Chianti Vespa Tour from San Gimignano with Wine Tasting and Lunch
Ride through the hills of Tuscany on a vintage scooter, visit a local estate and enjoy a local meal
Exploring Chianti on your own sounds dreamy until you're lost, stressed, and stuck with tourist traps. Skip the hassle and ride like a local on this small-group Vespa tour from San Gimignano. With a professional escort leading the way, you’ll zip through scenic countryside, stop for wine tastings, tour a working winery, and enjoy a long lunch in the hills. No GPS, no guesswork, just pure Tuscan joy.
- Meeting point
- Vespa orientation and safety check
- Chianti hills scenic ride
- Photo stops in the countryside
- Winery tour
- Wine tasting
- Tuscan lunch
- Ending point
Leave the crowds behind and start your day in San Gimignano, meeting your tour escort in Via San Giovanni, the main street that cuts through the heart of this iconic hilltop town. Here, you’ll be introduced to your Vespa, an Italian icon ready to take you deep into the heart of Tuscany. After a quick safety briefing and rental check, you’ll hit the road in a small group, riding through rolling hills, olive groves, and rows of cypress trees. The ride is smooth and scenic, with plenty of photo-worthy views along the way. You’ll stop at a local winery for a guided visit and a proper Tuscan lunch, with wine tasting included. After the experience, you’ll ride back to the starting point, with your head full of views and your heart full of Chianti.
Chianti Vespa Tour with Wine Tasting and Lunch Description
Your 7.5-hour small group tour includes:
Professional tour escort
Original Vespa scooter rental (automatic)
Fuel and helmet
Scenic ride through the Chianti countryside
Visit to a medieval village
Guided tour of a local winery
Wine tasting of regional wines
Traditional Tuscan lunch at the winery
Group size of 15
San Gimignano meeting point
Your experience starts in Via San Giovanni, San Gimignano, just steps away from the town’s famous towers. After checking in and meeting your escort, you’ll receive your Vespa and all necessary equipment. Drivers must show a valid license and credit card and be able to confidently operate the scooter. If you’re not comfortable driving, a shared Vespa option is available—or you may be offered an alternative vehicle if available.
The ride through Chianti
There’s no better way to explore Tuscany than on two wheels. Your route winds through some of the most breathtaking parts of the Chianti region, known for its vineyard-dotted hills, stone farmhouses, and postcard-perfect landscapes. You’ll pass by sunflower fields, olive groves, and small medieval villages, with stops for photos and to soak it all in. This is the kind of ride where the journey really is the destination.
Visit to a winery
Midday, you’ll stop at a historic Chianti winery surrounded by vineyards. A guide will walk you through the winemaking process and into the cellars where the magic happens. Learn how the region’s famous wines are made—Chianti DOCG, Super Tuscan blends, and more—and taste them for yourself.
Tuscan lunch
After your tour, sit down for a relaxed lunch overlooking the countryside. Expect traditional dishes like pecorino cheese, cured meats, fresh pasta, and seasonal vegetables, all paired with house wine. A vegetarian option is available upon request. It’s not a tourist meal—it’s a real Tuscan table.
Return to San Gimignano
With full bellies and satisfied smiles, you’ll ride back to San Gimignano along scenic roads. The tour ends at the same meeting point in Via San Giovanni, leaving you free to continue exploring the town or simply head home with your helmet full of memories.
What you get with this tour
Frequently Asked Questions
What to bring?
A valid international driver’s license is required. Please also bring along a credit card to guarantee your rental. Closed-toe shoes, sunscreen and sunglasses are also recommended.
Is there any chance my tour might be canceled?
In case of extreme weather, the tour may be modified or canceled for safety reasons. You’ll be offered an alternative or a refund.
Is this tour run by The Tour Guy?
No, this tour is operated by one of our trusted and vetted partners in Tuscany.
What if I have concerns about my ability to drive the Vespa?
All drivers must have experience operating a scooter. If the staff believes you’re not confident or safe, they may reassign you as a passenger or, if available, offer an alternative like a tuk-tuk or Fiat 500.
What happens if it rains?
The tour runs rain or shine, and rain gear is provided. In case of unsafe conditions, the itinerary may be changed or postponed.
Is lunch included in the price of the tour?
Yes, a full traditional Tuscan lunch is included, served at a local winery. Vegetarian options are available upon request.
What if I have food allergies, intolerances, or other dietary requirements?
Please let us know at the time of booking. We’ll do our best to accommodate your dietary needs.
Can I ride alone or do I have to share a Vespa?
To have a Vespa to yourself, you must book two spots. Single bookings will be paired with another passenger unless otherwise arranged.
Is this tour wheelchair accessible?
Unfortunately, pets are not allowed on this experience.
Can infants join the tour?
No, infants cannot sit on laps and infant seats are not available. This tour is not suitable for very young children.
Is this tour recommended for pregnant travelers?
We do not recommend this tour for pregnant travelers due to the movement and terrain involved.
Is this tour suitable for children?
Passengers must be at least 13 years old, and drivers must be 18 or older with a valid license. This is not recommended for younger children.
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