Siena Tours

Take the stress out of planning a day in Tuscany on this half-day small-group tour of the Chianti wine region from Siena, including transport. Enjoy an air-conditioned ride over to two popular wineries to taste wines and oils locals love. Plus spend some free time in Monteriggioni, and catch a glimpse of the town’s well-known medieval castle.

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this day trip from Siena. Led by an expert guide, travel to the cellars to learn about the production process and meet the locals behind the delicious red wine. Then, pause at a family-run winery for an authentic Tuscan lunch before exploring the village of Montalcino and the abbey of Sant'Antimo. Stop for additional tastings along the way and conclude with transportation back to Siena. Group size is reserved to eight people for a more intimate experience.

There’s only one way to see Tuscany: from above. And the best way to do that is via hot air balloon. This 1-hour hot air balloon flight from Siena takes you above Tuscany to get a breathtaking view 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) as you get a commanding view of the countryside and surrounding ancient villages and towns. Upon landing, enjoy a nice glass of sparkling wine to celebrate the amazing trip through the Tuscan heavens.

Leave the planning and driving to someone else on this daylong winery tour specializing in Brunello di Montalcino—a wine produced in the vineyards around the town of Montalcino. Visit historic wine cellars and vineyards, have lunch in a winery in the hill town of Montalcino itself, and visit a winery in the nearby Nobile di Montepulciano area for good measure.

Explore southern Tuscany with your own private guide on a full-day wine and food tour from Siena. Visit Pienza, Val d'Orcia, Montalcino, and more as you take in small towns, a 14th-century monastery, and sample Brunello di Montalcino, the famous wine of the region. Ride in comfort in a luxury Mercedes vehicle with a private guide who shares the best of the region.

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.

Spend an enchanted evening at a winery estate in Chianti on this half-day tour from Siena. Travel through the scenic landscape of Tuscany to reach the winery estate, then take a tour of the winery, capped off by wine tasting. Afterward, find your seat at a festively decorated table situated in the vineyards for a barbecue dinner accompanied by wine and music.

Tuscany is world-renowned for its wine, so ensure you get an insider’s glimpse into the industry during a tasting tour of the vineyards surrounding Siena. Receive personalized attention in a small group limited to 12 as you visit a historical cellar and educate your palate to recognize subtle flavors with the help of a sommelier. Plus, a choice of morning or afternoon departure means you can slot this tour into even the busiest of sightseeing schedules.

Take a tour of Siena with a local, and get the lowdown on the city that the guidebooks can’t give. In a small group that’s limited to just ten people, you’ll explore Siena by foot to discover the history behind the UNESCO-listed Piazza del Campo and its nearby monuments, and sample classic food from Tuscany with Chianti wine.

Spend an afternoon in the wine town of Montalcino, tasting the prestigious Brunello di Montalcino and learning about wine production. This tour from Siena that tasting of local wine paired with salami and cured meat. Admire views of the Tuscan countryside from the pretty hill town and discover the region’s generations-old winemaking traditions.

Visit San Gimignano, Monteriggioni, and Montalcino on a day trip from Siena, and discover medieval architecture, wine, and stunning views of Tuscany. With ample free time in each of the hill towns, the tour also includes lunch at a Monteriggioni winery plus samples of Chianti and Brunello di Montalcino wine.

Take a private cooking class with a local chef-instructor at their home during this half-day culinary experience in Siena. Learn to prepare a 4-course Italian meal, then enjoy the lunch or dinner that you helped to make with your host. You’ll also sample a selection of red and white wines from Tuscany.

Giddy up! Traverse the hills of Tuscany via a unique mode of transportation with this guided horseback tour from Siena. Roam the rolling hills, some clad in grapevines, others blanketed with olive groves, as you and your horse calmly explore the region. Pass through rustic villages, all while learning about the history of the place from your guide. See stunning scenery that you would not have had the chance to encounter.

When visiting Florence, spend a delicious day winery hopping in the renowned Chianti wine region. Visit three of the best estates for tastings of Chianti Classico and other top varietals, plus a gourmet lunch of Tuscan specialties. There's also time to soak up countryside culture and history with a stop in San Gimignano or Monteriggioni, two of Tuscany’s best-preserved medieval towns.

Are you a curious and thirsty traveler looking to uncork some of Tuscany's wine secrets? Come to the Tuscan Wine School for an informative and fun class to learn about Tuscany's most important, traditional wines led by an English-speaking local expert. Discover the history and legends behind Tuscany's most significant wines and learn to swirl, smell and sip your way through the different types and styles of wine. The tasting of wines is enhanced by a series of different sample foods, and food pairing tips will be discussed, leaving you able to make better choices when choosing from local names in the city's restaurants.

Indulge in one of Italy's most beautiful cities, Siena, during this sightseeing tour. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo, the superlative square that is home to the Palio, a wild horse race that takes place every July and August. Stroll the streets with your guide learning about the history of the place. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket. 

Discover the treasures of one of the most beautiful cities in the world with a monolingual local guide and immerse yourself in its art, culture and traditions as the horse race the Palio, which takes place twice a year. With a small group you will explore the best that Siena has to offer. Your guide will accompany you along the ancient streets of Siena through the most beautiful sites such as: Piazza del Campo, Palazzo Pubblico, Palazzo Tolomei, Palazzo Salimbeni, the ancient via Banchi di Sopra, the Basilica of San Domenico, the Sanctuary of St. Catherine of Siena, the Baptistery and the Cathedral. You will visit also the inside of the Cathedral (ticket not included), if you choose the Cathedral option, where you will admire the works of art of important Italian artists, such as Michelangelo, Donatello and Bernini.

See the hills of Tuscany in true Italian style with this action-packed day trip on a Vespa scooter from Siena. Set off on your scooter through the Tuscan countryside, your guide leading the way, as you and other scooter-riding participants make your way to a Chianti winery for lunch. Tour the vineyards and cellars, sample some wine and indulge in an antipasto lunch before heading back to Siena.

Explore Tuscany beyond Florence or Siena with a full-day wine tour. Get picked up at your hotel for a small-group tour to visit local wineries and relax over lunch in the town of Montepulciano. Learn about how wine is made and taste regional specialties including Brunello. Meet the people behind the wine without the hassle of a rental car or navigating between wineries.

See Tuscany in classic Italian style by exploring the rustic region via a vintage Fiat 500, the classic, beloved and diminutive Italian automobile. Get picked up at your hotel in Siena and then ride to the stunning hilltop town of Monteriggioni, cruising through the rolling hills of Chianti along the way. Stop at a local vineyard and sample some delicious Italian wines with a hearty lunch of local fare. Follow the guide in a caravan. The number of participants on this small-group tour is limited to just ten, so you’re sure to get plenty of personalized attention from the guide.

Following our experienced English-speaking guide, you will live “la Dolce Vita” driving an authentic Vespa 125cc. We propose you two itineraries to choose: a) We will take you to a small medieval village situated in the heart of the area, driving along the enchant of Orcia Valley (Val d’Orcia) which is UNESCOs Heritage. or b) Trasimeno Lake will offer you its wonderful landscape with the history of the old town and the peace of its waters. The tour will end up in our winery. Here you’ll discover all steps of wine making and you’ll enjoy a fantastic tasting of our wines accompanied by a delicious Tuscan menu with a first choice, a platter of cheeses and cured meats, plus dessert. Driving experience on a scooter is requested. Those who do not feel confident enough about riding on their own, can opt for riding with one of our expert escorts. We provide: Original Vespa scooter (automatic transmission) and Helmet A valid driving license is required

Ciao, I’m Alessandro, the owner of Siena Tartufi. I’m a truffle hunter from 20 years. I have 3 dogs, Moka and Freddie a Lagotto Romagnolo and Pepita, a black Labrador. I really love going outside with my dogs looking for truffles . In every season there are different types of truffle that will be collected and you can do it with us... My hobby is my job and my passion!

Get an authentic taste of northern Italy on this 4-hour cooking class in Siena. Led by a local chef, learn how to craft a delicious spread of Tuscan favorites, including bruschetta, crostini and pici, thick, hand-rolled pasta originating in Siena. Afterward, enjoy the fruits of your labor as you savor your creations with your group and a glass of vino. Group size is reserved to 15 to keep this experience as intimate as possible.

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.