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Montecatini Terme to San Gimignano

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Chianti Views

Tuscany’s Chianti region is a hassle to explore with public transport, and the country roads are confusing to navigate on your own. With this private day tour, cover more ground and focus on the views rather than the map with a private driver. Set off directly from your accommodation in Montecatini for a scenic drive through Chianti, including stops at two picture-perfect villages. Cap off your day with time to explore San Gimignano.

Montecatini Private Day Trip To Chianti & San Gimignano

9 hoursFree Cancellation

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Siena, S.Gimignano & Chianti Tasting Small Group from Montecatini

Departing from Montecatini Terme with roundtrip hotel transfer, this full-day escorted tour immerses you in the heart of Tuscany. Explore Siena, with its medieval streets, Gothic cathedral, and charming squares. Wander its historic alleys, admire centuries-old palaces, and soak in the vibrant local atmosphere. Then visit a charming estate at the foot of Monteriggioni Castle. Discover the estate’s history, and enjoy a guided wine tasting along with fragrant olive oils and artisanal vinegars, paired with traditional Tuscan cold cuts, cheeses, and bruschette. Continue to Monteriggioni, a walled medieval village frozen in time, before concluding in San Gimignano, the “Town of Towers,” with its artisan shops, narrow streets, and panoramic views over the Tuscan hills. Return to Montecatini Terme with unforgettable memories of Tuscany’s history, flavors, and charm.

Siena, S.Gimignano & Chianti Tasting Small Group from Montecatini

11 hours to 11 hours 30 minutesFree Cancellation

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Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme

Check out the must-see towns of Tuscany on a day trip to San Gimignano, Siena, and Chianti from Montecatini Terme. Travel with a tour leader so you get the lowdown on the towns’ history, then explore each one. Hear tales of the Palio di Siena horse race and visit Piazza del Campo, walk amid the medieval San Gimignano towers, and savor Chianti wine and pecorino cheese at an authentic Tuscan wine estate. It's a great way to experience Tuscany with minimum fuss.

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme

9 hoursFree Cancellation

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Bella Toscana - San Gimignano plus 2 Chianti Wineries and lunch

Bella Toscana - San Gimignano plus 2 Chianti Wineries and lunch

8 hoursFree Cancellation

Price varies by group size

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Head south into the Tuscan hills on a day trip from Montecatini Terme to the medieval towers of San Gimignano. These excursions explore the UNESCO–listed town center, featuring the Piazza della Cisterna and the Collegiata’s 14th-century frescoes. While walking the stone streets, you can visit local gelaterias or climb the Torre Grossa for views of the surrounding vineyards. Most itineraries add a stop at a nearby Chianti estate for a wine tasting or a visit to a traditional olive oil mill. Guided tours handle the rural navigation and provide historical context on the rivalries that shaped this 13-towered skyline.