Tuscany is a famous tourist destination in central Italy for many reasons. Its sweeping landscapes, rich history, culture, art, architecture, food and wine bring hundreds of thousands of visitors to the city of Florence and the Tuscan countryside every year. Tuscany boasts so many iconic spots, like the Leaning Tower of Pisa and the Duomo Cathedral in Florence and the Piazza del Campo in Siena where the annual Palio festival and race is held.
Tuscany is also home to the famous works of Michelangelo, Botticelli and Brunelleschi. An authentic experience and exploration of the most beautiful places in Tuscany, however, lies in the many cities, villages and towns scattered in the gorgeous, lush greenery of this region. Here are some of the best places in Tuscan countryside to include on your next trip.
Most charming towns and villages in Tuscany
1. Siena
Siena is one of Italy’s most charming medieval cities that sits over three hills with Piazza del Campo as its heart. Siena’s population is that of a small town but it is indeed classed as a city and in peak travel season, tourists often outnumber residents. Rich in culture and history Siena is a must-visit on any trip to Tuscany. James Bond lovers will recognize this city from the Quantum of Solace movie and chick flick bingers will recognise locations from The Twilight Saga and Under the Tuscan Sun. You can explore Siena in a day trip from Florence, but we recommend staying for at least two days to take in the beauty of this city.
Things to do in Siena
- Climb up the Torre del Mangia and enjoy the mesmerizing views of the city from the top of the tower.
- Explore the treasures within Piazza del Duomo and visit the Cathedral, the Crypt and the Piccolomini Library.
- Enjoy the various experiences that Piazza del Campo has to offer, especially the bi-annual event Palio di Siena.
Explore Siena and San Gimignano along with Rome, Florence and Venice on this 2 week Italy trip
2. Lucca
Lucca stands tall at the foot of the Apuan Alps and is known as Tuscany’s city of 100 churches. Lucca holds traces of ancient history across the city, and they shine through its various attractions. Glimpses of its Roman history can be seen in the shape of the Piazza dell’Anfiteatro and the archaeological remains under the 12th-century church of Saints Giovanni and Reparata. Marvel at the various churches, villas and towers from the 12th and 16th centuries and the city walls that stand firm to this day.
Things to do in Lucca
- Visit the Puccini Museum dedicated to Giacomo Puccini, one of Italy’s greatest composers and learn about his life.
- Enjoy a bike ride or take a walk over the old city walls of Lucca and be amazed by the panoramic walkway that overlooks the city.
- Explore the Basilica of San Frediano which is one of the oldest churches in the city and a great example of Lucca’s religious architecture.
3. San Gimignano
San Gimignano is a town in Tuscany which is famous for its medieval architecture and tall towers that offer amazing views that will leave you speechless. It has been recognized as a UNESCO World Heritage Site since 1990 with its medieval streetscape and the 14 towers that stand tall and survived from the original 72 built by San Gimignano’s patrician families. The beautiful town of San Gimignano can be explored on foot within a day.
Things to do in San Gimignano
- Climb to the top of the tallest remaining tower in the town – the Torre Grossa to enjoy the best view of San Gimignano.
- Sip the famous and delicious local white wine Vernaccia di San Gimignano and enjoy a great gelato here.
- Stroll through the town and explore various attractions such as the Duomo di San Gimignano and the Palazzo Comunale.
Visit San Gimignano on this 7 Day Florence and Cinque Terre Itinerary
4. Cortona
Easily one of the most beautiful places in Tuscany is the charming town of Cortona in the Chiana Valley. This town is enclosed by walls from the Roman era and sits atop a hill offering breathtaking views of the surrounding valley as well as views of Lake Trasimeno on the horizon. This town houses many cultural sites that take you on a deep dive into its Etruscan heritage. Be sure to visit the picturesque sunflower fields and sip on local wine while in Cortona.
Things to do in Cortona
- Visit the Santa Margherita whose history dates back to the 13th century and is one of the many architectural treasures of Cortona.
- Explore a part of the iconic Girifalco Fortress which was constructed for military purposes and has undergone many changes through time.
- Pay a visit to Franciscan Hermitage Le Celle, which is the first monastery built in 1211 by Saint Francis of Assisi.
5. Montepulciano
Montepulciano is one of the best small towns in Tuscany to stay in, set in a strategic corner of Tuscany. Montepulciano is a beautiful starting off point from which you can explore the nearby attractions and villages. It is the largest hill town in southern Tuscany and is famous for its beautiful Renaissance buildings, churches, magnificent central square and breathtaking views. This walled hill town is built on a narrow and sloping limestone ridge in the heart of the Vino Nobile.
Things to do in Montepulciano
- A trip to Montepulciano is incomplete without exploring its main square, the Piazza Grande, surrounded by 15th-century buildings.
- Marvel at architecture from the Renaissance period at Madonna di San Biagio Church.
- Be mesmerized by incredible never-ending views from the top of the Palazzo del Comune, a beautiful tower.
6. Pitigliano
Pitigliano is a magnificent town carved into the Tofu Rock in the Tuscan Maremma countryside and stands at the crossroads of the valleys of Meleta, Prochio and Lente. It is one of the prettiest towns in Tuscany. It is also famously known as ‘Little Jerusalem’ because of its large Jewish community from the 16th century. Pitigliano is a hidden jewel that houses art, culture and history and is a must-visit on your trip to Tuscany.
Things to do in Pitigliano
- Enjoy spectacular views of the town at night and during the day from the Sanctuary of the Madonna delle Grazie before entering Pitigliano.
- Visit the Jewish Ghetta and explore the Synagogue, the Cellar, the Tirual Baths and the Forno delle Azzime bakery.
- Step into the oldest building in the town- the Church of San Rocco for some positive vibes.
7. Pienza
Located in southern Tuscany, Pienza is a small town known as the city of cacio (cheese) and a UNESCO World Heritage Site. It is set on top of the hill overlooking the Orcia Valley and is very close to Montepulciano. This charming tiny town is known as the ‘ideal city of the Renaissance’ and features the perfect mix of architecture, food and tradition. Enea Silvio Piccolomini (who later became Pope Pius II) envisioned Pienza to be a Utopian city. The narrow streets of Pienza will transport you into a beautiful Renaissance painting.
Things to do in Pienza
- Enjoy unique and breathtaking panoramas of the Val d’Orcia Valley from the hanging garden of Palazzo Piccolomini.
- Walk down to the Romanesque church, Pieve di Corsignano with origins in the 7th century.
- Savour every bite of the Pecorino of Pienza, a cheese made from sheep’s milk.
Explore the most beautiful villages on this 7-Day Tuscany Itinerary
8. Fosdinovo
Fosdinovo village is one of the Orange Flag villages of the Italian Touring Club and no doubt ranks among the most beautiful villages in Tuscany. This historic village in the Val di Magra and Luni plains was a gateway to the Lunigiana region. Fosdinovo is also famous for its conserved castle-fortress and is a popular attraction in Tuscany. It is famous for excellent quality extra virgin olive oil and wines. Be sure to taste the delicious wines while in Fosdinovo.
Things to do in Fosdinovo
- Visit the beautiful Malaspina Castle, a well-conserved fortress set atop a hill.
- Explore the 13th-century church, Parish Church of San Remigio and marvel at the Baroque-style temple.
- View the white marble façade and 15th-century wooden statue of the Virgin Mary of the Compagnia dei Bianchi Oratory.
9. Monteriggioni
Find yourself transported to the past on your trip to the medieval village of Monteriggioni. Considered one of the best places in the Tuscany countryside, this memorable village has remained intact as a mirage of the Middle Ages. The village overlooks the Via Cassia offering stunning views of the Valdelsa territory. It is one of the Orange Flag villages of the Italian Touring Club and has been mentioned by Dante in his works.
Things to do in Monteriggioni
- Walk through the stunning Monteriggioni Castle from the 13th century and enjoy views of Siena from its towers.
- Find traces of the village’s medieval origins preserved well in the Church of Santa Maria Assunta.
- Tour of the village through the ‘Monteriggioni in Arme’ educational route featuring imitations of medieval and Renaissance weapons and armour.
10. Suvereto
This stunning village of Suvereto is located between the hills and the Etruscan Coast’s Sea. The village stands out for its rich history and art. The cultivation of olive trees and vines in this region dates back to the 19th century and is well-known worldwide. It is only a quick 10 kilometres from the sea and stands on one of the hills of Mediterranean scrub offering beautiful views of the region.
Things to do in Suvereto
- Prepare to be amazed by the beautiful views of the village from the Rocca Aldobrandesca Castle.
- Explore the 18th-century Church of the Madonna di Sopra la Porta.
- Visit the Doll Museum and see the intriguing collection of a variety of dolls of all ages and types.
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11. Tavern d’Arbia
Tavern d’Arbia is a small village in Tuscany. This quaint village offers a glimpse into Tuscany’s beauty. Slow your life down and enjoy periods of rejuvenating rest in the slow-paced Tavern d’Arbia. This village is 8 kilometres from Siena making it the perfect place to enjoy the best of both worlds. Enjoy the hustle and bustle of Siena during the day and the serenity of Tavern d’Arbia at night.
Things to do in Tavern d’Arbia
- Stay in a cozy place and enjoy the homely life of this beautiful village.
- Stroll through the village and explore the local shops and markets.
- Enjoy local food and drink at the local restaurants.
12. Colle di Val d’Elsa
Home to the famous Italian architect and sculptor, Arnolfo di Cambio, this gorgeous city makes for a perfect day trip from Siena. Explore the newer parts of the city and move upwards to reach the parts of the city that are reminiscent of the past. In Colle di Val d’Elsa handicrafts began as early as the 1300s and it then became the first hub of the glass manufacturing industry. It is famously called the Italian Bohemia where the local artisanal excellence of crystal making is a link between modernity and tradition.
Things to do in Colle di Val d’Elsa
- Visit the Museum of Crystal set up inside an old glass factory and partake in the many workshops to make glass and crystal objects.
- Explore the San Pietro Museum through its collection of sacred artworks.
- Learn about the history of the Etruscan period through artefacts in the Ranuccio Bianchi Bandinelli Archeological Museum.
We at Go Real Travel are excited to take you on a magical exploration of Tuscany’s best places so prepare to be amazed by the beauty of these hidden gems.