Tuscany Day Trip to Chianti, Siena & San Gimignano from Florence

<p>Tuscany Day Trip to Chianti, Siena & San Gimignano from Florence</p>

Enjoy a small group tour to the true gems of Tuscany with intimate access to your expert tour guide.

Take a walking tour of Siena, one of Italy’s most picturesque and well-preserved Medieval towns, and learn about the famous Palio horse race, one of the most dangerous and unique sporting spectacles in the world.  Spring to Autumn, the guided walk includes a visit to Siena's Cathedral.

Discover one of Tuscany’s classic gems – the town of San Gimignano – a Medieval town with such unique and beautiful architecture it has been designated a UNESCO World Heritage site.

Indulge in an all-inclusive lunch of local ingredients and regional specialties at an authentic Tuscan family farm.

Relax in a comfortable, air-conditioned vehicle (never more than 8-person capacity).

Enjoy an intimate group of 14 or fewer fellow travelers.

  • Details
  • Description
  • Cancellation Policy
  • Related Photos

Tour/Activity Details


10 hours


9:00 am on Monday, Thursday & Saturday (November to Mid January)

9:00 am on Monday and Saturday (Mid January through February)

8:30 am on Monday, Wednesday, Friday & Saturday (March & April)

8:30 am  - Daily except Tuesday (May through October)

Hotel pickup is NOT included; you will meet your guide at Piazza della Repubblica (specifics on your E-Ticket).  Rates are per person in US dollars.  Please order online or call 212-852-4822 to order or for more information.


Tour Details

Before leaving Florence, you’ll be treated to a local secret – the jaw-dropping view of the city from the Piazzale Michelangelo - from which you can take postcard-perfect photos of the Arno, the Ponte Vecchio, the Duomo, Palazzo Vecchio, the Bargello and the bell tower of the Badia Fiorentina.

Then you'll head 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 II, 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 before escorting you to the doors of the breathtaking Siena Cathedral. You don’t have to go in, but we highly recommend that you do.

Walking the hills of Tuscan towns will make you hungry and thirsty, so your next stop is an authentic Italian family farm where some good friends will give you a behind-the-scenes tour of the 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, it's time to 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.



  • Expert, English-speaking Tour Leader throughout (may be split between 2 vehicles for journeys)
  • Lunch & wine tasting in Chianti
  • Comfortable, air-conditioned transport
  • Professional driver (separate to Tour Leader)
  • Small groups of only 14 people or fewer


Not Included

  • Gratuities
  • Hotel Pick-Up/Drop-Off



  • Must be at least 18 years of age to taste wines.
  • Please note that the Cathedral of Siena is closed on Sundays during this tour's visiting time, and is also subject to closure on other days due to special celebrations and festivities.  If this occurs during your visit, your guide will run an alternative itinerary that includes an explanation of the Cathedral from the outside and there will be no refund or discount.
  • Please remember that the Cathedral of Siena is a holy place and attire must be appropriate for the visit.  Both men and women are asked to wear clothing that covers ast least the shoulders and knees.  Your guide cannot be held responsible for denied entry due to improper dress.
  • 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.
  • This tour includes a full lunch. If you have any dietary requirements please specify them on the order form and guides will do everything they can to accommodate you.
  • Unfortunately this tour is unable to accommodate guests with mobility impairments, wheelchairs or strollers.


Sites Visited

  • Siena
  • Chianti farmhouse
  • San Gimignano


Hotel pickup is NOT included; you will meet your guide at Piazza della Repubblica (specifics on your E-Ticket).  Rates are per person in US dollars.  Please order online or call 212-852-4822 to order or for more information.

Cancellation Policy

There are no refunds. All sales are final.

Change policy

If changes are allowed on a tour or activity, a $20.00 per reservation change fee will be applied for any change to a reservation. Please note that some tours and activities do not allow any changes. Date changes can only be made only if we can confirm availability on the new date. While we cannot guarantee any changes can be made, all change requests must be submitted a minimum of 24 hours prior to the tour departure and must be handled on an individual basis through our Reservations Center.

Related Photos

Use the form below to select the date for your reservation. Calendar defaults to first available date. Please verify your date selection prior to submitting your order.

<< March 2018 >>

If you are unable to select a date, it means the tour is unavailable on that date.

Calendar Key

Rates All rates are in US Dollars

Event Date:

March 26, 2018

Desired Time:

08:30 AM