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Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano

350 Reviews 4.84 out of 5 stars Based on 350 traveler reviews collected by Cool Shore Excursions and TripAdvisor | Recommended by 97% of reviewers |
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Florence, Italy
Don't miss out!
On average, this is booked 16 (0) days in advance.

9 hours (approx.)
Mobile ticket
Offered in: English
Instant confirmation

Overview

When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, wander the storybook streets of the UNESCO-listed village San Gimignano. Indulge your taste buds with a seasonal lunch and wine tastings at a family-run farm in the Chianti region, and visit the remarkably well-preserved medieval town of Siena, home to a magnificent cathedral and the famous Palio horse race. Group size is limited to 14 for a more personalized experience.

What's Included

  • Expert English-speaking tour leader
  • Piazzale Michelangelo
  • Free time in San Gimignano and Siena
  • Gratuities
  • Hotel Pick-Up/Drop-Off
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Meeting Location

Meeting point

Piazza della Repùbblica
50123 Firenze FI, Italy

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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Tuscany

Your driver and tour leader will pick you up in a comfortable, air-conditioned transport in central Florence and drive you through the hills of Tuscany. You'll pass the best panoramic viewpoint of Florence and pause for pictures.
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1 hour 30 minutes Admission Ticket Free

San Gimignano

Indulge your imagination with a stop at San Gimignano, a town of such unique architectural beauty it has been designated a UNESCO World Heritage Site. You'll have free time to explore its winding streets on your own. Please note that the private option does not include a guided tour of San Gimignano. Guests will instead enjoy extended free time to explore the town at their own pace.
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1 hour 30 minutes Admission Ticket Free

Tuscany

Walking the hills of Tuscan towns will make you hungry 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 each dish.
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3 hours Admission Ticket Free

Siena

Siena is one of the best-preserved examples of medieval Italian architecture in the world. Spared German bombing in WWII, 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.
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2 hours Admission Ticket Free

Piazza del Campo (pass by)

One of the highlights your tour leader will recommend during your free time. Pause amidst the square where fervent horses race to win the honor of bringing home the palio - a handpainted silk banner of the highest regard.
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Duomo di Siena (pass by)

If time allows, a visit to the Siena Cathedral, a Tuscan gem, during your free time won't disappoint!
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Piazza della Repubblica

At the end of the day, hop aboard your comfortable private coach bus back to Florence. We've taken care of the logistics so all you have to do is enjoy the food, the sights, and the scenery.
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1 hour Admission Ticket Free

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Additional Info

  • Confirmation is instant and will be received at time of booking
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Those with dietary restrictions need to contact us after booking the tour so we can arrange your lunch. Unfortunately, we cannot accommodate vegans or those with celiacs.
  • Tickets for the Siena Cathedral are not included in the tour price. If you wish to visit the Cathedral, your tour leader will assist you. The Cathedral is closed on Sundays and for certain holy days.
  • In order to get into the city center, we utilize small luxury minivans. This allows us to avoid the parking lots outside of the center requiring us to walk. Your guide may need to split time between vehicles on groups larger than 8.

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CET). Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

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Activity code: C-15693P28

Traveler Photos

Reviews

4.84
350 reviews

Average 4.84 out of 5 stars based on 350 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor

5 stars
305
4 stars
35
3 stars
10
2 stars
0
1 star
0
Don't miss out!
On average, this is booked 16 (0) days in advance.

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What's Included

Activity name

  • Expert English-speaking tour leader
  • Piazzale Michelangelo
  • Free time in San Gimignano and Siena
  • Designated professional driver
  • Siena Cathedral (exterior)
  • Gourmet lunch and wine tasting in Chianti
  • Chianti farmhouse & vineyard
  • Air-conditioned transport
  • Gratuities
  • Hotel Pick-Up/Drop-Off

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Specialized infant seats are available
  • Unfortunately due to the nature of this tour it is not suitable for guests with mobility impairments or with wheelchairs, or strollers.
  • This is a walking tour. Guests should be able to walk at a moderate pace without difficulty.
  • Those with dietary restrictions need to contact us after booking the tour so we can arrange your lunch. Unfortunately, we cannot accommodate vegans or those with celiacs.
  • Tickets for the Siena Cathedral are not included in the tour price. If you wish to visit the Cathedral, your tour leader will assist you. The Cathedral is closed on Sundays and for certain holy days.
  • In order to get into the city center, we utilize small luxury minivans. This allows us to avoid the parking lots outside of the center requiring us to walk. Your guide may need to split time between vehicles on groups larger than 8.
  • Please note that this description is an example, and your experience may vary depending on the season, day of the week, and group size. Regardless of where your tour goes, you always have an excellent experience.
  • Please note: This tour offers multiple options. Take a moment to choose the one that best suits your interests.
  • This tour/activity will have a maximum of 14 travelers

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