Discover the renowned Chianti wine region and the medieval town of San Gimignano on this semi-private tour from Florence. Explore local wineries, savor a traditional Tuscan lunch, and learn about the charming streets of the UNESCO-listed San Gimignano. With a maximum of 8 passengers per Mercedes van, this personalized experience offers an intimate introduction to the highlights of Tuscany. From the carefully curated wine tastings to the personalized transportation, this tour promises an unforgettable journey through the heart of Italy’s winemaking legacy.
Key Points

- This tour offers a deep dive into the renowned Chianti wine region, including visits to local wineries for tastings of Chianti wines and olive oils.
- Travelers will also explore the medieval town of San Gimignano, a UNESCO World Heritage site known for its well-preserved skyline and tower houses.
- A traditional Tuscan lunch is included, showcasing the region’s culinary heritage with locally-sourced specialties and accompanied by Chianti wines.
- The tour accommodates a maximum of 8 passengers per Mercedes van, providing a personalized and immersive experience.
- Hotel pickup and drop-off within Florence’s historic center are offered for a seamless start and end to the day’s adventures.
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Contents
- Key Points
- Tour Overview
- Inclusions
- Pickup and Drop-off
- Tour Details
- Cancellation Policy
- Chianti Wine Region
- Medieval Town of San Gimignano
- Traditional Tuscan Lunch
- Recap
- Our Top Picks in Florence
- More Wine Tours in Florence
- More Private Tours in Florence
- More Tour Reviews in Florence
- Not for you? Here's more things to do in Florence we have recnetly reviewed
Tour Overview
This small-group tour from Florence allows visitors to discover the renowned Chianti wine region and the medieval town of San Gimignano.
The tour includes visits to local wineries where guests can enjoy tours and tastings of Chianti wines and olive oils. Travelers will also have the opportunity to savor a traditional Tuscan lunch during the excursion.
The tour operates with a maximum of 8 passengers per Mercedes van, ensuring a personalized and intimate experience. Wheelchair and stroller accessibility, as well as infant seats, make the tour suitable for a variety of travelers.
With free hotel pickup and drop-off in the historic center of Florence, this tour provides a convenient and immersive way to explore the Chianti countryside.
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Inclusions

The tour includes a wine tasting and olive oil tasting, where visitors can savor the flavors of the Chianti region.
Plus, a traditional Tuscan lunch is provided, allowing travelers to enjoy the local cuisine.
Bottled water is also included throughout the day, ensuring guests stay hydrated.
On top of that, the tour includes transportation via an air-conditioned vehicle, and gratuity is covered, eliminating any out-of-pocket expenses for the traveler.
This comprehensive package allows participants to fully experience the charm of the Chianti wine region and the medieval town of San Gimignano without having to worry about the logistics, making it an attractive option for those seeking an authentic Tuscan adventure.
Pickup and Drop-off

The tour offers free hotel pickup and drop-off within Florence’s historic center, categorized as the ‘A zone’.
Travelers not staying in this designated area can instead meet the group at the Hotel Boccaccio. This convenient pickup and drop-off service ensures a seamless start and end to the day’s adventures.
Whether you’re staying in the heart of Florence or elsewhere, the tour company makes it easy to join the small group. With a maximum of 8 travelers per Mercedes van, you’ll enjoy a personalized experience as you’re whisked away to explore the stunning Chianti region and medieval town of San Gimignano.
Tour Details

Along With the convenient pickup and drop-off service, the tour accommodates a maximum of 8 travelers per Mercedes van, ensuring a personalized experience as guests are transported to the stunning Chianti region and medieval town of San Gimignano.
The tour is accessible, with wheelchair and stroller availability, and it’s located near public transportation. Infant seats are also provided, making it a family-friendly option.
With a mix of cultural exploration, wine tastings, and a traditional Tuscan lunch, this semi-private tour offers an immersive and well-rounded introduction to the highlights of Tuscany.
Travelers can feel confident in the tour’s reliability, as it’s subject to weather and minimum traveler conditions.
Cancellation Policy

Travelers can cancel their reservation up to 24 hours in advance for a full refund, though the tour is subject to weather and minimum traveler conditions.
If the tour is canceled due to inclement weather or insufficient participants, customers will receive a full refund.
The tour operator reserves the right to modify or cancel the tour at any time for safety reasons.
Clients should review the cancellation policy carefully before booking to ensure they understand the terms.
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Chianti Wine Region

Situated in the heart of Tuscany, the Chianti wine region is renowned for its picturesque rolling hills, medieval hilltop towns, and world-class red wines.
Spanning across several provinces, this historic viticultural area produces the iconic Chianti Classico, a DOCG-designated wine made primarily from the Sangiovese grape.
Winemakers in Chianti carefully nurture the vineyards, ensuring the grapes reach optimal ripeness and develop the signature flavors of cherries, plums, and spice.
Visitors to the region can explore charming towns like Greve in Chianti, tour family-owned wineries, and savor the rich, food-friendly Chianti wines paired with traditional Tuscan cuisine.
The Chianti wine region offers a truly immersive experience in the heart of Italy’s renowned wine country.
Medieval Town of San Gimignano

After exploring the renowned Chianti wine region, the tour moves on to the captivating medieval town of San Gimignano. This UNESCO World Heritage site is renowned for its well-preserved skyline, which features an impressive collection of tower houses that have earned it the moniker ‘the Medieval Manhattan.’
Visitors can wander through the charming winding streets, admiring the historic architecture and soaking up the timeless ambiance. The town’s main square, Piazza della Cisterna, is a particular highlight, with its graceful fountain and striking Gothic buildings.
With its blend of history, culture, and scenic beauty, San Gimignano offers a truly memorable experience for travelers on this Tuscan adventure.
Traditional Tuscan Lunch

The tour includes a traditional Tuscan lunch that showcases the region’s renowned culinary heritage. Guests savor a selection of locally-sourced specialties, such as handmade pasta, farm-fresh produce, and artisanal cheeses, accompanied by the area’s renowned Chianti wines.
This authentic dining experience promises to delight the senses and transport guests to the heart of Tuscany. The meal is served in a charming setting, allowing travelers to enjoy the rustic ambiance of the Chianti countryside.
The traditional Tuscan lunch is a highlight of the tour, providing a memorable taste of the local culture and cuisine. Guests can expect to:
- Indulge in the rich, bold flavors of Chianti wines
- Savor the homemade quality of the pasta and other dishes
- Appreciate the freshness and seasonality of the ingredients
- Enjoy the convivial atmosphere of a traditional Tuscan meal
Semi-Private Deep Wine Chianti and San Gimignano From Florence
“This experience was exceptional. Our driver Gabriel was amazing, enthusiastic, engaging and informative about the various destinations. We visited …”
Recap
This semi-private tour from Florence offers an immersive introduction to the highlights of Tuscany.
Discover the renowned Chianti wine region, explore the charming medieval town of San Gimignano, and savor a traditional Tuscan lunch.
With free hotel pickup and drop-off, transportation, and gratuity included, it’s an efficient and personalized way to experience the best of this iconic Italian region.


































