Tours/Siena/Hidden Castles & Chianti Wine Experience– Small Group
Viator · group up to 15 pax

Hidden Castles & Chianti Wine Experience– Small Group

4.5(179)Siena1 hour
VIATOR4.5(134)TRIPADVISOR4.6(45)

Description

Visit two charming family-run wineries in the heart of the Chianti region, learn about local winemaking traditions, and taste 7 exquisite wines paired with bruschetta, salami, cheese, and extra virgin olive oil. Between tastings, stop at the medieval village of Monteriggioni for free time to explore or relax before returning comfortably to Siena. travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people. Note :Wine tastings take place in English, with your tour leader providing translation support when needed. A moderate amount of stairs and walking is involved During special events, opening times can change The tour itinerary may change, but all tour stops will be visited

Tour Options

Low Cost Chianti Half Day
  • Low Cost Chianti Half Day 2:00: 3 glasses of wine and snacks
Low Cost Chianti Half Day Tour
  • Low Cost Chianti HD - 13:00: 3 glasses of wine and snack
Premium Chianti Half Day
  • 2:00 pm: Chianti & Castle Small-Group Tour from Siena with 7 wines
Premium Chianti Half Day 1:00
  • 1:00pm: Chianti & Castle Small-Group Tour from Siena with 7 wines

Itinerary

30 min

Start your trip at Siena Station Ferrovia, where you will meet the staff. You will recognize them by their green shirt. You will travel by minivan.

60 min

Between the two tastings, enjoy some free time in Castellina in Chianti, a picturesque village surrounded by rolling vineyards, perfect for a relaxing walk or a coffee break.

90 min

Enjoy an authentic wine experience in the Chianti region, visiting one charming family-run winery and tasting of 3 wines with bruschette, bread and olive oil.

60 min

Second tasting experience featuring Tuscan wines, olive oil, and local products.

30 min

Stop for some free time in Monteriggioni, a beautiful medieval walled village. Take beautiful photos of the Tuscan landscape and visit local shops.

30 min

Return to Siena. Relax on the ride back after an unforgettable afternoon in the Chianti countryside.

Highlights

Wine, Olive oil and balsamic vinegar sampling
Two wine tastings in Chianti
travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people.
Local products tasting (bruschette, salami, cheese)
Expert multilingual tour leader and driver-guide
Tasting of 7 wines in total
Travel by air-conditioned minivan or minibus

What's included

Included
Wine, Olive oil and balsamic vinegar sampling
Two wine tastings in Chianti
travel in an air-conditioned minivan for up to 8 people or a minibus for up to 30 people.
Local products tasting (bruschette, salami, cheese)
Expert multilingual tour leader and driver-guide
Tasting of 7 wines in total
Travel by air-conditioned minivan or minibus
Not included
Gratuities

Traveller Ratings

4.5
179 reviews
5
128
4
31
3
7
2
5
1
8

Important Information

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Specialized infant seats are available
  • Suitable for all physical fitness levels
  • Customers must be able to climb and descend stairs.
  • Please note that during low season from November 16th to March 14th Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough passengers to meet requirements (4pax are required). In the event of this occurring, you will be offered an alternative or full refund

Reviews(179)

D
Doredi_B
June 5, 2026
Amazing tour

The entire tour was wonderful and informative. The locations we saw were so beautiful and the wine was amazing. The hosts at the wineries were very enthusiastic about sharing their knowledge and history of the vineyard

Operator response

Dear Customer, Thank you for your feedback! We are delighted to hear that you enjoyed the tour, the beautiful locations, and the wine experience, as well as the enthusiasm and knowledge shared by the winery hosts. We truly appreciate your support and hope to welcome you again soon. Kind regards, My Tour in Italy

L
Lindsay_H
May 30, 2026
This was a good tour,...

This was a good tour, however, small group to me means 10 people or less. This was definitely closer to 30 plus people, and felt a bit like herding cats. The vineyards were nice, and well prepared for us. The two towns we visited were lovely. Overall, was an ok trip. I would have liked to see more of the actual vineyards rather than just the tasting rooms.

L
Linda_L
May 29, 2026
Did not occur

The reason for the rating THIS NEVER OCCURRED IT WAS CANCELLED 1 DAY prior to the booking I paid the tour well in advance then was offered another tour yes offered another tour 1.Not 8 but 20 people 2.No tuscan villa wine tasting it was a winery 3.No maps provided with all the non guide tikmes all day 4.The second half of the day waste of time as we had 1 1/2 hours to browse a wine making town with few shops open then 5Not 20 but 30 people sitting in a garden tasting red wine no wine tour at all and to offer a toilet in the open garden was disgusting

W
Whitney_l
May 27, 2026
We loved everything about...

We loved everything about this tour! Both wineries were fabulous and we loved exploring at the other stops. Luca was a wonderful guide, so full of information, kind and funny, and most of all so patient!

Operator response

Dear Customer, Thank you for your feedback! We’re very happy to hear you enjoyed the tour, the wineries, and Luca’s guidance. We truly appreciate you sharing your experience with us. Best regards, my Tour in Italy

M
MICHELLE_N
April 26, 2026
Best tour of our trip

Fantastico! Winery tastings were informative, fun and delicious. The bonus stops in two little towns put this over the top for me. Really great experience and our guide V and driver Fernando were wonderful.

Operator response

Dear Customer, Thank you for your feedback! We’re glad you enjoyed the winery tasting, the extra stops, and your guide V and driver Fernando. Hope to see you again soon! Best regards, my Tour In Italy

R
Raquel_D
April 3, 2026
The experience was nice....

Such a beautiful day in Tuscany! The views were incredible, the wines were amazing, and everything was perfectly organized. Highly recommend! We had an excellent tour guide (Val) and driver (Dontorel).

Operator response

Dear Customer, Thank you for your feedback! We’re glad you enjoyed the day in Tuscany and that the guides made your experience special. We appreciate your recommendation and hope to see you again soon. Best regards, my Tour in Italy

S
Steven_S
March 28, 2026
A great and varied afternoon not soon to be forgotten

The 2 wineries visited were both very nice…the wine at the 2nd (along with the balsamic vinegar) was exceptional. 2 historic site stops in addition made this a complete experience. Actually compared to some tours this felt like a great value!

Operator response

Dear Customer, Thank you for your feedback! We’re so happy you enjoyed the wineries, especially the wine and balsamic vinegar at the second stop. It’s great to hear the historic sites are added to the experience too. Best regards, my Tour in Italy

C
Christina_P
November 9, 2025
Great guided experience with Luca

Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in Tuscany.

Operator response

Dear Customer, Thank you for sharing your feedback with us! We’re delighted to hear that Luca provided such knowledgeable guidance and helpful restaurant recommendations. It’s wonderful that you enjoyed the wineries, the cities, and the stunning Tuscan views. Your feedback means a lot to us, and we hope to welcome you again soon for another memorable tour! Best regards, My Tour In Italy

R
R5932ROruthm
October 15, 2025
Fabulous tasting and countryside in comfort.

We loved this! I wanted to be in the countryside for a Sunday afternoon and this was a great choice. Very comfortable 8-person van. Terrific guide. Beautiful drive in countryside going to two small towns I couldn't have gotten to on my own. Two very different and marvelous tastings with great hosts. Tour was exactly as promised only better.

1 people found this helpful
Operator response

Dear Customer, Thank you for sharing your feedback! We’re delighted to hear you enjoyed the peaceful countryside, the comfortable van, and the tastings. It’s great to know the tour exceeded your expectations. We hope to have the pleasure of welcoming you again on another adventure soon! Best regards, My Tour In Italy.

N
NaomiterB
October 7, 2025
Perfetto!

Thank you so much to Valesca and Massimo for providing us with an amazing tour! I would recommend it to people who'd love to learn more about wine. We loved it! Grazie mille

Operator response

Dear Customer, Thank you for sharing your feedbck with us! We’re delighted to hear that you enjoyed the tour with Valesca and Massimo and found it informative and enjoyable. Your recommendation means a lot to us, and we’re thrilled that you had such a great experience learning about wine. We hope to welcome you back on another tour soon! Best regards, My Tour In Italy.

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