Journey into the heart of the Chianti Classico region and step back in time. This full-day tour balances world-famous wine with medieval history, taking you from the iconic towers of San Gimignano to a private visit at a majestic Chianti Castle/Winery. The day's adventure culminates in the remarkably preserved walled fortress of Monteriggioni, where you will enjoy a memorable, full-course Tuscan dinner. It's an experience that captures the true essence of Tuscany's rustic charm, historic grandeur, and culinary excellence.

Itinerary
The tour departs from Siena and heads first to San Gimignano, the 'Manhattan of the Middle Ages,' for free time to explore its UNESCO-listed historic center and towers. Next, we journey into the beautiful Chianti countryside for a visit and wine tasting at a historic Chianti Castle/Winery. Finally, we arrive at the fortified town of Monteriggioni for an exquisite full-course dinner before returning to Siena.

Destinations
Siena (Departure/Arrival)

San Gimignano

Chianti Castle/Winery

Monteriggioni

Activities
Wine Tasting (Chianti Classico, Super Tuscan) at a historic estate.

Explore Historic Towns & Villages (San Gimignano, Monteriggioni).

Gourmet Full-Course Dinner Experience inside the walls of Monteriggioni.

Visit a Historic Chianti Castle/Winery.

Enjoy Scenic Views & Photo Opportunities.

Duration
Full Day (Approximately 8-10 hours)

Highlights
World-renowned Chianti Classico and Super Tuscan wines at a historic Chianti Castle/Winery.

Explore the UNESCO-listed “Town of Fine Towers,” San Gimignano, with free time to wander its medieval streets.

Indulge in a delicious, full-course Tuscan dinner with wine pairings inside the medieval fortress of Monteriggioni.

Enjoy the picturesque landscapes of the Chianti wine region.

Benefit from the expertise of a professional local guide/Tour Leader.

What’s Included
Luxury, air-conditioned transportation.

Professional local guide/Tour Leader (Multilingual: English, French, Italian, German-speaking).

Pick-up and drop-off from designated points in Siena (outside the historic center).

Winery tour and tasting fees.

Full-Course Tuscan Dinner with wine included.

FAQ
Q: Where does the tour depart from? A: This tour departs from Siena. Specific pick-up points outside the restricted traffic zone (ZTL) will be confirmed upon booking.

Q: Is lunch included in addition to dinner? A: A full-course dinner is included. Lunch is not, allowing you free time for a snack or light meal in San Gimignano.

Q: How much walking is involved? A: Expect moderate walking on the cobblestone streets of San Gimignano and Monteriggioni. Comfortable shoes are essential.

Q: What should I bring? A: Comfortable shoes, a bottle for water, sun protection, and your camera.