Top Activities on the Ground in Siena

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.

See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

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.

Siena has one of the most intact medieval cityscapes in Italy, and with this walking tour, you can take in the hill town’s top sights in just two hours. Skip the hassle of following a map and instead head straight to the highlights with a guide. Stroll past Piazza del Campo, the town hall, and the Basilica of San Domenico, plus stop in the cathedral to marvel at works by Donatello and Bernini.

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.

We were born here in Tuscany, we rent our e-bikes at discounted prices. We will provide you with all the information about our places and the best itineraries, both for beginners and for the more experienced. Cycling in our countryside is something unique. Like in a movie ....

Skip the dry guidebook and hassle of following a map and discover the medieval streets of Siena with a personal guide at your side who knows how to bring its history to life. Take in the top sights plus find hidden-away corners far from the tourist crowds, learn history and lore that most tourists miss, and create a personalized itinerary that suits your pace and interests.

Take a break from the crowds in Siena, and spend an afternoon in the wine town of Montalcino on this group tour. Don't worry about hiring a car to get there, with transportation all sorted. Learn about Brunello di Montalcino wine and its production, along with wine tastings paired with local snacks. Admire views of the Tuscan countryside from this hill town as you discover the region’s generations-old winemaking traditions.

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.

Stroll the charming Medieval streets of a Tuscan hill town with this 2-hour private tour of Siena. Learn about Siena's hidden gems from a knowledgeable guide in between visits to its most popular sights.

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.

Once you have booked the tour, you can go to our rental point to pick up your bikes, so you can leave with our Virtual Guide who will accompany you step by step. The tour is a ring of about 23 km in the Maremma Natural Park, designed to be accessible and to be experienced in 2 - 3 hours including stops. You cycle among some of the most representative views of the park, with passages between ancient olive trees, Mediterranean scrub and coastal landscapes. The route includes the Collelungo area and the Collelungo Tower, with panoramic stretches towards the sea and towards the mouth of the Ombrone, one of the most characteristic environments of the protected area. It is an ideal tour for a relaxed half day. Bring water, a snack and a charged phone to enjoy the ride with serenity.

Once you have booked the tour, you can go to the rental point to pick up your bikes and leave with the Virtual Guide who will accompany you step by step. This ring e-bike tour starts near Siena and follows a fairly easy route, ideal for cycling calmly through Tuscan landscapes, history and small villages. The itinerary develops on minor roads with little traffic, dirt roads and short cycle paths, resulting in smooth and non-technical. From the first kilometers you enter the Sienese countryside, among hills, vineyards, cultivated fields, farms and tree-lined rows. Along the way you reach Montaperti, a town linked to the famous battle of 1260 between Siena and Florence, today immersed in a rural context of great charm. The tour also touches Pianella, Pievasciata and the area of Pieve a Bozzone, among authentic views, quiet streets and typically Tuscan atmosphere.

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.

Discover Siena from a different perspective on sightseeing and scavenger hunt of the city. Solve riddles and clues that lead to the next location, showing all the city highlights. Solve interesting puzzles, have fun, and learn new things about the city. Explore the city and find hidden gems at your own pace. Try a new type of experience with your smartphone, the perfect mix between a walking tour, sightseeing, and a scavenger hunt. Enjoy the tour in English, Italian

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.

Enjoy an unforgettable half day e-bike guided tour in Chianti region, one of the most known wine region in the World. You’ll cycle surrounded by vineyards and olive groves, while enjoying the amazing views of the Tuscany countryside. The bike tour will take you to PIevasciata before to come back to Siena along the Eroica route, on paved and gravel roads. During the ride we’ll stop in a winery for a Chianti wine tasting.

Easy fully guided e-bike tour to discover the beauty of the Maremma natural park in 1 day. With a 30 km circuit, you will enjoy a fun cycling experience by visiting the best spots in the park. You will see the ruins of an ancient and beautiful abbey, from the top of a hill overlooking the sea, you will enjoy a breathtaking scenery, from there the park will be at your feet. You will have a relaxing picnic on a wild beach, you will discover the "Porte Vinciniane" and you will take wonderful photos from the bird-watching refuge from which you can admire the unspoiled nature of this place. This is the perfect opportunity for an active day with your family or friends.

Discover the beauty of Belcaro hill, Siena, on a 6km hike that offers breathtaking views and an immersion in nature. This loop itinerary will take you through typical farms, vineyards and cool woods, making every step an opportunity to admire the Tuscan landscape. With a difference in height of 200 meters, it is ideal for nature lovers looking for an authentic experience just a few steps from Siena. - 6 km hike with open views and typical Tuscan landscapes - Moderate level loop itinerary - Discover farms, vineyards and cool woods along the way - Perfect for lovers of nature and Tuscan culture

Come with me to discover the lost town of Vitozza! Walk with me through the breathtaking city of Sorano and then descend into the hidden trails underneath to finally reach the ancient town of Vitozza, the Matera of Tuscany. In this town people dug their houses inside the tuff rock since time immemorial and lived in it until the 18th century. We will enter inside some of these houses and wander around the remnants of the old castles (Vitozza had 3) that overlook the town, to see how people used to live in such an incredible environment. At the end of the hike it would be possible to taste a glass of local wine in an incredible wine cellar dug inside the tuff rock. ATTENTION: The wine tasting is optional and available only upon request.

Castiglione della Pescaia is a fortified village overlooking the sea, a balcony overlooking the Tyrrhenian Sea. From here you can enjoy a panorama of rare beauty, among the most "rich and sweet in the Maremma". The view ranges from the Uccellina mountains to the heights of Punta Ala, from the coast drawn between the intense green of the pine forest and the blue of the sea; below, in the plateau (ancient kingdom of Lago Prile), the marsh of the Diaccia Botrona stretches out, with the elegant and evocative Red House in the foreground, one of the most representative examples of civil engineering that recalls the impressive reclamation work desired and built under the Lorraine. The well-preserved village has exposed stone streets, ancient portals, niches and arcades that chase each other ... all enclosed by mighty turreted walls. Castiglione della Pescaia is one of the most efficient tourist resorts of the Tyrrhenian Sea and in its canal port cradled fishermen's boats and "habituès" boats.

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition to it, this tour has an Arts footprint. We'll lead you through some hidden sculptures, located throughout the landscape, as a warm up to our stop at the Chianti Sculpture Park, where you'll visit some contemporary sculptures and installations. We'll build on to the arts experience by stopping at the hamlet of Scopeto, where the film "Letters to Juliet" has been shot. Least, but not last, it will be wine time right after at the Scopeto Winery, where you can further develop your reconnaissance of the territory by tasting one of its maximum expression: the Chianti Classico. We then, climb back to our comfortable ebikes to return to Siena

Explore the landscape of Tuscany on a private, full-day cycling tour from Siena. With the full attention of your guide, follow a route along the Via Francigena, an ancient pilgrimage route that once linked Canterbury to Rome and a popular destination for photographers. Rest and refuel after a day of activity with a three-course lunch and wine pairings at a Tuscan vineyard. Hotel pickup and drop-off is included.