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What is the prettiest town in Tuscany? There are so many choices, with a ton of beautiful towns and countryside in Tuscany. But which one is the prettiest? The answer, like many things in life, will likely depend on your personal preference.
Some people might say that Siena is the most beautiful town in Tuscany. Others might say Lucca is stunning. And honestly, they’re all really beautiful, so it can be hard to choose just one as the best town. Though, it can be important to narrow down your options, especially if you can only visit one during your trip to Italy.
Don’t panic though, this article will help you come to a decision. Together let’s go through the choices and by the end of this post you’ll be able to come to your own conclusion to what is the prettiest town in Tuscany.
Quick Info on Tuscany
Currency: Euro
Language: Italian
Daily budget: 120 Euros for a midrange budget. A budget traveler could definitely do it for less by cutting food and drink costs and going for the cheapest possible accommodation. If you’re in Tuscany to experience the food and wine though, the above is a good estimate for a midrange budget.
How to get around: Getting between towns in Tuscany can be a little trickier than getting to and from bigger cities in Italy. The best way to get around Tuscany is definitely by car as it gives you a lot of freedom. However if you don’t have your own wheels, buses are you’re best choice for getting between the towns with public transport. Otherwise there are some regional trains between some of the Tuscan villages, but many smaller cities don’t have a train service.
Electronics: The Italian electrical outlets provided will be 3 vertical holes in a vertical column. If you are using sockets that are different from those at home, you may need to use a plug adapter. Plug adapters that are not equipped with a middle prong will be the best choice when you go to a two-prong plug. Apart from that, just be aware that your electronics need to be 110V compatible, otherwise you’ll also need a power transformer.
Is Tuscany safe?: Yes, violent crimes are not common in Tuscany and the area is safe for tourists.
Best Time to Visit Tuscany
The best time to visit Tuscany is Spring, followed by Autumn, and then Summer. All three are beautiful but the shoulder seasons will be less crowded.
About Tuscany
Tuscany is a region located in central Italy. The area is known for its beautiful landscapes, art and history. Tuscany is also home to some of the world’s best wines. The region has a Mediterranean climate, with warm summers and cool winters.
Tuscany is a popular tourist destination, with visitors from all over the world coming to experience its unique culture and scenery. From Florence to Siena to Pisa, there are many interesting places to explore in Tuscany. And of course, no trip to the region would be complete without tasting some of its delicious wines!
The Contenders for the Prettiest Town in Tuscany
Volterra (Golden Mountaintop Town)
Volterra is one of the most beautiful mountain top towns in Tuscany. It is known for its stunning views, its quaint cobbled streets and its medieval architecture. The town has a long history dating back to the Etruscan era, and there are many interesting things to see and do here.
If you’re looking for a truly unique and memorable experience, be sure to add Volterra to your list of must-visit destinations in Italy!
Accommodation picks: Camere la torre (budget), Agriturismo Villa Felice or Agrihotel il Palagetto (midrange), Il Sogno di Annalisa Suite or Hotel San Lino (lux)
Montalcino (Epic Views & Amazing Wine)
Nestled in the heart of Tuscany, Montalcino is a quaint town with stunning views. The rolling hills and winding roads are dotted with olive trees and vineyards, making it the perfect place to enjoy some delicious wine. There are plenty of wineries to choose from, as well as charming cafes and restaurants.
If you’re looking for a relaxing getaway, Montalcino is the perfect destination.
Accommodation picks: Anna Camere (budget), B&B del Musico (midrange), Hotel Dei Capitani or Drogheria e Locanda Franci (lux), Castello Di Velona (absolute splurge)
Pitigliano (Cliffside Town)
Pitigliano is a cliffside town in Tuscany, Italy. The town is situated on a plateau of tufa rock, overlooking the Lago di Mezzano. The town’s history dates back to the Etruscan period, when it was known as Piticulum.
Pitigliano is home to numerous historical and architectural landmarks, including the Palazzo Orsini, the Cathedral of Santa Maria Assunta, and the Church of San Rocco. The town’s picturesque setting and rich history make it a popular tourist destination.
Accommodation picks: Residenza Gregorio VII (budget), Da Titta or Cerchio Verde (midrange), La Casa Degli Archi or Agriturismo Poggio Delle Conche (lux)
Barga & The Garfagnana (Colorful Hilltop Town)
Barga is a colorful town located in Tuscany, Italy. The town is known for its picturesque streets and beautiful architecture. Barga is a popular tourist destination for those who want to experience the true beauty of Italy. The town is home to many historical and cultural attractions, making it a must-visit for any traveler.
Accommodation picks: Villa Gheradi (budget), Villa Moorings (midrange), Agriturismo Chioi or Renaissance Tuscany Il Ciocco Resort & Spa (lux)
Bagno Vignoni (Hotsprings in Tuscany)
Bagno Vignoni is a town in tuscany that is home to hotsprings. The springs are located in the center of town and are a popular spot for locals and tourists alike. The waters of the springs are said to have healing properties, and many people come to Bagno Vignoni to relax and rejuvenate.
The town is also home to a number of restaurants, cafes, and shops, making it a great place to spend a day or two.
Accommodation picks: La Locanda del Loggiato (midrange), Albergo Le Terme or B&B L’orto Delle Terme (lux)
Montepulciano (Hilltop Classic)
Montepulciano is a hilltop town in the province of Siena, Tuscany, central Italy. The town is best known for its wine, produced from the Sangiovese grape, and its medieval and Renaissance architecture. It is also a popular tourist destination for its Spa resorts and art galleries.
Accommodation picks: Casale Le Civette (budget), B&B L’Agnolo Di Caroti Cinzia or Il Rondò Botique Hotel (midrange), Villa Cicolina or Residenza Fabroni (lux), Terra Antica Resort, Winery and Spa (splurge)
Siena (Grand and Accessible)
Siena is one of the most beautiful and well-preserved medieval cities in all of Italy. Situated in the heart of Tuscany, this city is known for its red-brick buildings, picturesque piazzas, and stunning Duomo. A visit to Siena is like stepping back in time – and it’s no wonder why this city is such a popular tourist destination. From the moment you arrive, you’ll be charmed by Siena’s old-world atmosphere.
There’s plenty to see and do in Siena. Be sure to visit the Duomo, an iconic Gothic cathedral with a magnificent exterior and equally impressive interior. For views of the city, head to Il Campanile di San Domenico or one of Siena’s many lookout points.
Accommodation picks: Casacenti (budget), B&B Il Corso or Hotel Santa Caterina (midrange), Il Battistero Siena Residenza d’Epoca or Grand Hotel Continental Siena – Starhotels Collezione (lux)
Fosdinovo (Sea Views & a Castle)
Fosdinovo is a municipality located in the province of Massa and Carrara, in the Italian region of Tuscany. The town is situated on a hill in the valley of the Magra river, and it overlooks the Gulf of La Spezia. Fosdinovo has a population of about 2,500 people.
The town’s name is derived from the Latin word for “fossil”, because of the many fossilized shells that can be found in the area. The town is known for its castle, which was built in the 12th century by the Malaspina family. The castle has been restored and it is now open to the public.
Fosdinovo is also home to a museum dedicated to the work of Italian poet Giosuè Carducci.
Accommodation picks: coming soon
Montefioralle (Small Village on a Hill)
Montefioralle is a small village located on a hill in Tuscany, Italy. The village is known for its picturesque streets and views of the Tuscan countryside. Montefioralle is a popular destination for travelers looking to experience the authentic Tuscan lifestyle.
The village is home to a number of restaurants and cafes, as well as a few shops selling local artisan goods. Visitors can also explore the nearby vineyards and olive groves, or take a short drive to the city of Florence.
Accommodation picks: coming soon
San Gimignano (Classic Tuscany)
San Gimignano is a beautiful town located in the heart of Tuscany. This historic town is known for its medieval architecture and stunning views. Visitors can explore the many shops and restaurants, or take a leisurely stroll through the streets.
San Gimignano is the stunning place to relax and enjoy the beauty of Tuscany.
Accommodation picks: coming soon
Suvereto (Medieval Vibes)
Suvereto is a medieval town in tuscany that has a long and rich history. The town is situated on a hilltop and has stunning views of the surrounding countryside. Suvereto is home to many historical buildings and monuments, as well as a number of excellent restaurants and cafes.
Accommodation picks: coming soon
Santa Fiora (Riverside Hamlet)
Nestled in the Tuscan hills, Santa Fiora is a charming riverside hamlet that offers visitors a taste of traditional Italian life. With its winding streets and quaint stone houses, Santa Fiora is the perfect place to slow down and enjoy some la dolce vita.
There are plenty of things to do in Santa Fiora, from strolling through the picturesque streets to enjoying a leisurely lunch by the river. Visitors can also explore the nearby countryside, where they’ll find rolling hills dotted with vineyards and olive groves.
Accommodation picks: Hotel Eden (budget)
Monteriggioni (Walled Village)
Monteriggioni is a walled village in Tuscany. The village is located on a hilltop and has views of the Tuscan countryside. The village has a medieval feel to it with its stone walls and narrow streets. There are many shops and restaurants in the village. Monteriggioni is a great place to visit if you are looking for a unique experience in Tuscany.
Accommodation picks: B&B Torre Della Chiocciola or Fattoria Il Casone guest house (midrange), Il Piccolo Castello or Borgo San Luigi (lux)
Florence (Big City, Gorgeous Architecture)
Florence is the capital city of Tuscany, in central Italy. It’s known for its Renaissance art and architecture. The Duomo, a cathedral with a terracotta-tiled dome engineered by Brunelleschi, is a standout.
Other major sights include the Baptistery’s bronze doors and the Giotto bell tower, plus the Uffizi Gallery’s paintings and sculptures. The city is also home to specialties like leather goods and Chianti wine. It’s also the most populated city in Tuscany and you’ll most likely pass through here to the other towns in the area.
Accommodation picks: Borgo Oblate or Il Diospero B&B (budget), B&B Monte Oliveto or Residenza Vespucci (midrange), Villa Cora or Hotel Brunelleschi (lux)
So, What is the Prettiest Town in Tuscany?
That’s a tough one, it really depends on what you value in a countryside town. While all of the towns are gorgeous I’ve narrowed it down to my two favourites below.
Personally, I think Montelcino or Pitigliano are the prettiest towns in Tuscany. Montecino has epic views of the surrounding countryside, and Pitigliano is a stunning site with the town perched on top of a cliff. You’ll see some epic sunsets and countryside views in both towns.
Accommodation in Tuscany
There are a ton of places to stay in Tuscany, so you’ll want to do a bit of your own research if you’re choosing a town or village outside my recommendations. I’ve noted my favourite options where possible under the places above, so you can check out my suggestions there.
One thing to be aware of in regards to hotels, is that many of the rooms and hotels themselves are older style. Some have been built as far back as the middle ages. This means you’re staying in buildings with a lot of history but they may not look as shiny and new as you’d hope.
What to bring to Tuscany
It really depends on the season you’re visiting but here are a few must haves:
- Sandals or nice flats, because heels + wine + uneven footpaths sometimes equal disaster.
- Some pretty dresses for the countryside
- A nice jacket for the evenings
- A sunhat in summer
- A steady grip (for that wineglass, girl)
- Space in your suitcase for your taking some bottles home