Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Experience Tuscany on a Vespa with a guided tour from Siena, featuring vineyard visits, wine tasting, and a delicious light lunch in Chianti's scenic hills.
The Vespa Tour with Lunch & Chianti Winery from Siena offers a lively way to explore the rolling hills of Tuscany. For $168.36 per person, this 6.5-hour adventure combines scenic riding, wine tasting at a Chianti winery, and a relaxed lunch made with local ingredients. The tour departs from Piazzale Carlo Rosselli in Siena, with options to ride your own Vespa or join a guide on a scooter, making it accessible for different comfort levels. While the tour includes professional guides, helmets, fuel, and taxes, additional services like hotel pickup are available at extra cost. It’s best suited for those aged 18 and above who have some experience driving a scooter, as passing a driving test is required on-site.
Though reviews highlight the tour’s strengths—breathtaking views, knowledgeable guides, and delicious wine tastings—there are notable considerations. Some guests mention long waits due to mechanical issues or delays, and a few report that the wine tasting was brief or that the guidance was limited. Still, the balance of scenic riding, cultural stops, and wine experiences makes this a compelling option for those eager to see Tuscany from a spirited perspective.


This tour kicks off at Piazzale Carlo Rosselli in Siena, where guests are fitted with helmets and given a brief safety overview before setting out. The ride begins with a convoy led by a professional guide, passing through striking Tuscan landscapes of vineyards, olive groves, and rustic villas. The route includes a notable pass by Monteriggioni, a hilltop village surrounded by medieval walls, which serves as a scenic photo stop.
Travelers have the option to drive their own Vespa or hop on behind a tour escort. This flexibility is especially helpful if you’re less confident in your riding skills. The ride emphasizes tranquil country roads that showcase the charm of the Chianti region, often described as breathtaking by past participants.
If wine interests you, we've examined these other wine experiences in Siena

Midway through the tour, guests disembark at Casale dello Sparviero, a picturesque estate accessible via a long avenue lined with cypress trees. The winery tour includes visits to vineyards and cellars, offering guests insight into local winemaking traditions. The wine tasting features red Chianti wines, with some reviews mentioning that only two glasses are served, which might feel brief but still provide a good taste of regional flavors.
Guests often find the wine and lunch pairing to be a highlight. The light lunch includes fresh dishes typical of Tuscany—often a simple mix of meats, cheeses, and bread—designed to complement the wines. The setting of the winery is praised as gorgeous, with many saying it’s a perfect backdrop for photos.

Following the vineyard visit, the tour continues with free time in Radda in Chianti, an appealing town known for its medieval architecture and viewpoints. Later, the group visits Monteriggioni, a medieval hilltown encircled by original walls. The time allocated here allows for strolling the streets and soaking in the historic atmosphere.
Past guests appreciate that these stops provide a break from riding, enabling them to explore at their own pace. However, a few mention that the stops are relatively brief, and the overall sightseeing is somewhat limited, focusing mainly on the towns rather than extensive tours.

The safety and driving test is a key part of the experience, required for anyone wishing to drive their Vespa. The test typically involves a parking lot maneuver and a turning exercise. Past reviews reveal that some guests with motorcycle experience find the process straightforward, while others have reported difficulties or crashes, especially if they are less experienced.
The tour guides are strict about safety, and the vehicles are well-maintained. However, some reviews point out that delays or vehicle issues can affect the schedule, especially if a Vespa experiences mechanical problems. It’s important to pass the safety test and have adequate Vespa experience for your own safety and enjoyment.

Past feedback indicates that guides are knowledgeable and friendly, often sharing interesting facts about Tuscany’s landscapes and towns. Conversely, some reviews mention that guides do not engage in detailed commentary or lead comprehensive sightseeing tours, instead focusing on driving directions and basic safety instructions.
The pacing of the tour is generally described as relaxed, with ample breaks for photos, driver switches, and rest. This makes the experience accessible to those who prefer a less hurried exploration, though drivers should be prepared for a full day of riding.
While in Siena, here are other experiences we've covered

The lunch at the winery is described as light but fresh, often consisting of local meats, cheeses, and bread, paired with Chianti wines. Vegetarians can request a vegetarian menu in advance, which is available upon request. Some reviews mention that only two glasses of wine are served during the tasting, which some consider brief, but others appreciate the quality over quantity.
Guests often commend the genuineness of the food and the scenic setting of the estate. The wine tasting is usually part of the vineyard tour, providing an opportunity to learn about Chianti winemaking and taste different red wines from the region.

The maximum group size for this tour is 16 travelers, ensuring a personalized experience. The meeting point is centrally located in Siena, with optional hotel pickup available at extra charge. The tour operates rain or shine, with weather contingencies that may involve route modifications or full refunds if conditions prevent the experience.
Participants must be at least 18 to drive, and a valid driver’s license is required. The tour provider emphasizes that prior Vespa experience is necessary for drivers, and safety measures are strictly enforced.

This tour offers a unique way to see the Chianti countryside, combining scenic riding, wine tasting, and visits to authentic towns. The price includes the Vespa rental, guide, wine tasting, and lunch, which many guests find cost-effective given the experience.
However, the mixed reviews highlight the importance of prior Vespa experience and accepting that the guided aspect may be limited. The tour is best suited for active travelers comfortable on a scooter, seeking an adventurous way to explore Tuscany’s landscapes and wine culture.
The Vespa Tour from Siena provides a fun, scenic, and cultural journey into the heart of Tuscany. Its main draws are the stunning views, wine tasting at a charming winery, and the possibility to ride through historic villages and countryside. The guides are generally knowledgeable and friendly, adding to the relaxed atmosphere.
While some reviewers note delays or limited guidance, most agree that the experience is memorable and worthy of the cost. It’s an excellent choice for adventurous spirits who enjoy riding scooters, exploring small towns, and sampling regional wines. For those less experienced on a Vespa or seeking more extensive sightseeing, it’s worth considering additional preparation or alternative tours.
“The tour itself was great. However, a Fiat 500 in our group was having mechanical issues, and we spent a large part of the tour waiting on the road…”
Do I need prior Vespa experience to join?
Yes, prior Vespa driving experience is necessary, and you must pass a safety test on-site before riding solo.
What is included in the tour price?
The tour includes guide, helmet, fuel, taxes, winery tour with tasting, and a light lunch with typical dishes.
Can I join if I prefer not to drive?
Absolutely—you can opt to ride on a scooter with a tour escort instead of driving yourself.
Are vegetarian options available for lunch?
Yes, vegetarian menus can be requested in advance.
What are the age requirements?
Participants must be at least 18 years old to drive, and 13+ to be a passenger.
What happens if the Vespa breaks down?
The vehicles are well-maintained, but in case of mechanical issues, the guide will handle repairs or replacements as needed.
What if the weather is bad?
The tour runs rain or shine. In case of heavy rain or wind, the route may be modified, or a full refund will be offered.
Is hotel pickup included?
No, pickup is optional at an additional charge.
How long is the tour?
The entire experience lasts approximately 6 hours and 30 minutes.
Where does the tour start and end?
It begins and ends at Piazzale Carlo Rosselli in Siena.
Can I cancel if my plans change?
Yes, free cancellation is available up to 24 hours before the tour start.
What makes this tour different from other Tuscan excursions?
The combination of Vespa riding, scenic towns, and winery visits makes this tour especially lively and immersive, perfect for those seeking an active day in Tuscany.