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Tuscany Day Trip from Florence with Chianti, Siena and San Gimignano

Spend a Beautiful Day in Tuscany

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, and all you have to do is indulge your senses with wine, food, and medieval architecture that exists nowhere else in the world.

Your day starts in central Florence where you’ll meet your small group of 18 people maximum and your friendly expert tour leader. Then, you’ll hop into our private transport vans, and we’ll drive through the beautiful countryside to Siena, one of the best-preserved examples of medieval Italian architecture in the world.

Walking the hills of Tuscan towns will make you hungry and thirsty, so your next top 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 — and of course, plenty of Chianti wines.

After indulging your taste buds, we will 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.

Tour Highlights

  • Roundtrip Transportation from Florence
  • Guided walking tour of Siena
  • Visit inside Siena Cathedral (closed on Sundays and religious holidays)
  • All-inclusive lunch at a Tuscan farm and vineyard with local Chianti wine pairings
  • Visit to San Gimignano
  • View Calendar
    • Live Guide
    • Roundtrip Transportation from Florence
    • Lunch and wine pairings in Chianti
    • Guided Walking Tour of Siena
    • Guided Visit inside the Duomo di Siena

  • This tour meets in front of Cafè Lietta n.6/7/8 red, in Piazza della Libertà. Please arrive 15 minutes prior to tour start time. We do not have the luxury of waiting for guests, and no refunds can be provided for late arrivals after tour departure.

  • English
    • This tour includes a full lunch. If you have any dietary requirements please let us know in the Comments section at checkout, and we will do everything we can to accommodate you.
    • Unfortunately, we are unable to accommodate guests with mobility impairments, wheelchairs or strollers on this tour.
    • Please note that the Cathedral of Siena is closed on Sundays during our visiting time and subject to closure during special celebrations/festivities, including the Easter ceremonies. If this occurs during your visit, we will run an alternative itinerary that includes an explanation of the Cathedral from the outside.
    • Siena Cathedral is a holy place and attire must be appropriate for the visit. Both men and women are asked to wear clothing that covers at least the shoulders and knees. We cannot be held responsible for denied entry due to improper dress.

FAQ

  • Expand/Collapse Where is the meeting point?

    This tour meets in front of Cafè Lietta n.6/7/8 red, in Piazza della Libertà. Click here for map.

    Please arrive 15 minutes prior to tour start time. We do not have the luxury of waiting for guests, and no refunds can be provided for late arrivals after tour departure.

  • Expand/Collapse What does 'Fat Tire Tours Approved' mean?

    We've been perfecting our tours since 1999, and we are always looking for new ways to improve our tour menu for our guests. We are committed to expanding the activities offered during your stay in Florence to make for an unforgettable experience. So for all of the experiences that we aren't able to deliver on our own, we've hand-selected the best local providers to offer a wide-range of unique and fun activities for our guests. With anything Fat Tire Tours Approved, you still receive our spectacular customer service ready to assist you in any way we can, 24/7, as well as the guarantee that we have hand selected the best possible partners to supplement our tour menu.

  • Expand/Collapse Is lunch included with this tour?

    Yes! This tour includes a full lunch at a stunning Tuscan farm house and vineyard.

    If you have any dietary requirements please let us know in the Comments section at checkout, and we will do everything we can to accommodate you.

  • Expand/Collapse What time do I need to get there for my tour?

    Please arrive 15 minutes prior to tour start time.

    We do not have the luxury of waiting for guests, and no refunds can be provided for late arrivals after tour departure. It is imperative to be on time for this tour.

  • Expand/Collapse What is your cancellation policy?

    We're happy to offer free changes and 100% refund up to 24 hours before tour* Failure to cancel a reservation at least 24 hours prior to scheduled departure may result in forfeited travel funds. Fare difference may apply.

    *See restrictions here

  • Expand/Collapse What is your weather policy? What if it rains?

    Our tours run rain or shine, and we encourage all guests to consult the weather forecast and plan your dress accordingly.

    In the summer months, please prepare for the heat by bringing/wearing adequate sun protection, and staying hydrated. Even if you are accustomed to high temperatures, air-conditioning is not always available in Italy.

  • Expand/Collapse Are reservations required?

    Yes, reservations are required for all tours. 

  • Expand/Collapse Is this tour offered in any other languages, or only English?

    All scheduled tours are in English, but private tours can sometimes be scheduled in other languages, given we have a tour guide who speaks the language of your choice.

  • Expand/Collapse Is this tour appropriate for children?

    Absolutely! This tour is a great overview of the beauty of Tuscany for all ages. However, the visit to the Chianti vineyards and lunch do include lots of wine-related content as well as wine pairings during lunch, and the legal drinking age in Italy is 16 years old.  However anyone under the age of 18 must be accompanied by an adult on our tours.

  • Expand/Collapse What is the number to call if I am lost and trying to find the meeting point?

    If you are having difficulty finding the meeting location for your tour, please call us at +39 06 9480 4888 and our staff will be happy to help you find your way.

  • Expand/Collapse My group size is larger than the dropdown menu allows, how can I book?

    Please contact our Private Tours team to see what options we have.

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