Immerse yourself in the heart of the historic Chianti region on this unforgettable guided tour. Discover the rich history, meet welcoming locals, savor world-class wines, and uncover hidden gems. Experience Tuscany like never before and feel like a true Tuscan for a day.

Itinerary

Start Time:
The tour begins in Siena between 8:30 a.m. and 9:00 a.m.

Vagliagli – Medieval Village & Iconic Film Spot
Enjoy a scenic drive to the picturesque village of Vagliagli, known for its medieval charm and its appearance in the movie Letters to Juliet. Explore the area’s history and capture breathtaking photos at this stunning location.
First Winery – Boutique Estate Experience
Visit a family-run boutique winery operating since the 1970s. Meet the winemaker and learn about the wine-making process, from vineyard to glass. Taste exquisite wines and extra virgin olive oil crafted on the estate.
Radda in Chianti – Historical Stop
Take a moment to delve into the history of Radda in Chianti, a quintessential Chianti town. Stroll through its charming streets and snap more memorable photos.
Medieval Castle & Authentic Tuscan Lunch
Head to a stunning medieval castle dating back to the 12th century. Relish a sumptuous Tuscan lunch featuring appetizers, first and second courses, and dessert. Each dish is perfectly paired with wines produced on-site, carefully selected to complement the meal. Afterward, explore the estate, including its aging cellars, during a private guided tour.
Gaiole in Chianti – Ancient Fortress Visit
Conclude your journey with a visit to a fortress from 1100 AD in Gaiole in Chianti. This estate produces a unique selection of Chianti Classico and Supertuscan wines, which you’ll have the chance to taste after exploring the wine cellars.
Location

Chianti – The Historic Wine Region
Chianti Classico, symbolized by the iconic Black Rooster, is one of Italy’s oldest and most renowned wine regions, with records dating back to the 13th century. Beyond its extraordinary wines, the area boasts medieval villages, ancient castles, and stunning vistas, making it a truly unique destination.

Included

Guided tour with Franco as your expert tour leader and/or driver
Visits to select boutique wineries, medieval castles, and estates
Wine tastings, including Chianti Classico, Super Tuscans, and extra virgin olive oils
Traditional Tuscan lunch at a local osteria or farm castle with vegetarian and vegan options
Scenic drives and historical insights
Duration

8–9 hours

Embark on this remarkable journey through the Chianti Classico region and savor the best of Tuscany’s wine, history, and culture.