Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni
Overview
Available languages
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 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
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
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
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
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
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
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
Reviews
2,055 reviews
Total reviews and rating from Viator & Tripadvisor
Well worth it !!
Chris C,
Aug 18, 2025
- Viator
5.00So glad we took the tour. We would never have been able to see all the places, rent a car, be on time, etc. If we hadn't been on an organized tour like this. The guide (short guy with an orange bandana for a flag) was exceptional & and organized our large group very well (and the bus driver as well). Not having to think about any logistics was great after 5 days of having to plan everything. All of the locations on this trip had value. We spent enough time in each place to get a thorough experience without being bored. And also leaving a little for us to come back and see. The walled cities are incredible, Sienna so rich in history, and the wine tasting was very fun. I'd recommend this particular trip without hesitation. They said we would be home by 7, and we were 2' early. Over 20k steps in walking overall, so the time on the air-conditioned bus between locations was welcome to relax out of the sun (94 degrees). Also, the Gelato in San Gimanagno was as good as they said it would be. Four-time world champion in ice cream.
Great day with kids!
Mike L,
Aug 14, 2025
- Viator
5.00Great time, busy day but fun! Kids saw and did a lot. They loved the wine tasting and made friends with other kids (and adults) on the trip!
Get to know a region...
Corrado S,
Aug 8, 2025
- Viator
4.00Getting to know a region like Tuscany even through a short Tour can serve to return pears more days.
Long day but eventful!
Dameion D,
Aug 5, 2025
- Viator
4.00Roberta & Juan Carlos - Siena tour Roberta was great & knowledgeable. It was a long day with a lot to see. The wine tasting at the end was a nice treat. John Carlos our bus driver saved the day when the bus broke down just about 20 mins on our way back to Florence. We were stalled for about 10 mins but during the entire time Juan Carlos never gave up & the bus started again! We arrived back to Florence in one peace and all was well. Thank you Roberta & John Carlos for an eventful evening!
Trip to siena ,chianti ,monteriggioni and San Gimignano
Maria K,
Jul 21, 2025
- Viator
5.00Filippa and Gabriel our guides were very friendly to all of us, very well informed about the history of all the places we visited and all the time ready to assist.
Related Experiences
Operated by Ciao Florence Tours Srl