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3-Week Italy Itinerary: Italy's Greatest Hits

If you’ve got more than two weeks to spend on your vacation in Italy, you might have found lots of great suggestions for a 2-week Italy trip and be wondering what to do with your third week. Sometimes it’s as simple as tacking another week onto an existing 2-week itinerary, but it’s sometimes easier to look at the whole three weeks together.
I call this suggested 3-week Italy itinerary the “Italy greatest hits” itinerary, because you’ll hit almost every major tourist destination in the country. This itinerary includes the Italy “holy trinity” of Venice, Florence, and Rome, and it also gets you to the Ligurian coast (where you can visit the popular Cinque Terre), the city of Siena (one of the most loved spots in Tuscany), the Amalfi Coast, and the famous excavated city of Pompeii.
Best of all, having three weeks in the country means you’ll get to see all of that without rushing around like a maniac.
Itinerary Quick Overview:

Itinerary Assumptions

The main assumption I’m making here is that you’re buying “open-jaw” plane tickets – flying into one city and out of another. This maximizes your time in Italy because it doesn’t require you to back-track to return to your arrival city for your flight home. Since this is a three-week itinerary, however, you could shave a day or two off of some of these destinations if you needed to fly in and out of the same city. I leave the decision of where to cut in your hands.

Who Might Like This Trip

This itinerary is a good option for people who haven’t been to Italy before and so therefore have all the big must-see places on their list – but who aren’t intending to be in a new city every day. This itinerary allows for a little slowing down between transit days (no stop is fewer than a two-night stay in a hotel), and there are several day trip options you can either take advantage of to cover more ground or skip to relax even more.


For this itinerary, you’ll fly into Venice (VCE) and out of Naples (NAP).
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This itinerary is easy to do on public transportation (train and bus). If you want to rent a car for a day or two to get out of the main population centers, the places I’d recommend doing that are Liguria, Tuscany, or the Amalfi Coast.
Note that driving along the Amalfi Coast, while a well-known thing to do, is challenging on narrow roads when huge coaches are coming at you. You can choose to rent a scooter for the day and make the trip that way, too.
In every case, however, parking is generally a pain in the city centers (and sometimes not even possible, as in the case of the Cinque Terre), so inquire with your hotel about parking options if you’re renting a car for more than one consecutive day. You may also want to read these driving tips for Italy before you get there.

3-Week Italy Itinerary: Italy’s Greatest Hits in Three Weeks


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You’ll arrive at Venice Marco Polo Airport, likely in the morning. Get to your hotel, get situated, and go out to explore the city on foot. Visit St. Mark’s Basilica, the Doge’s Palace, and any other churches or museums on your must-see list, but otherwise just enjoy wandering through the islands. On day two, you can continue exploring the islands, or take a half-day trip – the other islands in the lagoon (Murano, Burano, and Torcello) can be visited easily by vaporetto, or you can take the train to nearby Verona. Should you prefer to just continue trying to get as lost as you possibly can on the islands, that’s also perfectly fine.
You’ll take a morning train to the Ligurian coast after your second night’s stay in Venice. You can choose just about any spot on the beautiful Ligurian coast and have a great couple of days – but most people will gravitate the more well-known Cinque Terre towns or the city of Portofino. Either area is a fine option, and that’s what I’m going to focus on below, but if you want to explore a bit further I suggest you look at a map of Liguria and consult a guide that specializes in the area. The city of Portofino is about 5.5-6 hours away, with 1-2 changes, and the Cinque Terre towns are about 5-6 hours away, with 1-2 changes, so don’t forget to bring some snacks along for the train ride (or be prepared to buy sandwiches and drinks from the vending machines in the station).
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Liguria – Cinque Terre or Portofino

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You’ll arrive in either Portofino or Cinque Terre (or any other Ligurian coastal town you like) in the mid-afternoon from Venice, get settled into your hotel, and explore the town a bit. The next day can be spent in and around the water or (if you’re in the Cinque Terre especially) hiking, or a combination of the two. The scenery is the main “sight” here, so you don’t really have to worry about museums or galleries that you’d be missing by spending all your time outdoors.
You have a bit of time the next morning to get in one last swim or a short hike before getting on a train bound for Florence. If you’ve got the time and are interested, you can even make a 1-2 hour stop in Pisa en route in order to get that “leaning tower photo” everyone wants. The train trip from the Cinque Terre to Florence takes about 2.5-3.5 hours, depending on the route and any transfers you might need to make, and doesn’t include time spent in Pisa if you decide to do that.
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You’ll arrive in Florence by mid-afternoon, which means your first day is about settling into your hotel and exploring on foot. It’s an excellent time to start sampling gelato in the city, too. Walk or take the bus up to the Piazzale Michelangelo in the early evening to see the sun set over the city at least once during your stay.
It is helpful to book as many of your museum/gallery visits in advance as you can to avoid waiting in lines, so check out the schedules for places like the Uffizi and Accademia. You won’t need to book a visit to the Duomo or Bargello, but both are worth visiting. Note that you can also stop in at the secret ticket window in Florence to see what last-minute bookings are available if you don’t book before you leave home.
Normally with four days in Florence, I recommend using one of them for a day trip to Siena – but since that’s the next stop on this itinerary, you can choose another Tuscan town for a day trip or rent a car for a day or two and just drive around aimlessly (it’s helpful to rent a car with a GPS unit in these cases). Other day trip options include Lucca (by train), San Gimignano (by bus), and even Bologna (by high-speed train).
You’ll take the bus to Siena on the morning after your fourth night’s stay in Florence. There is a train, but the bus is faster and the bus station is closer to the historic center than the train station. It’s about a 1.5 hour trip by bus.
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Since it’s a short transfer from Florence to Siena, you’ll have most of your first day in Siena rather than just an afternoon (unless you choose to take a later bus). Arriving mid-day may give you the impression that Siena is packed to the gills, but the city is a magnet for day trippers – just wait until the evening and the majority of the crowds will disappear. You can visit Siena’s must-see attractions (especially the Duomo and Baptistery) at a leisurely pace over the next day and a half, so feel free to wander slowly through the picturesque city center. It’s quite hilly, so slow may be just the pace you can manage. Don’t miss an evening passeggiata in the Campo, preferably with a gelato in hand.
After two nights in Siena, you’ll head for Rome the following morning. You can take a train from Siena to Rome (about 3-3.5 hours, with one change) or take a SENA/Eurolines bus (about 3.5 hours, departing every other hour).
Note that if you’re visiting during the summer, the famous Siena Palio horse race runs on July 2 and August 16 each year, and the city will be extremely busy and hotels booked solid around those dates.
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When you get to Rome, settle into your hotel and explore your neighborhood. While you may not have time to get into any of the big sights on your first half-day in the city, it’s not a bad idea to head for the Colosseum in the evening anyway to see the monument all lit up. It’s quite a first night in Rome.
You’ll have three full days in which to explore Rome. One of them should be mostly set aside for Vatican City – an organized tour (highly recommended, as they help you speed past the long Vatican Museums lines as well as give you some sense of what you’re looking at) that includes both the Vatican Museums and St. Peter’s Basilica is likely to run six hours or more, including a stop for lunch. I like seeing the ancient sites first (Colosseum, Forum, Pantheon, etc.) and then doing the Vatican on the following day. Other options include browsing through colorful outdoor markets, exploring the pretty Trastevere or Monti neighborhoods, visiting any number of churches/museums/galleries throughout the city, or taking a walking tour – or some combination of all of those. If you’re a history nut and the Roman ruins and upcoming Pompeii visit aren’t enough, consider a day trip to Ostia Antica to see the ruins there – pair it with a stop at nearby Ostia Lido and you’ll get a bit more beach time in, as well.
After four nights in Rome, you’ll take a morning train to Naples and then immediately head for the Amalfi Coast. You can get there by train (to Sorrento, followed by a bus to the Amalfi Coast), by bus (from the Naples Airport near the city center to Sorrento, followed by a different bus to the Amalfi Coast), or by boat (to Sorrento or some the Amalfi Coast towns) – or you can rent a car and make the spectacular coastal drive yourself.
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Amalfi Coast

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If you haven’t had enough relaxing yet during your trip, this is your opportunity to kick back. It’s not a direct transfer from Rome to the Amalfi Coast, so it’s the most tedious travel day of the whole trip – but once you get to the coast, you’ve got essentially nothing to do but relax. If you’ve got a car, you can explore beyond the popular towns along the main road, but even without your own transportation you can visit each of the towns of the Amalfi Coast, along with nearby Sorrento (not technically part of the Amalfi Coast, but a common base for exploring the area) and some of the islands – all by bus or boat. Still need more of a history fix? A day trip to nearby Paestum could be ideal. If four nights in one place along the coast seems too much, consider splitting your time with two nights each on the coast and then on one of the islands. It’s a similar but definitely distinct flavor when you’re on an island and the day trippers have gone.
After four nights on the Amalfi Coast, you’ll take the bus back to Sorrento and from there you’ll take the Circumvesuviana train back to Naples’ main train station.
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You’ll likely get a raised eyebrow or two when you tell people you’re including Naples in your Italy trip – the city has a bit of a PR problem – but after nearly three weeks in the country I think you’re good and ready for Naples. And if you’re prepared for Naples, you’ll leave wondering what all the raised eyebrows were for in the first place.
Once you get settled into your Naples hotel after leaving the Amalfi Coast (which I hope is in the historic center of the city for maximum atmosphere), you’ll have the rest of the day to explore. There are several fantastic museums and art galleries in the city, but the one at the top of any must-see list is the National Archaeology Museum. Find time for this during your day, and otherwise enjoy wandering through the old city – stopping frequently for pizza and to walk into any church with an open door – and perhaps taking the tram up to the top of the hill that overlooks the city center for a staggering view of the bay and Mt. Vesuvius.
On your last day, you’ll take a day trip to nearby Pompeii and Herculaneum. Both were wiped out by Vesuvius in 79 A.D., and it’s easy to do a DIY day trip that includes both – or you can join a guided tour (many depart daily from Naples). This won’t take you all day, so you’ll be back in Naples’ city center in time to do a bit more wandering (and pizza eating, of course) before you fall asleep in Italy one last night.
The Naples Airport is very close to the city center, so have someone at the hotel front desk arrange a taxi to pick you up whenever you need it, and you can begin planning your next Italy trip on the flight home.
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photo by Jason OX4