perspective that's different from a non-Italian.

Let's put it that way. So I like to read some of those to really understand what's great. And then I go back 20, 30 years and see what's still standing in a spot for so long that I need to go to. I mentioned earlier that I used to live in Rapallo.

There's a coffee shop in Rapallo that's been around since the 70s that they sell a particular style of biscuit in the morning. I'm not a biscuit eater, but this biscuit with their coffee is like amazing. It's called canepa, C-A-N-E-P-A. And so it's not like I need to go to Italy to have that, but when I'm there or nearby, that's the only thing I eat for the week or whatever it is of time that I'm in Italy.

In Rome, there's a place called Panella, P-A-N-E-L-L-A. They make out of an old school coffee machine, kind of looks like a samovar almost. They pull espresso and then they whip it with a zabaglione, egg yolks and sugar. And they make this cream. And so you can go get an espresso with espresso zabaglione cream on top.

That is to die for. And I could literally, Chris, tell you 150 of these things, okay? But the point is, is that none of these are like undiscovered gems that no one's ever heard of. They've been around for 30 years, 50 years, 100 years, doing their thing, selling their one item that makes them spectacular.

And so every town you go to will have this, from big or small. And it's just a question of you seeking them out and finding your own that's exciting to you. You may not like coffee. And so those two examples I gave you are terrible, right? That's fine. But you'll find the thing that makes the Italians, the locals, super proud and makes everybody write about it and talk about it and eat it and drink it and experience it themselves.

- And if you're someone like me and you're a bit of an over-optimizer trying to find the perfect place, is Italy the kind of place that you can fall into a trap of just walking down the street and picking the wrong place? Or is it just like, just go pick any place that looks crowded with people that look like they're speaking Italian and you're gonna have a great meal?

- The latter, for sure. If you find where the Italians are, you're gonna have a blast. If you find a menu in seven languages, beware, you have your hackles up, but know that if you're gonna follow the Italians and get lost and be off the beaten path, and it might be a little uncomfortable 'cause you may not speak Italian and you may not know where you're going.

Trust your instincts, trust your nose, you're gonna find something great. - And you can get back with Google Maps. Like it's not, you're not lost. - Or you could tell people, "Hey, I don't know where I'm going. Can you help me?" And they will help you. They're not gonna take advantage of you.

They're not brutal people. They're lovely, wonderful people. If you start it by saying, "Oh, I'm so happy that I got lost here. How do I get back?" (laughs) They'll help you right out. - Our next partner has a product I literally use every day. I started taking AG-1 from Athletic Greens because I wanted an easy way to get my daily nutritional insurance and optimize my immune system.

And it's been in my routine for almost a year. Because when you take one scoop of AG-1, you're absorbing 75 high quality vitamins, minerals, whole food source superfoods, probiotics, and adaptogens to help you start your day right. Every morning, I mix it up with some cold water, add a few ice cubes because it tastes so good cold, and head to my office feeling focused and energized for the day, which is a feeling I absolutely love.

I also love that it has less than one gram of sugar and no GMOs, nasty chemicals, or artificial anything. To make giving it a try easy, Athletic Greens is gonna give you a free one year supply of immune supporting vitamin D and five free travel packs with your first purchase.

All you have to do is visit allthehacks.com/athleticgreens. Again, that's allthehacks.com/athleticgreens to take ownership over your health and pick up the ultimate daily nutritional insurance. I just wanna thank you quick for listening to and supporting the show. Your support is what keeps this show going. To get all of the URLs, codes, deals, and discounts from our partners, you can go to allthehacks.com/deals.

So please consider supporting those who support us. Any parting thoughts? We didn't go too deep into specific things, but I feel like you left people with a few ideas of what to try. Any other standouts? - We'll talk a little bit about Airlift, getting to and from Italy, because there's a couple of gems here you wanna know about and a few you can avoid, right?

So Alitalia, which is actually an acronym, it's now a dead airline. It's the old state airline that Italy used to have. It died in 2019, 2020. But it was A-L-I-T-A-L-I-A, Alitalia. It literally means to Italy or the wings of Italy, depending on how you translate it. But it was the acronym for always late in takeoff and late in arrival, which is not nice.

They're dead now and their resurrection is called ITA Airlines. It's the same thing. I would sort of avoid them if I could. They're just meh at best. The business class is fine, but economy's pretty terrible. But all of your U.S. carriers, your Delta, United, American, et cetera, they all fly nonstop from Gateway Hubs to Rome and some to Milan.

But the best experience getting to Milan is gonna be on Emirates. Now Emirates flies from JFK to Milan, and then that same aircraft continues on to Dubai, and then it goes back. So I would recommend if you can get on business class or ideally first on that flight, do so.

Emirates just recently made changes to award redemption for that particular route, which is a bummer. But sometimes on Emirates partners like Alaska and others, you can still find it. So take a look at that. As a general rule of thumb, I would actually prefer to fly through Paris if you're gonna fly on Air France La Premiere.

If you're flying in true luxury, then take a nonstop from North America to Italy. Just that extra stop, even though it adds another hour or two, it's such a nicer experience than flying United Polaris. But there is gonna be a new United Polaris flight from San Francisco to Rome nonstop coming up starting in May, and that'll definitely help with lift from the West Coast.

In terms of getting around inside of Italy, none of the airlines that fly intra-Italy are great, so don't splurge for business. Business class in intra-Italy is literally just an empty economy seat. It's blocked off. So it's not necessarily something I would say is worth two or three times the price.

- Which by the way, seems to be this case with almost every European airline. If you're booking an international flight using points in business and you get the intra-Europe flight in business for free, why not? But you will be wildly underwhelmed if you've never had that experience because it's literally just a blocked seat in between you.

- Exactly. - And in fact, if you're traveling with someone, depending on the airline, sometime that seat is actually blocked. Like you can't actually lift up the armrests. - There's a thing there. - Yeah, so if you actually wanna sit next to whoever you're traveling with, you actually can't in those seats.

So I totally agree there. Any other points, miles tricks? Normally I would do a location episode and do it separately because most of the people I talk to about countries aren't as dialed in on points and miles, whereas you might be. Anything there? - Yeah, so I mean, definitely on the hotel side, take a look at using Hyatt points for properties in big cities, especially through the SLH properties.

Take a look at using Hilton points. There's a few higher end Hiltons that are sometimes not that egregious. Usually they're pretty bad. And then there are a handful of Marriott properties, especially those on Sardinia, that are usually exceptionally expensive, but sometimes allow point redemptions. So usually it's shoulder season, like end of May or early September.

But if you can get one of those Sardinian properties, it's normally 2,000 euro a night, and it's 60,000 Marriott points. Jump on that twice and then some. On the airline side, I do like to fly through Northern Continental Europe. Germany, Switzerland, France, even sometimes the UK, when doing points redemptions, because I find that the value of the ticket that I'm usually redeeming for would be greater than the price that I would pay for either a nonstop flight from the States.

I can get a better experience, better bang for my buck out of doing that. - Cool, all right. Well, Lee, I feel like I'm ready both for lunch, by the way. Now I'm both hungry, but I'm also excited for a trip to Italy. I don't know when it'll happen, because two kids traveling, we're still recovering from the trip to London and Paris, but I'm excited whenever it happens.

- Just want to call out, Chris, I have done weekend trips with kids to Italy before. It's not an insane idea. You can do it yourselves. Choose one city and go, and spend three nights. - I don't think that sounds as fun as you make it seem. - Sounds like you're not in.

- Your kids are older than ours. I don't know if a weekend trip with a seven-month-old is gonna be fun. - Yeah, not really too exciting when they're that little. - Cool, well, thank you for doing this. - Thank you, I appreciate the opportunity, and dai, andiamo in Italia.

Let's go to Italy. - That was so awesome, but Lee and I did not get to spend as much time as I wanted talking about points and miles and tactics to get to Italy, as well as how to use your points to stay there. So I'm gonna run through a few things, but I'm also gonna share an amazing service I've been using for finding hotel deals with points.

So when it comes to flights, all the major U.S. carriers, United, American, and Delta fly to Rome from their hubs. There's a few flights from each of them, mostly from more East Coast hubs to Milan, and then just a couple flights to Venice from the New York area, Atlanta, and Philly.

Don't forget that Air Canada also flies from Montreal and Toronto to Rome, and from Toronto to Venice. So if you're nearby, that's another good option. But there are a couple other airlines that while you can't use points or miles on, I do wanna flag. There's Norse Atlantic Airways, which I talked about on the London episode.

I'll just bring it up because it is so inexpensive to fly from JFK to Rome. When I looked on a date in August, it was $328 on Norse Atlantic versus 900 on the cheapest flight on all other airlines. So huge savings there. It's definitely a budget airline, though they are flying Dreamliners, which is nice.

So if you're on the East Coast, that could be worth looking into, or if you can get there. There's also an airline called La Compagnie, which is I think is a French airline that flies from Newark to Milan. It's interesting because it's an all business class airline, but their flights are as low as $3,000 round trip in business, which is a lot less than other airlines.

Then finally, another airline that we haven't talked about, you might not know, is called Neos. It's Italy's second largest airline, has really affordable flights to Milan from JFK. I found them as low as $500 round trip online. So that's another one. So obviously if you're using points and miles, though, none of those are options, and you're gonna be focusing on airlines that are part of major alliances that you can transfer points to, and that's usually gonna be Delta, American, United, Air Canada from North America.

Emirates also, as Lee mentioned, that flight from JFK to Milan. And then also, if you're willing to change planes, Air France, KLM, Virgin, British Airways, Lufthansa, Swiss, there are a ton of airlines that you can fly to change planes on. But I wanna share a little bit high level of some searches I just did to get you a sense of what's possible.

I went on United's site, I looked for the next month, and it seems very, very easy to find an economy flight for 30,000 points. So that is great. I imagine if you have points in any transferable program, you could transfer to some airline that's part of Star Alliance, whether that's Air Canada, Avianca, or United, and book something really affordable in economy.

If you're looking for business, I did find some flights. I found a flight through Frankfurt in October and in April, and the lowest prices I found were about 70,000 points one way on United. However, let me walk through an example of how the way you search for some of these flights can make a huge difference in the value you're getting.

So I just looked for a few weeks from now, April 4th, San Francisco to Rome. I found a flight on United's website for 81,000 points that changes planes in Frankfurt. So I thought, okay, that's not a bad use of points, right? 80,000 points for a business class flight. Yes, there are some dates you could find it for 70, but that's a pretty good deal.

However, I went to point.me, I did the same search, and what it'll do is not just look at where there's availability, but it'll look at the cost to book that flight on all the different airlines you could transfer from your credit card programs, and find out things like if you transferred Capital One or Amex points to Avianca, you could actually book that flight for 63,000 points instead of 81,000 on United.

Or because there's a 20% bonus right now, you could transfer from Citi to Avianca, and you only need 53,000 points. So for a $3,600 flight, if you only need 53,000 points, that means you're getting 6.8 cents per point. And even if you booked with Chase or United and you booked it for 81,000, you're still getting four and a half cents per point.

And when I looked at the cheapest flight with one stop in economy that day, it was almost $1,000. So the crazy thing is if you wanted to use that 53,000 points in Citi and book in the travel portal, you would only get $530. So you couldn't even book a coach flight there.

And if you took the 80,000 points on Chase, if you had a Chase Sapphire Preferred, you'd be able to use that 80,000, and you'd be able to book $1,000 ticket. If you happen to have a Chase Sapphire Reserve, you'd get one and a half cents in the portal. So that 81,000 points would get you a little more than $1,200, which would actually cover the economy flight.

However, we're talking about a business class flight. So the reason I love transferring points to airlines is because in circumstances like this, if you find the availability, you can usually get a business class flight for not too far off from what you would have gotten an economy flight for if you were just redeeming in the portal or you had had a cashback card in the first place.

So if we assume that in a given year, you spend $30,000 on your credit card and you manage to optimize such that you're on average getting back two points per dollar, or if you had a cashback card 2% back, then that $30,000 getting 2% cash back would earn you $600, but in points, you'd be earning 60,000 points.

Well, that $600 is definitely not gonna book you a business class flight to Italy. You would need $1,200 just to book the coach flight, but you could actually take those points and transfer them from Citi or Cap One or Amex to Avianca and get this flight. So I hope that example is helpful.

I just wanted to share a few other examples I found 'cause I know not everyone has points in every single program, but I looked on American and I found a round trip flight for 115,000 points in business. I even found a nonstop in business for 100,000 points, which is one way, but in July, which is the peak travel season for Americans going to Italy.

So that was interesting. And then finally, I did a fun search for the Emirates flight because if you wanna get to JFK and fly JFK to Milan, you get a chance to do it on Emirates. You could do it on a first class cabin if you want with points that has a shower.

It's really unbeatable, private suites on the plane. It's very hard to find those flights. And if you find the right time and the right days, which takes some work, you can get in business or first on Emirates for under 100,000 points. Now, is it really worth doing that when you could go for 53,000 on Lufthansa or Swiss Air or Air France or another airline?

That's really up for you to decide. It is a unique experience that you probably won't have on any other airline, but it also means that you could probably go two for the price of one when you compare the cost. So that's up to you to decide. But I will say, when you're doing these searches, in general, the way I approach it is, there's a bunch of airlines that fly the route I want.

First, I'll go and search on some of these airline websites because they have an easy calendar. You can go to the American website and see a month at a time. Unfortunately, you can only see from one destination. So you can search from your destination. But sometimes what unfortunately happens is that American, for example, might not have award flights from San Francisco to Dallas, but they might have Dallas nonstop to Italy.

And so you might be willing to spend a couple hundred dollars to fly to Dallas if the flight from Dallas all the way to Italy is free and in business class. So you do have to do a bit of searching from some of the different hubs where airlines fly from.

But most of those airline websites, one of the advantages is you get a calendar for the month. So on United, you get this. On American, you get this. A lot of different airlines have this option. So you can search a wide set of dates and see when the sweet spots are.

However, I strongly encourage people to consider that once you've found it, don't necessarily book on American, don't necessarily book on United, because there might be a partner airline that's much cheaper to book on. And that's where Point.me comes in and can be so valuable. I use it almost every week when I'm helping friends search for flights, when I'm searching for flights for us.

The only knock I have on it is that there isn't a multi-day search on their website. So if your dates aren't flexible, you don't even need to go to the airlines. You can say, I'm looking at this day, or even if they're flexible within one or two days, great.

But if you're looking at, I wanna go somewhere and I could go anytime, Point.me might be tricky because you have to search a day at a time. That said, I would argue, if you're willing to go in an off season, pick a time that would be good. You could still search there and you might find something right away.

But if you don't, it can be a little bit burdensome. But I did wanna point two things out on Point.me. First, as I've said in the past, if you wanna get your first month for $1, you can sign up for the monthly standard plan. And just to be clear, 'cause it's a little confusing, don't go to the, I have a code field, sign up for the standard plan with monthly billing that's $12 a month, and all the way at checkout, if you put all the hacks, you'll get your first month for $1.

However, for the month of March, if you do go to the services page, there is a field that says, I have a code, and there's a complimentary starter pass, which gives you access for 24 hours, which normally costs $5. If you use all the hacks there just in the month of March, 50 people can get that access.

A lot of people are listening to this show. I can't promise it'll still be available when you try, but the $1 for your first month should. So definitely consider checking it out. I am happy paying customer at Point.me. I think it's a really great product. I've heard so many people have had a great experience.

And if all of this is too complicated, they do also have a consulting service where they will just, for $200 a passenger, book your entire flight for you with their concierge. So that's definitely something to consider if you don't wanna deal with this. If we go back to our business class example, if your alternative is, I'm not going to use my points optimally because it's too much work, and I don't wanna try to do this, well, in that example, if 53,000 points is able to get you a $3,600 flight, it would absolutely have been worth you paying an additional $200 for a concierge to go look into this and figure out a way to make it work.

And by the way, if they don't find anything, they only require a $25 search fee to get started. So it's a pretty low risk option for people who aren't willing to spend the time to go do some of the searching their own, but still wanna get those really, really outsized values from their points.

So that's flights, but let's talk about hotels because there's so many great options in Italy. But before that, I wanna talk about Aways, which is a really awesome service I started using. And it's basically become my de facto way I search for hotels with points these days. And what I love about it is they show you the cash price right next to the award price.

But even more than that, they show you the award availability. So they make it so easy to find which hotels have availability, and you can look at a calendar view of when they're available, and you can compare the cash and the award price to see if it's a good deal.

It works for Hilton, Marriott, IHG, and Hyatt, and they actually let you filter on your balances with those programs or your balances at Chase, Built, and Amex. And they'll factor in things like how Marriott and Hilton give you fifth night free and show you the price respective to that.

Unlike Point.me, they actually have a free option so you can go in and search for the real-time cash and award pricing and get availability for free. And they do this for over 1,000 cities and over 25,000 hotels around the world. Unlike Point.me, they do have a free service that gives you access to the cash and award prices and the award availability.

However, I've been playing with the premium version. They give you features like being able to search for your free night certificates, being able to filter on the pricing for getting your fourth or fifth night free depending on the hotel chain. But the real thing that I love is that you can get a wider view of the award pricing.

So with the gold plan, you can get a seven-day view, and with the platinum plan, you can get a 30-day view. But I heard a little rumor that by the end of this week, that'll switch to be a calendar view you can browse for the whole year. So if you're eyeing a property, like let's say the St.

Regis in Rome, and you wanna see when you can get the best deal, you'll be able to click through the whole year. So like I said, you can use the product for free, but if you want all the features, you can use the gold or the platinum plan, and you can get a five-day free trial.

So you can actually go in and play around with this right now for free. But for all the Hacks listeners, I got them to offer $10 off the platinum plan forever, not just your first year, forever. If you just go to allthehacks.com, slash aways with a Z, A-W-A-Y-Z. I'll also put the link in the show notes.

Definitely go check it out. You can use it for free for five days, or even the free version of it forever. But I will highlight a few of the hotels that I found when I was doing some searching, just to get you an idea of some amazing outsized value you can get.

So within Hyatt, and I'll just caveat that if anyone listening isn't familiar, unfortunately, on March 28th, Hyatt is gonna change the prices of a lot of their hotels. And it's not all of the hotels, and not all of them are going up, but the award cost for 214 Hyatt hotels and resorts is going to change.

On average, everything's going up about 5,000 points per night, but some hotels are going down, and you still have, by the time this comes out, in five or six days to go in and search, which honestly is a perfect opportunity if you have a trip to plan to go use the five-day aways free trial to go find out if you can find a way to get a value from your points before it gets devalued.

I'll put a link in the show notes to all the hotels that are changing categories, so you can see if they're in that list. Obviously, if the hotels you wanna go to aren't, then there's not a lot of rush to do any booking. But if there's a trip you know you wanna plan, and there's a Hyatt hotel you know you wanna stay at that is going up in price, definitely get that booked before the 28th of this month.

But just as some examples, within Hyatt, the Park Hyatt in Milan looks beautiful. When I looked at a few dates, it was about $1,040 a night, but you could book it for 40,000 points, which means you can get 2.6 cents per point, which is amazing. Though, in Milan, there's also the Hyatt Centric, which costs a lot less at 470, but is only 15,000 points per night, so 3.1 cents per point value, which is really great.

And then there's a few Hyatt small luxury hotel properties that are part of that little collection they have that you can get for similar values, like the Hotel Ding Hill Terra, which I found for 29,000 points a night, which is really nice. On the Marriott side, the St. Regis in Rome and Venice both look beautiful.

Both are over $1,200 a night, but I found the one in Rome for 75,000 points a night, which works out to about 1.7 cents per point, which is really big for Marriott, because Marriott points often are kind of more around the 0.7 cents value. And then at the St.

Regis in Venice, which when I looked was about $1,300 a night, but I found it under 100,000 points, which similarly is kind of double the value in terms of what you get for your Marriott points. So there are some really great spots for Marriott, and all that goes down by 20% if you book five nights.

So don't forget that you get your fifth night free on Marriott, and you also get the same thing on Hilton. And so if you look at Hilton in Rome, there's the Cavallari Hotel, which is a Waldorf Astoria property. I found it for a few different dates for 80,000 points a night.

But if you don't have Hilton points, Amex transfers one to two, so you only need 40,000 Amex points. So that was a $746 a night property, which means on the Amex point side, you're getting about 1.9 cents per point. Or if you book at five nights and get your fifth night free, that bumps up to about 2.4 cents, which is still a much better deal than using the portal to get one cent per point with Amex.

Obviously, like in the example earlier, you can get much more value on some of these international business class flights. But honestly, if you're not looking to fly business and you want your points to go further, you might be more interested in flying economy and staying in hotels. Or maybe you're just someone who doesn't care about the flight experience, you just like a really nice hotel.

I totally support that as well. So those are a few of the points options. I'm not gonna go through every single hotel and every single property, because when I looked, there were so many. Marriott has 63 hotels, Hilton has 33, Hyatt had 52, and it looks like IHG has another 49.

So that all adds up to probably 200 hotels you could use your points and miles at. So hopefully that gives you a little bit of an overview of how you might wanna use your points and your miles to get to Italy, to stay in Italy. Definitely reach out to me.

Let me know what you think of the Aways product. I have reached out and talked to John, the CEO of the company, and he's definitely open to product feedback as well. So feel free to send them an email if you have suggestions. There are a bunch of other updates that I've already sent him that some of which he said are coming as soon as this week.

So I'm really excited to see how that product evolves. But most of all, I'm really excited to have another tool in the hotel toolkit, because the only site I knew of was a site called AwardMapper, which stopped updating things as hotels changed hands and changed their rates, and it really became unreliable.

So really excited that we have a couple tools that you guys can use to book your next trip with points and miles and find really great deals. So if you wanna check out point.me, don't forget the promo code, AllTheHacks. And if you wanna check out Aways, don't forget to go to allthehacks.com/aways, A-W-A-Y-Z.

(upbeat music) So I would love to hear if anyone is going to Italy, plans a trip to Italy, uses any of this advice, or even has other tips they wanna share, please send them my way. This whole country series is going to be a thing. I'm gonna be doing it probably every four to six weeks.

So please let me know what you think. Let me know if there are countries that are at the top of your list, and we'll see what's next. Right now, I'm trying to get Brandon Presser, who I did the Japan episode with, to do one on Iceland, because it turns out he knows just about as much, if not more, about Iceland as he does about Japan, which is hard to believe, but really exciting, because Iceland has been at the top of my list for a long time, and I've never been able to go.

We even threw out the idea of trying to fly to Iceland and do the episode there, but two little kids is likely gonna make that challenging. So thank you so much for listening. I hope you enjoyed this episode, and I'll see you next week. (upbeat music) (upbeat music) (upbeat music) (upbeat music) (birds chirping) you you