Description
Ride a Vespa along quiet, scenic roads through the rolling hills of the Chianti countryside, right in the heart of Tuscany, where some of the region’s most famous wines are produced.
This unforgettable experience starts in San Gimignano, the iconic medieval hilltown, and takes you through breathtaking landscapes of vineyards, olive groves, and panoramic country roads. Along the way, we’ll stop at carefully selected viewpoints for photos and short breaks, while our expert staff shares insights into the history, culture, wine, and olive oil traditions of the area.
If you do not have a driving license, have little experience, or simply prefer not to drive, you can comfortably join the tour as a passenger with one of our guides — the fun is guaranteed either way. Couples may also choose to share one Vespa, enjoying the ride together.
During the tour, you’ll enjoy a guided visit to the medieval town of San Gimignano, worldwide known as the “Medieval Manhattan” for its impressive towers. You’ll have time to admire the historic center, soak in the views, and stop for a taste of the world-famous Dondoli gelato.
After the Vespa ride, the experience continues at a local winery, where you’ll enjoy a typical Tuscan light lunch paired with a guided wine tasting. The tasting also includes extra virgin olive oil and balsamic vinegar, all produced locally. There will be an opportunity to purchase and ship genuine Tuscan products directly from the winery.
Who can join
– Drivers must present an original driving license (no photos or copies)
– Passengers do not need a license
– Children (6–11 years) can participate as passengers with a guide or expert driver
– Infants (0–5 years) may join as passengers on our fun Tuk-Tuk (Ape Calessino)
– Vegetarian, vegan, and gluten-free meals available upon request
Notes
-All scheduled times are approximate and may vary due to traffic or weather conditions
-Long pants and closed shoes are recommended
-A short lesson is given before the ride to ensure everyone can drive safely
-Vespa sharing discounts are calculated on the final balance
FUN IN TUSCANY
WHAT’S INCLUDED
MEETING POINT
Porta San Matteo, San Gimignano
BOOKING METHOD
- Reservations required
- Payment on the time of booking
- Free cancellation up to 24 hours in advance This experience requires good weather. If it’s cancelled due to poor weather, you will be offered a different date or a full refund
Christine –
Everything about this tour exceeding my expectations. The staff were all friendly, knowledgeable, and very fun! Not only were we able to ride vespas through the beautiful Tuscan countryside, but we also stopped and visited a few villages and towns in the country. To top it all off, we had a delicious lunch with a wine and olive oil tasting.
Charlene –
Did the wine tasting tour and vespa as it was my birthday. Was a really fun trip. I was alone but both Daniels made sure I had a good time on my birthday and I made friends with the group I was in. I didn’t get the hang of the vespa but then Daniel took me around in a tuktuk instead which was equally as fun! The wine places we visited were really informative and I think pretty good wine.