
Chianti and Castles Tour from San Gimignano Small Group
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 1 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Chianti and Castles Tour from San Gimignano Small Group worth booking?
Chianti and Castles Tour from San Gimignano Small Group is a 6-hour experience in San Gimignano, Italy, from $65 per person. It scores 57 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 1 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 57 / 100
- Rating
- 5/5 (1)
- Duration
- 6 hours
- From
- $65 per person
Enjoy a half-day journey from San Gimignano to the picturesque wine region of Chianti. Begin your adventure with a visit to the charming village of Castellina in Chianti, followed by a delightful wine tasting at a nearby
What you get
About this experience
Enjoy a half-day journey from San Gimignano to the picturesque wine region of Chianti. Begin your adventure with a visit to the charming village of Castellina in Chianti, followed by a delightful wine tasting at a nearby vineyard. Stroll around Monteriggioni, a medieval village where you can admire the ancient walls. At a beautiful wine estate, take part in a wine tasting savoring the rich aroma and ruby-red tones of Chianti wine crafted from Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes.
What's included
Included
- Visit two wineries in the Chianti area
- Expert multilingual guides
- Wine, oil and balsamic vinegar tasting
- Travel by air-conditioned minivan
- Alcoholic Beverages
Not included
- Gratuities
- Lunch
What you'll see and do
San Gimignano
Start the trip from San Gimignano, Porta San Giovanni for a half day tour on board of a minivan. Reach Castellina in Chianti by admiring the landscape. Our drivers can give you information during the trip.
60 minutes here
Castellina In Chianti
Enjoy free time to visit Castellina in Chianti. In the heart of the town you can admire the ancient Rocca (15th century), an imposing tower with its keep offering a breathtaking view over the rooftops of the town. The Church of San Salvatore, of 15th-century origin and renovated in neo-Romanesque style after the damage caused by World War II. Explore the covered street in which one can find workshops and restaurants. Amidst secret passages and small loopholes overlooking the panorama of the Tuscan hills.
60 minutes here
Strada Statale 222 Chiantigiana
Enjoy a wine tasting in a winery in the Chianti area. Here you can taste the Chianti wine. The beautiful ruby red colour and the characteristic aroma with hints of violet are the special features that reveal the identity of one of the most famous wines in the world: Chianti. This wine comes from the skilful blending of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes. On this journey, discover the breathtaking and unspoilt landscapes that have cradled the Chianti vineyards for centuries, giving you a harmony of colours that can only be found on the hills of this region.
60 minutes here · Admission included
Monteriggioni
Enjoy a stroll around Monteriggioni medieval village. The castle of Monteriggioni dates back to the second two decades of the 13th century and was founded by the Republic of Siena to defend its borders against the rival city, Florence; the two cities clashed for centuries, until the capture of Siena in 1555.
60 minutes here
Strada Statale 222 Chiantigiana
Enjoy a wine tasting in a winery near Monteriggioni. You will be able to taste wines from a quality cellar that true connoisseurs will certainly recognize, surrounded by a magnificent landscape, in a magical and pleasant atmosphere.
60 minutes here
San Gimignano
Hop on the minivan for the trip back to San Gimignano, where our drivers will drop you off at Porta San Giovanni.
60 minutes here
Where it starts and ends
Meeting point
San Gimignano
Meet our driver in front of Porta San Giovanni.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Meet our driver in front of Porta San Giovanni.
Options you can book
WINTER
Chianti and Castles Tour from San Gimignano Small Group
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- MyLuxuryDrive
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Only Adult 18 years old and above are allowed for wine and any other alcoholic beverages
Photos






Traveler reviews
1 verified traveler reviews for Chianti and Castles Tour from San Gimignano Small Group. Ratings and reviews provided by Viator and Tripadvisor.
Perfect day with family (grown children)
Daniel was excellent. Everything was perfect. The village, the wine tastings and the castle. Would definitely recommend.
Response from the operator: Dear Barbara, Thank you for this beautiful review! Best wishes, My Luxury Drive
via Viator
Good to know
- Duration
- 6 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $65 to $119
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 57
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Chianti and Castles Tour from San Gimignano Small Group: questions travelers ask
Practical detail on this experience, plus the wider planning questions for San Gimignano.
How much does Chianti and Castles Tour from San Gimignano Small Group cost?
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Prices start at $65 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in San Gimignano usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Chianti and Castles Tour from San Gimignano Small Group take?
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Plan for about 6 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 San Gimignano is not rushed.
Is Chianti and Castles Tour from San Gimignano Small Group worth it?
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It holds an Outty Ranking of 57 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 1 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in San Gimignano, and how flexible the cancellation terms are.
Can I cancel or reschedule Chianti and Castles Tour from San Gimignano Small Group?
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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 Chianti and Castles Tour from San Gimignano Small Group suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 6-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Chianti and Castles Tour from San Gimignano Small Group?
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Around 0 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 San Gimignano 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 San Gimignano and add a light layer if any part of the 6-hour experience runs outdoors or after sunset.
Where does Chianti and Castles Tour from San Gimignano Small Group 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 San Gimignano 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 San Gimignano?
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On Outty we rank every San Gimignano experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Wine and food tasting in an organic family winery, Tuscan Cooking Class, Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano. 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 San Gimignano?
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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 San Gimignano?
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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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