Weekend & Day Trips from Siena, Italy

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.

Asciano

25 km southeast of Siena is the quiet little town of Asciano nestled in the Ombrone River Valley.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.

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.

Buonconvento

Buonconvento is known to be one of Italy’s most beautiful villages. Visitors driving into Buonconvento are greeted by medieval walls and architecture.

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.

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.

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.

Fiesole

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

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.

Greve

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.

Livorno

Visitors wanting to spend the entire day in Livorno should visit during the Effetto Venezia Festival.

Lucca

The attractions in Lucca are centered around the town’s ancient history including Piazza dell ‘Anfiteatro, and archeological remains housed beneath the 12th-century churches and villas. The walls around the fortress are now used as a pedestrian promenade and are one of the main attractions in the city now.

Montalcino

Visitors driving around the countryside of Montalcino can see one of the most notable examples of French Romanesque architecture found any more in Italy at the Abbey of saint’ Antimo. Montalcino is surrounded by forests, olive groves, and vineyards and was declared part of a UNESCO World Heritage Site in 2004. Spend the day wine tasting and sampling honey or exploring the ancient sites and monuments.

Montepulciano

Nobile wine is produced in Montepulciano, and the countryside is covered in vineyards and wineries. The Piazza Grande is the center of town often showcases special events such as the annual barrel racing contest each August. Several other villages surround Montepulciano including Pienza and Bagno Vignoni, a thermal village.

Monteriggioni

When visiting Monteriggioni, visitors should park in the lot at the base of the bill then climb the short ascent to the village. The Church of Santa Maria Assunta is part of the original construction and faces the Piazza di’ Roma. The best time to visit is in July during the Medieval Festival of Monteriggioni where people dress in Medieval clothing with live performances, acrobats, bards, and theater.

Monteroni d'Arbia

Monteroni d'Arbia is home to a medieval mill complex dating back to the early 14th century, and the mill pond is even still intact. Visitors should stop by Cuna, a fortified farm that was established in 1224, and The Castle of San Fabiano which was constructed around 1100. The formal gardens at the castle are still maintained, and there are often special exhibits that can be toured and events.

Pienza

Pienza is in the south of Tuscany and means “the city of Pius” after Pope Pius II who was born there when it was named Corsignano.

Pisa

Pisa is famous for more than just the Leaning Tower, though the tower is one of the most famous attractions in the world.

Pistoia

Pistoia is also famous for its thermal baths that royalty has used for health benefits and spa treatments. Visitors who love outdoor sports will enjoy exploring the mountains, and just outside the city is the Zoo of Pistoia and Pinocchio Park. For some of the world’s finest artisan chocolates, explore the Tuscan chocolate valley, which comprises Pisa, Prato, and Pistoia.

Portovenere

The medieval town of Portovenere is a UNESCO World Heritage site on the Gulf of Poets in Liguria Italy.

Prato

One of the most iconic parts of Prato is the pulpit designed by Donatello and Michelozzo at Cathedral of Santo Stefano. Pope Francis once spoke from the pulpit, and the church holds a religious relic that once belonged to the Virgin Mary. The interior of the church is decorated with historic frescoes created by Filippo Lippi. Other great attractions to see when visiting Prato include Palazzo Pretorio which is the Prato Civic Museum, the Castello dell’ Imperatore built in the 13th century, and check out the place where the world-famous biscotti di Prato is made. Prato

Rapolano Terme

The rugged landscape of Rapolano Terme is known for the therapeutic thermal springs that have been used in traditional Roman baths for centuries. The spas offer hydro-massage, mud baths, and many other relaxing skin treatments.

San Gimignano

Visitors to San Gimignano can visit the remaining 13 of the original 72 towers built in the 14th century to represent the wealthiest families in the region. Other great attractions to visit in San Gimignano include Museum of Sacred Art, Ornithological Museum, more than ten historic churches, The Ruins of Castelvecchio and the Natural Reserve of Castelvecchio. Guided tours of the town are also available.

Val d'Orcia

Pienza is known as the ideal city and features the world-famous Palazzo Piccolomini. Other great places to visit in Val d'Orcia are the fortress at Castiglion d’ Orcia or Radicofani, a hilltop town with ancient towers, and Montalcino which is still surrounded by a medieval wall. Visitors interested in religious history or medieval architecture should check out the Abbey of Sant’ Antimo. There are also many thermal baths to relax at or museums to explore.

Volterra

Visitors can still walk parts of the 4th-century perimeter walls and visit the Acropolis where there are two ancient temples and several ancient buildings. Several other historic Roman buildings can also still be visited including the remnants of the Roman Theater, and places where the Twilight Movie was filmed. Volterra