Chianti and Castle Small Group Tour with Wine Tasting from Siena

Overview

Available languages

English

Italian

Spanish

5 hours

Mobile ticket

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.

Additional Info

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

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

What‘s Included

Wine, Olive oil and balsamic vinegar sampling

Two wine tastings in Chianti

Local products tasting (bruschette, salami, cheese)

Tasting of 7 wines in total

Travel by air-conditioned minivan or minibus

Gratuities

What To Expect

Siena

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.

30 minutes • Admission Not Applicable

Castellina In Chianti

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.

1 hour • Admission Not Applicable

Options

Chianti & Castle Tour

1:00pm: Chianti & Castle Small-Group Tour from Siena

Chianti & Castle Small-Group

2:00 pm: Chianti & Castle Small-Group Tour from Siena

Reviews

4.49

172 reviews

Total reviews and rating from Viator & Tripadvisor

123

Great guided experience with Luca
Christina P,
Nov 9, 2025
- Review from Viator
5.00
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.
Fabulous tasting and countryside in comfort.
R5932ROruthm,
Oct 15, 2025
- Review from Tripadvisor
5.00
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.
Perfetto!
NaomiterB,
Oct 7, 2025
- Review from Tripadvisor
5.00
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
Tour host was extremly...
Jeremy P,
Oct 6, 2025
- Review from Viator
5.00
Tour host was extremly knowledgeable and created a friendly atmosphere on the mini-bus. The 2 wine tasting experiences were excellent, but contrasting. One being more of a family vine yard located on an old Tuscan farm in the hills, the other being a dedicated tasting / function venue, hosted by a charismatic Sommelier. Quality of wine superb and from my hazy memory exceeded the 7 glasses advertised! Only down side was disorganised pick-up at station. Having a wine tour notice on bus and having host there at stated meet time, 15 mins before departure. Italian speaking driver turned several clients away before host arrived. Still a 5-Star tour though, as rest of afternoon made up for this.
Great tour, lovely guide! Fantastic wine!!
markpE6895ZK,
Oct 5, 2025
- Review from Tripadvisor
5.00
Great trip, with entertaining, helpful and friendly guide “Val”, and safe driver “Sal”. Comfortable air conditioned mini coach, with a visit to 2 wineries and 2 small towns. Enjoyed the day, but…. This trip would be far better with an extra 30 minutes in each location. Felt rushed, would have been nice to either explore more, or sit and relax and enjoy a nice glass of Chianti!!
Valeska was a wonderful...
Dane H,
Oct 4, 2025
- Review from Viator
5.00
Valeska was a wonderful tour guide and both tastings were great! We had thought about going to a couple of vineyards on our own but it was well worth the little bit extra for the tour. I definitely recommend it.
Recommended tour
j rgensT4094ZC,
Oct 3, 2025
- Review from Tripadvisor
5.00
That was a wonderful day! Tour guide was great. The program was very well put together. The bus driver is also recommended. All in all, this tour is highly recommended,
You’ll have to get...
Emma G,
Sep 26, 2025
- Review from Viator
5.00
You’ll have to get transportation to the meeting point. Make sure to wear walking shoes and check the weather. Guides are knowledgeable and friendly. Highly recommend for groups or even if traveling solo!
Great tour
Camille C,
Sep 25, 2025
- Review from Viator
5.00
It was a wonderful tour. Luca was informative and had a great sense of humor. The wineries we visited were welcoming and the tasting great. I highly recommend this tour.
Relaxing and enjoyable experience in Tuscany.
Angie B,
Sep 24, 2025
- Review from Viator
5.00
It was relaxing. Love our guide, don’t remember her name, a nice girl from Venezuela who spoke several languages, had a very engaging voice . The driver was nice and patient, nice little towns we visited. Delicious wine!