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Chianti & Castles: Day Trip from San Gimignano + Wine Tasting
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Witness the beauty of Tuscany with a scenic tour
This six-hour day trip travels from San Gimignano into Chianti Classico, combining guided visits and wine tastings at two estates with a stop in Castellina in Chianti. The itinerary also includes tastings of extra virgin olive oil and balsamic vinegar, plus time to walk along a cypress-lined avenue and take in the Tuscan countryside. Roundtrip minivan transport is included for groups of up to eight participants.
What's Included
- Roundtrip from San Gimignano by minivan (max 8 participants)
- Wine tasting and guided tours of two popular wine estates
- Oil and balsamic vinegar tasting
- Visit to Castellina in Chianti
What's Not Included
- Gratuites
Prices and discounts
Opening hours
Meeting Point
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Chianti & Castles: Day Trip from San Gimignano + Wine Tasting:
126 Via San Giovanni Siena
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Average Duration
Duration: 06:00
Cancellation Policy
Cancellation allowed up to 24 hours before the event.
Not Wheelchair Accessible
Additional Information & Description
Chianti & Castles takes you from San Gimignano into the Tuscan countryside for a six-hour day of wine, scenery and historic towns. The route explores Chianti Classico, pairing time among its rural landscapes with visits that bring the region’s wine-making into focus.
Guided visits to two wine estates
Two wine estates welcome you for guided tours and wine tastings, giving you more than a single stop on the region’s wine trail. One winery is tucked away in the Chianti Classico countryside; another is recognized by wine connoisseurs for its quality. The tastings are a chance to sample the wines where they are produced, with the estate tours adding context to what reaches your glass. Extra virgin olive oil and balsamic vinegar tastings are also included, extending the day’s flavours beyond wine.
A walk along a cypress-lined avenue
The landscape is part of the visit, rather than simply the view from the vehicle. You’ll have the chance to wander along one of Tuscany’s characteristic cypress-lined avenues and take photographs of the surrounding countryside. This is a distinct moment away from the estate tastings: time on foot to look along the line of trees and capture the rural scenery that gives this part of Italy such a recognizable appearance.
Castellina in Chianti and historic surroundings
A visit to Castellina in Chianti adds a named town stop to the day. The wider route also takes in ancient churches, medieval castles and towns, bringing a historical dimension to the countryside excursion. These stops shift the emphasis from the region’s produce to its built surroundings, with opportunities to stroll through places shaped by their older buildings.
Departure, group size and tickets
Roundtrip transport from San Gimignano is included in a minivan carrying a maximum of eight participants. Arrive at 126 Via San Giovanni 15 minutes before departure. Live guiding is available in English, Italian and Spanish. Tickets are delivered instantly and can be presented on a smartphone. Gratuities are not included.
Frequently Asked Questions about Chianti & Castles: Day Trip from San Gimignano + Wine Tasting
It includes roundtrip minivan transport from San Gimignano, guided tours and wine tastings at two wine estates, oil and balsamic vinegar tastings, and a visit to Castellina in Chianti.
The minivan carries a maximum of eight participants.
The day trip lasts six hours.
Live guiding is available in English, Italian and Spanish.
Yes. Tickets are delivered instantly and can be presented on a smartphone.
No. Gratuities are excluded from the tour.
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