Italy: Best first-time Italy itineraries for 3 days to 2 weeks

Planning a first trip to Italy can be daunting. Unlike France, where Paris is the obvious focus, and the UK where London is the obvious focus, Italy provides so many options that you’ll feel like you are missing something big no matter where you decide to go. I get a lot of questions about Italy itineraries on this site and I end up typing the same answers so frequently that I decided to create an article that should cover the topic for nearly all first-time Italy visitors.

Racing through Italy will make for a miserable trip

One great thing about Italy is that its ‘Big 3′ tourism cities (Rome, Florence, Venice) are each under two hours apart by train. Rome to Florence takes 90 minutes and Florence to Venice takes 1 hour 53 minutes, but they are also all quite crowded and hectic, so trying to race between them in a few days will most likely make you hate Italy.

Venice is a rare exception as either 1 or 2 nights is probably best, and we will discuss that below. Aside from that you really don’t want to race. If you don’t have at least 6 nights to spend in Italy, you’ll want to visit just one or two cities and then see more on a future trip.

If you’ve only got 3 days in Italy spend them in Rome

Venice is amazing and you’ll definitely want to see it in person at some point, and Florence is packed with many of Italy’s most interesting sights, but Rome is still the king of the hill and it’s the place you should focus if you’ve only got 3 nights in Italy.

Three nights gives you two full sightseeing days and those will be so packed in Rome that you’ll realize that trying to add anything else would be insane.

Rome in 3 days highlights

On the day you arrive it will take some time to check into your hotel and get oriented and probably have a meal, so it’s hard to do much or any sightseeing on your arrival day. Your departure day will probably just be you having breakfast and scrambing to check out of your hotel in time to catch a train or a flight, so don’t count on much (or any) sightseeing that day. This gives you two full days to see Rome’s top sights.

• Full day: Colosseum, Ancient Rome, Pantheon, Spanish Steps, Trevi Fountain
• Full day: Vatican Museum, St. Peter’s Basillica, Sightseeing bus tour or walking tour

During those two full days you’ll have time for lunch and a gelato and then a nice sit-down dinner near your hotel, but the main sights generally don’t stay open into the evening so you’ll usually finish sightseeing before dinner. The Spanish Steps and Trevi Fountain are always open (and free), so visiting those in the evenings can be nice.

Rome is also fairly chaotic, so 3 nights is enough for most people

As one of the world’s most famous and historically important cities, you’d be right to assume that it would be packed with amazing sights. The problem is that Rome feels fairly disorganized and a bit gritty, so most people prefer not to linger there. For example, crossing the streets near the main attractions can feel dangerous and there will be people everywhere going in all directions. That isn’t true in most large European cities, so Rome is just not a place to relax for most people.

With 4 or 5 nights you can add a day or two in Florence OR Venice

If you’ve got exactly 4 or 5 nights to spend on your first Italy trip it’s STILL recommended to do the 3 nights in Rome. Your best options are these:

• All 4 or 5 nights in Rome
• All 4 nights in Rome with a one-day Florence day trip
• Do 3 nights in Rome and 2 nights in Florence
• Spend 3 nights in Rome and take a train to Venice for 1 or 2 nights

As we’ll see just below, the shortest recommended visit to all of the Big 3 is six nights. So if you’ve only got 4 or 5 nights it’s really best to choose Florence OR Venice and save the other for your next trip. Better still, add at least one night to your Italy stay and do the best fast trip discussed just below.

6 or 7 nights in Italy: Fastest recommended trip to Rome, Florence AND Venice

If you want to see the best highlights of Italy in the shortest amount of time, this is your best option. You’ll need 6 or 7 nights and you’ll be moving quickly the whole time, but at least you’ll be able to check pretty much every major item off your Italy bucket list. And you’ll almost certainly want to come back again because Italy is really as enchanting as people claim.

Fast Italy trip in 6 or 7 nights:

• Land in Rome and spend 3 nights there
• Take a train (90 minutes) to Florence and spend 2 or 3 nights there
• Take a train (2 hours) to Venice and spend about 24 hours there

Of course you can do these three things in the reverse order, but most long-distance flights land in Rome (or Milan) so this is the best way to do it if you are starting your trip in Italy. On the other hand, if you are coming from France or Switzerland it’s much easier to go from there to Venice and end your trip in Rome.

Why you want to go to Florence?

While Florence isn’t quite as famous or showy as Rome or Venice, it really is the heart of Italy. Florence is the capital of the Tuscany region in Italy, and that makes it the best introduction to much of the country’s best food and wine for a first-time visitor. The city is also the birthplace of the Italian Renaissance and it was literally the most important city in Europe for hundreds of years not all that long ago.

If all of that weren’t enough, Florence is also about 90 minutes by train from Rome and under 2 hours by train from Venice, so it’s the ideal place to stop in between to understand Italy on a deeper level than you can if you only visit both super-crowded Rome and Venice.

Highlights of Florence in two full sightseeing days

The highlights of Florence aren’t quite as famous as those in Rome, but many travelers decide this is their favorite stop in Italy.

• Florence Cathedral and Giotto’s Tower (Famous and worthwhile)
• Uffizi Gallery (Birth of Venus and Primavera by Boticelli)
• Accademia Gallery (Michelangelo’s David)
• Ponte Vecchio Bridge and Palazzo Vecchio (Famous bridge and plaza)
• Tuscan food, gelato, and wine

Why go to Venice and why not stay too long

Having been a tourist city for hundreds of years now, Venice is unlike anything else you’ll ever see and you have to experience in person at least once. The main island is totally car (and bike) free and the only way to get around is to slink through the passageways and cross bridges that are each more stunning than the one before.

That said, Venice is packed every day of the year with tourists, cruise passengers and day-trippers on bus excursions, to the point that it’s frustrating. Think about Venice as a theme park such as Disneyland or Disney World. It’s amazing to visit them for the first time ever, but after dealing with those crowds all day the idea of spending a second day there is a bit less appealing.

Highlights of Venice in 1 or 2 sightseeing days

The main attraction is wandering around and enjoying the views of the canals and gorgeous buildings, not to mention the gondolas.

• St Mark’s Square (crowded all day and lovely at night)
• St. Mark’s Basilica (cathedral overlooking the square)
• Rialto Bridge (Venice’s most famous sight)
• Doge’s Palace (The main palace and museum if you only see one)

Spend 24 to 48 hours in Venice if you can:

From about 10am until about 5pm every day Venice is packed, but from 5pm until 10am the following morning the crowds are MUCH thinner. With this in mind, the best sightseeing times are the evenings and the mornings, although you’ll still want to visit some attractions during the day because that’s the only time they are open.

The key is to splurge a bit for a hotel or hostel on the main island and preferably near St. Mark’s Square. The restaurants around the square are full in the evenings, but most of the walkways are not so you’ll be able to appreciate Venice in a way that the day-trippers can’t. Spending one night is enough as long as you use the evening and morning for some exploring, and two nights is better as long as you avoid the worst of the crowds in the middle of the days.

Places to add if you’ve got 8 or more days in Italy

Needless to say, if you’ve got 8 or more days on your first Italy trip you’ve got the option of staying even longer in Rome, Florence, and/or Venice. But in my experience most people want to move quickly and see more things so I’ll discuss the best options for those who want to see more.

Day trips from Florence (1 to 4 additional days)

Another popular reason to stop in Florence on your way between Rome and Venice is that it’s the ideal base for most of Italy’s best side trips. You can literally stay a week in Florence doing something really great every day, so it’s all down to how much time you have.

Pisa (half day)

To be honest, the city of Pisa is kind of a dud for tourists except for the Campo dei Miracoli (Field of Miracles), which includes the Leaning Tower, a lovely cathedral, and the Baptistry. Pisa is about an hour from Florence by train and the tickets are cheap. The main station in Pisa requires a walk of about 30 minutes to reach the Leaning Tower, but there is another smaller train station about a 10-minute walk away if you are in a hurry.

Cinque Terre (1 to 2 days)

The “Five Lands” are five small fishing villages that were quiet and isolated up until the 1990s when some travel writers (Rick Steves) began recommending them for their charm and photogenic views. These days the Cinque Terre are so overrun with visitors (especially during warm months) that local authorities are considering limiting visitor numbers and those who do come sometimes regret it.

The most photographed village in the Cinque Terre is Vernazza so if you want to take a train from Florence and visit just one, that’s probably the best one. When the weather and conditions allow you can hike between the five villages (for a fee), although the path isn’t easy in some spots.

Siena (1 day)

Siena (80 minutes from Florence by train) is another important Tuscan town that will remind you somewhat of Florence, but it’s usually much less crowded with international tourists so it’s typically more pleasant.

The large brick town square is one of the top attractions and it’s a nice place to eat or relax except during the two days per year (July 2 and August 16) when the square hosts a horse racing event that packs the place with enthusiastic locals. The nearby cathedrals are also notable and worth a look.

Tuscan hill towns (1 or 2 days)

Tuscany has many hills surrounded by valleys and most of those hills have medieval or older towns built on top of them for defensive purposes. Some of them are reachable by train (at least the area below the towns), while others are best reached by rental car. Visiting one or more of these cities is a wonderful contrast to the busy cities because they are truly small and simple towns with great local food and wines on offer.

Montepulciano, Montalcino, San Gimignano, and Volterra are some of the better ones, although each can get pretty crowded on popular summer weekends.

Milan (1 day, if that)

Milan is Italy’s major business city and it’s internationally famous for fashion houses (and Italy’s banks), but it’s actually not much of a tourist city. The Last Supper is in Milan, although you’ve got to make reservations long in advance in order to see it. The main cathedral in Milan is one of Italy’s finest and most interesting, and the shopping area that surrounds it is also very impressive.

Aside from those things, Milan probably isn’t worth a special stop. It’s the main transit hub for long-distance trains so there’s a decent chance you’ll be at least visiting the main train station. If you do decide to stay it’s probably best to make it just one night. Trains from Switzerland to Venice will change in Milan, so if you’ve got time that could be a good time for a visit.

Lake Como (1 or 2 days)

Basically, Lake Como is a collection of small towns around a picturesque lake that is primarily a warm-weather getaway for residents of Milan. If you’ve got an extra day or two then it can be a nice place to visit, but it’s not nearly as beautiful as many of the nearby towns in the Italian and Swiss Alps, and you probably aren’t going to see George Clooney or his friends.

The easiest town to reach by train is Varenna (about an hour from Milan Central) and from there you can take frequent and inexpensive ferries to Bellagio, Menaggio, and other small towns. From November through March Lake Como is pretty dead and maybe not even worth the trip.

Southern Italy (1 to 5 days before or after Rome)

If this is your first trip to Italy it’s probably best to focus on the places mentioned above, but you’ve got some interesting options a bit south of Rome as well. I’d recommend focusing your next Italy trip on the section below, and you might include a visit to Sicily as well.

Naples (Day trip from Rome or Sorrento)

Naples is another of Italy’s largest cities and it’s partly famous as the legit birthplace of pizza. It’s only about 70 minutes from Rome by high-speed train, so it can be done as a day trip.

Naples is also famously gritty and somewhat dysfunctional with almost no green space and a history of problems with petty crime. For those reasons many people choose to just visit during the day to have a look and visit the amazing Naples National Archaeological Museum, which houses many of Pompeii’s greatest finds.

Sorrento (1 to 4 days as a base to explore the whole area)

Once in Naples you can (and probably should) change for the suburban Circumvesuviana train that takes you to Sorrento, which is the end of the line, in 72 minutes. You’ll pass the Pompeii ruins about halfway on that ride, so it’s easy to reach them from Sorrento as a day trip.

Sorrento is a lovely seaside town that is an ideal place to base yourself to explore this part of Italy. Not only can you use it for a day trip to Naples and also Pompeii, but you can catch a bus (or taxi) from the Sorrento train station to explore the Amalfi Coast with its main highlights being Positano and Amalfi itself.

You can also take a ferry from Sorrento to Naples, as well as to the Isle of Capri, which is another famous and worthwhile destination just an hour away. The Blue Grotto is the main attraction, but shopping and eating are also popular in the warmer months.

Europe resources

Book