Siena & San Gimignano with Tuscan Dinner

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Full details

An all-around Tuscan extravaganza

Enjoy a captivating afternoon exploring Siena and San Gimignano, two of Tuscany's most enchanting cities, and conclude the day with a picturesque sunset and dinner at a charming boutique winery nestled in the scenic Chianti countryside.

Our guide to Siena & San Gimignano with Tuscan Dinner

Siena graces a picturesque landscape, surrounded by vineyards and olive groves, and stands as one of Italy's most captivating medieval cities. Led by an expert guide, you'll uncover the town's most remarkable sights, and marvel at the splendid Piazza del Campo, where daring horses race in the Palio competition twice a year.

Explore quieter backstreets and learn everything about the Contrade (the 17 medieval city districts that compete against each other in the Palio) and enjoy a flavorful surprise: a tasting of a local speciality. Next, your journey takes you to San Gimignano, a UNESCO World Heritage Site and a splendid example of an ancient walled town. Renowned as "the city of beautiful towers" or "Tuscany's Manhattan," San Gimignano boasts a distinctive skyline and is among Italy's best-preserved towns, often featured in film settings.

During your leisurely exploration, traverse the cobblestone streets and discover the towering structures that once served as residences. As the sun descends behind the vineyard-clad Chianti hills, immerse yourself in the authentic atmosphere. Later, relish an authentic Tuscan dinner and indulge in a wine tasting within the charming confines of a delightful boutique winery.

Savour the delectable flavours of a traditional meal expertly paired with exceptional wines, and relish the privilege of a private tour of the estate's wine cellar.


  • Apr-Oct - Daily, Nov-Mar - Mon, Wed & Fri

Start Times:

  • Nov to Mar 1.00 pm, Apr to Oct 2.00 pm


  • Approx. 8 hours


Terms and conditions

Terms and conditions for Siena & San Gimignano with Tuscan Dinner

  • You will receive a voucher for this experience. Please read it thoroughly.
  • The itinerary is subject to change without notice.
  • This tour runs rain or shine.
  • Gratuities to guides are appreciated but never obligatory. 
  • Please note that the tour meeting time is 15 minutes prior to the start time. No refunds or re-bookings can be provided for late arrivals or no-shows after tour commencement or departure.
  • Comfortable walking shoes are recommended.
  • Please inform us of any food intolerance or allergy in advance.
  • We regret to inform you that this tour is not suitable for guests with wheelchairs or with impaired mobility.
  • Please inform us of any food intolerance or allergy in advance.
  • Please note that Italy's law doesn't permit selling alcoholic beverages to teens under 18 y.o. so clients under this age will be served non-alcoholic beverages.
  • Children under 18 years must always be accompanied by an adult. Please specify the child's age at the time of booking.
  • Cancellation Policy: If you cancel at least 72 hours in advance of the scheduled departure, there is no cancellation fee. If you cancel within 72 hours of the scheduled departure or do not show up for the tour, there is a 100% cancellation fee.