My Two-Week Italy Itinerary (Rome, Positano, Florence, Cinque Terre)

Italy had been nothing short of an incredible trip! Although I took hundreds of photos during these two weeks, no clever composition or expensive camera could have captured the full experience of being there in person. Instead, I'll give you my itinerary so you can experience it for yourself instead!

We went to the following cities in order:

  • Rome (May 14-16)
  • Positano (May 16-20)
  • Florence (May 20-24)
  • Cinque Terre (May 23 while in Florence)
  • Rome (May 24-25)

Key takeaways and advice: 

  • You can pretty much explore all of Rome in 2-3 days
  • You CANNOT just walk into any restaurant/gelateria and expect it to be exceptional - do research on the best places to eat beforehand and you'll have a much better cuisine experience!
  • Also, they don't like giving samples x)
  • Don't ever leave your backpack on the floor, even if it's near you! We almost got robbed. Here's the story!
  • Positano was my absolute favorite, although Rome and Tuscany had its own amazing features as well. When I go back, I'll spend the most time in Positano, more time in Florence, and the same amount of time in Rome


May 14 - Trevi Fountain (it was a travel day so we took it easy!)

May 15 - Colosseum, Palatine Hill (right next door), Sistine Chapel, St. Peter's Basilica, Castel Sant'Angelo

May 16 - Train and ferry to Positano!

Food Recommendations:



May 16 - Dinner at Ristorante Santa Croce (right next door to our Airbnb!)

May 17 - Eat at Da Adolfo and enjoy the free ferry ride back to downtown Positano

May 18 - Amalfi Coast day trip (highly recommend!!! 5/5)

May 19 - Explore downtown Positano and chill by the beach (there is a LOT to look at and experience!)

May 20 - Ferry and train to Florence, Tuscany!

CLICK HERE for my top food recommendations in Positano!



May 20 - Explore the magnificent Duomo

May 21 - Cooking Class and Lunch at a Tuscan Farmhouse with Local Market Tour from Florence (5/5 HIGHLY recommend!!! Seriously our best experience in Tuscany so far. We made delicious pasta from scratch!!)

May 22 - Explore the Uffizi GalleryPonte Vecchio and the surrounding areas

May 23 - Cinque Terre day trip from Florence (the cities themselves were incredible but you're mostly paying for the transportation and logistics)

May 24 - Train back to Rome!

Food Recommendations:


May 24 - Explore the Piazza della Repubblica and surrounding areas, including a lovely bookstore and an incredible underground market at Eataly (described by the NY Times as "an Italian Amusement Park for Foodies")

May 25 - Fly home!

Our dinner view of the Piazza della Repubblica

Our dinner view of the Piazza della Repubblica

Have you ever been to any of these places? Let me know in the comments below which place you would love to add to your bucket list! Also, feel free to ask any questions about my trip - I'll be happy to answer them for you!

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