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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
  • Siena: exclusive opening of intimate and secret sights and the Cathedral
  • Wonderful views of Tuscan rolling hills and Chianti countryside
  • Enjoy the Visit to the cellars and vinejards together with a typical Lunch in a cozy Chianti Winery
  • Taste three excellent Chianti wines
  • Picturesque, Medieval village famous for its colors and charm

Added Safety Measures in Place


  • Gray Line Caf Tour’s Staff Assistance at the meeting point
  • Transport by air-conditioned Coach with Wi-Fi on board
  • Licensed Tour Escort
  • Visit to the cellars, vineyards and 3 course typical Tuscan lunch in a Chianti Winery
  • Tasting of three different Chianti Wines, balsamic vinegar plus “vin santo”
  • Guided Visit in Siena led by Professional local Guide
  • Cathedral and Libreria Piccolomini inside visit & skip-the-line Ticket (if option selected)

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

Please Note

• Mandatory: Participants must present, together with the ID Card, their EU Green Pass or their own country document to proof one of the following: - to have received full vaccination; - to have received first vaccination at least 15 days ago; - to have had Covid-19 infection in the past 6 months; Those who will not present the required documents, will not be entitled to any refund. All participants must wear an FFP2 mask

  • It is recommended that participants wear comfortable shoes and appropriate clothes to visit museums or places of worship.

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, of which you can admire the magnificent architecture and the splendor of the polychrome marbles. You will experience an amazing inside Guided Visit of the famous Siena Cathedral (if option selected), together with its Libreria Piccolomini, to discover the beauty of its treasures and works of art. You will visit the not-to-be-missed floor (during the opening period), decorated with the art of mosaics to create storytelling masterpieces, St. John the Baptist by Donatello, the rose window by Duccio di Buoninsegna, the marble pulpit by Nicola Pisano, the Library which kept a rich collection of manuscripts.

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
Apr 30 2022
We enjoyed this day trip all though the timing of the several visits could have been a bit better.Arriving in San Gimignano the church was not open to visit.At opening hours the line for tickets felt too long and slow to leave us enough time to visit it.Lunch was really good - but too much time at the winery => there was no visit to the winery, all we saw was a vessel (I've visited wineries before in different seasons, I know what can be seen)We had the guided tour in Siena - which was really good, a really good guide! But as we took this tour we only had 15min of free time in Siena which made our visit to this lovely town feel very rushed.
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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