Day trip

Medieval Castles & Chianti Wine Tasting Tour with Lunch

Medieval Castles & Chianti Wine Tasting Tour with Lunch

Activity provider: Tuscan Escapes by Papilio

From US$ 169.33 per person

Explore the Chianti countryside on this full-day tour that takes you to impressive medieval castles and top regional wineries and their cellars. Enjoy a typical Tuscan meal in the company of your expert wine tour guide and taste fine wines as well.

About this activity

Free cancellation
Cancel up to 24 hours in advance to receive a full refund
Covid-19 precautions
Special health and safety measures apply. Learn more
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Duration 8 hours
Check availability to see starting times.
Live tour guide
English, Italian
Small group
Limited to 8 participants


  • Visit the Castle of Brolio as well as the hilltop town of Radda in Chianti
  • Tour 2 different wineries and taste fine Chianti wines
  • Enjoy a Tuscan meal at a wine estate
  • Meet a local wine producer and learn about the wine-making process
Full description
The first stop on your full-day tour of Chianti will be at the walls of Castello di Brolio, where you’ll get an up-close look at the picturesque vineyards. It was here that Baron Bettino Ricasoli introduced the world to Chianti red wines, known around the world for their distinctive taste and easy drinkability, and for the straw flasks, which at one time covered the bottles. Next stop on the tour is Castle of Brolio as well as the hilltop town of Radda in Chianti. While visiting the castle and its grounds, you’ll learn about its origins and history, and then enjoy a tasting of it's wine. Enjoy lunch here, it will consist of local, traditional Tuscan specialties.  In the afternoon it will be time to visit to a third winery. Meet the local producer and tour the estate that has been in the hands of the same family for many centuries. Visit the old cellars and learn about the traditions of the Chianti folk, while savoring and learning about great Chianti wines. The estate’s wines are made from Merlot, Sangiovese, Cabernet Sauvignon, Chardonnay, and Pinot Bianco grapes. You’ll sample 4 different wines, including 1 white wine, 2 red wines, and a special dessert wine, all of which are in limited production and only available at the villa.
  • Traditional Tuscan lunch
  • Tour of 2 wineries with wine tastings
  • English-speaking expert wine tour guide
  • Transportation by air-conditioned vehicle
  • Castle of Brolio visit
  • Hotel pick-up
  • Tips/gratuities
Covid-19 precautions
Safety measures in place
  • All areas that customers touch are frequently cleaned
  • You must keep social distance while in vehicles
  • The number of visitors is limited to reduce crowds
Traveler requirements
  • You are required to bring and wear a mask

Select participants and date



Meeting point

Meet at 09:30 at the Church of San Domenico (under the large tree), Piazza San Domenico, 53100 Siena

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Important information

Know before you go

  • It may occur that a visit to the farm is not possible on the day of your tour in this case you will enjoy your traditional Tuscan meal at a typical local trattoria
  • You will be required to make your way to the designated meeting point as there is no hotel pickup included on this tour
  • Gratuities have not been included in the price of this tour
Customer reviews

Overall rating

5 /5

based on 6 reviews

Review summary

  • Guide
  • Transportation
  • Value for money
  • Safety

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Our Guide was simply “Superb” in every way! She was extremely knowledgeable about the wine industry, the countryside and the history of the Castle we visited, as well as, the history of wine growers in Italy! The Location she choose for our lunch in Tuscany, was awesome, the food selection, preparation & taste was incredible. We were served on the patio with an unbeatable view of the winery, and oh, what a charming dining facility! It was my sister & brother-in-law 50th Anniversary, and this tour could not have been more perfect and more memorable! Thank you to everyone!

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October 29, 2019

A fun and informative day. Our guide, Daniel was very knowledgeable and gracious.

November 5, 2021

Very nice day

Nice excursion, very interesting guide (David) pleasant atmosphere for dinner, we enjoyed the small group of 7 people, great organization.

April 23, 2019

Product ID: 47300