This beautiful excursion takes you through the delightful hills of the Chianti countryside

Siena, San Gimignano and Greve in Chianti with Wine Tasting in a typical Winery

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Travel through the delightful hills of the Chianti countryside


  • 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
  • Picturesque, medieval village famous for its colors and charm


  • Transport
  • Tour escort
  • Local guide
  • Museums entrance fees
  • Wines tasting and local products sampling


  • Optional Gratuities
  • Lunch

Please Note

  • It is recommended that participants wear comfortable shoes.
  • The English language is always guaranteed for the tours. Local guiding service in Italian, Spanish, French and German is always guaranteed for a minimum of 4 people.
  • CANCELLATION POLICY: there will be no penalty for cancellations of tour or service communicated in writing to Caf Tour & Travel up to 48 hours before departure time of the tour or service. Less than 48 hours before departure time of tour or service 100% of the total price will be due and no reimbursement will be granted. No reimbursement will be granted to any client who is not at the place of departure at the time established; similarly, no reimbursement will be granted to clients who lose contact with the guide or who do not complete the tour.
  • This tour has 2 passenger minimum requirement and is subject to cancellation if this minimum is not met. In the unlikely event of such a cancellation, a refund will be provided or an alternative will be offered
  • Children policy: under 3 years free, from 4 to 12 years 50% discount.
  • Tour departs at 08:30am from Piazzale Montelungo at Gray Line Florence - Caf Tour & Travel yellow Street Sign. Please arrive at the meeting point 15 minutes before
  • This tour does not operate on Dec 25 or Jan 1.

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100% of reviewers liked this tour
Jan 12 2017
loved the tour, great places to visit, very good tour guide guide and bus driver.
Dec 28 2016
Oct 26 2016
Loved the way the tour was conducted. So many places seen, so much history was related by local guide esp in siena. And there was enough free time to have one's own experience of each place. Very good!
Feb 16 2016
Very nice cities and landscape. We hoped for a visit to a vineyard, but this was not included. We did taste local wine and got a poosibility to buy chocolate and sweets.
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As we approach Siena, you will see an enchanting view of Monteriggioni from the panoramic windows of the bus; enjoy the spectacle of a small, medieval village enclosed by its famous walls, which remain standing to this day.

Upon arrival in Siena, we will meet up with a local guide (at our disposal for two hours), who will take us on a comprehensive tour of the historic center. We'll start at the famous Basilica of San Domenico, a jewel of Renaissance art that was built in the 13th century and dedicated to St. Catherine of Siena.

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

The tour continues with a visit of the Museum and Oratory of a Contrada*(exclusive opening), where we can experience the atmosphere of the authentic and most intimate soul in 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 for 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 that are normally not disclosed to the public.

The guided tour of Siena ends in its most beautiful square, Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point. You'll have free time to continue exploring the city and to eat lunch (not included).

In the afternoon, we reach San Gimignano, a small but world-famous walled town located on a hilltop. It has remained intact throughout the centuries, and is renowned for its tall towers, wonderful frescoes, and many other valuable works of art: here we will be led to the heart of the historical center where you will have free time to explore its fascinating discovery.

In the evening, crossing the gently rolling hills of Chianti , we will arrive at a small and typical winery where, after a short walk in the ancient vineyards, we will visit the suggestive barrique room and taste four fantastic wines. This local sampling produced zero food miles. Finally, we will 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.

  • When the Museum and the Oratory of the Contrada are not accessible, will be replaced with the interior visit of the Cathedral or another site of particular historic and cultural interest