Tuscany Day Tour: Explore Medieval Siena, San Gimignano, Monteriggioni with Chianti Wine Tasting

Embark on a full day tour of Tuscany, exploring the medieval towns of Siena, San Gimignano, and Monteriggioni. Indulge in a Chianti wine tasting and soak in the breathtaking views. A perfect day-out to relax and replenish your spirits.

Duration: 10 hours, 30 minutes
Cancellation: 1 day learn more
Highlights

The tour starts from Florence and leads you to the atmospheric Medieval gem of Monteriggioni. It was built in 1203 and became a strategic garrison town with its 14 towers, Dante called it the “ring-shaped citadel”. Here you can steep yourself in the past and prepare yourself for the wonders of Siena

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Here your local guide will reveal to you its main beauties: the stunning Piazza del Campo, an open-air fish bowl, surrounded by softly-washed Siena stone architectural masterpieces. It really is a showpiece place, worth lingering in and drinking in the richness of the past. Visit Piazza del Duomo and be impressed by the imposing Cathedral, one of the finest achievements of Italian Gothic. Before leaving Siena you will be served a light lunch in a cozy restaurant where, together with genuine Tuscan products, you will savour traditional pastries.

After your free time for lunch in Siena, continue on to San Gimignano: the home of the renowned Vernaccia wine. This Medieval town is listed as a UNESCO World Heritage Site, and once you’re there you’ll see why. The secret lies in its soaring towers that seem like skyscrapers! It is a jewel of art and architecture and also boasts one of the best ice-creams in the world! Here you’re free to stroll around or just stop and take it all in.

Next, Chianti calls. You will visit a rustic wine estate where, after drinking in the landscapes, you can taste and sip quality wines and try the plonk along with oils and local products.

This is a tour made for the spirit and the flesh. A perfect way to mix quality culture and cuisine.

Points of Interest

  • Florence

  • Monteriggioni

  • Siena

  • Piazza del Campo

  • Duomo di Siena

  • San Gimignano

  • Piazza della Cisterna

  • Gelateria Dondoli

  • Chianti Road

What's Included
  • Professional guided tour of Siena (headsets not included in semi-independent option)
  • Free time to explore San Gimignano and Monteriggioni
  • Wine tasting experience at a Chianti estate (2-3 wines)
  • Sample regional products and extra-virgin olive oil
  • Travel in comfort with a fully-equipped GT Coach, including free Wifi
  • Assistance from an expert, multilingual Tour Leader
What's Not Included
  • Gratuities
  • Hotel pickup and drop-off
  • Siena Cathedral tickets (approx. 7€ pp)
  • Lunch
Additional Information

Experience a full day exploration of the prime attractions in Central Tuscany, complete with a delightful Chianti wine tasting. Traverse through the stunning rural scenery to your first stop, the radiant city of Siena, known for its unique square and Gothic-style town hall. Next, navigate towards San Gimignano, often referred to as the Medieval New York, and Monteriggioni, a castle perched atop a hill offering panoramic views. No trip would be complete without a stop at a Chianti winery where the finest Italian wines are waiting to tantalize your taste buds. It’s an ideal day out to unwind and rejuvenate your senses.

  • A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements
  • May be operated by a multi-lingual guide
  • Please note that the given order of the visits may change
  • Please inform us of any food intolerance or allergy in advance
  • Kindly note that the Semi independent option does not include the professional guide in Siena
  • LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
  • HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax
Location
Piazzale Montelungo
TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.5
(1410 Ratings)
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Tammy_s
Aug 9, 2024
Well organized tour - Very well organized tour. Lots to see in each locale. Nice to have free time to explore after guided portions. Wine tasting was fun. Lots of moving parts were well done
Review provided by Viator
David
Aug 8, 2024
Excellent tour - Our tour guide was awesome. The whole trip was put together very well. The wine tasting was a fun adventure. The bus was air conditioned and comfortable.
Review provided by Tripadvisor
Patriciamq4612ez
Aug 3, 2024
The best - The best Gabrielle and Luca second to none!! A dream tour!!! Super recommended!!! The beautiful places and both guide and driver are the best Patricia
Review provided by Tripadvisor
O4584xkfranka
Aug 1, 2024
I definitely recommend it. - Excellent tour, super recommended. It is a very complete tour! Very friendly staff, Roberto and Cesi (the guides) and Lucca the driver.
Review provided by Tripadvisor
Guide32737964542
Aug 1, 2024
Siena trip - Great trip and the guides Roberto and Cecile were really fun and helpful as well as Luca driving really well and safety the whole trip
Review provided by Tripadvisor
64xabierj
Aug 1, 2024
Very pleasant tour of Tuscany - It has been a very complete excursion, with very good guides (Roberto, Ceci and Luca the driver). A highly recommended tour.
Review provided by Tripadvisor
V1412lwmarios
Aug 1, 2024
Beautiful Tuscany - Everything great!! Very timely and very good explanations!! Many thanks to Ceci, Lucca and Roberto for such a good experience!!!
Review provided by Tripadvisor
Amyrn7553og
Aug 3, 2024
Good experience for Tuscany - Driver Luca has taken us through the tour nicely and smoothly, the trip has been great. Our guide Gabriele has been very friendly and fun, making the tour an unforgettable experience.
Review provided by Tripadvisor
Claudiabm2585tq
Aug 1, 2024
Very good treatment, excellent organization - Excellent wine tasting, very organized excursion. I really liked Siena, very interesting story, the guide explained great.
Review provided by Tripadvisor
Mary_d
Aug 7, 2024
Great scenery - The trip to Siena and San Gimignano was good. It would have been much better if we had only an English speaking tour guide for both places. The guides English were poor. Our trip in San Gimignano did not have a tour and we felt we missed a lot of information. The trip to the winery was terrific. Overall, this is the first tour with Vivator that the guide was not great. It was hard to understand the guides English. The guides did not tell us anything about each area and what to do. We were basically dumped and then carted back in the bus -very disappointing. The bus driver was rude , he would not let us drink coffee or eat because he didn’t want to have to clean the bus. However, they had no problem asking for tips at the end. Very entitled!! This is a low one for Vivator!!
Review provided by Viator
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up to 15 guests
1 Adult
September 2024
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