How To Plan The Best 10 Day Trip to Italy

If you’re looking to plan the best 10 day trip to Italy, look no further! Whether you want to ditch the classic Rome-Florence-Venice route or you hope to experience those cities through a unique lens, we’ve got you covered. We’ve created two separate 10 day trip to Italy itineraries for whichever path you wish to take. Or you could even combine the two! No matter what your heart desires, we’ll help you craft the perfect Italy itinerary.

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Itinerary Option 1: Classic Italy With a Twist

If you’re wondering what to do with 10 days in Italy, we have all the answers. For travelers who want to experience the hidden gems of the more well-known cities of Rome, Florence, and Venice this 10 day trip to Italy itinerary takes you on a more curated tour.

Days 1-4: Rome

• Accommodation:
  • Donna Camilla Savelli – This hotel is a converted 17th-century monastery in the Trastevere area. The rooftop terrace offers views of the city, including Saint Peter’s Basilica.
  • Palazzo Manfredi – This hotel is so central that it perfectly overlooks the Colosseum. You truly can’t beat this view!
• Activities:
  • Golf Cart Tour – Sightseeing in Europe is no joke!! It’s not uncommon to be walking 20-30k steps a day. So what better way to explore such a sprawling city than to take in the sights in a golf cart! This golf cart tour is such a blast, allowing you to hit all the major sights without exhausting your body. And it’s a great time-saver if you’re not planning to spend a lot of time in Rome.
  • Capuchin Crypt – Under the Church of Santa Maria della Concezione, you’ll find the bones of over 4,000 friars. Spooky!
• Food/Dining:
  • Romeow Cat Bistrot – While not super specific to Rome, who doesn’t want to check out a cat cafe wherever their travels take them?
  • Food Tours – We here at Travel The Unexpected are obsessed with Eating Europe. We’ve joined their food tours in many cities, and they’re always the highlight of the trip. They do an excellent job of providing cultural and historical insight, hands-on learning, and top-tier dining. Some of the restaurants they bring you to are either impossible to get a reservation at or offer add-ons that aren’t open to the public. Our two favorites in Rome are the Trastevere Tour and their Golf Cart Food Tour. The Trastevere tour is great, but it is their most popular tour in Rome, so of course we have to recommend an even more unique and niche tour… like their Golf Cart Tour. Here, you can explore Rome without doing too much walking, especially once the food coma hits!
  • Ristorante da Pancrazio – Dining at this restaurant will deeply immerse you in Roman history. This is the site of the former Theater of Pompey and is also the site of Julius Caesar’s assassination. This was one of the stops on Eating Europe’s Trastevere Food Tour when we went, but you can also make your own reservation.

Days 5-7: Florence / Tuscany

• Accommodation:
  • Hotel Brunelleschi – Sleep inside a medieval tower with direct views of Brunelleschi’s Dome. Their tower suite is absolutely gorgeous and is the perfect place to come home to after a long day of sightseeing.
• Activities:
  • Mysteries & Legends Free Tour – Sandemans is a free tour aggregator that partners with on-the-ground tour companies to provide tip-based walking tours all around Europe. On this tour, you can learn all about the “dark side” of Florence, including tales of ghosts, serial killers, and more.
  • Vintage Fiat 500 Tuscany Tour – Explore Tuscany in style in a vintage Fiat 500. This tour departs from Florence and brings you to a wine estate where you can sample wines and indulge in a light lunch. Don’t worry about getting lost – a guide will be nearby at all times.
  • Giunti Odeon – This place is heaven on Earth for book or film lovers. It’s part bookstore, part movie theater that shows older, classical films. You can’t hear the film from the first floor, allowing you to browse and read in peace. But you can head upstairs to the balcony to enjoy the film with sound. It’s also a great place to escape the heat and take a load off during the summer months.
  • Move On Italian Pub & Record Store – For the ultimate photo op, head to the upstairs room of Move On. If you time it right, you could snag the patio table overlooking the Cathedral of Santa Maria del Fiore. The streets below are always hectic with tourists, so it’s a great place to people-watch.
  • Olive Harvesting – Tuscany is known for truffle hunting and wine tastings, but did you know that you can help harvest olives? This is a super seasonal activity, but if you happen to be in Florence between October and November, we can’t recommend it enough. This tour comes from the family-owned company, Our Tuscan Farm. They offer picnics, cooking classes (including one for kids – how cute!), and wine tastings, but the olive harvesting truly stands out as a one-of-a-kind experience.
  • Vintage Fashion Tour – If you’re hoping to bring home a truly original piece with a bit of Italian history but don’t know where to start, this tour is for you. While you could pop into vintage stores on your own, this tour takes the guesswork out of which stores are best, and they’ll help you communicate with the sellers.
  • Perfume Workshop – Learn from one of the premiere perfume makers in the world and go home with your own, unique souvenir. You’ll leave with not only a new scent but also with the understanding of which scents go together and how to distinguish true made-in-Italy perfumes.
• Food/Dining:
  • Food Tours – Want to discover Stanley Tucci’s secret wine window? You can do exactly that on Eating Europe’s Sunset Food & Wine Tour. OR, if you want an even more immersive experience and want to work for your food a little, you can go on Eating Europe’s Tuscany Truffle Hunt.

Days 8-10: Venice

• Accommodation:
  • Hotel L’Orologio – This is a clock-themed hotel right in the heart of Venice. Much of the artwork and design centers around clocks. Even your bathroom mirrors will resemble them!
• Activities:
  • Venice Carnival – The Venice Carnival typically takes place during the two weeks leading up to Lent. If you want to experience the vibrancy and tradition of the carnival, it’s a truly remarkable experience. And if you can secure an invitation to a masquerade ball, you will have a night of opulence you’ll never forget. But if you’re not interested in the Carnival, do not, we repeat DO NOT, visit Venice during this time. I mean, do what you want, of course. But we advise against it given how absolutely crowded the city is with the festivities. It’s wall-to-wall people, and you will not truly get a sense of Venice as it is the rest of the year during this time.
  • Ca’ Macana Mask Making Workshop – If you are planning to visit Venice during the Carnival, we highly recommend avoiding the souvenir shop masks and making your own. Ca’ Macana is a renowned family-run business that maintains ancient tradition while providing a modern flair. If you don’t want to make your own, they have some truly stunning and creative masks for purchase.
  • Libreria Acqua Alta – This is a floating bookstore where the books are stored in gondolas in case of a flood. While this place is a bit of a social media gimmick, it’s still a fun visit for any book lover. And there are cute cats that hang out in the store! It might just be worth the visit if you want to snap a gondola photo without the hefty price tag. There just so happens to be a gondola outside the bookstore that patrons are allowed to sit in to get their photo op. Just be aware that due to flooding, there may be times when the gondola is inaccessible.
• Food/Dining:
  • Dine in a Local Home – Nothing says immersive experience like getting an exclusive cooking demo and meal in the home of a local Venetian. You’ll be served authentic recipes that may very well come from a family cookbook!
  • Nino & Friends – While not exactly an unexpected find, we cannot stress enough how much we love this shop. This is a chain of chocolate/candy stores in Venice, and I still dream about their lemon candies on a weekly basis. They offer a seemingly never-ending supply of samples. Honestly, you could skip a meal by coming here. It’s one of our top souvenir choices to bring home for loved ones or coworkers.

Itinerary Option 2: Off The Beaten Path Italy

If you’ve already been to the major cities in Italy, or if you just want to escape the tourists, this 10 day trip to Italy itinerary is for you. You’ll experience the authenticity of small Italian towns like Verona alongside some more well-known and luxurious destinations such as Milan. And not only are we taking you to the most unique hidden-gem spots in Italy, but we’re also recommending unique places to stay and some one-of-a-kind activities.

Days 1-4: Milan & Verona

• Accommodation: We recommend lodging in Milan for all of these days and doing a day trip to Verona. Rather than changing hotels again, visiting this nearby location allows you to explore more of Italy without having to pack and unpack yet again.
  • Château Monfort – This whimsical hotel is a former palace, and each room is inspired by fairy tales and operas.
  • Magna Pars L’Hotel à Parfum – If you’re a perfume lover, we highly recommend staying at this perfume factory-turned-hotel. There’s even an on-site perfume lab. You just know this hotel smells good!
• Activities:
  • Monumental Cemetery of Milan – You’ve never experienced a cemetery like this before. The tombs are truly ornate pieces of art. There’s even a tomb that resembles the Last Supper.
  • Day Trip From Milan to Alba – Who wouldn’t want to take a trip to the world capital of white truffle? But if somehow that’s not your thing, you can also enjoy a wine tasting at a family-run winery and visit a UNESCO castle during this special day trip.
  • Juliet Club – This adorable spot in Verona brings volunteers together to answer love letters sent from all around the world. You, too, can embrace your inner romantic and respond to a letter. A visit here is a MUST for Shakespeare fans.
  • Juliet’s Tomb – While all of the tourists go to Juliet’s balcony, you can skip the crowds and opt for this spookier spot located in the underground crypt of the church of San Francesco al Corso.
• Food/Dining
  • Bar Luce – This unique bar in Milan was designed by renowned and quirky film director Wes Anderson. It’s part of Fondazione Prada, an art museum with unusual and immersive exhibits.
  • Nottingham Forest – This bar in Milan serves up cocktails so unique that they’re often added to recipe books worldwide. And the drinks come in fun and unusual containers, from test tubes to skulls.
  • Gusto 17 – Experience unique flavors of gelato at this artisanal ice cream shop. You can even suggest a future flavor you’d like them to offer. Come back weekly to try their new offerings.

Days 5-7: Matera

• Accommodation:
  • Sextantio Le Grotte della Civita – Spend the night in this cave hotel where the rooms are carved into ancient stone. You’ll feel transported back in time, but with the modern comforts of heated floors and soaking tubs. This is an exceptional hotel for couples and our favorite hotel in Matera.
  • Sant’Angelo Luxury Resort – This is another luxurious cave hotel. Many rooms offer terraces overlooking the city of Matera.
  • La Dimora di Metello – If you’re looking for the ultimate relaxation experience at a lower price point, we recommend this spa hotel inside whitewashed caves. With the remote feeling of this hotel, you’ll find it easy to unwind here.
• Activities:
  • Sassi di Matera – People have been living in these ancient cave dwellings for over 9,000 years! Explore the cave streets or churches carved entirely into rock in the Sasso Caveoso and Sasso Barisano districts.
  • Crypt of the Original Sin – Take in incredible artwork literally painted into a cave. It’s often compared to the Sistine Chapel. Pro Tip: You can’t enter without tickets, so be sure to book in advance.
  • James Bond Tour – Embrace your inner 007 and check out some of the filming locations from No Time to Die.
• Food/Drink
  • Baccanti Restaurant – Expect a romantic night out when you dine at Baccanti. This restaurant is built inside a cave, and you can even partake in wine tastings in the stone tunnels beneath the restaurant.
  • Trattoria Lucana – Dine at this local favorite and Anthony Bourdain-approved restaurant.

Days 8-10: Naples

• Accommodation:
  • Atelier Inès – This hotel is a must for art lovers! They even have a sculpture studio inside the hotel. We recommend booking their jewelry-making workshop for a personalized and handcrafted souvenir!
• Activities:
  • Bourbon Tunnel – Tour this archaeological museum to experience underground Naples. You’ll see underground tunnels that served as a military hospital during WWII, hidden escape routes, old cars, a bomb shelter, and wartime graffiti.
  • Herculaneum – While most people go to Pompeii, Herculaneum is often overlooked. It offers a well-preserved glimpse into life before the eruption of Mount Vesuvius.
• Food/Dining:
  • L’Antica Pizzeria da Michele – Check out this spot from the film Eat Pray Love. They’ve only served two kinds of pizza since 1870: Marinara and Margherita. Don’t come expecting anything fancy – just classically delicious pizza served on paper plates.
  • Palazzo Petrucci – On the other end of the spectrum, we have Palazzo Petrucci, a fine dining, Michelin-starred restaurant overlooking the Gulf of Naples. You can dine right on the sand while observing the chefs in real time, thanks to the open-concept kitchen.

Logistics for Your 10 Day Trip to Italy Itinerary

Best Time to Visit:

The best time to visit Italy is in between the peak seasons. From April to June and September to October, you can escape both the massive throngs of people and the ungodly heat! These months offer more moderate temperatures – ideal for sightseeing and crafting the best 10 day trip to Italy that won’t have you sweating bullets the entire time. While Italy is never going to be entirely tourist-free, you’ll have an easier time checking out the major attractions during these windows. Especially for itinerary #1! If you don’t care so much about the weather and want even fewer crowds, visit between November and February.

Transportation Tips:

The idea of traveling around a foreign country for the first time, especially on a 10 day trip to Italy, can feel overwhelming. But we found Italy very easy to navigate by train. We recommend using Omio. This site aggregates the best trains and buses, and you can filter by time, price, and number of stops. You also don’t have to worry about validating your tickets at the station. If you purchase your ticket at the station and do not validate it, you could be fined! We don’t really recommend renting a car in the major cities since there’s so much foot traffic. Plus, these cities are incredibly walkable.

Cost:

How much does a 10 day trip to Italy cost? It definitely depends on your travel style. For budget-friendly travelers, we recommend $1,500-$2,400. For mid-range travelers, expect to spend $2,500-$4,000. And for our more luxurious travelers, you’ll likely spend anywhere from $5,000-$10,000. Your budget will also depend on where you’re comfortable cutting costs. For us, if a city doesn’t have any hotels that are truly unique or original, we’ll opt to cut costs there by staying at a more budget friendly hotel. If it’s your first time visiting Italy, you might opt for more guided tours to get a better lay of the land. But if you’re more familiar with a city, you might elect to forego some of the costlier tours and explore on your own.

You can see Italy in 10 days without breaking the bank if you plan ahead. We like to book in advance over a period of a few months leading up to the trip. This way, we’re spacing out our spending. It’s really easy to go overboard on spending when you land at your destination. You’re too excited to reel yourself in! Since Italy requires reservations for most restaurants, you can also plan ahead and gauge how expensive your meals might be, rather than randomly sitting down at a restaurant only to be shocked when you see the menu prices.

We’re also fans of travel credit cards here at Travel The Unexpected. The cost of a ten day trip to Italy can be drastically reduced by using credit card points to pay for flights and/or hotel stays. Check out our favorite travel credit cards on our Travel Tips page.

Booking Unique Stays & Experiences:

• Book early: Even though many of our suggestions are more off-the-beaten path, they can still book up fast! We recommend booking as far in advance as possible. Many tour companies and hotels will offer refundable options.
• Dining reservations: You need reservations at most restaurants in Italy. We recommend booking through TheFork, which is the European version of Resy or OpenTable. You can also always call the restaurant directly.

Packing Essentials:

• Comfortable shoes: Do not, we repeat, do not wear heels in Italy. Most streets are made of cobblestone, and it’s a disaster waiting to happen. We tripped multiple times just in sneakers! Trust us, if you’re planning a 10 day trip to Italy, your feet are going to be screaming by the end of it. If you must wear heels, opt for a wedge, which will give you more support. We recommend your sturdiest footwear, especially during the day while sightseeing. Our favorites are Brooks and Hokas.
• Smart casual attire: If you want to stand out and have everyone be able to tell that you’re a tourist, wear leggings. If you want to blend in with the locals, opt for smart casual wear. Linen, especially in the summer, is a great choice as it’s breathable yet classy. Italians are always well-dressed, especially during meals.
• Travel adapter: Italy uses Type C, F, and L plugs.

Other Unique Italy Finds

Check out our Italy page for even more unique finds to add to your trip.

We hope you’ve found these itineraries for the best 10 day trip to Italy helpful and that we’ve given you lots of inspiration for your next trip. No matter where you go or how you travel in Italy, you will have the time of your life. Let us know in the comments which itinerary you would choose! And remember, don’t just travel, Travel The Unexpected!