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
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
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
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
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 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 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
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
Reviews
2,179 reviews
Total reviews and rating from Viator & Tripadvisor
Fabulous...... just be ready for the hills
Karen C,
Sep 15, 2025
- Viator
4.00Beautiful places to visit and great to see more of Tuscany on this tour but heavy on the legs at times. Due to some construction taking place we were told that our bus had to park further away than usual and the walk in and out of Siena in particular took more effort than expected not least due to the gradient of some of the inclines. A wonderful tour but worth considering for anyone with mobility issues.
Tuscany Vibes
Ceri N,
Sep 13, 2025
- Viator
5.00Great cultural experience visiting beautiful medieval villages and wine tasting. Exceptional value for money, lovely air conditioned coach, very organised. My tips for the trip would be to expect elevated walks and a long day.
Liars
Emerson A,
Sep 12, 2025
- Viator
1.00I booked this tour with viator, but the tour was made with CIAO FLORENCE. It was the worst experiencie! We where in 13 people and when i bought It, It was informing that the vehicle hás 15 seats, but It was fone with a 60 seats bus, Full of people! I told to the representativos, but tbey Just ignored It!
Constantino and Simon...
Claude D,
Sep 10, 2025
- Viator
5.00Constantino and Simon were super welcoming and available while knowing very well the places visited. We loved the places visited and the comfort of the bus.
So big group: 57 persons. Not fair fir us or the guide
Leticia G,
Sep 10, 2025
- Viator
3.00The cities where increfible. I did not know that the group was going to be that big and combinig English and Spanish. To strict in times and rules. Dani was very professional handling that big group, but for us too uncomfortable when we needed to find a restroom or to buy something. I really liked the guide in Siena. Please, tell us how big is the group to allow me to have more info in buying the tour. I am giving three stars because the places were si beautiful.
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Operated by Ciao Florence Tours Srl