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Day trips & excursions

Siena, San Gimignano and Greve in Chianti tour with wine tasting in a typical winery

Based on 20 reviews
Availability: Every day
Duration: 11 hours
Language: English, Italian, French, Spanish, German
Mobile voucher accepted
Do this because
  • Visit two UNESCO World Heritage Sites
  • Siena: exclusive opening of intimate and secret sights
  • 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 and authentic experience of Siena and its traditions, thanks to a full guided tour of the old town and an exclusive admission to the heart of a typical contrada (district). Discover San Gimignano – the "Manhattan of the Middle Ages"! – and stop at a winery located in the Chianti area. Finally, be captivated by the colors and charm of one of the most picturesque Chianti villages.

Along the way that will lead you to Siena, the first emotion is the enchanting view of Monteriggioni from the panoramic windows of the bus: the amazing spectacle of a small medieval village enclosed by its famous walls, which remained standing to this day.

Upon arrival in Siena, you'll meet the local guide, at your disposal for two hours, who takes you to a comprehensive guided tour of the historic center, starting from the famous Basilica of San Domenico (inside visit), a jewel of Renaissance art built in the 13th century and dedicated to St. Catherine of Siena, of which preserves a relic.

You will walk along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, until you reach the spectacular Cathedral of the 12th century, of which you can admire the magnificent architecture and the splendor of the polychrome marbles.

The tour continues then with the visit of the Museum and Oratory of a 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 It is an intimate and secret place containing historical documents and wonderful relics of the famous Palio, as well as magnificent works of art which are normally not disclosed to the public.

The guided tour of Siena ends in its most beautiful square, Piazza del Campo, of which the Town Hall is the focal point. Free time to continue exploring the city and for lunch (not included).

In the afternoon you'll reach 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 until the heart of the historical center, where you'll have free time at disposal.

In the evening, crossing the gently Chianti rolling hills, you'll arrive in a small and typical winery where, after a short walk in the ancient vineyards, you'll visit the suggestive wine barrel room and taste 4 fantastic wines, sampling also locally produced zero food miles. Finally, you'll stop in the picturesque village of Greve in Chianti, to admire its famous main square flanked by arcades and browse through the local artisan shops to end a memorable experience in the heart of Tuscany.

Discover the budget version of this tour (without guide in destination)

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What's included
  • Stop in Siena (3 hours and 30 minutes approx.) with 2 hours of guided tour with professional local guide, inside visit to Basilica of San Domenico and Contrada Museum and Oratorio (exclusive opening)
  • Stop in San Gimignano (1 hour and 30 minutes approx.)
  • Stop in the Chianti area with winery guided visit, sampling of wines and zero food miles products
  • Free time in Greve in Chianti
  • Caf Tour's staff assistance at the meeting point
  • Transport
  • Tour escort
What's not included
  • Gratuities
  • Hotel pick-up/drop-off
Reduced price
  • Children (ages 0-3): free of charge
  • Children (ages 4-12): reduced
  • Please note that you must show a document proving children’s age upon request

Piazzale Montelungo

Meeting point:

In front of Caf Tour & Travel - Gray Line yellow street sign.

What to remember
  • *When the Museum and the Oratory of the Contrada are not accessible, they will be replaced with the interior visit of the Cathedral or another site of particular historic and cultural interest
  • Please note that the order of the visits may change
  • For small groups, up to 8 pax, the tour escort could be replaced with an English speaking driver-guide, maintaining unchanged the entire program of the excursion
  • Comfortable shoes are suggested
  • Walking pace: moderate
  • This tour may be conducted in 2 languages
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  • Duration of the tour: 08.30am - 07.30pm
  • Check-in in time at the meeting point: 08.15am
  • From November to March: Monday, Wednesday, Friday, Saturday
  • From April to October: every day
  • Tour not available on 25 December and 1 January
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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.
What people say about this experience
Based on 20 reviews
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Great (8)
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