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Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni

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Overview

Available languages

Portuguese
English
Italian
French
Spanish

10 hours 30 minutes

Mobile ticket

A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.

Additional Info

Infants and small children can ride in a pram or stroller

Public transportation options are available nearby

Infants are required to sit on an adult’s lap

Specialized infant seats are available

Not recommended for travelers with poor cardiovascular health

Travelers should have at least a moderate level of physical fitness

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

Cancellation Policy

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

What‘s Included

Free time in San Gimignano and Monteriggioni Medieval towns

Siena tour with professional guide with Headsets (not included in the semi independent option)

Visit to a charming wine estate in the Chianti area with tasting of up to 2-3 Chianti wines

Expert multilingual Tour Leader

Sampling of wines, extra-virgin olive oil and regional products

Journey by fully-fitted GT Coach with Free Wifi on board

Gratuities

Hotel pickup and drop-off

Siena Cathedral tickets (approx. 7€ pp)

Lunch

What To Expect

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 . 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.

Options

Classic French tour

All inclusive tour in French: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Classic English Tour

All inclusive tour in English : Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Classic Spanish tour

All inclusive tour in Spanish: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Classic Portuguese Tour

All inclusive tour -Portuguese: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Portuguese - Semi independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Italian Tour -Semi Independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Spanish Tour -Semi Independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

English Tour -Semi Independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Classic Italian tour

All inclusive tour in Italian: Including 1 hour guided tour in Siena, Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

French Tour -Semi Independent

What is not included: Local Guide in Siena. What is included: Free time in Monteriggioni, Siena, San Gimignano and wine tasting in a Chianti winery

Reviews

4.59

2,444 reviews

Total reviews and rating from Viator & Tripadvisor

1794
423
139
42
46
  • Great Way to Visit Tuscany without the Hassle

    Y6359SFjanetm,

    Nov 10, 2025

    - Review from Tripadvisor

    4.00

    This was a great way to visit the beautiful towns of Siena, San Gimignano and Monteriggioni from Florence without the hassle of arranging transport yourself. Roberto was a great host and it was very well run. Would recommend this tour and company for anyone wanting to get a taste of Tuscany in a short time. The only downside was that the tour was in 3 languages (English, Italian & Spanish) which made the commentary a bit tedious on a 11 hour tour. I booked and English tour so maybe this should eb mentioned when booking?

  • Exceptional experience

    D1279CJesters,

    Nov 9, 2025

    - Review from Tripadvisor

    5.00

    We did the tour with Constantine the guide and Patroclus the driver, both excellent. Costantino was always nice, kind and helpful, everything went perfectly and punctually from start to finish, thanks to them we discovered places that otherwise we could not discover not having a car, or we would have taken too long. Monteriggioni and San Gimignano are exquisite and unmissable medieval pearls! A nice experience also tasting local wines, even there everything or friendly and helpful staff. I love Tuscany, it's always nice to go back but this was our first group tour accompanied by a guide, and it was a great experience. Greetings from Cagliari! 😊

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  • Great moment.

    luismO6889EP,

    Nov 9, 2025

    - Review from Tripadvisor

    5.00

    Excellent experience, thank you very. Lucia the best guide in Europe. I really would like to know a good person. Great experience, great moment. Lucía 👏 respect 🙏

    luismO6889EP's photo 1
  • A delightful day trip!

    56Gingerella,

    Nov 9, 2025

    - Review from Tripadvisor

    5.00

    I was hesitant to book a group tour for myself, husband and adult son and be "one of those big tour groups" wandering around a city. But I was glad we decided to give it a try. This tour was just what we needed. We had a double decker bus and got to enjoy fantastic scenery as someone else did the driving along curvy steep hills. The company tour guide pointed out sites as we drove along and she kept us well informed of logisitics at each stop. We weren't on the bus too long at any one time as the spacing of the stops was well planned. Each stopping point was majestic with so much to see. We took the guided tour of Siena with a local guide and glad we did. A great way to pack in some highlights of Italy's treasures without all the hassle and stress!

  • Recommended

    luismariol422,

    Nov 9, 2025

    - Review from Tripadvisor

    5.00

    Very good experience and pleasant tour. Lucia and Zenij guides knew the places perfectly and were kind to us

  • Great

    A2296QNtamarac,

    Nov 9, 2025

    - Review from Tripadvisor

    5.00

    Zeni and Luzia Extremely careful and professional, attentive and very cheerful They were ready to answer any question Thank you

  • Full experience of Tuscany

    752valei,

    Nov 9, 2025

    - Review from Tripadvisor

    5.00

    We had a very complete tour with Lucia. He explained all the important history and data of the places we visited, as well as always kept a close eye on all the members of the group.

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  • Great Tuscany experience

    robertobX1342QM,

    Nov 9, 2025

    - Review from Tripadvisor

    5.00

    Excellent experience, all perfect. Guia Luiza and the driver Zenj were very professional and helpful. I recommend.

  • Wonderful tour

    Daneyis D,

    Nov 6, 2025

    - Review from Viator

    5.00

    The tour was very good the truth I highly recommend you can know and see several places in Tuscany. It is very worthwhile and although it is long it is not exhausting to enjoy. The views are amazing. Our guide Anna was wonderful and loving just like the very friendly driver.

  • Great tour to see multiple towns in one day

    damarisr394,

    Nov 6, 2025

    - Review from Tripadvisor

    5.00

    This tour was a great experience. We loved the fact that we got to see so many small towns around Tuscany. Our favorite was San Gimignano! Thank you to Francesca our amazing tour guide.

From €65.00

4.59
2,444 reviews
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