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Italy will always have a special place in my heart. It was my first international trip and although it was many years ago, it seems like yesterday. At the time, I thought it would be in my best interest to go with a tour group since I had very little experience traveling. It was great, but looking back I wish I had done it on my own and been able to spend additional time at some of the places that the tour glossed over. I was able to see and do an incredible amount in a fairly short amount of time and I felt as though I really got a taste for Italy as a whole. There is so much more to Italy than Rome. That being said, I decided to put together what I consider, the perfect two week itinerary for Italy. This is an itinerary for someone who really wants to see all the major sights and cities.

Day 1: Arrive in Rome

Spend the evening exploring the city. Night tours of the sights are offered or visit the Spanish Steps. People will gather here and play music at night. It was really beautiful.

Day 2: Rome -> Sorrento

On the way to Sorrento, about 2 1/2 hours outside of Rome, is Pompeii. Make sure you stop and explore a little. Pompeii has always fascinated me and had been somewhere I’ve been interested in visiting since reading about it in my 6th grade history class. Pompeii was an ancient Roman city that was destroyed and buried under ash when Mt. Vesuvius erupted in AD 79. It has since been excavated and the ash actually preserved the city underneath giving us a detailed look as to what life was like then. It’s pretty amazing. Sorrento is only about another 45 minutes away.

perfect itinerary italy pompeii ruins

Day 3: Sorrento/Capri

Spend the morning exploring Sorrento. It is a gorgeous little town that sits cliff-side above the Bay of Naples. It provides some beautiful scenery; it’s full of windy roads and waterfront views.

perfect itinerary italy sorrento

Early afternoon, catch the ferry to Capri for some lunch and shopping. Or hire a boat to take you to the Blue Grotto. Unfortunately, it was raining during my time there and the waters were to rough for the grotto.

perfect itinerary italy pompeii capri

Day 4: Sorrento -> Florence

It’s about a 6 hour drive but you’ll pass trough some beautiful scenery on your drive north to Florence. I would recommend spending the afternoon wine tasting in Tuscany on your way. It is a must do in Italy! I stopped at Castello il Palagio, a fourteenth century castle and farm. I was able to take a tour and enjoy some delicious Chianti.

perfect itinerary italy tuscany

Day 5: Florence

Explore all the beautiful sights in Florence. There are walking tours available or do it on your own. Take a stroll and do some shopping on the Ponte Vecchio, visit the Duomo and the Santa Croce.

perfect itinerary italy ponte vecchio

Day 6: Florence

Spend the day, taking in all the city’s art and visit the Uffizi, one of the best museums in Italy. It’s a gorgeous museum and has a large collection of works by famous Italian artists, such as Michelangelo, Leonardo Di Vinci and Botticelli. I would take a tour so you don’t miss any of the “must-sees.”

Day 7: Florence -> La Spezia

Get an early start and be try to beat the crowds to the Leaning Tower of Pisa. It’s a little over an hour outside of Florence. Continue onward toward the coast for another 2 hours to the stunning Cinque Terre. The Cinque Terre is a little difficult to access by car and if you do drive, chances are you will find parking difficult as well, so I would recommend riding in on the train and leaving your car at the station in La Spezia.

perfect itinerary italy leaning tower pisa

The Cinque Terre was one of the highlights of the trip for me. The Cinque Terre, meaning five lands, is a group 5 different towns sitting on the Italian Riviera. You can take a hike on a winding path through the hills of these five towns. The water and the towns, themselves are absolutely beautiful.

Day 8: Cinque Terre

Spend a relaxing morning at the Cinque Terre before catching the train back to La Spezia.

perfect itinerary italy cinque terre

Day 9: La Spezia -> Milan

It’s roughly a 2 1/2 hour drive to Milan from La Spezia. Arrive in the evening and enjoy dinner and/or a night out. Milan is full of good food and nightclubs.

Day 10: Milan

Do some sightseeing and shopping. Make sure you visit Milan’s Duomo, a massive Gothic cathedral; the Sforza Castle, a fortress full of museums and art by da Vinci and Michelangelo; and the Galleria Vittorio Emanuele II, the world’s oldest shopping mall. It opened in 1865 and has a glass and iron roof is quite amazing.

galleria vittorio emanuele

Day 11: Milan -> Venice

About 2 hours outside of Milan is the town of Verona. This was another of my favorite places and I definitely recommend a stop here on your way to Venice. Three of Shakespeare’s plays are set in Verona and there is even a building with a balcony overlooking a courtyard that is said be Juliet’s House. Other sights to check out are the Verona arena, a huge amphitheater; Castelvecchio, a castle that now houses a museum; and nearby Lake Garda.

Another hour and a half and you will be near Venice. Depending on what time you arrive and what your budget it is, you have two options. The first being to stay right outside of Venice and catch the first boat over in the morning. I would do this if you are arriving late or you are looking to save some money. A lot of the hotels directly in Venice can be quite pricey. Or, the second option, get on a boat asap and stay on Venice. You’ll have a little more time to experience it this way, but either would work. Venice is small and you don’t need a lot of time there.

Day 12: Venice

Explore the city. Take a gondola ride, eat some amazing food and check on some of Venice’s famous sights. Pay a visit to St. Mark’s Square, the Bridge of Sighs, the shops of some of highly skilled local craftsman, including glass blowers and lace makers. Also, stop by the Hotel Danieli, a hotel Princess Diana used to frequent and sip on one of their delicious Bellinis. Catch the last boat of the day back.

perfect itinerary italy venice

Day 13: Venice -> Rome

Almost 2 hours into your drive you’ll be in Bologna. I would recommend stopping here for a couple of hours. Bologna, a medieval city, is quite a bit different than some of the other Italian cities and I found it really interesting. Be sure to check out the Towers, Piazza Maggiore and the Whispering Walls.

perfect itinerary italy bologna

Continue on to Rome. In about an 1 hour and 45 minutes you’ll arrive. Visit any sights that you missed your first day. Visit the Colosseum, Trevi Fountain, the Forum, and the Pantheon.

Day 14: Rome

Visit Vatican City and take a tour of the Vatican. Don’t miss St. Peter’s Basilica, the gardens, the necropolis and of course, The Sistine Chapel.

perfect itinerary italy colosseum

I hope you love this perfect two week itinerary to Italy as much as I did. As mentioned before, this itinerary may not be ideal for everyone. It covers a lot in a short amount of time. That being said, it is definitely doable, but please adjust it to fit your personal travel style. Enjoy!