Discover the captivating essence of Tuscany on this immersive 5-hour tour. Departing from Siena, you’ll explore renowned Chianti wineries, medieval castles, and charming villages – all while indulging in exquisite local wines and cuisines. With a personalized experience for a small group, this excursion promises an unforgettable cultural journey through the heart of Italy’s renowned wine country. What secrets and delights await you in this picturesque corner of the world?
Key Points

- A 5-hour excursion from Siena to explore the Chianti region, including visits to two renowned wineries and scenic stops at ancient churches, medieval castles, and small villages.
- The tour is available in English and Italian, with a maximum group size of 8 participants.
- Comfortable transportation is provided via a climate-controlled minivan, with pickup services available for accommodations within a 10-kilometer radius.
- The tour requires a minimum of 4 participants and offers a full refund for cancellations up to 24 hours in advance.
- Participants must be able to climb and descend stairs, and the tour is not suitable for wheelchair users.
Tour Overview and Pricing

The Chianti and Castles Tour is a 5-hour excursion from Siena that takes visitors through the picturesque Chianti region, visiting Castellina in Chianti, two renowned wineries, ancient churches, medieval castles, and small villages.
Priced from $92.79 per person, the tour is available in English and Italian. Participants can cancel up to 24 hours in advance for a full refund, and they can reserve their spot and pay later.
The small-group tour, with a maximum of 8 participants, departs from in front of Hotel Minerva in Siena.
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Itinerary and Highlights

Where does the tour start? The Chianti and Castles Tour with Wine Tastings departs from Via Giuseppe Garibaldi, 72 in Castellina in Chianti.
Guests will visit two renowned Chianti wineries for tastings paired with local Tuscan cuisine.
The tour also stops at ancient churches, medieval castles, and small villages across the scenic Chianti countryside.
Travelers will enjoy breathtaking vistas of rolling hills and vineyards from the climate-controlled minivan.
The itinerary showcases the history, architecture, and world-famous wines of the Chianti region, providing an immersive cultural experience over the 5-hour journey.
Transportation and Group Details

Guests are transported via a climate-controlled minivan for the small-group tour, which has a maximum of 8 participants.
The tour departs from the meeting point at Hotel Minerva in central Siena. Pickup and drop-off services are available for an additional fee for accommodations within a 10-kilometer radius of Siena.
The tour requires a minimum of 4 participants to operate. If fewer than 4 are booked, alternative arrangements or rescheduling will be offered without a refund.
Participants must arrive 15 minutes before the scheduled departure time.
Important Information

Although participants must arrive 15 minutes prior to departure, the tour is not suitable for wheelchair users as they’ll need to climb and descend stairs. Plus, the tour requires a minimum of 4 participants, and if there are fewer, alternative arrangements or rescheduling will be offered without a refund.
| Requirement | Detail |
| — | — |
| Age | Only participants over 18 years can consume alcohol |
| Mobility | Participants must be able to climb and descend stairs |
| Minimum Participants | 4 |
| Cancellation Policy | Cancel up to 24 hours in advance for a full refund |
The tour promises breathtaking landscapes and immersive experiences at Chianti wineries, ancient churches, and medieval castles, making it a must-see for any discerning traveler.
More Great Tours NearbyCustomer Reviews and Ratings

The Chianti and Castles Tour has earned an impressive 4.5/5 overall rating from 319 reviews, showcasing the quality of the experience.
Travelers consistently praised the professionalism of the guides, who expertly led them through the picturesque Chianti region and engaging wine tastings.
The transportation in a climate-controlled minivan also received high marks, with reviewers noting the comfort and convenience.
While most felt the tour offered excellent value, a few suggested exploring more of the countryside.
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Starting in Castellina in Chianti

The tour departs from Castellina in Chianti, a charming medieval town nestled in the heart of the Chianti wine region.
Visitors are greeted by the town’s well-preserved historic center, featuring:
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Narrow cobblestone streets lined with local shops and restaurants.
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The striking Rocca di Castellina, a 14th-century fortress overlooking the surrounding vineyards and olive groves.
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The Church of San Salvatore, renowned for its beautiful Romanesque architecture.
From this picturesque starting point, the tour continues on a journey through the Chianti countryside, offering a glimpse into the region’s rich history and renowned winemaking traditions.
Exploring Chianti’s Renowned Wineries

After exploring the picturesque town of Castellina in Chianti, the tour delves into the region’s renowned winemaking tradition with visits to two esteemed Chianti wineries.
At the first winery, guests enjoy a tasting of the classic Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes that make up the celebrated Chianti blends.
The second winery offers a more in-depth experience, with a guided tour of the vineyards and cellars followed by a food-and-wine pairing, showcasing how the local terroir and traditional methods produce these world-class vintages.
Medieval Castles and Small Villages

Next, the tour explores several medieval castles and small villages dotting the Chianti countryside. Participants wander through the ancient stone walls and winding alleys of these historic sites, seeing the region’s rich past.
The highlights include:
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Discovering the well-preserved Castellina in Chianti, a quintessential Tuscan town with a distinctive fortress and panoramic views.
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Marveling at the impressive medieval architecture and fortifications of the castle in Monteriggioni, a remarkably intact hilltop village.
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Strolling through the charming streets of Radda in Chianti, a picturesque town known for its artisanal shops and traditional Tuscan cuisine.
The Sum Up

This Chianti and Castles tour from Siena offers a captivating blend of Tuscan culture, history, and world-renowned wines. Guests’ll enjoy a personalized experience, exploring stunning landscapes, medieval castles, and premier wineries. With a small group size and comfortable transportation, it’s the perfect way to take in the charm of Tuscany’s renowned wine region.
You can check availability for your dates here:More Wine Tours in Siena
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