Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.8/5
Based on 326 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano worth booking?
Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano is a 9-hour experience in Florence, Italy, from $185 per person. It scores 80 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.8/5 rating across 326 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 80 / 100
- Rating
- 4.8/5 (326)
- Duration
- 9 hours
- From
- $185 per person
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 tas
What you get
About this experience
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
Included
- 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
Not included
- Gratuities
- Hotel Pick-Up/Drop-Off
What you'll see and do
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.
90 minutes here
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.
90 minutes here
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.
180 minutes here
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.
120 minutes here
Piazza del Campo
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.
Pass by without stopping
Duomo di Siena
If time allows, a visit to the Siena Cathedral, a Tuscan gem, during your free time won't disappoint!
Pass by without stopping
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.
60 minutes here
Where it starts and ends
Meeting point
Florence
Please arrive 15 minutes prior to the start of your tour, your guide will be holding a green Walks sign. This tour meets by the Carousel in Piazza della Repubblica.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Please arrive 15 minutes prior to the start of your tour, your guide will be holding a green Walks sign. This tour meets by the Carousel in Piazza della Repubblica.
Options you can book
Small Group Tour
Group Tour
Private Tuscany from Florence
Siena, San Gimignano & Chianti: Enjoy a Siena guided tour, a gourmet lunch at a vineyard in Chianti, and free time to explore San Gimignano at your own pace.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Walks - Italy & Spain
Know before you go
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- 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.
Photos
What travelers are saying
Outty’s summary of the themes that recur across 326 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
7 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
6 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
4 mentionsThe tastings and food stops are a highlight for most reviewers.
Organization
2 mentionsPickup, timing, and logistics are described as running smoothly.
Traveler reviews
326 verified traveler reviews for Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano. Ratings and reviews provided by Viator and Tripadvisor.
Highly Recommended
Great day. Loved the tour and wine tasting. Very educational. The wine was fabulous and food was excellent.
via Viator
Good tour
Well organized tour with an informative guide. Francesca was helpful and pleasant, the drivers were courteous and the van comfortable.
via Tripadvisor
Heart of Tuscany Tour
The experience was a lot of fun, the towns included in the tour were beautiful, the planning was solid, and Anna was an amazing guide. She told lots of cool stories and answered all of our questions, we had a great time!
via Tripadvisor
Sandra was friendly and...
Sandra was friendly and pleasant, educational and informative, helpful and patient. Her English was excellent.
via Viator
This was by far the best...
This was by far the best tour we had while in Italy. Our tour guide Marco kept us all engaged for the entire trip and gave us a wealth of information. He was informative and funny too. We had a wonderful time with our teenagers. Great shopping in San Gimignano and delicious gelato. The wine tasting and lunch was delicious and plentiful. After lunch we went to Siena which while beautiful is very hilly so that was harder than we expected on full bellies. Overall an incredible trip which was comfortable in an air conditioned Mercedes van. Loved this tour and Marco was a fabulous guide!
via Viator
Good to know
- Duration
- 9 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $185 to $1349
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 114
- Verdict
- Strongly Recommended
Why this scores 80
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano cost?
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Prices start at $185 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano take?
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Plan for about 9 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Florence is not rushed.
Is Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano worth it?
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It holds an Outty Ranking of 80 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.8/5 across 326 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 9-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano?
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Around 114 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Florence can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Florence and add a light layer if any part of the 9-hour experience runs outdoors or after sunset.
Where does Florence Day Trip: Chianti Wine Tasting, Siena, San Gimignano start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Florence within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Florence?
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On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Florence?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Florence?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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