If you’re craving a mix of scenic riding, delicious food, and authentic small-town charm, the Afternoon Tuscany Vespa Tour from Florence with Wine Tasting offers a compelling package. This small-group adventure combines the thrill of zipping through Tuscany’s famed countryside on a Vespa with stops in the medieval jewel of San Gimignano and a relaxing wine and dinner experience at a local winery.
From the start, two things stand out: how smoothly the tour balances guided riding with free time for exploration, and the quality of the wine and food you’ll enjoy at the end. However, one thing to consider is that this tour requires a moderate physical fitness level due to the riding, and it’s best suited for those comfortable on a Vespa or similar scooter. This experience appeals most to travelers looking for a fun, active way to see Tuscany’s rolling hills and taste its delights firsthand.
Key Points

- Authentic Vespa experience: Ride through scenic vineyards and olive groves on paved roads, led by knowledgeable guides.
- Small group size: Limited to 8 participants for a more personal and flexible experience.
- Historic visit: Explore the medieval town of San Gimignano with ample time for sightseeing and shopping.
- Gourmet ending: Conclude with a guided wine tasting and dinner at a local winery, paired with delicious Tuscan dishes.
- All-inclusive: The price covers Vespa rental, transportation, dinner, wine, and guides, making it easy to enjoy without worry.
- Booking and logistics: Book 15 days in advance, with options for private pick-up at additional cost.
The Itinerary: What You Can Expect

You can also read our reviews of more tours and experiences in Florence.
Reaching the Chianti Area and Riding Vespas
The journey begins with a convenient pickup in Florence (near public transportation), and a comfortable ride in an air-conditioned minivan to the heart of Tuscany’s Chianti region. Once there, you’ll swap your conventional vehicle for a Vespa, ready to cruise along scenic, paved roads lined with vines and olive groves.
This part of the tour—about four hours of riding—offers travelers a chance to enjoy the countryside up close. The guides are licensed professionals who ensure safety and share insights into the landscape, local agriculture, and regional history, making the ride both fun and informative. It’s worth noting that you should have a moderate physical fitness level, as controlling a Vespa requires some balance and coordination, especially on winding roads.
Visit San Gimignano, the Medieval Marvel
After a few hours of riding, you’ll arrive in San Gimignano, a town famous for its medieval towers that dominate its skyline. Here, you’ll have about an hour for sightseeing and shopping. The town is a photographer’s dream, with narrow cobblestone streets, ancient walls, and a lively atmosphere.
Many visitors praise this stop for its charm and history. One reviewer called it “so cool,” emphasizing the town’s well-preserved medieval character. You’ll also get a taste of local life, perhaps picking up some regional specialties or simple souvenirs.
Gourmet Dinner and Wine Tasting
The final segment takes you to a local winery in the Chianti area. Here, you’ll enjoy a guided tasting of regional wines—probably Chianti Classico—paired with a dinner featuring Tuscan-style dishes. The dinner is noted as being delicious, with some guests ordering bottles to ship home, eager to relive the taste of Tuscany.
The reviews highlight the hospitality at the winery, describing it as “beautiful and pristine,” which adds a special touch to this part of the experience. After dinner, you’ll hop back into the minivan for a leisurely one-hour ride back to Florence, concluding this memorable day.
What We Love About This Tour
Knowledgeable Guides: Several reviews praise the guides for their expertise and friendly attitude, making the experience both educational and personal. One reviewer said, “Christian was amazing!! We had a blast.” This attention to guiding adds value beyond just riding and tasting.
Incredible Views and Authenticity: Riding Vespas through vineyards and olive groves is a highlight, offering a sense of freedom and intimacy with the landscape. The scenery is often described as “amazing,” and the small group size allows for flexible stopping and personalized attention.
High-Quality Food and Wine: The dinner and wine tasting at the winery are consistently praised for being delicious and well-curated. Many guests appreciate the opportunity to sample regional wines and enjoy a traditional Tuscan meal in a beautiful setting.
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Considerations and Practical Tips

While this experience is highly rated, it’s important to be aware of a few practical considerations. You need a valid driver’s license (no photocopies or photos accepted), and drivers must be at least 18 years old. The ride requires moderate physical fitness, so if you’re prone to balance issues or have mobility concerns, you might find the riding challenging.
Weather can impact the tour—since it’s outdoor and involves riding Vespas—so checking the forecast before booking is a good idea. The tour offers free cancellation up to 24 hours in advance, providing some peace of mind if weather looks uncertain.
The small group limit of 8 travelers enhances the experience, making it more intimate and flexible. Private pickup and drop-off are available upon request for an extra fee, which can make logistics easier if you’re staying outside Florence.
Analyzing the Value

At $230.48 per person, this tour offers a comprehensive experience that combines adventure, culture, and gastronomy. When you factor in the included Vespa rental, guided visits, dinner, and wine tasting, it becomes a fairly good value—especially considering the small-group setting and the chance to explore Tuscany away from tourist crowds.
Many travelers consider the cost justified, given the high-quality guides, the scenic riding, and the chance to taste authentic regional wines and dishes. The fact that bookings are usually made 15 days in advance also indicates its popularity among travelers seeking a unique way to see the Tuscan countryside.
Who Is This Tour Best For?

This tour appeals most to adventurous travelers who enjoy outdoor activities and are comfortable on two wheels. It’s also ideal if you’re eager to combine sightseeing with authentic food and wine in a relaxed, small-group setting. Families with kids over a certain age and adults of all ages who appreciate a mix of fun and culture will find it a memorable experience.
However, if you prefer a more relaxed, less physically demanding way to see Tuscany, or if you’re uneasy on a scooter, this might not be the best fit. It’s also best suited for those willing to plan ahead and embrace a slightly active, immersive day.
FAQ

Do I need a driver’s license?
Yes, you must have a valid original driver’s license to operate the Vespa. No photocopies or photos are accepted.
Is this tour suitable for kids?
Yes, it’s described as family-friendly, but children should be comfortable riding or being a passenger on a Vespa. The tour recommends travelers have a moderate fitness level.
What if the weather is bad?
The tour requires good weather; if canceled due to poor weather, you’ll be offered a different date or a full refund.
Can I request private transportation?
Yes, private pick-up and drop-off are available upon request at an extra cost.
How long is the riding portion?
Riders will spend about four hours riding on paved roads through the Chianti countryside.
What’s included in the price?
The fee covers Vespa rental, air-conditioned transportation, guided visits, dinner, wine tasting, and small-group service.
Is there a recommended age for participants?
Drivers must be at least 18 years old, and a valid license is required. The tour is suitable for those with a moderate physical fitness level.
To sum it up, the Afternoon Tuscany Vespa Tour with Wine Tasting offers a unique way to explore Tuscany’s stunning landscapes with a dash of adventure. It’s perfect for those who love outdoor activities, authentic regional experiences, and a small, friendly group. With knowledgeable guides, excellent food and wine, and unforgettable scenery, this tour can turn a typical day into a treasured memory—just be ready for some riding and a little physical activity.
More Food & Drink Experiences in Florence
- Sunset semi private Chianti Tuscany Wine Tasting Tour from Florence
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