Top Siena Outdoor Activities

If you've only got limited time in Siena, make sure you maximize your experience of the Tuscan hot spot on a sightseeing tour that includes skip-the-line entry. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo and stroll the streets with your guide, learning about the history of the place and leaving the navigating to someone else. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket.

Commence your journey at the iconic Piazza del Campo, immersing yourself in the vibrant atmosphere of Siena's renowned square. Delve into the city's history at Palazzo Pubblico, an architectural marvel serving as the seat of governance. Meander through historic streets, passing Palazzo Tolomei and Palazzo Salimbeni, both UNESCO-listed treasures. Continue to the Basilica of San Domenico, housing the relics of Saint Catherine, before a visit to the Sanctuary of St. Catherine of Siena. Admire the Baptistery and opt for a guided tour of the awe-inspiring Siena Cathedral, adorned with masterpieces of Italian artistry.

Explore the Tuscan countryside by horseback during this special small-group riding tour. Get access to unique corners of the Crete Senesi and Val d'Arbia landscape on rustic horseback trails. Tours are suitable for beginners and can be adapted to all riding levels. Riding helmets and complimentary soft drinks are included.

Get views you can't find anywhere else on this hot-air balloon ride over Tuscany. Starting in Siena, float above the countryside and take in scenic views of the low-rolling hills, some clad in grape vines, others crowned by a rustic ancient villa. Ascend as high as 2,000 feet (609 meters) and enjoy seeing the countryside and surrounding ancient villages and towns. Upon landing, enjoy a glass of sparkling wine to celebrate your experience.

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in Chianti and enjoy exclusive wine tastings at renowned estates. This tour is tailored for wine lovers and nature enthusiasts, offering a rich cultural experience through Tuscany's famous landscapes. With expert multilingual guides, savor the essence of Chianti’s rich heritage and take in the stunning scenery that has inspired countless artists and wine aficionados.

Get up close and personal with Tuscany’s ineffable scenery, and explore with ease, on a full-day tour by electric bike. Meet your guide in Siena, get familiar with your bike and helmet, and head into the Chianti Hills. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local farm/winery, where you can enjoy a traditional meal and generous wine tasting.

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.

Avoid the hassle of organizing transport and winery visits in Tuscany on your own. This small-group experience simplifies a day in Chianti, combining scenic travel with curated tastings at local wineries and time to explore Monteriggioni’s medieval charm. Enjoy a relaxed, well-paced outing that lets you focus on the region’s flavors and landscapes rather than the logistics.

Begin your unforgettable e-bike adventure in Castellina in Chianti, exploring the stunning Tuscan hills, vineyards, and historic villages at your own pace. Thanks to the electric assistance, this tour is accessible to all fitness levels, allowing you to fully enjoy breathtaking, postcard-perfect landscapes without the strain of challenging terrain. Combining gentle exercise, nature, and culture, this experience offers a truly unique way to discover the beauty of Chianti in a single day.

Avoid the challenge of navigating Tuscany’s rural roads and finding hidden countryside trails on your own with a guided horseback ride from Siena. This gentle journey carries you through rolling hills, vineyards, and olive groves, reaching quiet landscapes that cars can’t access. Ride at a relaxed pace while taking in the region’s natural beauty and rural charm without any planning or navigation stress.

Open the doors of the Sienese countryside on horseback and immerse yourself in the breathtaking landscapes of the Tuscan countryside. Cross vineyards, rivers, olive groves and roads with cypress trees. See and touch the flora and fauna of the Sienese countryside with a guide who will explain the various plants and animals and the history of the places you will encounter during the tour. The walks in the Sienese countryside are suitable for everyone, from beginners to experts. The horses used for the tours are well trained and calm, suitable for everyone. Stop for a picnic in the shade of the river in the Siena area or for a tour and tasting in a winery. Spend an unforgettable day and discover Tuscany with different eyes as you ride your horse, seeing and touching the historic countryside and traditions of Siena.

Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.

Discover the medieval charm of Monteriggioni on a private luxury e-bike experience, ride scenic Tuscan roads, enjoy a curated lunch paired with fine wines, and end with an exclusive winery visit scheduled just for your group. More than a bike tour, this is a curated Tuscan experience for couples, families, and small groups seeking an authentic, relaxed, and elevated way to explore. Led by a professional local cycling guide, far from crowded routes, your ride is tailored to your pace, allowing you to fully enjoy the landscape and timeless atmosphere. Premium e-bikes ensure a smooth, accessible ride with minimal effort. The experience concludes with a refined lunch and wine pairing in a carefully selected winery, featuring a private dining room reserved for you and a private cellar visit without overlapping guests. A seamless Tuscan day blending cycling, culture, landscape, and fine wine — designed for comfort, privacy, and authenticity.

Get an extra boost from your electric bike on a half-day bike tour of the Chianti region. Follow your guide through a picturesque landscape of gentle hills with vineyards, olive groves, and small villages, stopping at a 12th-century castle and a winery. Your tour includes a wine tasting, bottled water, and use of all necessary equipment.

This e-bike tour in the Val d’Orcia is unique because it combines sustainable travel with an immersive cultural and culinary experience in one of the most fascinating regions of Italy. Highlights include: The tour will start from our store in Via Giacomo Matteotti 1B in San Quirico d'Orcia. We will visit UNESCO World Heritage sites such as Pienza, Monticchiello and Bagno Vignoni, each of which offers breathtaking landscapes and a rich history. We will savor local flavors with traditional Tuscan dishes in a medieval village. We will explore the campaign responsibly with e-bikes, reducing your carbon footprint. Of course you will be accompanied by our guide! So what is included? E-bike rental; Helmet; Bottle of water; Padlock; Paper map; Our local guide; Lunch; It's not just a ride: it's an unforgettable journey in the heart of Tuscany!

Explore Tuscany outside Siena on this small-group day trip, visiting San Gimignano and Montalcino. Don't worry about hiring a car, as all transportation is arranged. Take a break from the city as you discover medieval architecture and scenic views of Tuscany, with ample free time in each of the hill towns. The tour also includes a visit to a Montalcino winery, with the opportunity to sample Chianti and Brunello di Montalcino.

The Best Way to Discover Siena: Scavenger Hunt & Self-Guided Tour. Play, learn, and walk! Explore at your own pace with a 100% self-guided activity. Start anytime (24/7) with no guides or schedules. Pause for a traditional Ricciarelli almond cookie in a local pastry shop or enjoy the medieval atmosphere of the Piazza del Campo and resume whenever you're ready—even the next day. This unique team-building activity is perfect for couples, families, and groups. The "Complete City" Package Everything you need in one app: Interactive Game: Solve puzzles and discover 10+ major attractions, plus hidden gems revealed along the way. Cultural Context: Read the history and legends of each site as you explore. Insider Tips: Access hand-picked local restaurant and shop recommendations. What you will visit: Pinacoteca Nazionale, Baptistery of St John, Palazzo Piccolomini, Loggia del Papa, Tower of Mangia, Pubblico Palace, Fonte Gaia, Santa Maria della Scala, Facciatone, and the Duomo di Siena.

The hot air balloon tour is a magical experience, a true adventure carried out in total safety by flight professionals. Our pilots, all with great experience, are ENAC certified commercial pilots. They will guide you during your trip, sharing with you detailed information about hot air balloons and satisfying all your curiosities about the flight and its navigation. Don't wait any longer, immerse yourself in this extraordinary adventure.

Discover the folklore of Siena with an exciting urban trek that will take you to discover the 17 fountains of the district. Drive 8 km through historic streets as you explore the city famous for the Palio no i suoi three-thirds. This treasure hunt-like tour offers a unique way to immerse yourself in the local culture and discover the secrets of Siena. - Explore the 17 historic fountains of the district on an interactive tour - Enjoy an 8 km trek with a difference in altitude of 200 meters - Discover the rich culture and folklore of Siena, famous for the Palio - An experience suitable for all lovers of walking and history

This quad tour is much more than just a ride – it’s a journey into the most authentic side of Tuscany, following scenic dirt and country roads far from mass tourism, with breathtaking views around every corner. In 4 hours, you’ll experience the perfect blend of adventure, culture, and nature, discovering iconic spots such as the Sentiero del Nobile, San Biagio Temple, Madonna della Querce, and the famous zig-zag cypress road. You’ll explore hidden gems you wouldn’t find on your own, including Gladiator movie locations, the legendary Quercia delle Checch, and peaceful woodland trails. With your expert guide, every kilometer will be safe, exciting, and full of local stories. The perfect experience for travelers who want to live the real Tuscany, filled with thrill and beauty.

Join a journey through the breathtaking hills of Chianti aboard our state-of-the-art and high-speed ATVs. Pass through scenic trails amidst the iconic landscapes of Tuscany, enveloped by fields of shimmering gold and verdant vineyards, immersing yourself in the unrivaled beauty of nature. Experience the excitement of riding our quadricycles firsthand as you explore the Chianti Area under the expert guidance of our seasoned escorts. Feel the adrenaline surge as you discover hidden treasures and marvel at the stunning vistas along the best routes. Join an exclusive winery experience with panoramic views, savoring every sip while absorbing the tranquility of your surroundings. After this journey, return to the starting point where your ATV adventure began, ready to share your unforgettable experience with friends and relive the magic of Chianti's enchanting landscapes.

Visit San Gimignano and Volterra the easy way from Siena, on an intimate small-grop tour. Head to the hilltop town of Monteriggioni, then stop for a while in UNESCO World Heritage–listed San Gimignano, with its medieval towers and views over the Tuscan countryside. Drop into an alabaster workshop in Volterra, then indulge in a rustic lunch at a Tuscan farm. Learn about local history and culture along the way.

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.