Siena Tours

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.

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.

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.

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.

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.

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.

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.

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

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.

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.

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. 

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.

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.

Explore the beautiful Tuscan countryside in Italian style on an authentic Vespa scooter! Zip along hillside roads past historic villas, medieval villages, olive groves and vineyards. Stop at a local farm and winery for a fresh Tuscan lunch and tasting of Chianti wines. Drive your own Vespa, or ride with an experienced guide if you prefer.

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.

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.

Saddle up to explore the stunning countryside of the Chianti wine region on this private half-day horseback riding tour from Castellina. Suitable for all abilities, you’ll ride through scenic vineyards, olive groves, and medieval villages, and stop along the way for a typical Tuscan lunch and wine and olive oil tastings.

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.

Taste your way through Tuscany with this full-day wine tour of Montalcino, Pienza, and Montepulciano from Siena. Visit the charming town of Pienza and stop for one wine tasting each in Montepulciano and Montalcino.

Travel off-road through the Chianti valley on this day-long Tuscan wine tour. As your guide drives a vintage SUV, you'll gaze out at the gentle green hills and grapevine groves that typify the landscape. Stop at three wineries to sample several varietals of wine along with local products such as honey and olive oil, then relax over a traditional Tuscan picnic for lunch at your final stop. The tour starts and ends in the village of Castellina in Chianti.

Combine three of Italy’s most vital delights—wine, landscapes, and history—on this tour of the 15th-century Castello Tricerchi Montalcino wine estate. Exploring in a group no larger than 15, discover 600 years of history, including the chapel, the vineyards, and the cellars. Round off your visit with a tasting of three signature wines—Brunello di Montalcino, Rosso di Montalcino, and a Toscana IGP—paired with delicious local nibbles.

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.

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.

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.