Disclaimer: This post contains affiliate links. If you click through and make a purchase, I may receive a small commission (at no additional cost to you). This helps support and run my blog. I only recommend products I personally use and love. Thank you for your support.

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.

perfect itinerary italy trevi fountain

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 too rough for the grotto.

perfect itinerary italy pompeii capri

Day 4: Sorrento -> Florence

It’s about a six-hour drive but you’ll pass through 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 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 of five 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 Mi