So you’re daydreaming about exploring the best small towns in Tuscany? You’ve landed in the right place.
After exploring Tuscany by car a couple of times, we know the most beautiful small towns and the best villages worth visiting, how to get there, what you need to know, and when to visit.
So, are you ready to learn more about the beautiful villages and best towns in Tuscany?
Here are the most stunning towns to visit while being in Italy:
Our Top 3 Favorite Towns In Tuscany
1. Volterra
2. San Gimignano
3. Montepulciano
Best Smalls Towns In Tuscany Worth Visiting
Tuscany is one of the most beautiful regions in Italy.
The area is filled with amazing art and architecture, especially in Tuscany’s capital, Florence, and in Siena.
But exploring the smaller towns close to the most visited cities near Florence is also a great idea.
The true beauty of Tuscany reveals itself when you get off the beaten track.
⭐ Travel Tip: Keep an eye out for local festivals or markets. Mingling with the locals takes your Italian experience to a whole new level.
Volterra
Volterra is a stunning medieval town. The hilltop town is one of our personal favorites.
There’s something captivating about Volterra.
Its ancient walls add to the charm, making you feel like you’re stepping back in time.
We made our stay even more special by staying at a nearby agriturismo.
Imagine waking up to the sound of chirping birds and the scent of fresh Tuscan air.
It was the ideal countryside retreat.
The best way to see the cities in Tuscany is by car. We created a guide on driving in Italy for tourists, so that you feel comfortable visiting the Tuscan countryside.
BOOK YOUR STAY AT THIS AGRITURISMO PODERE CAMPAINI
The Etruscan Museum in Volterra is a must-see.
It showcases various artifacts from the Roman past.
The Roman Theatre in Volterra is surprisingly well-preserved and also worth visiting.
If you’re in the mood for shopping, local workshops sell hand-carved alabaster pieces.
They are a Volterra specialty, so don’t miss out on these Italian souvenirs.
In Volterra, you get the best of many worlds including history, scenic beauty, and local culture.
The best part is Volterra is not as crowded like San Gimignano or bigger cities like Siena and Florence.
It’s no wonder it’s high on our list of Tuscany’s must-visit small towns.
San Gimignano
San Gimignano is called the medieval Manhattan for a good reason.
The hilltop town has many towers and from afar it looks like a tiny version of Manhattan’s skyline.
You can climb up Torre del Podesá (Torre Grossa) for a view that stretches across the Tuscan hills.
It’s a must-see and currently the only tower you can get up to.
San Gimignano also has some amazing, historical art.
Check out the frescoes in the La Collegiata (Collegiate Church). They tell stories from the Bible in colorful detail.
Of course, a trip to San Gimignano isn’t complete without tasting local gelato at Gelateria Dondoli.
They claim to have the world’s best, and they might be right.
Want to know about a hidden gem in San Gimignano?
You can visit the quieter Fonti Medievali.
It’s an ancient well that’s not only scenic but also steeped in history.
You find it at Via dell Fonte, just outside of the historical center.
For great photos without the crowds, the best time is early morning or late afternoon.
The soft light makes the town look even more magical.
One of our favorite memories was sipping a cup of coffee at one of the cafés at the main piazza.
While sitting there we witnessed an Italian wedding right then and there.
It felt like being in a romantic Italian movie.
So when you’re in San Gimignano, take some time to enjoy some time at the piazza.
Montepulciano
Next up is Montepulciano, a town that’s worth a visit.
It is a dream for wine lovers, and if you fancy a great view of the rolling hills of Tuscany.
Montepulciano and the area are famous for its Vino Nobile.
A red wine, rich and full-bodied. The best way to enjoy it is by sitting outside with family at a local bar, like I did.
For sightseeing, don’t miss the Palazzo Comunale.
It’s an impressive building that shows off the town’s architectural flair.
Also, walk to the western part of the city. From the city wall, you have an impressive view of the Tuscany region.
Another must-see is the Tempio di San Biagio.
This church is outside of the historical center. It stands alone in a scenic field.
Are you looking for the best wine tasting?
There are plenty of cellars to explore inside the old town of Montepulciano, as well as outside of the city walls.
In Montepulciano, you can sip wine, marvel at the architecture, and enjoy family moments.
It’s a place that offers a perfect blend of culture and relaxation.
Cortona
Cortona is another must-see town, especially if you’ve read or seen the movie “Under the Tuscan Sun.”
Walking its streets, it’s easy to see why it captured so many hearts.
The Museo Diocesano features religious art.
The MAEC is perfect for you if you’re interested in Etruscan artifacts.
For us, the hidden gem of Cortona is the view from the Belvedere at Piazza Garibaldi.
Castellina in Chianti
BOOK YOUR STAY AT THE BORGO PIETRAFITTA RELAIS
Castellina in Chianti is a hilltop town in the Chianti wine region.
It is a beautiful small town to relax while enjoying wine or the serene woodlands.
Castellina in Chianti was once an important Florentine outpost.
It feels like stepping back into the 15th century when you stroll through Castellina.
You can visit La Rocca, which is now the town hall.
It has an archaeological museum. You can also explore the many wine shops nearby.
We stayed in Castellina in Chianti to relax and to enjoy the Tuscan landscape.
Tips for Visiting The Towns In Tuscany
Starting your Tuscan trip in Florence like most travelers? Great choice!
Once you’re ready to explore Tuscany from the Tuscan capital, here are some tips to keep in mind:
Distances from Florence: Most of the towns are just a one to two-hour drive from Florence.
For instance, San Gimignano is about 35 miles (57 km), Montepulciano is around 68 miles (110 km), and Volterra is roughly 39 miles (63 km) away.
How to Get Around: While public transport can get you to some places, renting a car is the best way to experience the Tuscany region.
This allows you to explore villages at your own pace and you can enjoy driving along the winding roads up the hills.
Guided Tours from Florence: If you prefer to travel as convenient as possible, there are plenty of day trips from Florence to Tuscany.
They’re great for seeing highlights in one day and usually include insider experiences.
Where to Stay: You have plenty of great options.
Boutique hotels in the town centers offer comfort and convenience.
For a special experience, consider staying at a countryside agriturismo. This was our favorite choice. Imagine waking up amidst vineyards and olive groves.
You can also stay in Florence. There are many great options.
Read more about it in our Florence in 3 days, Florence in 2 days, and 1 day in Florence itinerary.
Best Time To Visit The Tuscan Towns
The best time to explore the Tuscan villages depends on what you’re looking for.
For mild weather and fewer crowds, consider visiting in spring (April to June) or fall (September to October).
Summer is peak season, so be prepared for high temperatures and more tourists.
And in case you’re experiencing Florence in the rain, visiting one of the towns in Tuscany is always a great option.
Final Thoughts About The Beautiful Towns In Tuscany
Sure, Florence and Siena are amazing and a must on every Tuscany bucket list.
But the small towns in Tuscany offer something more.
Our faves? Volterra, Montepulciano, and San Gimignano. These medieval towns have a truly unique flair.
Tuscany is packed with hidden gems and is one of the most beautiful regions in Italy.
On your trip to Tuscany, you surely will find your own favorite Tuscan town.
No matter if you join a guided tour or go on a road trip.
Make sure to enjoy the scenic overlooks, and browse local markets.
Sip coffee in a quiet café and wander through the streets.
You will fall in love with the villages while you visit Tuscany.
FAQs About The Best Small Towns In Tuscany
What are the best small towns in Tuscany?
The best small towns in Tuscany are Volterra, Montepulciano, and San Gimignano. Each offers unique things to do in a gorgeous medieval setting.
How do I get to the small towns in Tuscany?
To get to the small towns in Tuscany, you can take regional trains and buses, rent a car, or join a guided tour, usually starting from Florence or Siena.
When is the best time to visit the small towns in Tuscany?
The best time to visit the small towns in Tuscany is in late spring or early autumn to avoid the crowds and for milder weather.
Are guided tours to the towns in Tuscany worth it?
Yes, guided tours to the towns in Tuscany are worth it. They include transportation to rural areas, guides, and insider tips you might not get otherwise.
What should I look for when choosing which small towns in Tuscany to visit?
When choosing which small towns in Tuscany to visit, consider historical landmarks, scenic views, and local wine and food options.
