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Walking tours

Siena with Palio’s Contrada, San Gimignano and Monteriggioni with Chianti wines and food tasting

Availability: Daily
Duration: 1 day
Language: English, Italian, French, Spanish, German
Mobile voucher accepted
Do this because
  • Visit of two stunning UNESCO World Heritage Sites
  • Wonderful views of Tuscan rolling hills and Chianti countryside
  • Stop at a typical winery with tasting of four excellent Chianti wines
What to expect

Have a unique, authentic, and exclusive experience of Siena! Visit its magnificent ancient city center and discover the secrets of its “Contrade” (districts). Continue your journey through time by visiting San Gimignano and Monteriggioni. On the way back to Florence, taste famous wines and various typical delicacies. Along the way that will lead you to Siena, you will stop at San Gimignano, a small and world-famous walled town located on a hilltop, which remained intact through the centuries, renowned for its tall towers, wonderful frescoes and many other valuable works of art: here, you will be led to the heart of the historical center, where you will have free time at disposal for its fascinating discovery.

Upon arrival in Siena, after free time for lunch (not included), you will meet the local guide, who will take you on a comprehensive guided tour of the historic center, starting from its most beautiful square, Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point, and a pleasant walk through the Museum and Oratory of a Palio’s Contrada(*) (exclusive opening), where you can experience the atmosphere of the authentic and most intimate soul of the town. The “Contrade” (districts into which the city is divided) are the real core of local social life, where inhabitants of each district compete with each other, as they devote themselves to the preparation of the famous Palio horse-race. The Museum of a ”Contrada”, as well as its Oratory, is, therefore, the heart of the district. It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art, which are normally not disclosed to the public. You will proceed then to the spectacular Cathedral of the 12th century, of which you can admire the magnificent architecture and the splendor of the polychrome marbles.

In the afternoon, you will stop at the charming historical hamlet of Monteriggioni, an amazing small medieval village enclosed by its famous walls, which remained standing to this day, free time for inside visit. Then, crossing the gently Chianti rolling hills, you will arrive at a cozy winery, where you will taste four fantastic wines and sample balsamic vinegar and “zero food miles” products, to end this memorable experience in the heart of Tuscany with delicious Tuscan flavors (please note that the order of the visits may change).

(*)When the Museum and the Oratory of the Contrada are not accessible, will be replaced with another site of particular historic and cultural interest.

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What's included
  • Transport
  • Tour escort
  • Guided Visit in Siena with professional local guide including a Contrada Museum and Oratorio - Exclusive opening (depending on the selected option)
  • Siena Cathedral and Libreria Piccolomini Guided Visit and admission (depending on the selected option)
  • Sampling of Wines and “zero food miles” products
What's not included
  • Optional Gratuities
  • Lunch
  • Hotel pick-up and drop-off
Reduced price
  • Child (4-12)
  • Infant (0-3)

Piazzale Montelungo

Meeting point:

Gray Line Florence - Caf Tour yellow Street Sign

What to remember
  • It is recommended that participants wear comfortable shoes and appropriate clothes to visit museums or places of worship
  • There is a possibility of cancellation after confirmation if the minimum number of passengers is not reached. In the event of this occurring, you will be offered another date or an alternative tour or full refund
  • The local guide service could be provided in two languages. The tour escort service is multilingual
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Daily at 8.30am (please reach the meeting point 15 minutes before)

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Caf Tour & Travel - Gray Line Florence
Booking fee
Good news! No extra fees are applied to this booking.
Cancellation policy
Unfortunately, we can't offer you a refund nor can we change or cancel your booking for this particular product, due to our partner's policy.

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