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

4.6
3,252 reviews
5
2,497
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506
3
153
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51

Definitely worth the day!

We are not usually tour bus people, so this was different for us. Siena and San Gimignano were very fun experiences. Nice quaint cities that we walked around in for the time we were given. Definitely worth it. The first city Monteriggioni was small and some may have found it worthwhile, but we didn't. The wine tour was not as one would expect...they were more concerned about trying to sell us wine than educating us about their process and history. Overall it's worth the day and the price to experience this trip.

Deepalk_BAug 14, 2026VIATOR

A day in Tuscany

Very good experience, the sites Siena and Gimignano were spectacular and the wine tasting was very simple but informative. Perhaps there was not enough time to see the sites better. The guide Federico was excellent, super attentive to everything and everyone and with perfect organization. The trip with the driver Raúl was impeccable.

L8194UJluisrAug 14, 2026TRIPADVISOR

Between Siena / Monteriggioni / San Gimignano

A day to dazzle your eyes. Lorenza, our guide, was always attentive, dynamic, and passionate in all her explanations.

459st_phanevAug 14, 2026TRIPADVISOR

Tuscany

Federico and Raúl made us have an unforgettable day. Very well organized in terms of the time dedicated to each activity and the punctuality of the departures. It is an excursion that, without a doubt, is worth it.

mariasR4029AQAug 14, 2026TRIPADVISOR

Very Good day in family in the Chianti

Lorenza was a very good guide, very Good day in beautiful city !

cl_mentm294Aug 14, 2026TRIPADVISOR

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