15 Best Day Trips from Siena

Written by Jan Meeuwesen
Updated on
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Siena is a fantastically historic medieval location in the heart of Tuscany.

Located in northern Italy, this small city attracts hundreds of thousands of visitors to its UNESCO World Heritage streets every year.

It’s an incredible place to experience Renaissance era art and see medieval buildings in their old yet preserved detail, but the narrow alleys can become congested even at the quietest times, and it won’t be long before you are itching to get out into the Tuscan countryside to escape it all.

Luckily, Siena is surrounded by quaint country villages and rolling hills, while a diverse display of Italian history, culture and most importantly, food and wine, is just waiting to be discovered and tasted nearby.

Further afield, it’s possible to visit Florence, explore the spectacular coastline of Cinque Terra, and see the iconic leaning tower of Pisa, all just a day trip away from Siena.

1 . San Gimignano

San GimignanoSource: canadastock / shutterstock
San Gimignano

Start your adventures outside Siena by visiting the old medieval town of San Gimignano.

People have lived here for thousands of years and its illustrious history extends back to the 3rd century BC. The real attraction, however, is the UNESCO World Heritage historic center, which dates back to the 13th Century AD.

San Gimignano has managed to preserve its unique medieval tower houses over the centuries; the skyline today is still dominated by these imposing structures, with 14 of them still standing tall and proud above the town.

Walk the old streets, tour the towers and experience an authentic piece of Tuscan history at San Gimignano.

Suggested tour: From Siena: San Gimignano, Montalcino & Wine Tasting

2. Monteriggioni

Monteriggioni, ItalySource: GagliardiImages / shutterstock

The walled town of Monteriggioni is found nestled amid the Tuscan hills in the countryside near Siena.

The town has preserved its significant medieval fortifications and is still entirely ringed by defensive towers and walls.

Visiting Monteriggioni is like taking a step back in time a few hundred years, with Renaissance era houses and churches still lining the cobbled streets.

The castles and walls were built to defend Siena in their many wars against bitter rival Florence.

It acted as an important defensive line for centuries, so much so that the poet Dante even referenced Monteriggioni in his famous works.

This really is one of the most fascinating historic sights to see around Siena.

Also included in: From Siena: San Gimignano, Montalcino & Wine Tasting

3. Lucca

Lucca, ItalySource: DaLiu / shutterstock

Lucca is another beautifully preserved walled city in Tuscany, and can be explored easily in a day.

Lucca’s walls are in fact the real reason to visit.

While the city has grown and modernized far beyond the original defensive encirclement that once protected it, the walls were never torn down, but left standing.

They are so wide that the locals began planting trees atop them and turned them into one long park that encircles the old city center, which can be walked or even cycled around for a unique tour.

Recommended tour: Pisa and Lucca Full-Day Tour from Florence or Siena

4. Montalcino

Montalcino, Tuscany, ItalySource: Don Mammoser / shutterstock
Montalcino, Tuscany, Italy

Montalcino is another beautiful, medieval town in the Tuscan hills, and while it’s nice to visit for the old architecture and quaint cobbled streets, a popular reason to visit is to try the renowned Brunello Wine that is produced here.

Brunello Wine has a highly guarded recipe and the secrets are kept well-guarded; production has been ongoing and refined for centuries.

Walk the streets of Montalcino and stop in the wine bars for a taste, or take a few bottles home to savor the delights of Tuscany later on.

5. Chianti Region Vespa Tour

Vespa TourSource: getyourguide.com
Vespa Tour

A more unusual and exciting way to see the historic towns and rolling hills of Tuscany is to join a Vespa tour from Siena that heads out into the Chianti Region.

These motorized bike tours will give you a road trip around the stunning countryside, taking in the best medieval towns, a few out of the way wineries, and of course, olive and cheese farms.

It’s a novel way to explore this beautiful region on the classic Italian Vespa.

Available tours: Full Day Vespa Tour from Siena

6. Livorno

Livorno, ItalySource: claudio zaccherini / shutterstock

Head to the coast from Siena to visit Livorno: the seaside city with one of the largest bustling ports in Italy.

This city caters to cruise ships throughout the year and is well provided with restaurants and bars serving freshly caught seafood and fine wines for the visitors.

The port is a spectacular sight, with all types of ships, cruise liners and yachts calling in at any time, while the old fortifications are still found staring out to sea along the length of the coastline.

Watch the ships in the port and then dine out at one of the many restaurants along the shore front.

7. Pisa

PisaSource: F_N / shutterstock

Pisa needs no introduction.

Just an hour and a half away from Siena, this is the home of the iconic Leaning Tower of Pisa, a must see for any first time tourist in Tuscany.

Head to the tower when you arrive to get that integral souvenir photograph, framed as if you were propping the tilted structure up, but then stay around in Pisa a little bit longer to explore everything else in the city.

Tour the old streets, visit the museums and walk the scenic riverbanks.

Recommended tour: Pisa and Lucca Full-Day Tour from Florence or Siena

8. Assisi

Assisi, ItalySource: canadastock / shutterstock

Assisi is a town of churches, cathedrals and Basilicas; a place which has played an integral role in the history of Christianity in Italy and Europe.

The most important religious site here is the Basilica of Saint Francis of Assisi: one of the most revered saints in the history of Catholicism.

This huge, multi-layered structure dates back to the 12th century, and Saint Francis is interred in a crypt here, making it an important place of pilgrimage as well as an historically interesting medieval basilica.

Available tour: Assisi and Cortona Full-Day Tour

9. Rapolano Terme

Rapolano TermeSource: www.termesangiovanni.it
San Giovanni Terme, Rapolano Terme

Half an hour away from Siena, nestled in the countryside, the perfect escape from the city is waiting to be found at Rapolano Terme.

Rapolano Terme is an ancient Roman Town, and the Romans came here for one reason: to bathe in the hot baths.

Centuries later and the tradition still continues; tourists are able to visit this small town to indulge in the hot baths and spas that make for a relaxing retreat from Siena.

10. Colle di Val d’Elsa

Colle di Val d’Elsa, ItalySource: Michele Alfieri / shutterstock
Colle Di Val D’Elsa

A trip to Colle di Val d’Elsa is one of the easier day trips to make from Siena, as this hilltop town is just half an hour away from the city and easily accessible, even by public transport.

The town has an old and a new section, with modern buildings contrasting with the old medieval ones.

The ancient tradition of crystal glass making has been successfully passed down through the generations here, and has become a prized skill that is on show to visitors wanting to learn more about its intricacies.

11. Perugia

Perugia, ItalySource: joyfull / shutterstock

Perugia is capital of the neighboring Umbria Region, known for its Renaissance architecture and its older Etruscan and Roman remains.

It’s an historic place, picturesquely perched upon high hilltops offering spectacularly scenic views out across Umbria.

During the Renaissance, Umbria was a thriving artistic center, and this is still reflected in the many galleries and cultural festivals which the city prides itself on hosting throughout the year.

The busiest of these festivals is the annual jazz music festival, held every summer.

12. Cortona

Cortona, ItalySource: francesco de marco / shutterstock

In the hills near Siena sits the ancient town of Cortona, a place with steep streets that always seem to be leading upwards.

This is the real, quintessential Tuscany, with ancient Etruscan and Roman roots mixing with Renaissance architecture.

The town offers sweeping views over Tuscany, and the nearby Lake Trasimeno was the site of the infamous defeat of the Romans by Hannibal and his elephants.

Recent years have seen the town’s tourism boom, in many ways thanks to it being the setting for the famous Hollywood movie ‘Under the Tuscan Sun,’ which has inspired generations of tourists to see Tuscany for themselves.

Available tour: Assisi and Cortona Full-Day Tour

13. Monte Argentario Peninsula

Monte ArgentarioSource: StevanZZ / shutterstock
Monte Argentario

Further away from Siena than many of the other Tuscan towns, the Monte Argentario Peninsula is a great place to visit to escape the crowds.

This mountainous area is connected to the main coastline by a small land bridge, and it is a wild, rugged place with beautiful windswept beaches and spectacular coastal views.

A world away from the medieval towns and hillside fortresses around Siena, it is spectacular in its own unique way.

14. Cinque Terre

Cinque TerreSource: Shutterstock
Cinque Terre

Cinque Terre is a long day trip away from Siena, but this spectacular coastal area north of Tuscany is worth the extra effort to get to.

It’s a UNESCO World Heritage site, comprising five coastal towns spread along wild cliffs.

This is an incredible coastal setting and a raw experience can be had walking and hiking the trails between the five towns.

The towns themselves are all unique, with complex histories and interesting cultures just waiting to be delved into by curious tourists.

Suggested tour: Carrara marble quarries Cinque Terre PRIVATE TOUR from Siena

15. Florence

FlorenceSource: Mikadun / shutterstock

Lastly, the final day trip from Siena should be to Florence.

Historically, these two powerful cities were arch rivals, constantly at war during the medieval period, in such a way that has distinctly shaped northern Italy’s history and culture.

Florence eventually conquered Siena, and today is the capital of the entire Tuscany region.

The city is literally stuffed with museums, historic buildings, castles and artworks.

It’s a real Italian masterpiece, not to be missed during your trip to Tuscany.

15 Best Day Trips from Siena:

  • San Gimignano
  • Monteriggioni
  • Lucca
  • Montalcino
  • Chianti Region Vespa Tour
  • Livorno
  • Pisa
  • Assisi
  • Rapolano Terme
  • Colle di Val d’Elsa
  • Perugia
  • Cortona
  • Monte Argentario Peninsula
  • Cinque Terre
  • Florence