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

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


Enjoy a once in a lifetime experience, to discover stunning Medieval gems, crossing the enchanting Tuscan countryside!

11 Hours
  • Mobile & printed vouchers accepted


  • Visit Two stunning UNESCO World Heritage Sites
  • Wonderful views of Tuscan rolling hills and Chianti countryside
  • Stunning guided visit to the Siena Cathedral and Libreria Piccolomini
  • Stop at a typical Winery with tasting of three excellent Chianti wines and Typical Chianti lunch
  • Picturesque, Medieval village famous for its colors and charm

Added Safety Measures in Place


  • Transport by air-conditioned bus with wi-fi on board,
  • Tour escort
  • Guided Visit in Siena with Professional local guide (depending on the selected option)
  • Siena Cathedral and Libreria Piccolomini Guided Visit and admission (depending on the selected option)
  • 3 course typical Tuscan lunch, Tasting of three different Chianti Wines, balsamic vinegar plus “vin santo”

  • Optional Gratuities
  • Hotel pick-up and drop-off

Please Note

  • It is recommended that participants wear comfortable shoes and appropriate clothes to visit museums or places of worship
  • Children ages 0-3 years old are free
  • Children ages 4 –12 years old: 50% discount

From US$62

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

11 Hours

Price Breakdown:


Departure Location & Details
Check in: 8:15 am
Departure: 8:30 am
Location: Piazzale Montelungo (Montelungo Square), in front of the yellow Street Sign Caf Tour – Gray Line

Return Location & Details
Return Time: 7:30 pm
Location: Piazzale Montelungo (Montelungo Square)
Tour Overview

Your memorable journey starts with the charming San Gimignano, 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 the tour leader will lead you to the historical center, where you will have around 2 hours of free time for a fascinating discovery.

A short distance from San Gimignano you will visit 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.
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 with its wine and typical products: tasting of three fine wines and balsamic vinegar followed by a Chianti style lunch: 3 course 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. Then strolling 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, you will get to the spectacular Cathedral of the 12th century (inside visit if option selected), of which you can 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.

Please note that the order of the visits may change
Verified user reviews powered by
4.0 / 5   overall customer review rating
a Gray Line customer
Oct 26 2020
Amazing tour, even during the pandemic season. Strongly recommend
Mr Michael Gay
Jan 12 2017
loved the tour, great places to visit, very good tour guide guide and bus driver.
Ms jacqueline thornton
Dec 28 2016
a Gray Line customer
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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