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

4.7
3,520 reviews
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51

It was a good experience in general

The tour guides Chiara and Antonio did a great job: punctual, friendly, and patient. As for lunch, the spaghetti was just ok. The wine tasting was very good.

676deboratOct 3, 2026TRIPADVISOR

Nice day in Toscana

Beautiful day, great experience, nice guides (Cecili and Daisy) and the spots were really charming

Quest03681944891Oct 2, 2026TRIPADVISOR

Lovely day trip

Beautiful day trip. We'll be back. Guides were lovely in particular Mya, who went above and beyond in assisting my husband who had mobility issues. Thank you too to our driver who assisted with mobility stroller. Thank you guys. Ger Campion

Pioneer799805Oct 2, 2026TRIPADVISOR

Pleasant day in Tuscany

It was a great experience, I managed to visit several cities practically and safely

840evertonaOct 2, 2026TRIPADVISOR

A taste of Tuscany in one day

It's a great experience with a smiling and friendly team! In Siena we would have liked a little more time because there are many things to see but we understand the timing with the other visits. I recommend it! :) Furthermore, we went without a meal (optional) in Siena, we went to a local restaurant very easily and it was very good, the prices were reasonable! The wine tasting had a great presentation, and the experience is super!

davys973Oct 2, 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