Are you dreaming of an unforgettable two-week trip to Italy but unsure where to start? Here’s the best of Italy’s two-week trip itinerary for you! We see many questions on social media about arriving in a city, and people ask, “What to do and see?” Italy is packed with history, stunning landscapes, and incredible food, and planning an itinerary can feel overwhelming—especially for a first-time visit.
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Realize that there is no “one-size-fits-all itinerary.” It will be a wild trip, but two weeks will give you enough time to experience Italy’s most famous destinations. We’ve carefully considered this itinerary, which will take you through Italy’s most iconic spots—Rome, Florence, Venice, Milan—along with must-see sights like the Cinque Terre and Bologna.
Can you see all of Italy in two weeks? No, but you can catch some of the highlights. This itinerary starts in Rome, as many flights come in and out, but you can reverse this guide and begin in Milan if you prefer. Please remember that our suggestions will also be determined by the time of year you visit. With this said… let’s dive in and view the ultimate – the best of Italy two-week trip itinerary and Italian adventure!
Check out several posts we’ve linked throughout this post for further detailed information. We wanted to limit the information in this post to mainly focus on the itinerary. Highlighted posts will give you all the additional information you need. You can also use the search bar!
Transportation by Train
Before we get any further, you should know a few things about trains in Italy. First, there are high-speed and regional trains that are completely different. High-speed trains are more expensive, but with your limited time in Italy, I suggest you put your budget aside and get to your next destination as quickly as possible. Booking in advance will usually save you money.
Regional trains (Trenitalia) are less expensive, slower, and flexible. These tickets are more flexible and can be bought when you arrive at the station. However, you must validate them before boarding.
Should You Rent a Car in Italy?
For this particular itinerary, you won’t need to rent a car. Our favorite mode of transportation is using the train. If you want to venture out into the countryside at any point, that’s when you might want to do so. Navigating the small streets and dealing with the dreaded ZTL Zones will cause a bit of stress you probably don’t want on your trip.
The Best of Italy Two-Week Trip Itinerary
ROME: 3 Days
Day 1: Arriving in Rome
I would recommend spending at least three full days in Rome. First and foremost, you will likely need to recover from jet lag. If you arrive in the morning, jump in and see as many sites as possible during this first day.
Days 2 & 3: Rome
I would recommend spending your time wisely, focusing on main attractions such as the Vatican and the Colosseum. Book your tickets for the Vatican and Colosseum in advance to avoid long lines. Many of Rome’s sites, such as the Trevi Fountain, Spanish Steps, and Pantheon, are within easy walking distance of each other. We have a fantastic post onThe Best 3-Day Detailed Itinerary for Rome.
FLORENCE: 4 Days
Day 4: Rome to Florence
Next up on your itinerary is Tuscany, one of the most beautiful regions in this country. Consider basing yourself in Florence. Taking the high-speed train from Rome to Florence will take about 1.5 hours. If you get an early train, you’ll have plenty of time to explore many sights on your first day.
Upon arriving in Florence, drop off your luggage and head to the streets. Some must-see sites are the Duomo, Accademia, and Uffizi Gallery. You will need entry tickets for each, and it’s best to book the Accademia and Uffizi well in advance. By all means, don’t miss all the little sites Florence has to offer.
If you can climb steps – venturing up to the dome in the Cathedral is spectacular and one of my fondest memories. I’m happy we did it when we were younger – but it will be a fantastic experience.
Day 5: Tuscany Day Tour
If you want to explore a bit of Tuscany, you can purchase many bus tours in Florence from various tour companies. We’ve taken several tours this way, visiting several towns in one full day. You can visit Siena, San Gimignano, Volterra, Pisa, etc. Each bus company will vary in terms of the amount of time and town, but I suggest you check their ratings online before purchasing. You can also quickly jump on the train and visit Lucca and/or Pisa for the day on your own.
Day 6: Visit Bologna
If you are looking for a day trip, take the high-speed train (45 minutes) and spend the day in Bologna. This city is known as the country’s food capital. You’ll be able to enjoy Bologna in one day. If you arrive earlier in the day, don’t forget to find the hidden canals!
Day 7: Visiting Cinque Terre
Depending on the time of year, I’m sure you’ve heard about this unique area – the five famous villages on the Ligurian coast. There are day tours available to you from Florence. It’s also possible to take the train and visit on your own. You would need to get to the town of La Spezia and from there take the Cinque Terre train to see the towns. No cars are allowed in the Cinque Terre. Visiting on your own will be a long day, so just be prepared. These towns are incredibly crowded during high season (March to September).
VENICE: 2 Days
Day 8: Florence to Venice
Take the early train from Florence to Venice, which takes about 2.5 hours. You have a good chunk of the day to explore when you arrive. St. Mark’s Square, St. Mark Basilica, and Doge’s Palace are located together and easily visited at one stop. If you go to the top of St. Mark’s Campanile (tower), you will have the best views of Venice. Don’t miss the chance to take a gondola ride on the Grand Canal and visit the Rialto Bridge.
Day 9: Venice
Use this day to explore the surrounding islands of Burano (known for its lace and colorful houses) and Murano (known for its glass-blowing factories and shops).
The Best of Italy Two-Week Trip Itinerary Continues…
VERONA: 2 Days
Day 10: Venice to Verona
The train ride to Verona will take 1.5 hours. Again, depending on your schedule, leave early to spend most of the day exploring Verona. A trip to Piazza Bra is a must to see the Arena di Verona. If you enjoy opera, check out the Information Office right across the street and catch a performance if it’s during the season. It was a spectacular experience for us in 2019. Of course, a trip to Juliet’s balcony is always a treat, but I’m sure you know the Capulet family’s house was not located there but in the vicinity near the River Adige.
Day 11: Visit Lake Garda (Spring/Summer/Fall)
Lake Garda is an easy day trip from Verona by bus, bus and train, or car. Again, this trip will be determined by the time of year you visit. If you aren’t interested in Lake Garda, consider the other option.
Day 11: OPTION – Visit Trento and/or Bolzano
Both these towns are excellent options other than visiting Lake Garda. It’s easy to take the train from Verona up north. Trento is about an hour’s ride (depending on the train), and Bolzano is about 1.5 hours. Both these towns have a German/Austrian influence and are fantastic to visit. Experience very different selections of food, too!
Milan: 3 Days
Day 12: Verona to Milan
The train will take you about 1.5 hours to arrive in Milan. Milan is, hands down, the fashion capital of Europe – perhaps the world. If you enjoy shopping… Milan won’t disappoint you. The Galleria Vittorio Emanuele II is Italy’s oldest active shopping arcade and a significant landmark of this city. It’s located next to the Duomo. If you want a unique experience, go to the top and walk on the roof of the Duomo. The sites are incredible. If interested, you must purchase tickets to see Leonardo Da Vinci’s Last Supper months in advance. Sometimes, you can find last-minute tickets, so always check. At this time, It is not open on Mondays so be prepared.
Day 13: Lake Como
Lake Como is beautiful depending on the time of year. The towns of Bellagio and Varenna are accessible by ferry. Stop for lunch at a café and take in the scenery. You can take the train yourself or find a tour that takes you on the bus.
Day 14: Winding Down
If you enjoy shopping, a trip to this outlet is a must. Be prepared to spend almost all day at the Designer Outlet Serravalle. A possible evening event might be to visit the canals of Milan located in the Navigli district. Another district to discover is the Brera district.
In Conclusion
And that’s a wrap on your two-week adventure through Italy! This itinerary offers a fantastic mix of history, culture, stunning landscapes, and incredible food. While there’s always more to explore, these stops will give you an authentic feel for Italy and its most unforgettable places.
To keep things manageable, this itinerary starts and ends in major international hubs—Rome and Milan—so finding flights in and out should be a breeze. Would you prefer a round-trip journey? Just hop on a high-speed train from Milan back to Rome, a quick and comfortable ride that takes about 3.5 hours.
I hope this guide helps you plan an unforgettable trip. And let’s be honest—Italy has a way of pulling you back, so don’t be surprised if you’re already dreaming about your next visit before you leave!
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We’ll be in Lake Como and then Lake Garda. When we head back towards Milan, do you recommend Brescia, Bergamo, or dipping down to Cremona? We’ll only have time for one of them.
This is the great thing about commenting on a post. We don’t have an opinion, but hopefully others will. We’ve only been to Brescia out of the three. It was lovely but don’t have a comparison for the towns. Sorry, Tom!
Great Blog! Thanks so much~
Thank you Joanne – appreciate your kindness!