Top Siena Wine Tasting Tours

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 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.

Sample Italy's flagship Brunello di Montalcino wine in the hills where it’s produced with this exclusive winery tour and tasting at a medieval castle. Join a sommelier for a stroll through the vineyards to learn about the history and production of Brunello at this family-run estate, then relax over a tasting that pairs three different wines with local specialties. Cap off your experience with a three-course Tuscan lunch.

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.

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. 

Visit San Gimignano and Montalcino on a small-group 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 Montalcino winery plus samples of Chianti and Brunello di Montalcino wine.

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.

Take your Tuscan wine tasting to the next level with this one-of-a-kind experience set in an authentic medieval aqueduct hidden below the historic city center. Settle in among brick vaults and tunnels dug directly into the stone to sip a selection of Brunello di Montalcino and Super Tuscan wines from the vineyards of Siena and Chianti, paired with local cheese.

Sip Tuscan wine in a medieval castle during a tasting session in Montalcino. Hosted by a professional sommelier, the experience ensures you get the lowdown on the wine as you taste it. Enjoy three varietals including a glass of the prestigious Brunello di Montalcino DOCG, along with local bread or breadsticks and olive oil.

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.

Tuscany is known for its excellent vintages, but the world of Tuscan wine can be overwhelming for a novice. With this informal wine class, you’ll get your bearings and learn to recognize the most important and storied wines of Tuscany. Delve into the history of Tuscany’s wine production, discover the different wine-producing areas and grapes, and sample a number of reds and whites from the region.

Explore some of the most popular Tuscan hill towns on this day trip to Siena, San Gimignano, and Monteriggioni from Florence. Enjoy visiting each town independently while also having the round-trip transportation organized in advance. Learn about the famous region from the tour leader on board the bus, listening to informative commentary as you travel.

A mere 6 km from Siena, immersed in the poetic and permeating beauty of the Senese countryside the small San Giorgino church, has since 1109 placidly observed the vineyard and olive trees of the surrounding fields, which have been under the stewardship of our family since 1977, where with love, tradition, dedication and innovative spirit we have produced wine and oil. We love to define our company as a harmoniously multifaceted reality that holds a myriad of souls inside of it. By fine tuning each one of the contrasting elements together, like an orchestra, we give life to unique products that are recognizable, inviting, and sincere: symphonies of genuine tastes, rooted in the culture of the land. This reality begins with our family: we are in 8 and all contribute in the company with our own specializations, following the entire production process, from the preparation at the vineyard, to the last step of commercialization.

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.

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.

Discover the fine food and wine of the Siena region with your own private guide on a full-day tour in Tuscany. Taste some of Tuscany’s great wine and cheese, take a cooking class, go to wine estates, and have a delicious lunch. Suitable for groups of up to eight people.

Discover the history of the Chianti region, visit Monteriggioni (a medieval castle and fortress), and stop by a boutique family-owned winery on this tour from Siena. Taste four different Chianti Classico wines paired with delicious Pecorino cheese, bruschetta, salame, and olive oil. Explore the historic cellar and learn about the wine production process.

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.

Taste your way through Tuscany with this full-day wine tour of Pienza and Montepulciano from Siena. Visit the charming town of Pienza and stop for one wine tasting each in Montepulciano. You also enjoy plenty of free time to explore each village on your own.

Discover the best of Siena’s traditional cuisine and food scene with the insights of a local insider guide on this small-group food tour. Set off with your foodie guide and group of just 12 fellow gourmands to visit the top artisan food shops, market stands, and other landmark eateries to sample a range of savory and sweet delicacies. Feast on charcuterie boards, pici pasta, ricciarelli cookies, and more as you explore the old town.

The owner will take you on a walk through the vineyards and olive groves of the Estate, we will visit the church of San Giorgino from 1100 to then go to the cellars and find out how our wine is born and ages (vinification and aging cellar in barrels and aging in bottle). At the end of the walk, tasting of wines and typical Tuscan products with one of the owners of San Giorgio a Lapi.

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.

Taste the best Tuscan and national wines, accompanied by a selection of tasty local pecorino cheeses in a suggestive Etruscan crypt. My wine shop is one of the oldest in Siena and specializes in Brunello di Montalcino as well as presenting famous labels such as Masseto, Sassicaia, Ornellaia and other top wines. An explosion of taste you won't forget!