One of the best things to do in Tuscany, besides drinking incredible wine and soaking in the lush countryside, is wandering through its medieval towns.

These towns are completely unique. They’re filled with charm, history, and views that feel almost unreal. It’s hard to find places like this anywhere else in the world. I highly recommend visiting at least a few during your time in Tuscany.

Here were some of our favorites:

Montepulciano

This one is at the very top of my list.

Montepulciano is a charming hilltop town with panoramic views over the Val d'Orcia. It’s not overly large, which makes it easy to explore, and it’s home to some of the best wine in the region.

Fun fact: it was featured in Twilight, so if you’re a fan, this is a must-visit.

For wine tasting, I highly recommend Cantina De’ Ricci. What makes this experience unique is that the wine cellar is completely underground. Walking through the historic tunnels and hearing the stories behind the cellar made it feel different from other tastings we did. The wine was excellent, and the setting was unforgettable.

After your tasting, spend time roaming the streets, popping into small shops, grabbing gelato, and relaxing in the main square. Montepulciano is the definition of a classic Tuscan medieval town.

Pienza

Another gem in Val d’Orcia, Pienza is known as the “ideal Renaissance city” and is part of a UNESCO World Heritage Site.

I was honestly hesitant about making the trip here, but it ended up being one of my favorites.

Pienza has some of the most breathtaking views of the Tuscan countryside. The streets are incredibly charming, and the overlook points feel straight out of a postcard.

You also have to try the pecorino cheese here, Pienza is famous for it. (Yes, this is the cheese commonly used in carbonara.)

While you’re there:

Walk through the historic center
Visit Palazzo Piccolomini
Have lunch at La Terrazza del Chiostro, which overlooks Val d’Orcia

You’ll park outside the town walls and walk up, but it’s very straightforward, just follow the signs.

Montalcino

Montalcino is a small medieval hilltop town overlooking Val d’Orcia and is world-famous for Brunello wine.

We visited Il Palazzone for a wine tasting, and it was such a special experience. We ended up being the only ones there, so it felt like a private tasting. We saw the vineyards, learned about their aging process, saw the barrels, and then sat down for a guided tasting.

The Brunello was incredible, one of my favorites from the trip.

Afterward, we headed into town for lunch. Montalcino is smaller and quieter, but absolutely worth visiting, especially if you’re planning a Brunello tasting.

Monteriggioni

This is the perfect quick stop if you’re driving between Siena and Florence.

Monteriggioni is a tiny fortified village built in the 13th century by Siena as a defensive outpost against Florence. The medieval walls are still fully intact, and you can actually walk along part of them.

The town itself is very small, there isn’t a ton to do beyond exploring the walls and enjoying a glass of wine in the main square, but the history and preservation make it worth the stop.

It’s located in the Chianti region, so the views shift slightly from Val d’Orcia’s rolling hills to more vineyard-covered landscapes. I had a lovely glass of Chianti in the square, and it was the perfect mid-drive break.

San Gimignano

We visited San Gimignano as a day trip while staying in Florence.

This town is known for its 14 surviving medieval tower houses that rise above the skyline. It feels slightly larger and more bustling than Montalcino or Monteriggioni.

You can:

Wander through shops
Grab lunch in a trattoria
Try award-winning gelato
Climb a tower for panoramic views

Like all the towns, the best part is honestly just getting lost in the narrow streets and people-watching in the squares.

Tips for Making Wine Tasting Reservations

There are endless wineries in Tuscany, which can feel overwhelming.

When choosing ours, I wanted a mix:

One with a beautiful vineyard setting
One with a unique, historic experience

That’s why we chose Il Palazzone and De’ Ricci, completely different vibes, both amazing.

Here’s what I recommend:

If you have specific wineries in mind, book 2–4 weeks in advance (especially in peak season).
If you’re flexible, ask your host for recommendations. They often have relationships with local wineries and can call on your behalf.
Most wineries require reservations, walk-ins aren’t always possible.

We didn’t have trouble booking, but Tuscany gets busy. If a particular winery is high on your list, don’t wait.

My Top 3 Medieval Towns

If I had to narrow it down to three:

Montepulciano: The perfect, classic, charming medieval town.
Pienza: The absolute best views of Val d’Orcia.
Monteriggioni: For history, uniqueness, and Chianti scenery.

You truly can’t go wrong visiting any medieval town in Tuscany. But these three offer the perfect mix of charm, views, history, and wine, everything you imagine when you picture Tuscany.

Must Visit Medieval Towns in Tuscany (+ Wine Tasting Tips)