The Most Amazing Day Trips From Siena

Siena is one of the best places to stay in Tuscany for basing yourself close to all the top cities and attractions in the region. However, the surrounding region is equally captivating.

From medieval hilltop towns to rolling vineyards and picturesque countryside, there are numerous opportunities for day trips from Siena that will allow you to immerse yourself in the beauty and charm of Tuscany.

Discover the 10 best day trips from Siena, each offering its own unique experiences and attractions. Whether you’re interested in exploring art, history, wine, or nature, these day trips from Siena will take you to some of the most captivating destinations in the region.

From the iconic city of Florence to the scenic landscapes of Val d’Orcia, each day’s trip promises an unforgettable adventure.

Continue reading to discover the best of Tuscany as you embark on these amazing day trips from the charming city of Siena.

Florence Duomo tickets churches in florence

10 Best Day Trips from Siena, Italy


Florence, the capital of Tuscany, is a must-visit destination on a day trip from Siena – though granted, it deserves more than just a day. This iconic city is renowned for its rich history, artistic treasures, and architectural marvels. Admire the breathtaking Florence Cathedral, with its magnificent dome and stunning facade. 

Explore the renowned Uffizi Gallery, home to a vast collection of Renaissance masterpieces. Walk across the Ponte Vecchio, a medieval bridge lined with shops. Visit the Accademia Gallery to marvel at Michelangelo’s famous sculpture, “David.” 

Immerse yourself in the vibrant atmosphere of Piazza della Signoria, surrounded by magnificent sculptures and the Palazzo Vecchio. Indulge in delicious gelato at Gelateria Vivoli, a renowned gelateria in Florence. Explore the grand Pitti Palace and its beautiful Boboli Gardens

Finally, visit the Basilica of Santa Croce, the burial place of famous Italian personalities. Florence’s cultural richness, artistic heritage, and architectural beauty make it an unforgettable place to visit on day trips from Siena.

You can easily get to Florence by train from Siena – there are regular departures and the trip takes around 1.5 hours. Once there, you can follow my itinerary as explained in my post How To Make The Most Of Florence In A Day.

Alternatively, you could join this Florence In A Day With David, Duomo, Uffizi & Walking Tour by Walks of Italy. It’s highly rated and a great way of exploring the city if you have a short time.

San Gimignano best day trips from Siena

San Gimignano

San Gimignano is one of the most beautiful towns in Tuscany with its medieval towers and well-preserved historic center. Just a short drive away, this UNESCO World Heritage site offers a glimpse into the medieval charm of Tuscany.

Explore the narrow cobblestone streets and marvel at the 14 remaining towers that once symbolized the power and wealth of the town’s noble families. 

Visit the Collegiate Church of San Gimignano with its impressive frescoes, and climb the Torre Grossa for panoramic views of the surrounding countryside. Discover local shops offering renowned products like saffron and Vernaccia wine. 

Indulge in a traditional Tuscan meal at one of the cozy trattorias, and savor the flavors of the region. San Gimignano’s unique atmosphere, rich history, and architectural splendor make it an unforgettable day trip from Siena that transports you back in time to the medieval era of Tuscany.

There are no direct trains from Siena to San Gimignano. To get there, you can opt for a combination of buses changing in Poggibonsi, or bus and train. Alternatively, you can rent a car or join a guided tour.

This guided tour of San Gimignano also goes to the Chianti Region and Montalcino. It also includes wine tasting.

Another of the best guided day trips from Siena to San Gimignano is this tour that also includes a visit of Volterra and a home cooked meal at a local farm.

Finally, you have the option of joining this day trip from Siena that goes to San Gimignano and takes you to the Chianti Region in time for a fabulous sunset.

Val D'Orcia

Pienza and Val d’Orcia

A day trip to Pienza and Val d’Orcia from Siena is like stepping into a postcard-perfect Tuscan landscape.

Pienza, a small town known as the “Ideal City of the Renaissance,” offers breathtaking views and exceptional Renaissance architecture. Explore the charming streets and visit Pienza Cathedral and Palazzo Piccolomini. Don’t forget to sample the town’s famous pecorino cheese.

From Pienza, venture into the picturesque Val d’Orcia, a UNESCO World Heritage site. This idyllic region is characterized by rolling hills, cypress-lined roads, and charming villages. Driving through the countryside is easily one of my favorite European travel experiences I will never forget. 

The combination of Pienza’s architectural beauty and Val d’Orcia’s scenic landscapes make this one of the most unforgettable day trips from Siena.

To make the most of Val d’Orcia, you are better off renting your own car or joining a guided tour. Otherwise, it’s a matter of taking several bus connections to Pienza.

This guided tour of Val D’Orcia also goes to Pienza and Montepulciano. It lasts up to 10 hours and includes wine tasting.

Best day trips from Siena
Photo by Tania Zbrodko @shutterstock


A day trip to Montepulciano from Siena offers a delightful journey through the rolling hills and vineyards of Tuscany. This charming hilltop town is renowned for its Vino Nobile red wine and medieval architecture.

Immerse yourself in the charm and beauty of Montepulciano, soak in the views of vineyards stretching into the horizon, and experience the rich flavors of Tuscan wine and cuisine. A day trip to Montepulciano from Siena promises an unforgettable journey through the heart of Tuscany.

Explore the picturesque streets, adorned with Renaissance palaces, churches, and hidden corners waiting to be discovered. Visit the impressive Piazza Grande, the heart of the town, and climb the Torre di Pulcinella for panoramic views of the surrounding countryside.

Indulge in wine tastings at historic cellars and sample the renowned Vino Nobile di Montepulciano. Visit the Contucci Palace, a historic winery offering guided tours and tastings. Don’t miss the chance to try local delicacies, such as pecorino cheese and pici pasta, at the traditional trattorie and enoteche.

It only takes 55 minutes to drive from Siena to Montepulciano, but the traveling time almost doubles if you use public transportation. If you don’t feel like driving, consider joining a guided tour.

This guided tour of Montepulciano also goes to Pienza and Val d’Orcia. It lasts up to 10 hours and includes wine tasting and transportation from Siena.

You also have the option of this small day trip from Siena to Montepulciano and Pienza. It includes lunch, pecorino cheese and wine tasting and the visit of a cellar in Montepulciano.

Volterra Siena day trips
Photo by FooTToo @shutterstock


A day trip from Siena to Volterra offers a look into the ancient Etruscan civilization and the medieval charm of Tuscany. Situated on a hilltop, this historic town boasts a rich history and stunning panoramic views of the surrounding countryside.

Immerse yourself in the timeless beauty and rich history of Volterra, appreciating its ancient heritage and distinctive atmosphere. A day trip to Volterra from Siena is a journey back in time, offering a glimpse into the fascinating past of this remarkable Tuscan town.

Explore the well-preserved Etruscan walls, visit the Roman theater, and wander through the winding streets lined with medieval architecture.

Discover the Alabaster Museum, showcasing Volterra’s traditional craft, and admire the impressive Fortezza Medicea, a Medici fortress that now houses various cultural exhibitions. Visit the Palazzo dei Priori, the oldest town hall in Tuscany, with its remarkable frescoes and art collections.

Indulge in local cuisine at the traditional trattorie, where you can savor authentic Tuscan flavors. Don’t forget to try the renowned local delicacies, such as the wild boar stew and pecorino cheese.

Volterra is less than one hour drive from Siena. If you wish to go there by public transport, you will have to take a bus to Poggibonsi and change there. The best way to go if you don’t want to drive if probably a guided tour.

You may want to join this guided tour to Volterra departing from Siena that also includes a visit of San Gimignano and lunch at a local farm.

Chianti Wine Region
Photo by Tomas Marek @shutterstock

Chianti Wine Region

A day trip to the Chianti wine region from Siena is a true delight for wine enthusiasts and nature lovers alike. Just a short drive from Siena, this picturesque region is famous for its vineyards, charming villages, and breathtaking landscapes.

Embark on a scenic drive through the rolling hills of Chianti, passing by vineyards, olive groves, and ancient castles. Visit renowned wineries and indulge in wine tastings, sampling the region’s acclaimed Chianti Classico wines.


Explore charming towns like Greve in Chianti, known for its vibrant market square and wine cellars, and Radda in Chianti, with its medieval streets and panoramic views. Discover the medieval fortress of Castellina in Chianti, and soak up the relaxed atmosphere of these picturesque villages.

Enjoy a leisurely lunch at a local trattoria, where you can savor traditional Tuscan dishes paired with exquisite Chianti wines. Immerse yourself in the idyllic landscapes, capture stunning photographs, and create unforgettable memories in the heart of the Chianti wine region.

To make the most of the Chianti region and taste wine without the worry of driving after drinking, you are better off joining a guided tour.

You may want to consider this guided tour of Montalcino that goes to the Chianti Region and San Gimignano too. It obviously includes wine tasting.

There also is the option of joining one of the Chianti Region day trips from Siena by e-bike. It’s a fun way of exploring the area!

Finally, there’s the option of this fabulous Chianti wine tour that also includes with lunch and transportation from Siena.

Photo by DaLiu @shutterstock


A day trip to Monteriggioni from Siena offers a journey back in time to a perfectly preserved medieval village. This walled hilltop town, with its iconic circular shape and 14 intact towers, exudes a magical ambiance.

Stroll through the narrow cobblestone streets, admire medieval architecture, and take in panoramic views of the surrounding countryside from the town’s walls. Explore the Piazza Roma, the heart of Monteriggioni, and visit the Church of Santa Maria Assunta with its beautiful frescoes.

Learn about the town’s history at the Monteriggioni Castle and Museum, which offers insights into medieval life and fortifications. Enjoy a leisurely lunch at a local trattoria, savoring traditional Tuscan cuisine and regional wines.

Immerse yourself in the medieval atmosphere, imagining the days of knights and feudal lords. Monteriggioni’s charm and historical significance make it an enchanting day trip destination, transporting you to a bygone era in the heart of Tuscany.

There is a direct bus from Siena to Monteriggioni that takes you there in around 3o minutes. Driving will take you more or less the same amount of time.

Otherwise, you may want to join this guided tour to Volterra departing from Siena that also includes a visit of San Gimignano, Monteriggioni and lunch at a local farm.

Cortona best day trips from Siena
Photo by Maciej Czekajewski @shutterstock


A day trip to Cortona from Siena takes you to a picturesque hilltop town steeped in history and art. Known for its Etruscan origins, Cortona offers a captivating blend of medieval charm and panoramic vistas.

Wander through its enchanting streets, lined with ancient buildings and adorned with flower-filled balconies. Visit the Diocesan Museum, housing exquisite religious artworks, and explore the Etruscan Academy Museum, showcasing artifacts from the town’s ancient past.

Climb up to the Medici Fortress, which offers panoramic views of the surrounding Tuscan countryside. Discover the birthplace of renowned artist Luca Signorelli and admire his frescoes at the Church of San Francesco.

Indulge in authentic Tuscan cuisine at local trattorie, enjoying dishes made with fresh local ingredients. Take a moment to relax in one of the charming squares, savoring the tranquility and the captivating atmosphere.

A day trip to Cortona offers a wonderful blend of history, art, and breathtaking scenery, making it a memorable excursion from Siena that transports you to the heart of Tuscany’s cultural heritage.

Driving from Siena to Cortona only takes one hour, but the drip is significantly longer by public transportation. For this one, you are better off actually renting a car.

Radda in Chianti
Photo by ermess @shutterstock

Siena’s Surrounding Hilltop Towns

A day trip from Siena to the surrounding hilltop towns unveils the true essence of Tuscany’s charm and beauty. Explore the enchanting towns of Montalcino, Castellina in Chianti, and Radda in Chianti, each with its own unique character and attractions.

In Montalcino, immerse yourself in the world of renowned Brunello di Montalcino wine. Visit historic wineries, sample exceptional wines, and enjoy breathtaking views of the Val d’Orcia.

Castellina in Chianti captivates with its medieval architecture and lively atmosphere. Discover its ancient fortress, wander through the picturesque streets, and savor local delicacies at traditional trattorie.

Radda in Chianti boasts a charming medieval center surrounded by vineyards. Explore its narrow lanes, visit the ancient walls and the Church of San Niccolò, and taste the excellent Chianti wines produced in the area.

Experience the idyllic landscapes, taste exquisite wines, and immerse yourself in the authentic Tuscan ambiance of these hilltop towns surrounding Siena. Each town offers a unique glimpse into Tuscany’s rich heritage, making for an unforgettable day trip experience.

To make the most of all the small towns near Siena, either rent a car or joing a guided tour.

You may want to consider joining this small group Brunello di Montalcino tour that departs from Siena. You will be visiting the small town, 3 wineries and have lunch included in the price.

You could also consider this guided tour of Montalcino that goes to the Chianti Region and San Gimignano too. It also includes wine tasting.


A day trip to the Maremma region from Siena is an opportunity to explore the wild beauty of Tuscany’s coastal and inland areas. This diverse region offers pristine beaches, nature reserves, and picturesque towns waiting to be discovered.

Visit Pitigliano, known as the “Little Jerusalem” for its historical Jewish presence and unique architecture. Explore its ancient streets and visit the impressive Orsini Fortress.

Head to the coastal town of Talamone and relax on its beautiful beaches. Enjoy water sports, sunbathe, or take a boat trip to explore the nearby islands.

Immerse yourself in nature at the Maremma Natural Park, where you can hike or bike through enchanting landscapes, spot wildlife, and enjoy scenic views.

Indulge in local cuisine, such as traditional Maremman dishes like wild boar stew or acquacotta, a vegetable soup.

Discover the charming town of Grosseto, with its historic center and medieval walls, and visit the nearby natural hot springs of Saturnia for a relaxing soak.

A day trip to the Maremma region offers a perfect blend of natural beauty, coastal relaxation, and cultural exploration, providing a unique and diverse experience in Tuscany.

To better explore the Maremma region, consider renting a car. It will take you two hours to get to Pitigliano, for example. Getting there by public transport requires 3 times as much.

You should also read my posts A Short But Useful Guide To Pitigliano and How To Visit Saturnia Hot Springs.

This post was written by Samantha Karen, the visionary behind Sam Sees World, a travel blog that captures remarkable journey across the globe. As an intrepid adventurer in her twenties, Samantha embarks on a mission to embrace the unfamiliar, while documenting her experiences to ignite wanderlust in fellow explorers. On Sam Sees World you’ll find invaluable insights on the finest attractions and unforgettable encounters.

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Read about the best day trips from Siena - via @clautavani

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