Best Small Towns in Tuscany… Under The Sun

Who doesn’t love Tuscany, amiright? But Global Debauchery isn’t here to tell you everything you already know about a place. No, it exists to help you travel deeper. And how do we do that? By telling you about all the best small towns in Tuscany you didn’t even know existed. Lesson of the day: Never count the little guys out. Because sometimes they can pack a real punch!

Get Your Beach On In Bolgheri

Tuscany’s Etruscan Coast boasts the beautiful rolling hills, vineyards, olive groves, and charming villages that you probably associate with Tuscany. But the sunny, sandy beaches and ocean vistas make it even more spectacular. 

Though vacationers flock to the beach towns for the summer sun and bicycle tours cycle through regularly, the Bolgheri area is still a hidden gem of Tuscany, relatively undiscovered and uncrowded. 

Accessible by train or car within a couple of hours of Florence, Pisa, or Rome, Bolgheri is at the heart of this region’s “Oil and Wine Road” (La Strada del Vino). Home to world-class wineries like Sassicaia, this road leading out of town is lined with cypress trees and has been declared a national monument.

It’s one of the best areas to dive deeper into Italy’s top-quality ingredients and food heritage. Wine and olive oil tastings, food excursions, and admiring the scenery are must-do’s here. You can easily self-drive, bicycle, or schedule a day tour to make the most of your trip.

Whether you prefer easy bike rides to the beach, hopping from town to town, walking to the village gelato shop, or tasting wines and olive oils, there’s something for everyone around this beautiful Italian village of Bolgheri, one of the best small towns in Tuscany.

bolgheri - one of the best small towns in tuscany

Contribution by: Michelle C. from Intentional Travelers


Bask Under The Tuscan Sun In Cortona

The beautiful Tuscan town of Cortona was made famous with the release of Under the Tuscan Sun, first the book by Francis Mayes and then the movie. This hilltop town sits in the eastern part of Tuscany, about an hour’s drive from Florence.

Start your tour of this charming town in the main square, Piazza della Repubblica, and admire its 13th-century buildings. A well-preserved town hall, clock tower, and former palace are some of the significant landmarks you will find. A top thing to do in Cortona is to visit on market day, Saturday, and watch the town come alive. 

Simply get lost in Cortona’s endless narrow alleyways, or “vicoli,” as Italians call them. The ancient streets in Cortona are steep, and almost all of them lead you to find incredible views of the Tuscan countryside. 

While strolling, you are bound to discover the town’s many churches from the 11th and 15th centuries. Situated on the outskirts of Cortona lies Santa Maria delle Grazie al Calcinaio, built in 1513, one of the most architecturally important Renaissance churches in all of Tuscany.

Don’t miss visiting this elegant Tuscan town.

cortona - one of the best small towns in tuscany

Contribution by: Renee from Dream Plan Experience


Wanderlust In Lari, One of The Best Small Towns In Tuscany

Lari is a little Italian town close to Pisa. And, if you want to explore Tuscany off the beaten path, it should definitely be on top of your list.

This cute medieval town developed around a hilltop castle and can easily be visited on a day trip from Florence.

Lari Castle, also called Castello dei Vicari, has been around for a thousand years. It’s worth climbing the few stairs all the way up for the gorgeous views alone. But the castle can also be visited if you wish.

If you want to see how artisan Italian pasta is made, pop inside Martelli Pasta Factory at the foot of the hill. They are a small family-run business and will do a quick free tour of the small factory for anyone who walks in.

Hungry after seeing all that yummy pasta? Stop by one of the restaurants or walk into a charcuterie for some delicious and locally prepared sausages and cheeses—you won’t regret it.

Lari is so small that it doesn’t even have a hotel and certainly doesn’t have a train station. You’ll either need to drive or take the train to the nearest town and then a bus to get there.

lari - one of the best small towns in tuscany

Contribution by: Laura from Travelers Universe


Get Medieval In Montepulciano

Medieval Montepulciano is what Tuscan dreams are made of. Situated atop a hill amongst the rolling landscapes of Tuscany, this town is the perfect place to escape it all. Oenophiles flock to this idyllic town to savor the delicious fruits of the region at the many wonderful wineries in Montepulciano. In fact, the area is world-renowned for its Nobile di Montepulciano, the infamous medium-bodied red wine with fruity aromas.

In addition to its enviable wine scene, Montepulciano promises a rich experience for history buffs in its medieval old town. Start your exploration at Piazza Grande, the famous historic square of Twilight fame. From here, make your way down the charming alleyways and admire the medieval architecture of this fortified city.

For additional context, pay a visit to Museo Cívico. This 14th-century building houses everything from archaeological finds to an art gallery. After a fun visit, you may wish to pick up a trinket along Il Corso—the main street in town—to commemorate the fun journey.

To reach Montepulciano, the nearest airport is Perugia Airport. In addition, Florence and Pisa provide suitable alternatives. Given its countryside location in Southern Tuscany, a rental car is highly recommended for getting around Montepulciano.

montepulciano - one of the best small towns in tuscany

Contribution by: Elena Pappalardo from The Carry-On Chronicles


Visit Perfectly Renaissance Pienza

One of the most beautiful towns in Tuscany is definitely Pienza. For connoisseurs, this charming medieval town is a highlight of any Tuscany trip. The old town is known as the “perfect Renaissance town “and enchants with unique charm and lots of flair. On top of the town, you can enjoy a magnificent view of the endless hilly fields of the Val’Orcia, and the picturesque cypress avenues are truly breathtaking.

Pienza has been on the UNESCO World Heritage Sites list since 1996, making it a real jewel of Tuscany. Walking through the center, you will discover dreamy squares and historically important buildings, and you can visit interesting museums. 

Really worth seeing are the imposing town hall and the beautiful Palazzo Piccolomini, both of which have been opened to the public as museums. The landmark and most important attraction is the impressive Cathedral of Santa Maria Assunta, located in the center.

The small town of Pienza is located about 120 km from Florence, where there is an international airport. You can book a day trip to Pienza from there, but it is also worth staying longer and exploring the surrounding countryside. Consider staying at the Agriturismo Marinello with a beautiful pool and a breathtaking view of the city!

pienza - one of the best small towns in tuscany

Contribution by: Martina from Places of Juma


Savor San Gimignano, One Of The Best Small Towns In Tuscany

San Gimignano is a beautiful medieval, honeymooning-type town in Tuscany, Italy. The town is known for its many towers, which were built by wealthy families who lived there during the Middle Ages. Today, San Gimignano is a popular tourist destination and really one of the gems of Tuscany.

The town sits on top of a hill. In earlier times, this provided protection, but today this provides amazing views of the surrounding landscapes. Navigating through the winding streets lined with stone buildings will bring you to the main lookout point, where you can see for miles.

One of the best things to do in San Gimignano is to enjoy the food and wine. There are excellent restaurants and cafes to pop into. Plus, many wineries offer tastings, as well. The town is also home to several gelaterias, which serve up some of the best in Italy.

San Gimignano is located about halfway between Florence and Siena. It is about an hour away from Florence and can be reached by car, bus, or on a group tour.

Once you have seen the town, make your way outside the walls for a local winery tour or, even better, a horseback ride through vineyards and olive trees.

san gimignano, italy

Contribution by: Dan Bagby from Honeymoon Always


Have A Spa Day In Saturnia

Tucked away in northern Tuscany is the stunning spa town of Saturnia. One of Italy’s hidden gems, Saturnia is world-famous for its scenic thermal baths and hot water springs.

Along the hillside is where you can find these epic hot springs. The cascading water spills into individual bright blue pools. The hot springs sit at a comfortable 37 degrees Celsius, the perfect temperature for a relaxing soak in the thermal baths.

A tip before your visit is to pack water shoes. There are small and slippery rocks on the ground of the hot springs. Water shoes will help keep your balance and provide a more comfortable experience. Also, the parking lot is a short walk from the hot springs. Do not park along the road, or you will get a ticket.

If you plan to stay the night in Saturnia, Terme di Saturnia Natural Spa & Golf Resort offers luxurious and epic accommodations. The five-star resort features a spa, golf course, restaurant, and numerous hot spring pools for a tranquil and revitalizing stay.

Saturnia is a unique and off-the-beaten-path destination. It is an absolute must-visit in Tuscany, Italy!

saturnia, italy

Contribution by: Alisha from Travel Today Work Tomorrow


Best Small Towns In Tuscany Got You Daydreaming?

Then start planning your next trip to Italy today. Take a Northern Italy road trip with these helpful driving tips (safety first!). And stop by some of these obscure but beautiful cities in Italy you’ve never heard of. With so much insider intel, you’ll have no shortage of things to do and see on your trip to Italy.