All the Hacks

🇮🇹 How to Travel to Italy Like a Pro

Published about 1 year ago • 14 min read

Hi all👋! Today we’re talking about one of the counties at the top of my list to return to: Italy. Based on the number of emails I’ve received, Italy is also among the top of yours. I went with Amy back in college, but that was 20 years ago. To help think about a trip to Italy, I spoke with my good friend Leigh Rowan (🎧 Ep 107). Leigh runs a travel company, Savanti Travel, and has visited Italy 40+ times. Today’s newsletter will tell you where to go, what to do, and how to do it.

This is my second newsletter on traveling to a specific country. I received great feedback about the first one (Japan), so let me know what you find these types of posts valuable. And if you have been to Italy or planning a trip, please share your thoughts with me too!

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🇮🇹 Italy: Overview

Everyone knows Italy is where one can enjoy great food, wine, and coffee, but more than that, it’s a country all about enjoying life. The Italian lifestyle is focused on the present moment. No hurrying. No rushing. No constant need to be busy. The people are out and about, strolling from cafe to cafe, being social, and enjoying Italy’s rich culture and beauty. It’s so ingrained in the lifestyle that this stroll (a traditional passeggiata) happens every evening.

“The thing that makes me feel most at home in Italy is that the Italians know how to live. They know how to live life, great food, wine, and coffee. But more than all of that, it's just this continual enjoyment of life.” -Leigh Rowan

🗺️ How to Approach Italy

Italy is the 5th most visited country in the world, with 60+ million visitors and 20 distinct regions to explore.

It can be overwhelming for first-time visitors with so much to see and do. Don’t worry about seeing everything in one go because there are more museums, churches, and sites to visit for a lifetime of trips to Italy. Consider your energy levels and aim for rest and relaxation activities.

Keep it simple (especially if it’s your first trip):

  • Start with Rome: Rome is known as the Eternal City because of its rich history and ancient monuments, like the Colosseum, the Roman Forum, and the Pantheon. These sites are some of Rome’s most popular tourist destinations and offer a glimpse into the city’s ancient past.
  • Visit Northern or Southern Italy: Northern Italy, including places like Venice, Milan, and the Italian Alps, is known for its stunning architecture, beautiful landscapes, and world-renowned art museums, such as the Uffizi Gallery in Florence. Southern Italy, including places like Naples, the Amalfi Coast, and Sicily, is known for its beautiful beaches, coastlines, architecture, and delicious food, particularly pizza and seafood dishes.

You might want to think about revolving your trip around one aspect of Italian life: food, art, history, or culture. Draw inspiration from travel shows, books, blogs, and social media to get ideas of what aspect you want to experience on your trip. Then focus on the places that best support that aspect. The next time around, select another.

🚗 Navigating Within Italy

Taking the train is often the most convenient and reliable way to travel from city to city. Train tickets can be purchased in advance; the cheapest rates are typically available between 30 and 60 days out.

Buses or private cars may be better for exploring the countryside. Renting a car can also be an option, but driving in Italy can be challenging because you’ll probably be going too slow, and the roadways are very small. The medieval streets were designed for cows and sheep, not humans or cars.

Flying within Italy is a manageable option for travel between cities, but it’s often a no-frills experience. Companies like Ryanair, EasyJet, and Vueling have many flights departing from major cities. While the option for business class may exist, it’s an economy seat with a blocked-off middle seat on many flights. I’ll make a note of one to avoid: ITA Airways. It’s the resurrection of a now-defunct airline notorious for its delays.

⌚ Best Time To Travel

There’s no wrong answer; it depends on what you want to discover.

Peak Season (June - August):

This is the busiest time to travel in Italy, with the largest crowds and the highest prices. The weather is generally warm and sunny, making it an excellent time for outdoor activities and beach trips.

  • Visit famous attractions like the Colosseum, the Vatican, and the Pantheon, but be prepared for crowds and long lines. You can also visit the Catacombs or the underground sites of Rome.
  • The Amalfi Coast is a popular summer beach destination. You can take a boat tour of the coast to see the scenery from the water or hike the famous Path of the Gods for panoramic views.
  • Many outdoor events and festivals occur during the summer in Italy.

Shoulder Season (April - May, September - October):

The shoulder seasons offer a good balance between good weather, fewer crowds, and lower prices. It’s a good time to explore Italy’s museums, galleries, and churches. April and May are particularly nice for outdoor activities and sightseeing.

  • Go hiking in the Italian Alps or the Dolomites
  • Visit Tuscany’s vineyards during the grape harvest season in September
  • Attend food and wine festivals such as the Fiera del Tartufo (Truffle Fair) in Alba

Off-Season (November - March):

This is the quietest time to travel in Italy, with the fewest crowds and the lowest prices. The weather can be cold and rainy, but winter sports are popular in the mountains. Many attractions, shops, and restaurants may have reduced hours or be closed during the off-season, so checking beforehand is essential.

  • Hit the slopes in the Italian Alps or the Dolomites for winter sports. Some popular spots are Cortina d'Ampezzo and Val Gardena.
  • Visit cities like Rome, Florence, and Venice without crowds.
  • Attend festivals such as Christmas in the Vatican and Carnevale.

🛵 Guides, Tours, & Meeting Locals

Booking a guide can be a great way to explore Italy, but you don’t have to. There are always free walking tours led by excited people ready to show off their town.

One exciting option is to take a sidecar tour of these different cities. You hop in a motorcycle sidecar while an experienced guide drives you around to explore the historical sites. While most options I saw are solo, there are options for group tours (each traveling in your own sidecar).

If you explore independently, use resources like Context Travel and Airbnb Experiences to see what’s offered in the area. If you Google activities, there are lots to see and do, so leveraging these resources to guide your options can prevent decision fatigue or the feeling of FOMO.

I always talk about the value of meeting locals everywhere I go. Life in Italy is very much about the present moment, but it doesn’t always feel that way in tourist places like the famous Piazza Navona. So if you want to experience locals, meet them where they live. In most of my experiences, locals are proud to show off their city, country, or neighborhood and are interested in where you come from and why you’re in Italy.

🍽️ Dining Expectations, Planning for Meals & Family Naps

Italians usually eat on a different schedule than North Americans:

  • Breakfast is light. It’s a coffee and a croissant or bread.
  • Lunch is a big affair. It can last as long as two or three hours.
  • Dinner takes place late. In the winter, don’t expect anything earlier than 7 pm; in the summer, an “early” dinner might be 8 or 9 pm.

To accommodate this schedule, it’s a cultural norm to take a break (and nap) from 12:30 until about 3:00. On Leigh’s family trips, they take a family nap to make sure they can make it to the late evening dinner schedules.

For restaurants on your must-visit list, it is essential to make reservations in advance. This is especially true for Pierluigi Restaurant (Rome) or Osteria Francescana (Modena). However, I wouldn’t try to plan out every meal to leave some spontaneity as well.

Websites like the Italian Michelin guide, Gambero Rosso, can help you discover great options. Whereas typical guides, blogs, and review sites will tap into the more popular places, some recommendations in Gambero Rosso offer richer and more meaningful experiences and affordable prices.

🇮🇹 Rome

The best way to experience Rome is by adding a mix of must-see tourist places and getting lost exploring places off the beaten track. There is a reason all roads lead to Rome.

🏃 Explore Rome Like the Tourist

The Coliseum, Pantheon, Trevi Fountain, and the Vatican are four of the most popular tourist destinations. Though they can be overcrowded, they are worth the visit, being maintained for over 2,000 years. It’s a good idea to pre-book some of these experiences and look for a unique one-off experience like the Breakfast at the Vatican. This experience allows you to visit the Sistine Chapel before it opens to the public and then enjoy breakfast at the Vatican cafeteria. If you want a more private experience, you can fully privatize your visit but be prepared to pay more.

🚶 Explore Rome Off The Beaten Track

Explore the little villages where Romans live. Have a meal in a piazza where you might be the only person who doesn’t speak fluent Italian. You’ll be welcomed in and eat an incredible meal while experiencing the sweetness of doing nothing that passes by in front of you.

🗺️ Northern Italy

Northern Italy is a region that boasts both natural beauty and a rich cultural heritage. From the enchanting city of Venice to the stunning Dolomite mountains, there is no shortage of places to visit and things to do in this part of Italy. Florence is an 80-minute train ride from Rome which displays a medieval village that is still alive and offers stunning sights, sounds, and food.

Venice attracts millions of tourists every year. Take advantage of St. Mark’s Square, the Grand Canal, and a famous gondola ride. However, the heart of the Veneto region lies not in Venice proper but in the surrounding area. Visit the rich farmlands, the Palladian villas, the stunning mountains, and the canal cities that make this area so rich.

But let’s also talk about other less favored places in the north.

One such destination is Umbria, known as the Green Heart of Italy.

  • With ancient villages dating back thousands of years, delicious food and wine, and fewer tourists than neighboring Tuscany, Umbria offers an authentic Italian experience that should be noticed.
  • The annual Corsa dei Ceri festival in Gubbio, where locals carry massive wooden slats with tall columns and saints on top through the medieval town, singing and playing music. It’s a party and a true celebration of Umbria’s history and culture.

Another destination is the town of Rapallo, close to the tourist location of Portofino.

  • You can use Rapollo as the place to stay, so you can visit popular sites without needing to stay there.
  • ParlaComeMangi highlights local cheese, salami, and prosciutto, which will be just as impressive (and much less expensive) as one in Portofino.

Northern Italy is a haven for foodies. While the Michelin guide or Gambero Rosso are great places to start, try looking for local places that are not necessarily starred but are still authentic and delicious. You could filter TripAdvisor reviews for the ones from Italian people to get a sense of what’s great or just be bold and ask locals for recommendations. Look for places that have been around for years and are still standing, as these are likely to serve great food that the locals love. Take advantage of the classic Italian coffee, and try the traditional biscuit in Rapallo, called Canepa, or the Espresso with cream from the famous Panella cafe in Rome.

🧭 Southern Italy

The warm and sunny climate makes it a popular destination for beach-goers and sun-seekers; however, the region is also home to numerous historic cities, each with unique culture, cuisine, and architecture. Popular destinations include Naples, Pompeii, and the Amalfi Coast, but here are some other places in the South to check out:

Sicily is the largest island in the Mediterranean Sea and offers a rich history, culture, art, and food.

  • Agrigento on the west side of Sicily boasts some of the best-preserved Greek temples in the world.
  • Palermo, located in the north of Sicily, is another must-see destination.
  • The Aeolian Islands, a chain of islands north of Sicily, offer beautiful beaches, mud baths, and incredible views of volcanoes.

Puglia is a rapidly growing tourist destination located on the heel of Italy.

  • It is known for its picturesque towns, olive groves, white sand beaches, and the famous ear-shaped pasta called Orecchiette.
  • It’s less expensive than other regions in Italy, such as Tuscany or Umbria, making it an affordable destination for travelers.

Ischia is a beautiful island across the Gulf of Naples from Capri.

  • The locals are friendly and proud to show visitors their island, and you can explore it with a rental car, Vespa, or a stylish little vehicle called an “ape.”
  • Ischia offers a glimpse into authentic Italian culture and is a more affordable alternative to Capri.

You can’t go wrong with Northern or Southern Italy unless you try to do too much. Instead, embrace and squeeze the most out of the few places you visit. Every town, big or small, has something they are known for. It’s about seeking it out.

✈️ Flights

Many US carriers, like Delta, United, or American, fly nonstop into Rome and Milan from their hubs (including an SFO flight starting next month). But there are other options to consider:

  • Emirates is the best option for getting to Milan from JFK (especially if you can use your points for business or first).
  • La Compagnie is an all-business-class airline that flies from Newark to Milan. While you can’t use points or miles, it’s usually much cheaper than other business-class options.
  • Air Canada also to Rome and Venice from Toronto and Montreal (Rome only).
  • Neos is Italy’s second-largest airline, with affordable flights to Milan from JFK.
  • North Atlantic Airways is another inexpensive option from JFK to Rome.

💳 Flights With Points and Miles

There are over a dozen airlines you could fly to Italy on using points, so with enough flexibility , you should be able to find a way to make it happen. The best way to increase your odds of finding availability would be to either book far in advance or book less than a month out. That said, I’ve booked plenty of trips with points 3-6 months out, so it’s not impossible.

When booking with points, it’s important to note that the way you search for flights can make a huge difference in the value you’re getting. For example, booking a one-way business class trip from SF to Rome on United’s website might get as low as 81,000 points, but that same flight could be booked for 63,000 points from Avianca’s mileage program, which is a transfer partner of Citi, Amex and Capital One. So you might want to consider a few tools that make the process easier:

  • is a new award search tool, but it’s quickly becoming one of my favorites. While it only supports 9 airlines, it regularly runs searches for all the routes for the next year, which means that, unlike every other tool out there, it supports unique searches like showing all flights to Asia with business class availability from a specific airport for the next year. It’s free to see availability for the next 60-90 days, but the pro version is only $7.99/mo and gives you access to a full year of availability. While I haven’t managed to secure any discounts for you all yet, this is my referral link.
  • is another fantastic tool if you’re searching for specific dates. It searches 30+ loyalty and 100+ airline programs for award availability and then walks you through the exact steps to take to transfer the points and book flights. I got them to offer our readers their first month for $1 if you use this link, select the standard monthly plan and use the code ALLTHEHACKS on the final checkout page. And if all this searching is too much work they also have a consulting service, where they’ll do all the searching work for ~$200/person (but if they don’t find anything you want to book, you’re only on the hook for $25).
    • Hack: if you sign up for a free Bilt Rewards account, you can use their free flight search tool (which is powered by the search engine) to find award availability on the 12 airlines that happen to be Bilt transfer partners (but the other 18+ loyalty programs on are excluded).
  • AwardLogic is a similar site to, and while they search a few less airlines/loyalty programs, their searches allow +/- 1day and results show up 10x faster than It’s also a little more expensive, but this link gets you a 3-day free trial.
  • SeatSpy is a great tool when you have a ton of flexibility. While you can only search for award availability on direct routes on 13 airlines, it shows results for the entire year at once. It also let’s you set up alerts for new availability. If you want to check it out with a 14-day free trail, you can click this link.

🏨 Hotels

Italy offers some of the world’s most iconic and unique hotels, like the family-run il San Pietro, which was built by hand into the side of a cliff overlooking Positano. Or the Hotel il Pellicano in Tuscany, which offers exceptional Michelin-starred food and an incredible experience. Or the Palazzo Manfredi, which offers one of a kind, unobstructed views of the Coliseum from its suites. These hotels are perfect for those seeking a once-in-a-lifetime experience and are ideal for bucket-list trips to Italy.

But there are always other options. For example, the most expensive hotel in Northern Italy outside of Venice is the Belmond on Portofino. But right around Portofino are places like Santa Margherita and Rapallo, which have 4- and 5-star hotels that are wonderful for a fraction of the price.

Chains like Hyatt, Marriott, and Hilton also have hotels throughout Italy and some of the best smaller luxury hotels are even part of Hyatt’s SLH program, offering outsized value for points. If you’re looking to book hotels with points, check out Awayz (below).

Reminder if you’re booking high-end hotels: we have a partnership that gives you free extra perks (e.g. upgrades, complimentary breakfast, resort credits) at hundreds of four-star and five-star hotels. You can learn more about that program here.

👍 Try Awayz

For years I’d been hoping someone would build an award search tool for Hotels, and they finally have. It’s called Awayz and it’s awesome. It makes it easy to find award availability and pricing (and even compare the cash price) at over 25,000 Hilton, Marriott, IHG, and Hyatt hotels. While you can do some searches for free, the premium version has many amazing features (like alerts, a calendar view, individual hotel search, and more). You can get a 1-day free trial of both premium plans here.

💭 Parting Thoughts

That was a lot. But a trip to Italy might be the medicine to slow down, rest, and enjoy living in the moment.

I want to thank Leigh Rowan for this amazing conversation and insider tips. Check out (🎧Ep 107) for more on traveling to Italy.

I also got an email from a listener (thanks Jeff!) who has traveled to Italy 30 times (particularly Milan), so I wanted to share some of the 3 tips he shared with me.

  • Get an AirBnb because it forces you to do things more tourists don’t do (e.g., go to a supermarket, or meet locals in the building).
  • You can rent a car by the minute using Share Now. You can see what cars are available in the area, reserve it for (say) 20 minutes to get in it, and off you go. It’s usually less expensive than a taxi and metro tickets (if traveling with a family)
  • The Rick Steves Audio Europe app (which is free) was perfect for a walking tour.

If you found this post enjoyable and thinking about traveling, you’ll love my post on Japan. It’s about where and what to do and planning the best trip ever.



The content on this page is accurate as of the posting date; however, some of our partner offers may have expired.

Editor’s Note: Special thanks to our partners:, InsideTracker and Awayz. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

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