Chianti and Medieval Monteriggioni with Wine

7 Hours
Group Activity

From (USD) $83 Per Adult / $42 Per Child

Chianti and Medieval Monteriggioni with Wine

7 Hours
Group Activity

From (USD) $83 Per Adult / $42 Per Child

Choose your date


Choose an available time

Adult (Ages 12+)

Child (Ages 3-11)

    For Groups of 20 or more, please contact our GoTo Crew.


      JavaScript is required to complete booking

      Chianti and Medieval Monteriggioni with Wine

      San Gimignano, Italy
      From (USD) $83 Per Adult / $42 Per Child
      • Chianti region: Wind your way via air-conditioned coach or minivan with a multilingual escort over hills and past vineyards, letting the rich landscape of the Chianti region relax and inspire you.
      • Monteriggioni: Get your bearings in this charming medieval town as you stand at the village's gates: the Porta Romana, which faces south toward Rome, and the Porta Fiorentina, which faces the Tuscan capital of Florence. Walk the ancient walls that have withstood the ravages of time. Take time to enjoy a coffee or gelato.
      • Wine and snacks: Visit a charming wine estate, enjoy a guided tour of the wine cellars, then sample what the winery produces, paired with sliced cold meats, bruschetta, and salami. Before your day ends, stop at one more winery for a tasting of wine and olive oil.
      About This San Gimignano Tour

      When you whisper the word Tuscany, what comes to mind? Lush vineyards and olive groves? Tall grasses swaying in the breeze in the shade of mighty cypress trees? Gently rolling hills punctuated by stone villages and fortifications? If you answered "all the above," then you already have a good idea of what you'll see on this GoBe tour of the Chianti region.

      Settle in for a comfortable ride through one of the most beautiful parts of Tuscany. The countryside of the Chianti is famous around the world for producing delicious wine. You'll get to sample the fruits of these fields with a wine tasting following a guided tour of one of the region's many wineries. Gain insight into the various stages of wine production, then sip beautiful Italian wine while feasting on a selection of traditional Tuscan delicacies, like salami and bruschetta. One taste and you'll discover the gourmet traditions that stretch into the distant past.

      Speaking of the past, you'll come about as close as possible to time travel with a visit to the village of Monteriggioni. Completely walled in and protected by 14 medieval towers, Monteriggioni hasn't changed much in the last 800 years. Explore the town and you'll feel as if you stepped back into the middle ages.

      Round out your Tuscan experience with a second wine tasting and a sampling of olive oil, another of the region's specialties. With the warmth of the sun on your back and the warmth of wine in your belly, your journey through the Chianti region will be one you'll always remember.

      A remorseful ghost

      The famous fortifications of Monteriggioni were built to protect the interests of nearby Siena in the broiling medieval wars of Northern Italy. The castle served its purpose well for over 300 years, until one dark night in 1554 when the town was under siege by the army of Florence. As the situation in Monteriggioni grew desperate, Captain Giovannino Zeti, the commander and an ex-Florentine himself, decided to surrender in exchange for a restoration of his Florentine citizenship and property. The deal was struck and Monteriggioni fell. But for Zeti, all did not end happily. He became a pariah. People say that even to this day, Zeti's ghost wanders the streets of the fortress he failed to protect, crying out, perhaps attempting to explain his corrupt bargain.

      Getting prepared
      Tour Participation Requirements
      Great photo opportunities Great photo opportunities
      Bring money Bring money
      Bring photo ID Bring photo ID
      Wear comfortable shoes Wear comfortable shoes
      Wear Hat Wear Hat
      Wear Sunglasses Wear Sunglasses
      Swim wear Swim wear
      Cancellation policy

      Full refunds issued for cancellations made 7 full days prior to the date and time of requested services. Cancellations made within the 7-day and 72-hour window will receive a 50% refund of purchase total. Purchases are non-refundable inside of 72 hours.

      100 countries, 915 cities… limitless possibilities


      All our tours are offered by expert local guides & operators


      Head off the beaten path with our unique tours & activities


      You can rely on our team of travel industry experts

      General disclaimer

      Your order is subject to TourTrek's Booking Ticket Agreement, including all TourTrek and GoBe policies incorporated therein.

      Have you been on this experience?

      Write a Review

      Fields marked are required.

      Please enter your review.


      Looking for other experiences in San Gimignano?

      To book this tour for a large group, visit ourGROUPS PAGE for special discounted group rates