7 Charming Towns in Tuscany You Shouldn't Miss (Beyond Florence)

Jul 3
6 min read

If it's your first time visiting Tuscany, it's easy to assume Florence is the complete experience.

While Florence is still one of my favorite cities in Italy, it wasn't until I ventured into the Tuscan countryside that I realized how much I was missing.

Rolling vineyards. Medieval hill towns. Long lunches in sunny piazzas. Quiet roads lined with cypress trees. It's a completely different side of Tuscany—and the one I find myself returning to again and again.

After more than 15 years of traveling through Tuscany, these are the towns I find myself returning to again and again—and the ones I recommend most often to friends and travelers joining me in Italy.

My tip: Don't try to visit all of Tuscany. Slow travel is part of the magic. Allow yourself to step into the day-to day life of Italians. Morning cappuccinos. People-watching. Long lunches with wine and pasta. Exploring without a schedule. Watching the sun set over the hills.

Pienza - Most Beautiful Hilltop Town

Why I love it - it's the most idyllic and beautiful hilltop town. It was designed by one of the popes to be the example of a perfect Italian town -- and it really is!
Don't miss - Pecorino cheese. This is cheese made from sheep's milk. It sounds strange--but just trust me. I honestly come back to Pienza just to buy fresh Pecorino cheese.

My story - On my first visit to Pienza, I stopped at Ristorante la Terrazza della Val d'Orcia to have a glass of red wine with Pecorino cheese and sliced meat. From the walls of the city, the countryside stretches out in front of you. We had just planned to stay for a short visit, and ended up staying for 3-4 hours, just soaking in the views. It's a slice of heaven.
Montepulciano - Wine & Renaissance Charm

Why I love it - Vino Nobile di Montepulciano is my favorite red wine. It's robust and yet incredibly smooth. Also great quality and value compared to the iconic Brunello di Montalcino.
Don't miss - Piazza Grande is the main square in Montepulciano. I recommend climbing the tower to see the medieval city from above. The views are spectacular. Tip: Montepulciano has streets with a steep incline, I'd recommend starting at the top, and then walking downhill.
My story - I took my clients to Cantina Contucci, right off of Piazza Grande. Adamo is 82 years old and has been working with wine for over 60 years and is part of the board that rates Italian wines from the region. We got to chatting. You can see how passionate he is about wine and the whole process.
Montalcino – For Wine Lovers

Why I love it - it's quiet, fairly flat, and relaxing. Time slows down and suddenly you're living la dolce vita
Don't miss - Wine tasting. If you're only planning one winery visit during your Tuscany trip, I'd make it here. Everyone talks about Brunello di Montalcino, but make sure to try Rosso di Montalcino. Made from the same grapes, but a younger wine. I love robust reds, and this one is really good. Go for Brunello for a very special occasion. I like lunch in the old town (across from the fortress) at Drogheria e Locanda Franci.
I recommend going wine tasting just outside of the medieval town, for the full experience. I love seeing the vineyards with grapes growing and the fermentation process before tasting the wine. It really helps me appreciate the wine so much more. Two wineries that I love are: Ciacci Piccolomini d’Aragona and Paradiso di Cacuci.
Bagno Vignoni - Tuscany's Most Unique Village

Why I love it - Unlike every other town on this list, Bagno Vignoni doesn't have a traditional piazza. Instead, its main square is filled with a centuries-old thermal pool, giving the entire village a peaceful, almost magical feeling.
Don't miss - The relaxing thermal baths and my favorite hotel Relais Osteria dell'Orcia.
I found Relais Osteria dell'Orcia in 2019, and have been going back ever since. I love having lunch in the garden, relaxing at the pool, and going to say hi to their pet donkey. It's my little piece of paradise. My clients are always asking to go back to the restaurant at the hotel (La Vecchia Posta) because the food is so delicious. I think it's because they use produce grown in their garden. This boutique hotel is just a 10-min walk on a quiet trail from Bagno Vignoni.
Greve in Chianti - the heart of Chianti wine country
Why I love it - The drive is just as memorable as the destination.
Don't miss - Azienda Agricola Montefioralle Winery is a small family-run winery with gorgeous views in the Medieval village of Montefioralle close to Greve in Chianti.
One of my favorite parts isn't even arriving in Greve—it's the drive there. Winding roads lined with vineyards, cypress trees, and little stone farmhouses make this one of those places where you'll probably want to pull over more than once just to take in the view. One of my favorite memories is stopping by the side of the road with my sister for a picnic of fresh mozzarella, crusty bread, pesto, and a bottle of red wine.
San Gimignano - Worth the Crowds
Why I love it - it can be touristy, but I love the towers and the medieval vibes
Don't miss - my favorite white wine in all of Italy: Vernaccia di San Gimignano - crisp, refreshing, and one of my favorite white wines in all of Italy.
I came here for the first time when I was living in Florence as a university student and loved the feeling of stepping back into a medieval town. And it was here that I discovered that Tuscany isn't just for red wine. Wherever I travel in Italy, I always ask if they have Vernaccia di San Gimignano!
Siena - Must-see day trip
Why I love it – Siena is smaller and, to me, even more charming than Florence. It feels exactly how you imagine Tuscany: narrow cobblestone streets, a breathtaking cathedral, and a cozy medieval atmosphere that invites you to slow down.
Don't miss – Piazza del Campo in the evening, Siena Cathedral, and Hotel Palazzo Ravizza.
My story – I love ending the day in Piazza del Campo with a glass of wine or a coffee at one of the cafés lining the square. As the sun starts to set, people gather in the middle of the piazza to catch up with friends, children run around playing, and there's an energy that's both lively and incredibly relaxed.
If you only have time for a day trip, I'd encourage you to spend the night if you can. Siena changes completely after the day-trippers leave. The streets become quieter, the piazzas fill with locals instead of tour groups, and the whole city feels more intimate.
One of my favorite discoveries here is Hotel Palazzo Ravizza. The hotel has a fascinating history—it was run by two sisters during World War II and was later occupied by Nazi troops. Today, it's peaceful and elegant, with a beautiful garden overlooking the Tuscan countryside and a grand piano that makes it feel like stepping back in time.

My Biggest Tip for Visting Tuscany

If I could give you one piece of advice, it would be : Don't race from town to town trying to see everything. Have a slow morning drinking a cappuccino and just people watch. Wander down side streets. Stop for a drink at sunset and just soak it in. The magic of Tuscany isn't found in how many towns you visit—it's found in the moments you slow down enough to notice.

Planning a Tuscany trip?

These are the towns I return to year after year, and many of them are included in our Florence & Southern Tuscany journeys.

If you're looking for a boutique, small-group experience that goes beyond the typical tourist itinerary, I'd love to show you my favorite corners of Tuscany in person.