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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.

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 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.

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.

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.

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, town hall, and Basilica of San Domenico, plus stop in the cathedral to marvel at works by Donatello and Bernini.

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.

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.

Discover Tuscany's stunning landscape, culinary delights and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Led by a local guide, admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with an optional visit to a winery. Group size is limited to eight people, ensuring personalized attention from your guide.

Discover the medieval streets of Siena with a personal guide at your side, and find hidden-away corners far from the tourist crowds. Create a personalized itinerary on this private 3-hour tour, departing from Piazza del Campo in the morning or afternoon. Walk past major monuments as you explore on foot.

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.

Sip world-class wine and watch the sunset on this day trip to Chianti and San Gimignano from Siena. Led by an expert guide, explore the medieval town of Monteriggioni and visit Chianti wineries for tastings. Then, head to the UNESCO-listed San Gimignano to see the sunset as you savor a traditional Tuscan dinner in a farmhouse overlooking the hills. Group size is reserved for eight people to keep the experience as intimate as possible. 

Get medieval on this guided tour from Sienna to San Gimignano and Volterra. Head to the marvelously diminutive hilltop town of Monteriggioni and then stop for a while in UNESCO world Heritage-listed San Gimignano with its plethora of medieval towers and commanding views over the Tuscan countryside. Finally, spend some time in an alabaster workshop in Volterra before indulging in a rustic lunch at a Tuscan farm. This small-group tour is limited to just eight people, ensuring plenty of personalized attention from the guide. 

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.

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.

Discover the fine wines and rich historical heritage of Chianti on a full-day trip from Siena. With a knowledgeable guide, travel through the sublime Tuscan countryside and visit castles cradled by rolling green hills and sprawling vineyards. Visit Castello di Brolio, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Ama. Pleasure your palate with fine samples of Chianti Classico wine during tasting sessions and feast on a traditional Italian lunch during your tour. Enjoy an intimate atmosphere on this small-group tour, limited to only eight people.

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.

Experience the Tuscan countryside from a perspective rare to visitors on a private Vespa tour with round–trip transport from your Siena hotel. In addition to navigating for you, your guide ensures the best views and stops for photo opportunities along the way. The day includes a Tuscan–style lunch and complimentary wine tasting with vineyard views.

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.

Participate in the Tuscan tradition of grape stomping on a private four-hour tour in the Chianti hills.  Explore a local vinyard with your private guide and discover the wine making process. In addition to living out your Italian dreams of crushing grapes with your bare feet, you’ll also enjoy a wine tasting, along with a homemade lunch.

Come and discover Siena and its incomparable historic centre with our morning walk that aims at showing you the main attractions but also discovering some hidden gems. You can understand this wonderful medieval city in many ways and taste some of its best local products.

See more of Tuscany with a private guide, and book a day trip to Monteriggioni, San Gimignano, and Chianti for your personal group of family or friends. After a pickup direct from your Siena hotel, you’ll travel by private vehicle into Tuscany to spend free time in the hill towns of Monteriggioni and San Gimignano. Hear tales of Tuscany’s history as you travel, and then return to Siena via Chianti, where a stop can be made for lunch or even a wine tasting (both own expense).

After a morning spent exploring the streets of Siena, see to your appetite with a lunchtime Sienese food tour. Enjoy a beautiful antipasto before enjoying a meal in a traditional Tuscan tavern. This culinary tour fits neatly into a long lunch break, making it easy to fit this tour into a full day of sightseeing.

Hop on a scooter to explore the rolling landscapes of Chianti on this 7.5-hour Vespa tour from San Gimignano. Settle on a Vespa and ride around vine-coated hills, cypress groves and old villages, soaking in the views of this famous wine producing region. Your tour includes a wine tasting and lunch, plus the option to ride as a passenger with an escort driver or to upgrade to drive your Vespa.