For as long as I’ve been writing about travel in Italy, I’ve gotten questions about Italy itineraries. When you’re so spoiled for choice, it can be hard to pick an itinerary that eliminates places you thought were “must-see” sights. But with a limited amount of vacation time, those are the hard choices that must be made. That’s why I’ve put together what I’m calling the perfect two-week Italy itinerary.
Find out how I make my own travel plans so you can tailor your trip to your exact needs with my article on how to create the perfect Italy itinerary for any trip.
The Italy itinerary you see below is quite similar to the itinerary I created for my own first trip to Italy many years ago. It’s ideal for first-time Italy visitors who don’t want to miss the highlights but may also want to add on a few other options for side-trips.
Here’s a brief look at my suggested two-week Italy itinerary, with more details below:
To avoid back-tracking geographically, your best option is to get an open-jaw ticket flying into Venice and out of Rome. Open-jaw tickets are often competitively priced with airfare that’s in and out of the same city, so they’re always worth considering. When your other choice is to back-track, an open-jaw ticket means you’re using your vacation time for your vacation wish-list – not in transporting yourself across the country. I’m all about efficiency, and I want you to have as much time as humanly possible to enjoy Italy (and not just its train system).
Speaking of the trains, this itinerary is easily do-able entirely on public transportation – trains and buses – so you don’t have to worry about renting a car or driving in Italy.
You could do this itinerary in the reverse order, starting in Rome and ending in Venice, but I recommend Venice as a starting point for any Italy trip that includes Venice on the itinerary – and particularly first-time visits to the country. The Venice airport is far smaller than Italy’s two major airports – in Rome and Milan – which means it’s easier to navigate, and there is absolutely nothing like having your first Italian experience be the surreal city on water. Approaching Venice from the airport on the mainland, gliding across the lagoon on a vaporetto or water taxi – well, there’s nothing quite like it.
Another reason I like Venice as an introductory city in Italy is that its lack of cars means the average tourist, gazing up in awe rather than looking where he or she is going, won’t get hit by a Vespa. In Venice, the worst that can happen if you’re not watching where you’re going is that you’ll fall into a canal. By the time you get to Florence, the “HOLYWOW I’M IN ITALY!” feeling should have dissipated a bit, so you’ll be better-equipped to pay attention to traffic.
One final note, before I dive into the itinerary details: Before anyone gets annoyed by something I’ve left out (or included), please read my caveats at the bottom of the page. After that, if you’re still upset, by all means let me know.
You’ll begin your Italy trip in Venice, one of my favorite cities on earth, in what is likely a flight arriving in the morning. Venice doesn’t have a real off-season. It’s always somewhat crowded, and that doesn’t stop it from simultaneously offering quiet and romantic corners. Many travelers think that by visiting Venice as only a day trip that they’re avoiding the worst of the crowds, but Venice is at its most busy during the day specifically because of the day-trippers and cruise-goers. By staying at least one night in Venice, you give yourself a chance to enjoy a city that can be difficult to love.
Venice has a few attractions that most people think of as “must-see sights,” but the main thing to do in Venice is to simply wander, explore, and get lost. And because the island is quite small, you can easily cover the whole of Venice in a day. Going into churches and museums then becomes easy to add to your itinerary.
Aside from aimless wandering, Venice’s main attractions include St. Mark’s Basilica and piazza, the Doge’s Palace, and the Rialto Bridge. Venice isn’t a town known for its nightlife, but when the day-trippers have departed you’ll be able to take one of the best nighttime strolls of your life.
Venice’s Santa Lucia train station has regular service to destinations all over Italy and into the rest of Europe. After two nights in Venice, you’ll leave on an early morning train for your next stop in the Cinque Terre, which will likely include a transfer in Milan. The trip will take about 6-7 hours.
Read more about what to do & see in Venice
The secluded charm of the Cinque Terre is what drew visitors here in the first place. These five villages no longer feel very secluded, as they’re often crowded with tourists who come to hike the trails that connect the towns and to marvel at buildings that seem to grow right out of the rocks. The Cinque Terre has become one of northern Italy’s most popular places to visit, and – like Venice – is often a day trip destination. That means spending the night gives you a better chance of seeing the best aspects of the area.
You’ll arrive in the afternoon in the Cinque Terre, in time to settle into your hotel and explore that town. You may even have time to hop on the slow train that runs between the villages to explore another town in the evening, perhaps even having dinner there before heading back to your hotel or apartment. Spending two nights gives you one full day in which to do all the hiking you’d like to do – if there’s time the first afternoon when you arrive to do some additional hiking, that’s a bonus.
There isn’t much to do in the Cinque Terre besides hiking, lying by the sea, swimming, and relaxing – so take your time and enjoy your hike (best to go first thing in the morning before it gets too hot), cool off with a swim in the afternoon, and feast on local seafood for dinner.
After two nights in the Cinque Terre, you’ll take a train bound for Florence. Because the trip is only 2.5-3 hours long (even with a change in Pisa), you don’t need to worry about an early start if you’d rather go for a morning hike. If you’re planning to stop in Pisa for 1.5-2 hours to see the leaning tower, however, I’d recommend getting an early train so you’ll have time for a Pisa visit and still get into Florence for a leisurely evening.
Read more about what to do & see in the Cinque Terre
Florence could easily be the focus of a two-week vacation in Italy all by itself, and you still wouldn’t see everything the “Birthplace of the Renaissance” has to offer. With four nights in Florence and three full days, you’ll have enough time to see the major sights at a slightly more leisurely pace and squeeze in a day trip if you so desire.
The “must-see” sights in Florence include the fabulous Uffizi Gallery, the Accademia, the pretty Ponte Vecchio, and the multicolored Duomo – but the list doesn’t end there. The good news is that the bulk of the city’s main attractions are concentrated in its historic center, which means that although this will be your first taste of Italian city traffic since your arrival in the country, you’ll mainly be focused on the parts of the city that are more pedestrian-friendly than they are choked with cars.
Since you cleverly stopped in Pisa en route to Florence, if you’re itching to see the Tuscan countryside before heading south to Rome then I’d recommend a day trip while you’re in Florence. Siena is perhaps the most popular day trip destination from Florence (after Pisa), and although it’s a large city now, there’s an historic medieval core that’s quite appealing. It’s the sort of place people fall in love with instantly, and when you get there you’ll probably understand why. Another popular day trip option from Florence is San Gimignano, a small walled town with a plethora of medieval towers. Both Siena and San Gimignano are easy to reach from Florence by bus. Keep in mind that both are popular day trip spots, which – like Venice – means they’re extra-busy during the day. If you can’t spend the night in either city, however, then a day trip is the next best thing.
After four nights in Florence, you’ll board a train the next morning bound for Rome. It’s a 2.5-3 hour trip.
Read more about what to do & see in Florence
Even without ever having set foot in Rome, no doubt you know just how important the city is – and has been – for more than two thousand years. Even with the gravitas of all that historic significance, Rome is very much a city on the move – a modern metropolis with no time to slow down for visitors. I’ll admit that the first few times I went to Rome I found it to be overwhelming and exhausting. I’ve come to respect Rome, and I’ve learned to love it, but it didn’t come easily.
Rome is big. It’s sprawling. (The bus/metro/tram network is intricate. Get to know it – it means you’ll avoid exhausting yourself by walking everywhere.) One of the things that helps immensely is giving yourself enough time to ease into Rome rather than trying to see everything in two days. Having five days in Rome means you won’t punish yourself with an overly-ambitious itinerary. You can go back to the hotel room for a midday break if you need it, or spend an extra hour in a piazza watching the fountain and eating gelato. In short, don’t beat yourself up about trying to “conquer” Rome. You’re on vacation, remember?
The “must-see” list in Rome is extensive. You can see the major sights of ancient Rome – the Colosseum, Roman Forum, Pantheon, Capitoline Hill, and Palatine Hill among them – in a day. It’s best to give Vatican City the better part of a day. There are museums and art galleries to visit, markets to scour, and lots of great Roman cuisine to enjoy. You might be content to savor Rome for your four full days in the city before you fly home, but if you can’t bear to be this close to Pompeii and not see the famous archaeological site, you can do a day trip to Pompeii from Rome.
Pompeii is actually a much easier day trip from Naples or even Sorrento, since it’s so close to those, but you can do Pompeii in a day trip from Rome. You’ll just need to plan on an early morning train, and make sure you’ve researched the train connections ahead of time. You can also book a guided tour of Pompeii from Rome to leave the logistical wrangling to someone else.
You’ll fly home from one of Rome’s airports, and if you’re fortunate enough to have a flight that doesn’t leave at the crack of dawn you might have enough time to check something else off your to-do list in the Eternal City before you head out of town. Even though this is the end of your trip, you might consider bringing your Italy guidebook on the plane in your carry-on bag – you’ll be able to start planning your next trip to Italy on the flight home, picking up on the Italy wish list where you left off this time.
Read more about what to do & see in Rome
I know some readers will have gotten to the end of the itinerary and will be horrified that I’ve left their favorite place off the list, or that I’ve included a place that they think isn’t worth the time. I hope these caveats will help explain why I made the suggestions I did.
You’re right. It’s impossible for one traveler to tell another traveler what constitutes the “perfect” itinerary. We can make good suggestions based on what we know of another person, but in the end each person’s travel style is going to make it impossible for one itinerary to be a “one size fits all” trip. Having said that, there’s a reason the “tourist trail” is easily identified. Many travelers hit the same spots, often in the same order, because most people want to see the same highlights. My guess is that even if this Italy itinerary isn’t perfect for your first-time trip, you can probably make it perfect with a small tweak or two.
You’re right. And yet most Americans are lucky if they get two weeks of vacation time in a year. If you’re fortunate enough to get more vacation time, or if you live in a country that’s more generous with its holiday time, then feel free to use this itinerary as a starting point from which you can add more cities to fill the rest of your trip. If you only have two weeks, remember that Italy will be waiting for your return.
Oh, but you can. This is a sort of snobby attitude that one type of travel (and traveler) is better than another. I’m not fond of that attitude. Just because you don’t visit all the places on someone else’s idea of a proper Italy must-see list doesn’t mean your trip somehow “doesn’t count” or that you didn’t do it right. Of course, if you only set foot in Italian airports on your way someplace else, then – yeah – you can’t say you’ve been to Italy in that case. Even I’ll call you on that one.
As mentioned, tourist traps often become tourist traps because there’s something cool to see or do there. No, you’re not the first person to snap a photo of yourself propping up the leaning tower of Pisa. And if you really want that photo? Then, by all means, go for it. There’s nothing original in my affection for Venice, and no one can convince me I shouldn’t love the city just because it’s often overrun with tourists.
Spot on. And I always choose quality vs. quantity when possible. I have a thing when I’m planning my own trips and I make the same recommendation to many other travelers – stay at least two nights in every place in every case where that makes sense. Changing hotels every day can get kind of exhausting, so that your trip becomes one endless stream of reception desks. I’d wager most people don’t want that to be their vacation theme.