Tuscany, Italy isn’t your typical destination! Tuscany is a feeling, a way of life, and a complete feast for the senses. The rolling vineyards of Tuscany are home to some of the best wineries in the world, beautiful farmhouses, medieval castles, and a very specific fresh scent that will forever remind you of your dreamy vacation.
Since Tuscany is a region that could take a lifetime to explore, it can feel overwhelming to plan a trip and to decide where to go. I started my handbag brand, Vogelle, while living in Italy and we source all of our leathers from Florence, so I am lucky enough to have spent a lot of time in this region. One of the most common travel requests I get is from people who need recommendations for Tuscany travel. So, let’s get into it, shall we?
Pour a glass of wine and get comfy. Here are the best towns to visit when visiting Tuscany!
Florence
Yes, this may be obvious, but Florence is the most popular town in Tuscany for good reason. If you’re traveling to Tuscany, start in Florence. It really is the main gateway to Tuscany. To get the most out of Florence, I’d recommend spending 2-3 full days exploring. Rick Steves coined Florence as the Cultural Capital of Europe, and I agree.
Where to Stay
Florence Hotel
Hotel Croce Di Malta
What to See
Duomo
Uffizi Gallery
Ponte Vecchio
Academia Gallery
PITTI PALACE & BOBOLI GARDENS
Piazzale Michaelangelo for sunseT
Siena
Siena and Florence were political and economic rivals during the Middle Ages, but Florence emerged as the dominant city in the 1500’s. Similar to Florence, Siena was a key center of the Renaissance, and you can see that when visiting this beautiful city. Only about an hour drive from Florence, Siena is a must when exploring Tuscany.
One of my favorite Airbnb stays ever was in Siena at the Airbnb linked below.
When driving from Florence to Siena, stop at Casa Emma winery. I was sent to this winery to capture content for my travel partner, IC Bellagio, and it remains one of my favorite wineries in Tuscany. Read the Casa Emma Winery full article here.
I’d spend 1-2 full days in Siena to see as much of the town as possible. Siena is also a great home base for those looking to explore some of the deeper areas of Tuscany.
San Gimignano
San Gimignano is one of the most breath taking and traditional hilltop towns in Tuscany. Easily reachable from Siena, travelers can reach it by car of via a tour bus. Visit the Podere la Marronaia winery in San Gimignano and enjoy a picture perfect view. I spent 2-3 hours visiting this winery and enjoyed wine, cheese, olive oil, and balsamic vinegar and it was one of the best days ever.
Montepulciano
Now, this is one of my favorites! Montepulciano is the southernmost town on this list known for its world-class wine and breathtaking views. This town really feels untouched and local, which I loved. After one of my visits with my handbag manufacturers in Milan a few years ago, I spent some time in Montepulciano photographing the bags and exploring the town. It remains one of my favorite places in Italy and I can’t wait to return.
The route to Montepulciano from both Siena and Arezzo is lined with some of the most stunning winery estates. I stayed for a few days in Montepulciano at the Airbnb linked below. I woke up every morning and walked to the coffee shop, explored the piazza, tasted all of the wine in town, and enjoyed the small family-run restaurants that lined the windy streets.
You could definitely do a day trip here and keep your home base in Siena, but to get the full experience, I’d recommend staying for a night or two in town. There’s something magical that happens in all of these Tuscan towns in the evenings when the tourists go back to their hotels in places like Siena and Florence. It creates space for visitors to experience what its like to be a local. Find a create outdoor table and soak up every moment of being under the Tuscan sun.
Honorable Mentions
There’s still so much of Tuscany left for me to discover and I’m already planning my next trip to this wonderful region. Below are a few Tuscan towns that are high on my list.
More Tuscan Towns
Cortona
Lucca
Arezzo
Volterra
Montalcino
Enjoy your next trip to Tuscany! If you’re looking for more hands-on planning, reach out to my partners at IC Bellagio. They’re a full service travel agency based in Lake Como, but they serve clients who are traveling to any destination in Italy. If you have any Tuscany recommendations that aren’t on this list, leave them in the comments below.
