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Explore Chianti’s highlights on this private day tour from Florence, including wine tastings, a Tuscan lunch, and visits to Siena, San Gimignano, and Monteriggioni.

This private tour offers a full-day exploration of Chianti’s scenic beauty and historic sites, all while following the ancient “Via Francigena” route. Priced at $325.04 per person, it appeals to those seeking an intimate experience, guided by expert drivers and local tastings. The tour lasts approximately 11 hours, starting early at 8:00 am with pickup from your Florence accommodation.
What makes this tour stand out is its combination of cultural exploration, culinary delights, and exclusive wine tastings at two biodynamic wineries. It’s perfect for visitors who want a well-rounded taste of Tuscany’s traditions. However, it’s important to note that the tour involves quite a bit of walking and sightseeing, which might be challenging for those with mobility issues.

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This tour begins with pickup from your Florence hotel, B&B, or private apartment. The air-conditioned vehicle offers a comfortable ride through the rolling hills of Chianti, marked by olive groves, cypress trees, and vineyards. The journey is smooth, allowing guests to relax while the driver shares insights into the area’s landscape and history.
The early start at 8:00 am provides ample time to cover all stops comfortably. As the drive unfolds, expect to see picturesque villages and learn about the routes taken by pilgrims and Crusaders centuries ago, following the “Via Francigena”.
The first destination is San Gimignano, a UNESCO World Heritage Site famous for its Medieval Towers. With about one hour allocated, visitors have the chance to walk within the historic walls and admire the skyline dominated by medieval architecture. The town’s narrow streets and towers offer a glimpse into Tuscany’s medieval past.
While exploring, you’ll see why San Gimignano is celebrated for its preservation of historic charm. The guide provides insights into its history, but the visit is mostly self-guided, allowing free time to explore shops or take photos.

Next, the tour moves to the Podere La Marronaia- Le Colonne Biodynamic Winery & Farm. Here, guests enjoy a delicious Tuscan lunch paired with wine tastings. This winery is known for its authentic Italian wine and food culture, specializing in biodynamic practices.
The 1 hour and 30 minutes spent here include a tasting of Chianti Riserva, Super Tuscan, Sangiovese, and Vernaccia di S.Gimignano. The lunch features lasagna or homemade pasta, bruschettas, Tuscan ham, Pecorino cheese, and more, providing a true taste of local flavors.

The next stop is Monteriggioni, a well-preserved medieval castle that dates back to the Middle Ages. With about 30 minutes allocated, visitors can walk around the fortress walls and enjoy views of the surrounding countryside. Monteriggioni’s narrow streets and castle towers offer a charming glance into Tuscan history.
This village is a favorite for its authentic medieval atmosphere and well-preserved architecture, making it a perfect quick stop for photos and exploring.
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Following Monteriggioni, the tour proceeds to Siena, where guests enjoy about one hour and thirty minutes of free time. Siena is renowned for its stunning Gothic architecture, including the Piazza del Campo and the Duomo. Guests can stroll independently, taking in the vibrant atmosphere and historic sights.
The guide leaves visitors with recommendations on must-see landmarks, but the pace is relaxed enough for self-exploration. Siena’s pietra stone buildings and church facades make for memorable photos.

As the afternoon progresses, the journey continues to Fattoria Lornano, a picturesque winery in the Lornano area. Here, guests enjoy a second wine tasting, sampling local wines such as Chianti and other regional varieties. This 1-hour visit allows further appreciation of Tuscan wine craftsmanship.
Apart from wine, the farm also offers tastings of balsamic vinegar, truffle, and extra olive oil, giving a comprehensive look at Tuscany’s artisanal food products.

After a full day of sightseeing, tasting, and exploring, the private vehicle takes guests back to Florence. The return trip offers an opportunity to relax and reflect on the day’s highlights, with air conditioning and bottled water provided throughout.
This tour is valued for its small-group, private format, ensuring personalized attention and flexibility. The expert driver not only navigates the scenic routes but also shares insightful commentary, enriching the experience. The two wine tastings at biodynamic wineries are carefully selected to showcase regional diversity, including Chianti Riserva and Super Tuscan varieties.
The lunch in a family-run Tuscan farm provides authentic flavors, making the experience more than just sightseeing. The tour’s perfect rating from two reviews reflects consistent positive feedback, especially for the knowledgeable guides and excellent wine selection.
The tour is designed for most travelers, with most participants able to join. It features private transportation, making it suitable for those who prefer a comfortable journey. The full-day schedule means comfortable shoes are recommended, especially for walking around towns and villages.
Cancellation is free up to 24 hours in advance, offering flexibility if plans change. The group discounts and mobile tickets make booking straightforward.
This experience appeals most to wine enthusiasts, history buffs, and those seeking an intimate, guided day in Tuscany. It balances cultural exploration with culinary delights and scenic drives. Visitors looking for a personalized experience with top-notch food and wine will find this tour particularly satisfying.
The “FRANCIGENA WAY” private tour offers a comprehensive day in Chianti, combining historic sites, scenic drives, and regional tastings. The expert guides, especially the highly praised Mr. Andrea, ensure guests gain rich insights into Tuscan culture and history while enjoying delicious food and wine.
While it involves several stops and some walking, the private transportation and flexible schedule make it manageable and enjoyable. This tour suits those who want a personalized, well-rounded experience of Tuscany in a single day, with the added bonus of exceptional wine and culinary highlights.
“Andre was wonderful. Great knowledge of the history of the area. Provided authentic tour into local history & culture.”
Is this tour suitable for children or those with mobility issues?
Most participants can join, but the tour involves walking around towns and villages, so mobility considerations should be taken into account.
What is included in the price?
The price covers private transportation, lunch with wine, two wine tastings, bottled water, and visits to specific wineries and towns.
Can I cancel the tour if my plans change?
Yes, cancellations are free if made at least 24 hours in advance. Cancellations less than 24 hours before the start are not refunded.
What kind of wines are tasted during the tour?
Guests sample Chianti Riserva, Super Tuscan, Sangiovese, and Vernaccia di S.Gimignano.
How long are the stops at each location?
San Gimignano: 1 hour; Podere La Marronaia: 1.5 hours; Monteriggioni: 30 minutes; Siena: 1.5 hours; Fattoria Lornano: 1 hour.
Is lunch included?
Yes, the lunch in the biodynamic winery features regional Tuscan dishes paired with local wines.
What makes this tour unique?
Its private, small-group format, two curated wine tastings, and the combination of historic towns and culinary experiences stand out.
Are the wine tastings in different wineries?
Yes, they take place at two different biodynamic wineries, offering diverse regional wines.
What guides the tour?
An expert local driver provides commentary and insights, with reviews praising guides like Mr. Andrea for their friendliness and knowledge.
How long is the overall tour?
Approximately 11 hours, beginning at 8:00 am and ending with the return to Florence in the evening.