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San Gimignano, Siena, Monteriggioni, Chianti: Day Trip with Wine Tasting & Lunch

Travel through the enchanting landscapes of Chianti and enjoy stunning Siena, marvellous Monteriggioni and the medieval Manhattan of San Gimignano. Along the way, you will visit a cozy winery and taste three fantastic wines.

Your memorable journey starts with the charming San Gimignano, a world famous walled town located on a hilltop, which remained intact through the centuries. This stunning town is renowned for its tall towers, wonderful frescoes and many other valuable works of art. Your expert guide will lead you to the historical center, where you will have around two hours of free time for a fascinating discovery.

A short distance from San Gimignano you will visit the charming historical hamlet of Monteriggioni. This amazing small medieval village is enclosed by its famous walls, which remained standing to this day. Here, you will have free time to explore inside.

From Monteriggioni, crossing the gently Chianti rolling hills, a short ride will take you to a cozy Winery, where you can relax and enjoy the fantastic world of Chianti. Enjoy tasting three fine wines and balsamic vinegar followed by a delicious Chianti style three course lunch with “zero food miles” products which ends with "cantucci e vin santo".

Later on, getting to Siena, you will meet your professional local guide who will lead you on a comprehensive guided tour of the historic center. Starting from the famous Basilica of San Domenico, a jewel of Renaissance art built in the 13th century and dedicated to St. Catherine of Siena, of which preserves a relic.

Stroll along the narrow medieval streets of the city, flanked by splendid palaces and historic shops, passing through Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point. See the spectacular Cathedral of the 12th century and admire the magnificent architecture and the splendor of the polychrome marbles.

You will also have some free time to end your perfect day enjoying the unique atmosphere of this amazing city, before the return to Florence in the evening.

Experience Includes

  • Visit two UNESCO World Heritage Sites Siena and San Gimignano
  • Wonderful views of Tuscan rolling hills and Chianti countryside
  • Tasting of three different Chianti Wines, balsamic vinegar plus “vin santo”
  • Guided visit in Siena with professional local guide
  • 3 course typical Tuscan lunch
  • Air-conditioned coach transportation
  • Tour escort and local guide in Siena

Experience Excludes

  • Optional gratuities
  • Refreshments


Monday, Wednesday; Friday and Saturday November to March. Daily from April to October

Departure location

Tour commences at Piazzale Montelungo (Montelungo Square), in front of the yellow Street Sign Caf Tour – Gray Line

Start times



Around 11 hours

Terms & Conditions

  • Itinerary subject to change without notice.
  • Please arrive at the departure location at least 15 minutes before the scheduled departure time.
  • This tour does not operate between 25 December and 1st January.
  • We suggest you wear comfortable shoes; appropriate clothing is recommended to visit places of worship.
  • 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.
  • Infants aged 0-3 years go for FREE.