Weekend & Day Trips from Siena, Italy

1. Arezzo

Arezzo is a city with ancient origins centered at the meeting place of four valleys in southeastern Tuscany. Known for being the site where Man of the Elm, a body that dates to the Paleolithic era, was discovered, Arezzo is also home to many other ancient places that visitors can see and explore. Some of the best sites to see in Arezzo include fortresses, the remnants of a Roman amphitheater, ancient cathedrals, and prolific artworks at the museums.

Spend the day in Arezzo for wine tastings, take a drive down the Route of the Setteponti, or take a walking tour of the city and visit The Medici Fortress which was built in the 16th century.

2. Asciano

25 km southeast of Siena is the quiet little town of Asciano nestled in the Ombrone River Valley. Many people love to travel to Asciano and the Crete Senesi Region to explore the picturesque landscapes and visit the medieval center. One of the most popular attractions in Asciano is the Saint Agatha Collegial Church which was first built in the 12th century. Much of the original structure remains, though some parts of the church have been updated.

Visitors can stop by the Museum Cassioli next to the church to view local Sienese art and the Corboli Museum just down the road to explore archaeology and artifacts from the Etruscan tombs. Spend the day and drive out to Monte Oliveto Maggiore monastery 10 km south of town.

3. Bologna

Bologna is found in Northern Italy and is the capital city of the Emilia-Romagna region. The bustling metropolitan city has been one of the great urban centers of Tuscany for centuries and is known for its historic architecture and a well-preserved city center with long porticoes that have been meticulously restored. Bologna is also where the world-famous University of Bologna is. The university is the oldest in the world and was declared a European Capital of Culture in 2000, UNESCO City of Music in 2006, and was inducted into the Creative Cities Network.

The best places to visit in Bologna include Piazza Maggiore with Basilica of St. Petronius, St. Stephen Basilica, the leaning towers—Torre Garisenda and Torre degli Asinelli, and the university campus. Visitors should also make sure to stop at a local café for authentic Bolognese food.

4. Buonconvento

Buonconvento is known to be one of Italy’s most beautiful villages. Visitors driving into Buonconvento are greeted by medieval walls and architecture. The small village is found at the convergence point of the Arbia and Ombrone Rivers and features museums housing art from some of Italy’s finest artists and the Sienese school of art, and ancient cathedrals dating back to 1100.

The best time to visit Buonconvento is during the Sagra Della Val d’Arbia in September. The popular event celebrates art, food, sports, and music. This annual festival started in 1805 and drew hundreds of visitors to the small medieval town.

5. Chianti

Known for Chianti Wine, this area of Tuscany is visited by people from all over the world who want to experience wine country. The Chianti Region covers the provinces of Florence and Siena but isn’t clearly defined on any map. The territory is perfect for spending the day wine tasting and driving through the picturesque countryside to visit small stone villages, olive groves, castles, fortresses, and ancient church parishes.

Most people visiting the Chianti region will spend the day in Siena or Florence, where there are many tourist attractions such as museums and historic sites. There are many different types of guided tours and walking tours that offer visitors a taste of the Chianti regions, depending on their preferences.

6. Colle di Val d'Elsa

Stop by Colle di Val d'Elsa on your way from Siena to Florence to enjoy this charming town known for crystal glass making, exquisite restaurants, and a medieval ambiance. During summer months there are monthly first Sunday markets and glass making shows that visitors can explore. There are also museums, the old historical center, and Volterra—an ancient fortress with walkable roads, that tourists can enjoy exploring all day long.

Colle di Val d'Elsa is only thirty minutes from Siena and is easily accessible by car or bus. Some of the best sites to visit are the Civic and Diocesan Museum, Archeological Museum, and Via Della Misericordia, where visitors can watch glass blowing presentations.

7. Cortona

Visitors wishing to explore hillside towns in Tuscany will love spending the day at Cortona. Marked by steep vertical streets, there are many historic and cultural sites to visit in Cortona such as Cortona Etruscan Museum and the Cortona Diocesan Museum set against Renaissance architecture.

The Piazza Della Republica is one of the most popular attractions and is the focal point of the city. The Medicean Fort is another great place to visit for sweeping views of the city and the Val di Chiana.

Some great times to consider coming to Cortona are during the bric-a-brac market that happens monthly, the crossbow competition, or Cortona Mediaeval Week that happens in the middle of summer annually. There are also many performing arts events happening all year round.

8. Fiesole

The charming town of Fiesole is one of the least touristy hillside towns near Florence. The town overlooks the valley and features numerous Tuscan villas with the most famous being Lorenzo di Medici’s Villa Fiesole. The streets in Fiesole are very narrow, and the town is best visited via city bus though personal vehicles are allowed. There are also many excellent restaurants in Fiesole such as Le Reggia Degli Etruschi and Trattoria Tullio. You’ll need reservations to dine at both of these highly sought-after restaurants. Tours of the Cathedral of Fiesole and other historic churches are available as well as the Roman baths and theatre at Fiesole are available. Fiesole

9. Florence

When people think of the Italian Renaissance, Florence is one of the most iconic places that comes to mind. Some of the most significant artworks in history are found in the museums, castles, and churches in Florence. Tourists to Florence can spend several days exploring historic sites such as the Cathedral, Baptistery, Accademia, Uffizi, the Bargello, and many art galleries and libraries. One of the most famous libraries, San Lorenzo, was designed by Michelangelo. Visitors who want to explore the Oltrarno, the newer part of Florence, can enjoy a walk through the Boboli Gardens, Pitti Palace, and climb the hill up to the San Miniato al Monte. There are many different tours of Florence offered by travel and tourism companies that visitors can tailor to their own interests.

10. Greve

Greve is known as the gateway to the Chianti region, and the world-famous vineyards are visible before you leave the city limits. Greve offers a tranquil ambiance with a quaint small-town atmosphere and is the headquarters for a local comune between Florence and Siena. There are many villa rentals, bed & breakfasts, and other accommodations in Greve for people who want to spend a few days visiting Tuscan wine country. A farmer’s market occurs every Saturday, and the town sits just below the Castle of Montefioralle and is at the crossroads of three historic roads once used for pilgrimages. The Main Square is the perfect place to visit for boutique shopping, local restaurants, and artisan workshops.