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

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting
from USD $70.58
Full day Tour in the heart of Tuscany region: San Gimignano - the "Manhattan of the Middle Ages", the most famous and picturesque Tuscan hill village together with the unique experience of Siena and its traditions, thanks to the comprehensive guided tour of the stunning old town. The picturesque Monteriggioni Hamlet and the relaxing stop at a Chianti Winery for a typical Lunch which includes the guided Tasting of 3 different Wines, extra virgin olive oil , balsamic vinegar and “vin santo”
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Due to the impacts of COVID-19, we are currently not taking new bookings for day tours.

In Brief

Firenze, Italy
11 hours
Day trip (destination A to B)
All entrance fees included
Important InfoInfo
This is a typical itinerary for this product

Stop At: Historic Centre of San Gimignano, Piazza del Duomo 2, 53037, San Gimignano Italy

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.

Duration: 2 hours

Stop At: San Gimignano Bell Tower, Piazza del Duomo, 53037, San Gimignano Italy

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

Duration: 5 minutes

Stop At: Centro storico di Monteriggioni, Piazza Roma, Monteriggioni Italy

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.

Duration: 30 minutes

Stop At: Chianti Road, Italy

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, extra virgin olive oil and balsamic vinegar followed by a Chianti style lunch: 3 course with “zero food miles” products which ends with "cantucci e vin santo".

Duration: 1 hour 30 minutes

Stop At: Centro Storico di Siena, Piazza Del Campo, 53100, Siena Italy

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

Duration: 30 minutes

Stop At: Centro Storico di Siena, Piazza Del Campo, 53100, Siena Italy

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

Duration: 30 minutes

Stop At: Piazza del Campo, 53100, Siena Italy

Piazza del Campo, of which the Palazzo Pubblico (Town Hall) is the focal point

Duration: 30 minutes

Stop At: Duomo di Siena, Piazza del Duomo 8, 53100, Siena Italy

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.

Duration: 15 minutes


  • Transport by G.T. air-conditioned vehicle with WIFI on board
  • Licensed Tour escort with live commentary on board
  • Shared or Private Professional guide in Siena (depending on the selected option)
  • Visit of a picturesque Chianti medieval village, famous for its colors and charm
  • Siena Cathedral interior Guided Visit including entrance fee (depending on the selected option)
  • 3 course typical Tuscan lunch in a Chianti Winery
  • Tasting of three different Chianti Wines, extra virgin olive oil, balsamic vinegar & “vin santo”
  • Entry/Admission - Duomo di Siena


Departure Time

8:30 AM

Departure Point

Piazzale Montelungo, Firenze FI, Italy

Returns To

Returns to original departure point

Additional Information

  • Confirmation will be received at time of booking
  • A dress code is required to enter places of worships and selected museums. No shorts or sleeveless tops are allowed. Knees and shoulders MUST be covered for both men and women. This dress code is strictly enforced and you will risk refused entry if you fail to comply with requirements.
  • Not wheelchair accessible
  • Stroller accessible
  • Near public transportation
  • Infant seats available
  • Travelers should have a moderate physical fitness level
  • This tour/activity will have a maximum of 50 travelers

Booking Information

You can present either a paper or an electronic voucher for this activity.

Cancellation Terms

This trip is fully refundable up to 96 hours prior to the commencement of your trip.

Booking Terms and Conditions

When you book this trip, you need to read and accept the terms and conditions for booking our day trips in excursions.

Scoring an average traveller rating of 5 out of 5 based on the last 24 recent reviews

The best way to see some of the most wonderful sights in Tuscany. The relaxation of the motor coach versus the stress of driving or train transfers was well worth the cost.
• Submitted 17 Sep 2019
Barbara? the general guide and Paolo, the guide in Siena, were both excellent. The trip was well organized and very informative.
• Submitted 26 Aug 2019
Great day trip and very well organised. We were colour coded depending on our choices and our Tour Guide was very professional. She spoke 4 languages and moved from one to the other very quickly. Our local guides were also fantastic. The wine and food tasting was intimate with no pressure to buy. Thank you for a wonderful day.
• Submitted 05 Aug 2019
Our group was not disappointed with this tour. The guides were outstanding and the pace of the day was quite reasonable.
• Submitted 24 Jul 2019
Made a choice to drop pisa from the itinerary and go for this tour instead. Did not regret it. Wine tasting session was very informative and generous. Opt for the tour of Siena. you do not want to miss out on learning about the town's rich culture and history.
• Submitted 03 Jul 2019
Very informative and interesting tour. Helena was a wonderful guide and the smaller tour size was nice. Enjoyed the tour of Siena. I have been to Siena before but was unaware of the history of the town, specifically the horse race, Until this trip.
• Submitted 20 Mar 2019
The day in Tuscany at the different towns was beautiful and interesting. We met some great people on board and the guides, especially our local guide in Siena, was terrific. We would highly recommend this tour....great value and different experiences made for a full day.
• Submitted 22 Oct 2018
Great trip from Florence to see some nearby cities and great sites! Siena and wine tasting were the highlight!
• Submitted 26 Sep 2018
AMAZING!!! great tour guides especially in Siena! one of the highlights in our italy trip!
• Submitted 10 Aug 2018
An excellent day, well run. Visited 4 places that were all amazing. The highlight was the enthusiasm with which our guide exhibited at the wine tasting.
• Submitted 09 Jul 2018
This is a great tour. Siena is an old and beautiful city well worth seeing. The Chianti trip is so much fun. Great wine and food. We highly recommend this tour.
• Submitted 06 Jul 2018
This was a fun tour, but keep in mind there is a LOT of walking...! Local tour of Siena was outstanding and very informative. Wine tasting was excellent and very well done. Pick up location is quite difficult to find...nowhere to sit..
• Submitted 18 Jun 2018
Excellent tour. Really well organised and the guides were fabulous. The Siena guide who explained the Contrada and the Palio was wonderful. I would have loved a little longer in San Gimignano. In Siena we also took the tour of the Cathedral spectacular but then we had no time to do any shopping but I guess you cant have everything. We had a fabulous day even though it was quite long. My only small criticism would be better instructions for finding the tour start point. There were lots of renovations at the train station so it was a bit of a challenge finding the bus stop.
• Submitted 16 Jun 2018
Very well organized tour, special thanks to our professional guide Tiziana!
• Submitted 23 Apr 2018
Great trip and good value for the price of the tour. Four stops all good. Obviously, when your making four stop you don't have as much time to explore as you want at each place but I'm glad we took this tour instead of one that just covers Siena. Be prepared for 11 hour day.....8:30 AM to 7:30 PM. Enjoy!!!
• Submitted 11 Apr 2018
Siena is one of my favorite towns. We loved the tour and our guide
• Submitted 09 Apr 2018
• Submitted 02 Apr 2018
Definitely value for money...very worthwhile trip...covered quite a fair bit with enough free time to roam around .
• Submitted 02 Apr 2018
Loved this tour. Long day but worth it.
• Submitted 31 Mar 2018
This tour was amazing!
• Submitted 29 Mar 2018
This tour was amazing!! Extremely informative with lots of things to see. Our tour guide was a doll, she was so sweet and very smart! Definitely recommend, my family and I loved this trip!
• Submitted 20 Mar 2018
We enjoy visiting these small towns, each with their own particular point of view and interest, and the trip went by very quickly. You take in a lot of interesting stuff.
• Submitted 19 Mar 2018
A great tour with a knowledgeable and informed guide who was most thoughtful and helpful. An enlightening visit which brought alive the history and traditions of the places visited. The bus driver was 'the best' and reliable in difficult driving conditions in the evening in the clouds of the Tuscan hills.
• Submitted 12 Mar 2018
This trip wad amazing! Our guide Alicia was delightful and informative. This trip was so worth it!! Beautiful country! Saw so much all in one day! Love, love Loved!
• Submitted 28 Feb 2018