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

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 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

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

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

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

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

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

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

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

Reviews

4.53

1,893 reviews

Total reviews and rating from Viator & Tripadvisor

1337
346
126
40
44
  • Fantatsic tour. We had an...

    Jayaraman R,

    Jun 28, 2025

    - Viator

    5.00

    Fantatsic tour. We had an awesome tour guide Frederico! On time, good locations and ample time. Good coaches

  • Comprehensive tour of...

    Pooja B,

    Jun 26, 2025

    - Viator

    5.00

    Comprehensive tour of medieval cities -longest stop was at Siena. There’s also a wine tasting. We opted for partial guidance which left us some free time in Siena. San Gimignano was our favorite

  • This was a great day trip...

    Jacqueline W,

    Jun 20, 2025

    - Viator

    5.00

    This was a great day trip - highly recommend!! Very impressed with the company’s communication before and during the trip. Made it very easy to find the location and the day was very well organised. Also very accommodating to different languages. Siena was amazing! Although perhaps don’t choose the walking guide option - it was with a different provider and wasn’t very informative and took up some valuable time. The wine tasting experience was awesome - way better than expected! And SAN Gimignano was the best! Climbed the tower and tried some world famous gelato

  • Roberto was very...

    Catherine R,

    Jun 17, 2025

    - Viator

    5.00

    Roberto was very organized. He sent messages with suggestions and directions back to the meeting point. We opted for free time in each place and it was a stress free way to explore the towns.

  • Day tour to Siena, San Gimignano and Monteriggioni with wine tasting

    Tasia J,

    Jun 16, 2025

    - Viator

    5.00

    Be prepared for a very long day. We had a great time, loved the full experience. We were lucky to have entertainment.

From EUR 55.25

4.53
1,893 reviews