If you’re in the popular Tuscan city known for its horse races, you might be wondering about the best day trips from Siena. Is it really worth it to leave one of the region’s most visited destinations?
Absolutely! While Siena itself is lovely, there are so many other hidden gems to visit in the surroundings. You can explore wine country and its many vineyards and wineries. Check out jaw-dropping art, historical landmarks, and medieval structures that are unique from Siena’s. Even head to the Mediterranean, where you can swim in turquoise waters.
All of these wonderful attractions and more are located within just an hour or two from Siena by car. Keep on reading to learn how to maximize your time in the area.
How We Created This Guide
As a seasoned resident of Siena for 6 years, the author of this article has dedicated himself to immersion. Seeking out the most authentic experiences in the area, he has explored the corners of Tuscany and uncovered plenty of hidden gems. Additionally, we – the team of Italy Travel Secrets – have accounted for suggestions from friends and travelers with experience around Siena.
Although we have drawn upon personal experiences, they certainly aren’t the only factor we took into account. When creating this guide, we also considered temporal distances indicated by Google Maps. So, the guide is organized according to the average amount of time it takes to drive to destinations from Siena.
Of course, weather, traffic, and other conditions vary, so there may be small discrepancies between the distances indicated and reality. Always remember to drive safely and respect all limits on the road.
Day Trips from Siena – Places within an Hour’s Drive
1. Pienza and the Val d’Orcia
Pienza is a beloved town that oozes Tuscan charm. It was designed with Pope Pius II’s vision of Renaissance planning in mind, adding to the town’s architectural beauty. Pienza is perhaps most known for its cheese- in particular, its pecorino cheese made from sheep’s milk.
The surrounding Val d’Orcia is a paradise for nature lovers. Its idyllic hills, thermal springs, and roads lined with cypress trees make for a perfect postcard-worthy landscape. Visitors can walk along trails or go on a bike tour through the countryside.
2. San Gimignano
The town of San Gimignano is famous for its skyline of medieval buildings, giving it the nickname of Italy’s Medieval Manhattan. It’s one of the prettiest towns in Tuscany and a UNESCO World Heritage Sight.
While you’re there, make sure to check out the 12th-century Duomo, which features Florentine frescoes on the inside. The towers, plazas, and the Palazzo del Podestà are other attractions that make San Gimignano truly special.
3. The Wine Towns of Montalcino and Montepulciano
Montalcino sits on a hill that overlooks the Arbia, Ombrone, and Asso valleys, composed of lush grass, trees, and vineyards. The town derives its name from a type of oak tree that once blanketed the land. It’s most noted for its full-bodied Brunello wine, noted for its tasting notes of wild berry and anise.
Not to be confused with Montalcino, the town of Montepulciano is another lovely wine town in the area. Wineries around the town are known for their production of Vino Nobile di Montepulciano DOCG, a ruby red wine that’s classified as one of the noblest. Check out La Città Sotterranea, a winding network of underground wine cellars connected by tunnels and stone stairs.
4. The Abbey of San Galgano
The Abbey of San Galgano is a testament to the religious history of Tuscany, but it also has a fascinating legend. It’s named after Galgano Guidotti, who lived during the 12th century. It is said that when celebrating his sudden religious conversion Guidotti pierced a stone with his sword, creating a cross. The stone still stands in the rock today, just a 10-minute walk from the abbey.
The abbey itself is a marvel, as it remains a ruin with no roof. The iconic stone walls and archways make an impressive scene, despite the fact that it was abandoned. The parts of the abbey include the chapter house, the cloister, and the scriptorium.
5. The Chianti Hills
The hilly Chianti region is a captivating landscape of enchanting forests, winding roads, and vineyards full of ripe grapes. It’s also famous for its many wines.
Chianti is home to a plethora of quaint Italian towns and villages. Although it’s impossible to mention all of the remarkable places, there are some that absolutely must be mentioned. Castellina di Chianti, Gaiole in Chianti, and Panzano in Chianti are some of the towns worthy of special attention.
Located in the province of Siena, Monteriggioni is a small comune with cultural and architectural significance. It’s even been mentioned in Dante’s Divine Comedy.
Monteriggioni is surrounded by a medieval wall that follows the hill’s natural contour and has 14 towers and 2 gates. Inside, you’ll find the lively Piazza Roma, the main square and social hub of the comune.
In the surrounding countryside, Romanesque churches and abbeys offer glimpses into past history and the lives of monks.
Volterra, famous as an important setting in the Twilight sequel, exudes historic charm and artistic allure.
Its rich Etruscan heritage can be explored in the Museo Etrusco Guarnacci, which features a collection of fascinating artifacts. The ruins of Volerra’s Roman theater, one of the best preserved in Italy, are another chance to dive into history.
Additionally, Volterra is renowned for its longstanding production of alabaster. You can find many alabaster workshops that showcase the intricacies of the art and carry on its legacy.
Top Day Tours From Siena
Day Trips from Siena – Places within 2 Hours’ Drive
Pitigliano is one of the three so-called “Tufa Towns”, towns in the Maremma region that have been built upon tufa rock. The edges of the town blend into the cliffside, making the stone buildings appear one with the tufa.
Pitigliano is small, but packed with nooks to explore. The historic center consists of narrow alleyways that pass by authentic restaurants and artisan shops. “Little Jerusalem”, the Jewish quarter, has a small Jewish community. It was once more prominent, but the 1938-1943 Italian racial laws forced many to flee from Pitigliano. Even today visitors can check out the synagogue and the Museum of Jewish Culture.
9. Poppi and the Conti Guidi Castle
The town of Poppi is nestled in the Casentino Valley and boasts stunning views of the surrounding country. It’s linked to the aristocratic Count Guidi family, who built castles in towns around Tuscany, including Poppi.
The Castello di Poppi dei Conti Guidi serves as the icon of the town. Standing proudly atop the hill, this 13th-century castle features winding staircases, colorful frescoes, and a magnificent library.
If you’re a fan of hot springs or simply enjoying nature, Saturnia is not to be missed. Just outside the town is the natural Saturnia Hot Springs. It’s made up of beautiful terraced pools full of pristine water that is said to have healing properties.
It’s a great destination if you’re looking to get away from the busier town of Siena and relax in a natural environment. The water is constantly at 99.5 degrees Fahrenheit (37.5 degrees Celsius), so it’s especially great for cooler days. Plus, Saturnia Hot Springs is free to enter!
11. Monte Argentario
Monte Argentario is a Mediterranean peninsula in the stunning Maremma region. You’ll come across coves with crystalline turquoise water and sandy beaches here.
12. Bolgheri and Castagneto Carducci
Another town near Siena, Bolgheri, is on the smaller and quieter side. The Bolgheri area is known for its production of red Super Tuscan wines, which use non-traditional grape varieties.
Many delightful vineyards and wineries, like Tenuta San Guido, produce Super Tuscans- just keep in mind that they often don’t come cheap.
Nearby is Castagneto Carducci, a commune most famous for its agricultural and seaside linkages. It’s only 15 minutes away from Bolgheri by car.
Unlike the other destinations in this guide, Assisi is not located in Tuscany. Instead, it sits in the neighboring region of Umbria, just across the Tuscan border. This entire town is a UNESCO World Heritage Site recognized for its art and historically significant buildings.
The Basilica di San Francesco, the icon of Assisi, stretches along the hillside and is full of paintings and frescoes. The UN has even recognized Assisi’s significance for its contribution to the spread of the Franciscan Order and its uninterrupted existence as a sacred city.
Assisi is certainly one of Italy’s hidden gems and shouldn’t be overlooked!
Day Trips from Siena by Public Transport
Renowned as the birthplace of the Renaissance movement, Florence is home to artistic treasures and simply breathtaking architecture. It’s one of the biggest cities in the country, so there is no shortage of things to do or see.
No trip to Florence is complete without visiting the applauded art museums. Check out the Uffizi art gallery to see The Birth of Venus, among the extensive collection of paintings and sculptures. The Accademia gallery is perhaps just as popular, as it houses Michelangelo’s Statue of David.
Other attractions include the looking Duomo, the Ponte Vecchio bridge over the Arno River, and the Boboli Gardens. Plus, the city’s culinary scene is nothing short of impeccable. Try the bistecca fiorentina, pasta with boar ragù, and the lampredotto.
Florence is just 1.5 to 2 hours away from Siena by train. Depending on your specific journey, you’ll either take one train or have a transfer, but the time will be roughly the same.
Just the name Pisa brings to mind the leaning tower that’s the symbol of the city. Built over the course of two centuries, the tower began to lean due to soft ground that couldn’t support the structure’s weight. Many flock to Pisa to take well-planned comedic photos, but that’s not the only reason to check out the city.
Visitors shouldn’t miss the Piazza dei Miracoli, the Duomo, the Baptistry, or the Knight’s square.
The travel time from Siena to Pisa by train is similar to Florence. Just 1 hour and 45 minutes to 2 hours by train will bring you right to the city with the symbolic leaning tower.
16. Rapolano Terme
One spring, the Terme Antica Querciolaia, preserves the travertine pool that treated the historic figure Giuseppe Garibaldi. The Terme di San Giovanni consists of pools and a spa that offers endless treatments. Both thermal spas feature luxurious modern-looking pools with luxurious amenities and restaurants.
Other attractions include the Saltalbero Adventure Park, the travertine ridge, and the Pieve Romanica di San Vittore.
By bus, the trip from Siena can take between 30 minutes and an hour and 45 minutes- it all depends on what time you want to leave.
17. The Abbey of Monte Oliveto Maggiore
The Abbey of Monte Oliveto Maggiore is a Benedectine monastery that’s located near the hill town of Asciano. The complex’s buildings were built from red bricks that contrast the surrounding greenery.
The abbey’s church is adorned with frescoes painted by famous Renaissance artists. The cloister, which is lined with Renaissance arcades, is a peaceful space dedicated to contemplation.
Plus, a surprise remains hidden underneath the abbey: a wine cellar. Participate in a free wine tasting as you admire the massive barrels containing wine made in the area.
On average, the bus journey from Siena to the Abbey of Monte Oliveto Maggiore takes approximately 2 hours. However, that duration can vary, especially if you take a combination of bus and train.