Italy Itinerary for Two Weeks

Italy is one of the most beautiful countries in all of Europe. With its incredible history, culture and arts, unbelievable cuisine, sky high peaks, world-class fashion, and crystal clear Mediterranean waters, Italy has a little something for everyone. Seeing everything Italy has to offer on a single vacation, however, can be a challenge. In fact, you could spend a whole month in Italy and still not see everything it has to offer. So, when you're making an Italy itinerary for two weeks, cramming everything you want to see into your trip can be near impossible.

We learned this as we were planning our trip, and had to, unfortunately, cut out a trip to Lake Como in Italy's Northern region, as it would've been wayyyy too hectic and on the go. Scaling our trip back a bit did, however, allow us to truly enjoy the spots we did go to, and left us wanting to come back to explore even more of Italy. And we even managed to get a good taste of ancient Rome, wine country and the Mediterranean. So, if you've only got a few weeks available to explore this beautiful country, here's an Italy itinerary for two weeks that will give you a good taste of what Italy has to offer, while also allowing you to slow down and appreciate each spot.

Day 1: Rome

A lot of international flights land in Rome, so chances are your Italy itinerary for two weeks will start (and possibly end) with a trip to this famous, historic city. After you check into your hotel, check out one of the city's world-famous sights, such as the Colosseum or the Vatican. If you can, try and decide what sight you want to see before you go, and book your tickets for it in advance. You can get "skip the line" tickets for both the Colosseum and the Vatican. We chose to see the Colosseum, and it was epic, but it was also very busy, so a skip the line ticket will definitely make your visit a little better and easier.

From there, spend some time taking in the streets of Rome. Head to a cafe, grab a slice of pizza, and sip on a Peroni. Rome has lots of incredible places to grab a bite to eat, and will certainly provide a great introduction to Italy's famous cuisine.

If you've still got some energy in the evening, head over to the Trevi Fountain. This incredible fountain can be super busy, but tends to have a bit less traffic later in the day. You could also check it out the next morning, as it is typically quite empty just after sunrise. Either way, the Trevi Fountain is a great free sight, and should definitely be included in an Italy itinerary for two weeks!

Days 2-6: Tuscany

The next day, grab a rental car and drive out into the Tuscan countryside. Tuscany is a large region, however you'll start to experience Tuscany a few hours outside of Rome, where the landscapes quickly starts to turn into green and yellow rolling fields, and ancient towns jut from the top of hills.

When we went to Tuscany, we spent two nights near a town called Montalcino, and another two nights near a town called Cortona. We stayed in old Tuscan villas at both spots (Capanna Suites and Villa di Piazzano), which I would highly recommend over staying in one of the towns or cities.

Once you're at your villa, you can either get out and explore the local wineries and towns, or you can simply lay back, sip a glass of Chianti, and take in the endless views from your vacation rental. Tuscany is truly a place where you can go at your own pace, and not feel like you're missing out on anything. We spent a lot of time at our villas when we were there, and those days of complete relaxation were some of our favourite on the trip!

Days 6-8: Venice

Venice is one of the most beautiful cities I've ever seen - but you have to spend at least a night or two there. Hear me out.

Venice receives tens of thousands of day trippers every day, making the tight, car-free streets near impossible to walk through. If you are in Venice early in the morning or in the evening, however, you can experience near empty streets, allowing you to take in the canals and historic buildings in peace. The best way to do this, though, is to spend a night or two so that you can easily get up early and walk around before the crowds arrive, and head out onto the streets a little while before bed when the crowds have left. We honestly headed back to our hotel during the afternoon just to escape the crowds!

So, if your Italy itinerary for two weeks can afford you two nights in Venice, do it. You'll get to experience one of the most beautiful cities in the world for a few mornings and evenings without the crowds.

To get to Venice from Tuscany, the easiest way is to drop off your rental car in Florence, and then hop on a train from there to Venice's main station, Stazione di Venezia Santa Lucia. Once you arrive, you'll likely need to take a water bus into the actual city. These typically run multiple times per hour, so getting from the train station to your hotel should be a breeze!

Days 8-11: Positano and the Amalfi Coast

Now, getting from Venice to the Amalfi Coast is a bit of a trek, but, trust me, it is very worth it. To get there, you'll need to take a five and a half hour train ride from Venice to Naples. Once you arrive in Naples, you'll need to either rent a car or have a private driver take you to wherever you're staying in the Amalfi Coast. I would recommend having someone drive you as opposed to renting a car. The roads along the Amalfi Coast are not for the faint of heart (you'll see what I mean!).

There are several nice towns along the Amalfi Coast, such as Amalfi, Praiano, and Ravello, however we stayed in Positano. Positano is essentially a town built into the side of the mountains. It's also probably the most visited town in the Amalfi. Because of this, there are lots of hotel, restaurant and bar options. We chose to stay a little bit outside of the main town, which was nice, however we did have about a 15 minute walk to get to the restaurants. Keep this in mind when you book a hotel here. As I said before, this town is built into the mountains, so check to see how arduous it is to get from the hotel you're considering to the main town area where all of the food and drinks are.

The main beach in Positano is Spiaggia Grande. It is an epic beach, as it's filled with beach umbrellas and has the town and mountains as its backdrop. Be aware, though, that it gets extremely busy. Luckily, Positano has a lot of smaller beaches that don't tend to get very busy - because they are hard to reach. To get to some of these beaches, you either need to take a water taxi, or take a very long (and I mean verrrry long) staircase down the sides of the mountains. We spent a lot of time at a beach called Arienzo Beach, which also had a private beach club on it. We did the beach club one of the days. It costs roughly 70 Euros, which includes a lounger and umbrella for the day, two drinks, lunch, dessert and a limoncello shot. Pretty good value if you ask me!

Lastly, no trip to the Amalfi Coast is complete without taking in the sunset over the Mediterranean Sea and the mountains. If you end up staying in Positano, the best spot to take in the sunset is across from the perfume shop on via Cristoforo Colombo.

Days 11-14: Sorrento and Capri

After a number of delightful days in Positano, head back up the coast to Sorrento, which is a bit more populated than the towns along the Amalfi, but very beautiful in a different kind of way. In Sorrento, the mountains are replaced with large cliffs, the lights of Naples twinkle in the distance, and Mount Vesuvius looms above the skyline. Sorrento is also filled with several resort-style hotels, which can be a nice way to chill out and relax towards the end of a two-week trip!

Sorrento itself has a nice downtown area to explore and of course great access to the Mediterranean, however one of the best things you can do here is actually visit the isle of Capri. Ferries depart to and from Sorrento towards Capri all day long - and it's only about a 20 minute ride! Once you're in Capri, you'll want to get away from the large tourist crowds lining the souvenir shops and restaurants right where the ferry port is. The main town of Capri is actually up the mountain, and that's where all of the fancy shops and restaurants are.

To get up the mountain, you'll need to take the funicular, which is only about a two minute walk from the marina. When you arrive in Capri, turn right as soon as you get out of the marina, and locate the funicular ticket box. The tickets to ride it are only about 2 euros. Make sure you buy two tickets so that you can easily get back down and catch your ferry. Once you're up in Capri, wonder around the streets, do some shopping and try some of the restaurants in the area.

Now, no trip to Capri is complete without seeing the Faraglioni, which are three famous rock outcrops that jut out of the Mediterranean. The only problem is that they're on the opposite side of the island from where the ferry drops you off. One way to experience them is to take a boat tour around the island, which will take you right up to them. Another way, if you take the funicular up the mountain, is to head to the Gardens of Augustus. From here, you'll get a perfect view of the Faraglioni from above, as well as the yachts (and occasional helicopters) that hang out around them.

Day 15: Rome

When you've had enough of the Amalfi and Sorrento Coasts (which I don't think is possible!), get a drive back to Naples, and then take a train to Rome for one last night in Italy. While you're here, spend some time walking the streets, seeing some of the sights you may have missed on the first night, such as the Pantheon, and enjoy the food before catching your flight the next morning.

There are many ways to create an Italy itinerary for two weeks. In fact, you could visit Italy several times and have an entirely new experience every time you visit - that's how vast and deep in culture this country is. Our Italy itinerary for two weeks gives you a taste of some of Italy's most captivating components, including the countryside, coast and, of course, its history. If you do decide to base your two week Italy itinerary on this one, I hope that it helps you see what a wonderful place Italy is, and leads you back there to explore even more.

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