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Small Group: Tuscany Day Trip From Florence With Chianti, Siena & San Gimignano

If you want to enjoy the best of Tuscany’s culture, food and history without the hassle of trying to find your way around its beautiful but often confusing country roads, our Tuscany Day Trip From Florence With Chianti, Siena & San Gimignano is the perfect trip for you. We’ll worry about getting you to the best spots, all you have to do is indulge your senses with wine, food, and medieval architecture!

Your day starts in Central Florence where you’ll meet your small group of no more than 18 people and expert tour leaders. Then you’ll hop into our private transport vans and we’ll spirit you out of the city and over to Siena, one of the best-preserved examples of medieval Italian architecture in the world.

Spared German bombing in World War 2, this time capsule of ancient, precarious-looking buildings is home to the Palio, one of the greatest and most dangerous horse races in the world. Your expert tour leader will immerse you in the unique history and culture of Siena as you explore its narrow streets and admire the breathtaking Siena Cathedral from the outside.

Walking the hills of Tuscan towns will make you hungry and thirsty so your next stop is an authentic Italian family farm where some of our good friends will give you a behind-the-scenes tour of the vineyards, winery, and wine cellars before sitting you down for a sumptuous, all-inclusive lunch of local, seasonal ingredients. Your meal will be paired with Chianti wines specially selected to perfectly complement the flavors of the dish. What’s more, you’ll also gain an insight into traditional Italian pasta making with a demonstration by a local cook for a true appreciation of the culinary expertise of the region.

After indulging your taste buds, indulge your imagination with a final stop at San Gimignano, a town of such unique architectural beauty it has been designated a UNESCO World Heritage Site. Shop for Tuscan culinary delicacies in the rustic, winding streets, or learn about the architectural marvels of the famous Medieval tower houses that punctuate the city like sentinels of times long past.

Experience Includes

  • An unforgettable Tuscany Day Trip From Florence
  • Expert, English-speaking Tour Leader (may be split between 2 vehicles for journeys)
  • Indulge in an all-inclusive lunch of local ingredients paired with specially selected regional wines at an authentic Tuscan family farm.
  • Comfortable, air-conditioned vehicle
  • Take a walking tour of Siena, one of Italy’s most picturesque and well-preserved Medieval towns
  • Small groups of only 14 people or fewer
  • Discover one of Tuscany’s classic gems – the town of San Gimignano

Experience Excludes

  • Gratuities
  • Hotel Pick-Up/Drop-Off


Varies, please see calendar.

Departure location

Piazza della Libertà, Cafè Lietta n.6/7/8 red, Florence, IT

Start times



Around 10 hours

Terms & Conditions

  • You will receive a voucher for this experience. Please read it thoroughly.
  • Itinerary subject to change without notice.
  • Gratuities to guides are appreciated but never obligatory.
  • Comfortable walking shoes are recommended.
  • 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.
  • This tour has a maximum capacity of 18 guests.
  • Unfortunately this tour is not suitable for guests with mobility impairments, wheelchairs or strollers.
  • This tour includes a full lunch. If you have any dietary requirements please contact us before booking and we will do everything we can to accommodate you.
  • The order of the sites visited may vary.
  • Cancellation Policy: A full refund will be given on cancellations made more than 72 hours prior to tour commencement. Cancellations received within 72 hours prior to the tour are non-refundable. We will, however, do our best to reschedule you for another tour. Please note, this is subject to availability and price changes.
  • Tours depart precisely at the scheduled tour start time. If you show up late or cannot find the meeting point, for any reason, refund requests are not honoured per policy. For most tours, it is not logistically possible to join the group after it has started.