San Gimignano, the medieval town known for its iconic skyline of towering stone structures, is a captivating destination that beckons travelers to enjoy its timeless charm. Embarking on an all-inclusive journey through this UNESCO World Heritage Site, visitors can savor the flavors of Tuscany with a delectable three-course lunch and a guided wine tasting experience. With private transportation and an expert English-speaking driver, this excursion promises to transport you to a world where history, culture, and culinary delights intertwine, leaving you eager to uncover the treasures that lie beyond the town’s enchanting walls.
Key Points
-
Explore the historic town of San Gimignano with its iconic towers and charming streets, and enjoy a private wine tasting at a local Chianti Classico winery.
-
Experience a full-day private trip from Florence, with comfortable Mercedes E-class transportation and an English-speaking driver for stress-free travel.
-
Savor a delightful three-course lunch featuring regional Tuscan cuisine, accompanied by a guided sampling of 5-6 local wines and alcoholic beverages.
-
Enjoy the timeless atmosphere of San Gimignano, a UNESCO World Heritage Site, and discover its cultural heritage at your own pace.
-
Benefit from a personalized itinerary, free cancellation up to 24 hours before the tour, and a lowest price guarantee with reserve now, pay later options.
Tour Overview

This full-day private trip from Florence takes visitors to the medieval hill town of San Gimignano and a renowned Chianti Classico winery.
In San Gimignano, you’ll explore the town’s historic towers and charming streets at your own pace.
The tour also includes a visit to a local winery, where you’ll enjoy a tasting of 5-6 wines, extra virgin olive oil, and balsamic vinegar.
Lunch, which features 3 courses and alcoholic beverages, is also included.
With private transportation in a comfortable Mercedes E-class and an English-speaking driver, this experience provides a hassle-free way to discover the beauty and flavors of Tuscany.
You can also read our reviews of more food & drink experiences in Florence
Transportation and Comfort

The tour provides private transportation in a comfortable Mercedes E-class.
Your dedicated English-speaking driver ensures a stress-free journey, allowing you to sit back and enjoy the scenic views.
Onboard WiFi keeps you connected throughout the experience, so you can document your adventure as it unfolds.
- Relax in the air-conditioned comfort of a private Mercedes E-class
- Benefit from the expertise of an English-speaking driver
- Stay connected with onboard WiFi for capturing memorable moments
Lunch and Wine Tasting
Complementing the scenic journey, the tour includes a delightful lunch and an engaging wine tasting experience.
The lunch features three courses, showcasing the regional cuisine. Guests will savor authentic Tuscan flavors, from fresh salads to hearty pasta dishes.
The wine tasting allows visitors to discover the renowned Chianti Classico wines. A knowledgeable sommelier guides the group through a sampling of 5-6 local vintages, as well as extra virgin olive oil and balsamic vinegar.
Alcoholic beverages are included, allowing guests to fully enjoy the flavors of the region.
This well-rounded culinary and oenological experience complements the exploration of the historic San Gimignano, creating a truly memorable day.
Exploring San Gimignano

After savoring the delights of the regional cuisine and wine tasting, visitors now turn their attention to exploring the captivating medieval hill town of San Gimignano.
This UNESCO World Heritage Site boasts:
- Iconic towers that punctuate the skyline, offering panoramic views of the surrounding Tuscan countryside
- Charming piazzas and winding streets lined with historic buildings and artisanal shops
- The impressive Duomo, a 12th-century cathedral renowned for its frescoes and Gothic architecture
Visitors can wander at their own pace, taking in the town’s timeless atmosphere and seeing its rich cultural heritage.
Winery Tour and Tasting

Following the tour of the captivating medieval town, visitors then embark on a winery tour and tasting at a renowned Chianti Classico estate. The winery experience offers a unique opportunity to learn about the region’s winemaking traditions and sample a variety of local wines. Guests are guided through the process, from vineyard to cellar, and invited to indulge in a tasting of 5-6 different wines, accompanied by extra virgin olive oil and balsamic vinegar. The experience is further enhanced by a delightful lunch, complete with alcoholic beverages, providing a well-rounded and immersive exploration of the Tuscan culinary and viticultural delights.
| Wine | Aroma | Body | Finish |
|---|---|---|---|
| Chianti Classico | Cherries, spice | Medium | Smooth |
| Super Tuscan | Blackberries, oak | Full | Lingering |
| Vin Santo | Dried fruit, nuts | Sweet | Elegant |
| Rosé | Strawberries, citrus | Light | Refreshing |
| Grappa | Herbal, warm | Robust | Intense |
You can also read our reviews of more wine tours in Florence
- Florence: Pasta Cooking Class With Unlimited Wine
★ 4.9 · 10,285 reviews - Florence: Pasta & Tiramisu Cooking Class With Unlimited Wine
★ 4.9 · 6,708 reviews - From Florence: Tuscany Day Trip With Lunch at Chianti Winery
★ 4.8 · 4,538 reviews - From Florence: Tuscany Wine & Food Tour with Guide
★ 4.9 · 1,746 reviews - From Florence: Val D’orcia Tour With Wine Tasting
★ 4.6 · 1,106 reviews - From Florence: Chianti Wine Tour With Tastings
★ 4.4 · 1,025 reviews
Booking and Participation

The tour is available as a private experience, exclusive to your group. This means you and your party will have the driver and vehicle all to yourselves, allowing for a more personalized and flexible itinerary.
-
Most travelers can participate in this tour.
-
Confirmation is received at the time of booking, or within 48 hours for last-minute reservations.
-
Unfortunately, the tour isn’t wheelchair accessible due to the medieval nature of the destinations.
Booking is easy, and free cancellation is available up to 24 hours before the experience starts.
With the lowest price guarantee and reserve now, pay later options, securing your San Gimignano wine adventure has never been simpler.
Cancellation and Pricing

Cancelling your San Gimignano wine experience is straightforward, with free cancellation available up to 24 hours before the tour starts. The price for this all-inclusive day trip is $967.16 per group of up to 2 people, with a lowest price guarantee and reserve now and pay later options available.
| Pricing | Details |
|---|---|
| Group Size | Up to 2 people |
| Price | $967.16 per group |
| Cancellation | Free up to 24 hours before |
| Guarantee | Lowest Price |
| Payment | Reserve now, pay later |
This ensures maximum flexibility and value for your money when booking this exceptional Tuscan wine and sightseeing adventure.
Highlights of the Experience

Immersed in the rolling Tuscan hills, the San Gimignano Wine Experience offers a captivating journey through the region’s rich cultural tapestry.
Travelers will:
-
Explore the medieval hilltop town of San Gimignano at their own pace, marveling at its iconic towers and charming cobblestone streets.
-
Indulge in a delectable lunch featuring local delicacies, complemented by a tasting of 5-6 Chianti Classico wines, extra virgin olive oil, and balsamic vinegar.
-
Revel in the comfort of private transportation and the attentive care of an English-speaking driver, ensuring a seamless and memorable experience.
Since You Asked
Can We Customize the Tour Itinerary to Our Preferences?
Yes, the tour itinerary can be customized to meet your preferences. The private nature of the tour allows for flexibility to adjust the schedule and activities based on your interests.
Are There Any Dietary Restrictions Accommodated for the Lunch?
Yes, the tour accommodates dietary restrictions for the included lunch. Guests can specify any dietary needs or preferences when booking, and the lunch menu will be tailored accordingly.
Is It Possible to Visit Additional Towns Beyond San Gimignano?
The tour allows for visiting additional towns beyond San Gimignano. However, the itinerary is focused on exploring the medieval hill town and a Chianti Classico winery, so visiting other towns would need to be discussed with the tour provider.
How Long Does the Total Tour Duration Typically Last?
The total tour duration typically lasts around 8-9 hours. Guests can expect to spend 2-3 hours exploring San Gimignano and 2-3 hours for the winery visit, including lunch and wine tasting.
What Is the Minimum/Maximum Group Size for This Private Tour?
The private tour is exclusive to your group, with a minimum of 1 person and a maximum of 2 persons. The tour is not wheelchair accessible.
San Gimignano and Wine Experience All Inclusive Lunch and Wine Tasting
The Sum Up
Enjoy the charming medieval town of San Gimignano and savor the flavors of Tuscany. Enjoy a private tour with luxurious transportation, an indulgent lunch, and a tasting of renowned Chianti Classico wines. This all-inclusive experience offers a perfect blend of culture, cuisine, and scenic beauty, making it an unforgettable journey through the heart of Italy’s enchanting countryside.
























