Ever wondered what adventures lie just beyond the terracotta roofs of Siena? Embark on a journey to discover Tuscany’s hidden gems with day trips from Siena, where every turn on the road leads to breathtaking landscapes and storied towns.

Setting out from Siena for day trips, you’re on the cusp of experiencing Tuscany’s incredible diversity. Here are the top day trip destinations to add to your itinerary:

  1. Pienza and the Val d’Orcia
  2. San Gimignano
  3. The Wine Towns of Montalcino and Montepulciano
  4. The Abbey of San Galgano
  5. The Chianti Hills
  6. Monteriggioni
  7. Volterra
  8. Pitigliano
  9. Poppi and the Conti Guidi Castle
  10. Saturnia
  11. Monte Argentario
  12. Bolgheri and Castagneto Carducci
  13. Assisi
  14. Florence
  15. Pisa
  16. Rapolano Terme
  17. The Abbey of Monte Oliveto Maggiore

Ready to uncover the heart of Tuscany with day trips from Siena beyond the city’s enchanting streets? Join us as we guide you through each destination, revealing the best of what they have to offer, from historical sights to natural wonders, ensuring your Tuscan adventure is nothing short of magical.

The Best Day Trips from Siena

Here are the best day trips from Siena that you can take during your vacation!

1. Pienza and the Val d’Orcia

The square of Pienza: a town rich in history and culture to visit on a day trip from Siena.
Piazza Pio II, in Pienza – Photo by Daniel Günther CC BY 2.0

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.

Read more: Bagni San Filippo – Explore the Wild Spa Town in Val d’Orcia

2. San Gimignano

The overview of the town of San Gimignano, with its beautiful watchtowers.
The medieval skyline of San Gimignano, Province of Siena

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

The square of Montepulciano is a place to visit on a day trip from Siena.
Palazzo del Capitano, in Piazza Grande, Montepulciano – Valeri Rossano, CC BY-SA 4.0, via Wikimedia Commons

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.

Read more: Bolgheri – Exploring the Charm of Tuscany’s Wine Country

4. The Abbey of San Galgano

The interior of the abbey of San Galgano, built in medieval times.
The interior of the San Galgano Abbey (Province of Siena) – Photo by Alessio Pellegrini CC BY-NC-SA 2.0

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.

Official Website: The Abbey of San Galgano

Location: Strada Comunale di S. Galgano, 53012 Chiusdino SI

Telephone: +39 0577 049312

Reviews: 4.7/5

Explore more: Tuscany Views – The 10 Best Sites to See the Region’s Beauty

5. The Chianti Hills 

The view of Monteriggioni: a beautiful town to visit when doing a day trip from Siena.
The village of Montefioralle, 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.

6. Monteriggioni

A typical house in Monteriggioni, Tuscany
Monteriggioni, near Siena

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.

7. Volterra

The historic center of Volterra can be reached in an hour's drive from Siena
The town of Volterra, Tuscany

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

8. Pitigliano

The breathtaking view of Pitigliano, just two hours by car from Siena.
The “tufa town” of Pitigliano is less than two hours drive from Siena

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.

We also recommend visiting the nearby towns of Sorano and Sovana.

Italy Travel Secret

Did you know that in Pitigliano, there is an ancient system of underground tunnels? These caves carved into the tufa, known as “Cantinoni” or “Cunicoli,” date back several centuries and were used for various purposes, such as food storage, wine production, and water supply. Some of these tunnels are still open to the public, allowing visitors to explore this fascinating underground network and discover the hidden history of Pitigliano.

9. Poppi and the Conti Guidi Castle

Poppi Castle still has excellent architecture, in the past it housed the aristocratic Guildi family
The mysterious Poppi Castle was owned by the aristocratic Guidi family – Photo by Mongolo1984, CC BY-SA 4.0, Wikimedia

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.

Official Website: Castle of the Earls Guidi

Location: Piazza della Repubblica, 1, 52014 Poppi AR

Telephone: +39 0575 520516

Reviews: 4.6/5

Explore more: 15 Castles in Tuscany – An Enchanting World of Timeless Beauty

10. Saturnia

The waterfalls of the mill of Saturnia are located a few hours by car from Siena
Saturnia, Cascate del Mulino – These hot springs are quite easy to reach from Siena

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!

Explore more: San Casciano dei Bagni – A hidden gem in the Tuscan countryside

11. Monte Argentario

The iconic view of Porto Santo Stefano: an ideal destination for a day trip from Siena
Porto Santo Stefano, one of the main port towns of 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. 

You can explore the port towns of Porto Ercole and Porto Santo Stefano, which feature medieval structures and religious sites. 

Plus, the town of Orbetello rests on a small strip of land connecting Monte Argentario to the mainland. Check out the unique Spanish Mill, go swimming, and see flamingos in the Orbetello lagoon.

Explore more: Southern Tuscany – Best Towns, Where to Stay, and Itineraries

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.

13. Assisi

The church of Assisi, very close to the city of Siena
Assisi, in Umbria, is one of the most recommended day trips from Siena

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!

14. Florence

A traveler reached Florence, starting from Siena by train.
Florence is easy to reach from Siena, by train and bus

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.

Read more: Florence In February – 10 Things to do on your Next Visit

15. Pisa

The Arno River in Pisa reflects the houses of the city.
The Arno river in Pisa

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.

Italy Travel Secret

Have you ever heard of the Giardino Scotto in Pisa? It is a public park located along Lungarno Gambacorti, a short distance from the Leaning Tower of Pisa. This garden, although often overlooked by tourists, provides a peaceful atmosphere and a breathtaking view of the city. What makes it unique is its history: originally owned by the noble Scottish family of Scotto, the garden was donated to the city in 1869.

16. Rapolano Terme

The historic center of Rapolano Terme, a destination that cannot be missed if you visit Siena
The historical center of Rapolano Terme – RiccardoT, CC BY 3.0, via Wikimedia Commons

The Comune of Rapolano Terme, home to two relaxing thermal springs, sits about 20 km east of Siena

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 frescoes inside the Abbey of Monte Oliveto Maggiore
Frescoes in the Monte Oliveto Maggiore Abbey

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.

Location: Monte Oliveto Maggiore, 53041 Asciano SI

Telephone: +39 0577 707258

Reviews: 4.7/5

Read more: Explore Buonconvento – Your Guide to an Authentic Tuscan Town

How We Created This Guide

The Val D'Orcia countryside - one of the best places to reach on a day trip from Siena.
The Val d’Orcia, one the the best day trips from Siena

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.

FAQs about Day Trips from Siena

Here are some frequently asked questions about day trips from Siena.

Where Can You Go by Train from Siena?

From Siena, you can hop on a train to various charming destinations. Florence, with its Renaissance wonders, is just a scenic train ride away. Arezzo, Pisa, and even Rome are also within reach. So, whether you’re up for art, history, or just a change of scenery, the train from Siena is your ticket to adventure!

How Many Days Is Enough for Siena?

If time is playing hard to get, a solid 2 to 3 days is a sweet spot. It lets you stroll through the medieval streets, marvel at the Cathedral, and perhaps indulge in some delicious Tuscan cuisine. But beware, you might find yourself wanting more of this enchanting city!

Where to Go After Siena?

If you’re in the mood for more history, Florence is just a heartbeat away. The rolling hills of Chianti are perfect for wine enthusiasts, while the coastal allure of Cinque Terre is a short journey if you’re craving seaside vibes. The question is not where to go, but where your heart desires next!


As you plan your day trips from Siena, think of it like picking ingredients for a perfect recipe. Each destination adds its unique flavor to your Tuscan adventure. So whether you’re drawn to Florence’s art, captivated by Lucca’s charm, or enticed by the beauty beyond, let Siena be your launchpad for a journey full of surprises. Enjoy every moment, soak in the experiences, and let the memories linger as souvenirs of your magical exploration. Safe travels, and may joy and discovery fill your days!