Curator’s statement
A trip to Italy often gets associated with wine. Endless bottles, rolling Tuscan hills, full of…wine. Before my alcohol-free trip, someone asked me, “You’re going to Italy and you’re not going to drink any wine?” I’m here to remind you there’s more to Italy than wine—and you should absolutely keep Italy on your travel list even when you won’t be partaking in the vino while the rest of your group is. Italy is the perfect trip for anyone looking to immerse themselves in history, indulge in local cuisine, and maybe enjoy a beach day or two. The reliable train system makes it accessible and easy to explore without a car and trips back to the airport.
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Days 1–3: Florence
From the top of Giotto's Bell Tower
Start your trip with a climb up the 414 steps up Giotto’s Bell Tower, where you’ll get amazing panoramic views of the city. There are helpful viewing landings throughout your climb for breaks or checking your progress. 414 steps will fly by! Purchase a Brunelleschi Pass for access to the other monuments like the Dome and the museum.
Shop the Ponte Vecchio and the local leather markets and vintage shops. One of my favorite activities in any city is window shopping and spending time exploring without a schedule and instead feeling the vibe of the city.
Appreciate some of the famous art, like Michelangelo’s David at the Accademia Gallery of Florence or the Uffizi Gallery.
For a break from the hustle and bustle and museum reading, take a walk across the river to wander the Boboli Gardens and Piazzale Michaelangelo. Keep in mind, these are entirely outside, so plan accordingly with the weather and wear comfortable shoes.
Days 4–6: Rome
The Roman Forum at sunrise
Take a sunrise bike tour of the monuments to see the city before the crowds. Fun fact: This was one of my favorite activities from our entire two weeks in Italy. The vibes were amazing at daybreak and the city was peaceful before everyone else was awake.
Venture to Vatican City and get tickets to St. Peter’s Basilica or the Vatican Museum to see the Sistine Chapel.
Explore the Roman Forum or enjoy one of the unique tour experiences at the Coliseum to immerse yourself in Roman history. Choose a guided tour to maximize your experience.
Animal lovers can make a pit stop at the Torre Argentina Cat Sanctuary, which is home to about 150 cats and is the assassination site of Julius Cesar in 44 BC. Yes, you just read that sentence!
The amazing thing about Rome is that there is history nearly everywhere you look! Don’t forget to check out the other amazing sites, including the Pantheon, the Spanish Steps, and the Trevi Fountain.
Days 7–11:
Positano from the sea
Make a reservation for a beach club like Arienzo. Beach clubs aren’t as wild as they sound. Arienzo had some vibey music, chair service, and a swimmable beach—and it came with lunch. They have fresh juices to choose from if you’re not indulging in alcohol.
Splurge on a boat day down the coast to Amalfi or to Capri. There is a lot of room to personalize this activity to meet your budget. Stop for lunch at your destination. This was probably our favorite day of the whole trip. It was amazing to be on the water, have a new perspective on the city, and anchor to swim whenever we wanted.
Wander through the winding streets lined with shops and get sandals made at Nana. You can pick the heel height and the strap color and design.
Enjoy a delicious, family style, energetic, farm-to-table dinner at La Tagliatta.
Days 12–13: Naples
Mt. Vesuvius from Naples
Visit one of the city’s castles, like Castel Nuovo or Castel Sant’Elmo.
Eat a margherita pizza in its literal hometown.
Take a day trip to Mt. Vesuvius and Pompeii. We opted for a guided tour and we were driven most of the way up Mt. Vesuvius. You can look into the volcano itself and earn yourself amazing views. On a clear day, you can see Capri.
Pompeii is a history buff’s dream and will appease even those less interested in other museums. The preservation of the city was a surprise to me, and I loved wandering the ancient ruins and learning about civilization before tragedy struck. This was a must-see.
Need to know
Taking the train between cities is an affordable and easy way to get around Italy. Starting and ending in different cities could save you time if you don’t have to get back to your starting airport.
Let your advisor book you a private transfer from Naples to Positano. Think air conditioning instead of having to carry your suitcase to the ferry and then up the stairs from the sea in Positano.
Try to avoid the peak of summer. Italy gets hot, especially inland, and the crowds can be intense. Trust me, the Sistine Chapel is much better enjoyed when you are not shoulder-to-shoulder during your viewing.
Air conditioning isn’t everywhere, so even if you’re inside, you might not be avoiding all of the heat in the middle of the day. Pack accordingly—think linens and sundresses.
If you can’t avoid the summer, plan accordingly and try to schedule your prime sites early. I can help you find your perfect times and tours.
There are over 60 Michelin-starred restaurants to choose from throughout this Italian tour!
Travel Advisor
Katie Boucher
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For more inspiration and insider recommendations, visit our Italy page.