Top Things to See and Do in Florence, Italy with a Stopover in Milan
EDITOR’S NOTE: THIS BLOG POST WAS ORIGINALLY PUBLISHED ON AUGUST 27, 2022 AND LAST UPDATED FOR ACCURACY ON JANUARY 8, 2025.
There’s nothing like going to sleep to views of New York City and waking up to the Italian Alps just a few hours later. Italy is a country that never stops calling me back. Over the years, I’ve strolled through Rome’s ancient streets, floated down Venice’s canals, marveled at Florence’s artistic masterpieces, soaked in the sun on the Amalfi Coast, and tasted my way through Naples. Yet Milan—a city celebrated for its fashion, culture, and contemporary charm—remained unexplored. So, when we decided to return to Florence and saw we could fly directly to Italy through Milan, choosing Milan as our starting point was an easy decision.
In this blog post, I’m sharing why a stop in Milan is a must if you’re planning on visiting Italy, along with my recommendations for the best way to spend five days in Florence.
one day in milan, Italy
24 HOURS iN MILAN WELL-SPENT
The first thing we did after stepping off our red-eye flight at Malpensa Airport (MXP), was pick up our rental car at Avis. We then drove about 50 minutes into the city of Milan. I booked an early arrival with our hotel in advance, the Sheraton Diana Majestic, Milan for only an additional 50 EUR which was well worth a bed at 10 a.m. After a restful couple of hours, we hit the streets to make the most of our one day (now technically half day?) in Milan. Luckily, the hotel is very well located and some of the biggest attractions were all within walking distance.
Here’s what we saw in 24 hours that I recommend:
Galleria Vittorio Emanuele II (shopping)
Duomo di Milano (to see)
Terrazza Aperol (the obligatory aperol spritz)
Mondadori Rizzoli Galleria (bookstore)
My only regret: not having booked more than one night. Milan is the perfect blend of old and new. A metropolis with as much history as it has fashion and design. Just walking the streets of Milan fills you with appreciation for it all.
FIVE DAYS IN FLORENCE, italy
The next day, we embarked on a three-and-a-half-hour drive south to Florence via Bologna. The goal of our trip to Florence was to try and have a more “local” experience since we had both been here before. So driving just felt right. Below is an overview of what we did in Florence over five days.
WHERE TO STAY IN FLORENCE, italy
We booked an apartment on the less touristy side of the Arno River - a gem I found on Airbnb called “Super Luxe Loft Apartment on the Arno with Terrace”. Owner, Dan, a traveler in his own right - has built this amazing home (Vagabond Home) that serves as a “warm landing space for other adventurous souls”. On our next visit to Florence, we’ll be booking his Airbnb Plus apartment, “Designer Apartment with Breathtaking Views”. Either way, you can’t go wrong with Dan, he’s an incredible host and you will fall in love with him as much as you will with his home.
THINGS TO SEE & DO IN AND AROUND FLORENCE, italy
Make it a point to at least catch one sunset over the Arno River.
Whether you’re standing on the Ponte Vecchio, strolling along the riverbanks, or finding a cozy spot at a riverside café, the view is unforgettable. It’s the perfect way to soak in Florence’s timeless charm and end your day on a serene note.
TAKE A SCENIC Drive through THE ROLLING HILLS OF Tuscany (stopping for wine tastings, of course).
A visit to Florence wouldn’t be complete without venturing into the rolling hills of Tuscany. Take time to explore the postcard-perfect countryside, where you can visit local wineries pouring the region’s world-renowned wines and stop in quaint villages.
ENJOY A MEAL AT CHARMING SANTAROSA BISTROT
Enjoy a wonderful meal at Santarosa Bistrot, tucked in Florence’s Oltrarno (“the other side of the Arno”) neighborhood. Known for its relaxed ambiance and picturesque garden seating, this charming eatery offers a menu inspired by Tuscan flavors with a modern twist.
TAKE A DAY TRIP TO MEDIEVAL SIENA AND STAY FOR DINNER AT MICHELIN-RATED GALLO NERO
Take a day trip to the enchanting medieval city of Siena, where narrow cobblestone streets and historic landmarks transport you back in time. After exploring the stunning Piazza del Campo and the iconic Siena Cathedral, unwind with a delicious dinner at Gallo Nero in the heart of Siena. Since I visited, Gallo Nero has earned a well-deserved Michelin star in 2024. It has also undergone a renovation, which I’m excited to capture on my next visit. Overall, a day trip to Siena is an unforgettable experience that blends history, flavor, and charm.
TAKE AN EVENING RIDE ON THE CAROUSEL AT PIAZZA DELLA REPUBBLICA
Take a charming evening ride on the historic carousel at Piazza della Repubblica, a classic Florentine experience. The whimsical, old-world charm of the carousel, with its colorful horses and playful music, offers a magical moment to cap off your day in the heart of the city. It’s a perfect way to soak in the atmosphere while enjoying a bit of nostalgic fun.
…AND IF YOU’RE LUCKY AND IT RAINS WHILE YOU’RE IN FLORENCE:
Start your day with a cappuccino at Antica Pasticceria Sieni, a local favorite for delicious pastries. Spend your morning or afternoon exploring the masterpieces at the Uffizi Gallery, immersing yourself in art and history. Afterward, stroll through the historic center, taking in the sights and sounds of Florence’s charming streets. For a little shopping, pop into Rinascente for high-end Italian fashion and accessories. And of course, don’t hesitate to stop for another pastry, no trip is complete without a second pastry—it’s Italy, after all!
ciao
Hope you enjoyed my Milan and Florence recommendations. Below is a quick video recap of my trip.
Feel free to reach out if you’re planning to visit Italy. It’ll always remain at the top of my list.