Tuscany Medieval Towns Tour with Wine Tasting
From€65
9 hours
Florence, Italy
About this activity
Discover Tuscany's medieval towns—Siena, San Gimignano, and Monteriggioni—on a guided tour from Florence, including a Chianti wine tasting and scenic countryside views.
Highlights
- Explore Siena's historic center
- Visit San Gimignano's medieval towers
- Discover Monteriggioni's ancient walls
- Enjoy a Chianti wine tasting
- Scenic drive through Tuscan countryside
Full description
Step back in time and immerse yourself in the rich history of Tuscany's medieval towns. On this full-day tour from Florence, you'll explore the UNESCO World Heritage site of Siena, renowned for its stunning cathedral and the historic Piazza del Campo. Wander through the charming streets of San Gimignano, famous for its towering medieval architecture, and visit the fortified town of Monteriggioni, which inspired Dante's 'Divine Comedy.' Along the way, enjoy a delightful wine tasting in the picturesque Chianti region, savoring the flavors of Tuscany's renowned wines. This tour offers a perfect blend of history, culture, and culinary delights, all set against the backdrop of the stunning Tuscan landscape.
Included / Excluded
- Guided tour of Siena, San Gimignano, and Monteriggioni
- Wine tasting in the Chianti region
- Transportation from Florence in an air-conditioned vehicle
- Meals and personal expenses
Meeting point
Start Location
Unknown location
Important information
Know before you book
- Tour operates rain or shine; dress appropriately for the weather.
- Wine tasting is included; bring ID if you plan to participate.
- Confirm the meeting point and time upon booking.
Know before you go
- Wear comfortable walking shoes for cobblestone streets.
- Bring a camera to capture the scenic views and historic sites.
- Check the weather forecast and dress accordingly.
Cancellation policy
Free cancellation up to 1 days before the activity starts
For a full refund, cancel at least 24 hours before the scheduled departure time.
Accessibility
- Stroller Accessible
- Easy Public Transport
- Infants Required On Laps
- Infant Seats Available
Good to know
- May be operated by a multi-lingual guide
- Please note that the given order of the visits may change
- 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
Traveler reviews
4.73,430 reviews
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Very Good experience
Very Good experiencie. Great guises Cecilia and Jesn Marco.
gonzalosJ8488LVSep 21, 2026TRIPADVISOR
Best way to go to toscany
Excelent great explsinations from cecilia y Jean Marco our guides. Great experience!!
PaulaCarvaSep 21, 2026TRIPADVISOR
Very nice tour
Amazing! Great guides and a very complete tour
melissajQ5652BFSep 21, 2026TRIPADVISOR
Wine tasting and country side
Was a great day out , well worth the money . The tour guides were amazing!! The sites we saw were lovely . Wine tasting was so good and funny had a great time
FellowTraveler628007Sep 21, 2026TRIPADVISOR
Beautiful!
Wear your walking shoes and comfortable clothes, you will be climbing stairs etc. The views are so worth it. Roberto was knowledgeable and kept things moving well. Highly recommend this tour.
Vanessa_BSep 20, 2026VIATOR
Additional information
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