Siena, San Gimignano and Chianti Wine Tasting from Montecatini

11 hours to 11 hours 30 minutes (approximately)
Pickup offered
Offered in: English and 2 more

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. Stroll through vineyards, 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.

What's Included

Roundtrip shuttle from your hotel in Montecatini Terme
Chianti wine tasting in the countryside
Free time in Siena, Monteriggioni and San Gimignano
Expert multilingual tour leader
Guided tours in the cities
Gratuities

Meeting and pickup

Pickup points
You can choose a pickup location at checkout (multiple pickup locations are available).
Pickup details:

The tour leader / driver will wait for you in front of your accommodation, with the white van, for a maximum of 5 min. In any case, we will contact you the day before departure to confirm the pickup time.

Itinerary

Duration: 11 hours to 11 hours 30 minutes (approximately)
  • 1
    Montecatini Terme

    After a good breakfast, at 8:30 your tour leader will be waiting for you right in front of your hotel, to take you on a memorable trip to the heart of Tuscany! The tour leader will be with you throughout the day, providing valuable advice and sharing some curiosities

    1 hour 30 minutes Admission ticket free
  • 2
    Siena

    One of Italy’s most enchanting medieval cities, Siena is famous for its beautifully preserved historic center, narrow cobblestone streets, and striking Gothic architecture. Admire the magnificent Piazza del Campo, the stage of the legendary Palio horse race, and visit the Siena Cathedral, with its intricate façade and stunning interior. The city is full of hidden corners, charming squares, and centuries-old palaces that invite leisurely exploration. You can explore independently or join an optional guided tour to learn the fascinating history and legends of this timeless city

    3 hours 30 minutes Admission ticket free
  • 3
    Monteriggioni

    Chianti Grand Tasting: Signature Wines, Olive Oils, and Vinegars in the Cellar After experiencing the timeless charm of Siena, we’ll take a 30-minute drive to a picturesque estate set at the foot of the medieval Monteriggioni Castle. Stroll through the vineyards as you learn about the farm’s fascinating history, then indulge in a guided tasting of exquisite wines, fragrant olive oils, and artisanal vinegars. Each sip and flavor will be paired with a generous Tuscan platter of local cold cuts, cheeses, and freshly toasted bruschette. It’s not just a tasting—it’s a journey into the heart of Tuscany, where every product tells the story of its land.

    1 hour 30 minutes Admission ticket free
  • 4
    Monteriggioni

    Nestled atop a gentle hill, Monteriggioni is a perfectly preserved walled village that seems frozen in time. Its medieval walls and fourteen towers stretch around the village like a protective crown, offering incredible views over the surrounding Tuscan countryside. Walk along the ancient ramparts, explore quaint streets lined with stone houses, and feel the atmosphere of a fortress that has stood for centuries. Monteriggioni is a small but unforgettable jewel of Tuscany, rich in history and charm.

    45 minutes Admission ticket free
  • 5
    San Gimignano

    Known as the “Town of Towers,” San Gimignano is celebrated for its unique medieval skyline and beautifully preserved historic center. Wander through narrow streets lined with artisan shops, traditional gelaterias, and historic palaces. Discover charming piazzas, visit small museums, and enjoy breathtaking panoramic views over the rolling hills, vineyards, and cypress trees that surround the town. San Gimignano perfectly combines history, culture, and the unmistakable beauty of Tuscany.

    2 hours 30 minutes Admission ticket free
  • 6
    Montecatini Terme

    It's time to return: just hop aboard your van and enjoy the journey to your hotel in Montecatini Terme, reminiscing about the wonderful day spent and recording every single moment in your memory!

    1 hour 30 minutes Admission ticket free

Additional info

  • Infants are required to sit on an adult’s lap
  • Specialized infant seats are available
  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
Supplied by Ranieri Tour operator

Tags

Day Trips
Full-day Tours
Bus Tours
Private and Luxury
Cultural Tours
Historical Tours
Culture
Small Group
Spring Break

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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