Chianti and Castle Wine Tour

From€49
5 hours
Siena, Italy

About this activity

Experience the essence of Tuscany with a guided tour through Chianti's vineyards, savoring local wines, and exploring a historic castle, all within a 5-hour excursion from Siena.

Highlights

  • Explore scenic Chianti vineyards
  • Taste renowned local wines
  • Tour a historic Tuscan castle
  • Learn about winemaking traditions
  • Enjoy picturesque Tuscan landscapes

Full description

Immerse yourself in the rich flavors and history of Tuscany on this captivating 5-hour tour from Siena. Traverse the rolling hills of Chianti, renowned for its picturesque vineyards and exceptional wines. Led by an expert guide, you'll visit a historic castle, delving into its storied past and architectural splendor. Along the way, indulge in tastings of the region's finest wines, each sip offering a taste of Tuscany's heritage. This excursion promises a delightful blend of culture, history, and gastronomy, making it an unforgettable addition to your Italian adventure.

Included / Excluded

  • Guided tour of Chianti vineyards
  • Wine tasting sessions
  • Visit to a historic castle
  • Meals and personal expenses

Itinerary

1

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.

Duration: 30 minAdmission: NOT_APPLICABLE
2

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.

Duration: 1 hourAdmission: NOT_APPLICABLE
3

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.

Duration: 1h 30mAdmission: NOT_APPLICABLE
4

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

Duration: 1 hourAdmission: NOT_APPLICABLE
5

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

Duration: 30 minAdmission: NOT_APPLICABLE
6

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

Duration: 30 minAdmission: NOT_APPLICABLE

Meeting point

Start Location

Unknown location

Important information

Know before you book

  • Tour operates rain or shine; dress appropriately for weather conditions.
  • Minimum booking requirements may apply; check availability in advance.
  • Confirm tour details and meeting points upon booking.

Know before you go

  • Wear comfortable walking shoes for vineyard and castle exploration.
  • Bring a camera to capture the stunning Tuscan scenery.
  • Consider bringing a light jacket, as temperatures can vary.

Cancellation policy

Free cancellation up to 1 days before the activity starts

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

Accessibility

  • Stroller Accessible
  • Easy Public Transport
  • Infants Required On Laps
  • Infant Seats Available

Good to know

  • 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

Traveler reviews

4.5
175 reviews
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7

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.

MICHELLE_NApr 26, 2026VIATOR

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).

Raquel_DApr 3, 2026VIATOR

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!

Steven_SMar 28, 2026VIATOR

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.

Christina_PNov 9, 2025VIATOR

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.

R5932ROruthmOct 15, 2025TRIPADVISOR

Additional information

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