Thinking about riding a Vespa through the rolling hills of Tuscany? This Vespa Tour with Lunch & Chianti Winery from Siena promises just that—a full day of scenic rides, wine tasting, and local food. It sounds like a blast, especially if you’ve dreamt of zooming through vineyards with the wind in your hair, but it’s worth looking at what this experience really offers before booking.
What we love about this tour is the chance to see Tuscany’s stunning landscapes from a classic Italian scooter—an authentic way to travel. Plus, the visit to a Chianti winery with a tasting and a light lunch provides a real taste of local flavors. However, a key consideration is that driving experience is a must, and the tour can be quite fast-paced, with some reviews mentioning logistical hiccups.
This is best suited for those who are comfortable on a Vespa and are eager for a blend of adventure and culture. If you’re after a relaxed, fully guided experience or aren’t confident on a scooter, you might want to explore other options. Still, for adventure lovers, it could be a highlight of a trip to Siena.
Key Points:

- Authentic way to see Tuscan scenery on a Vespa, with the wind and views as part of the experience.
- Includes a winery visit with tasting and a light lunch, giving you a nice break and some local flavors.
- Requires Vespa driving experience; beginners might find it challenging or unsafe.
- Guides are knowledgeable and friendly, enhancing the overall trip.
- Some reviews mention logistical issues, such as delays or miscommunications.
- Price includes helmet, fuel, taxes, and the winery tour, so it’s somewhat all-inclusive for the activities listed.
An Overview of the Experience

If you’re picturing yourself zipping along Tuscan country roads, this tour promises to deliver just that. Starting from Siena, you’ll hop on a Vespa—or get a ride with an escort if you prefer not to drive—that’s the core thrill. The ride takes you past charming villages, vineyards, and olive groves, with a guide leading the way, so you’re not just wandering aimlessly.
However, it’s important to note that you must be at least 18 to drive, and previous Vespa experience is strongly recommended. As some reviews pointed out, passing a driving test is a prerequisite, and the safety measures are strict—so don’t show up expecting to wing it without some experience.
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Traveling Through the Tuscan Countryside
The ride out of Siena is scenic, with vistas of rolling hills and rustic villas. You’ll pass through the medieval village of Monteriggioni, which is always worth a quick stop for photos and a stretch. The roads are tranquil and perfect for a Vespa, especially if you’re comfortable handling one. If not, you can ride as a passenger with a guide, which some reviewers appreciated.
The Winery Visit and Lunch
Midway through the tour, you’ll stop at Casale dello Sparviero, a charming farmhouse embedded in lush surroundings. Here, you’ll tour vineyards and cellars, offering a glimpse into traditional Chianti winemaking. Guests rave about the gorgeous winery setting and the delicious wine tasting, with some describing the wines as not to be missed.
Lunch is served afterward—a simple but tasty spread of fresh, local dishes, with vegetarian options available if requested. Reviewers have called the lunch “light” but satisfying, perfect after a morning of riding. The wine tasting includes a few glasses, usually reds, with advice to spit rather than swallow if you plan on driving afterward.
The Full Itinerary Breakdown
Stop 1: Outskirts of Siena and Monteriggioni
The tour kicks off from Piazzale Carlo Rosselli in Siena. From there, you’ll follow your guide out of the city, winding through scenic roads. One highlight is passing through Monteriggioni’s medieval walls—a small but picture-perfect hilltop town that’s worth a quick stop. Here, you can enjoy the views and take photos, which many reviews mention fondly.
While in Siena, here are other experiences we've covered
- Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch
- Guided tour of the cellars with wine tasting and lunch
- San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
- Chianti and San Gimignano – 2 Wineries with Pairing Lunch
- Cooking Class: Italian Authentic Recipes with Lunch
- Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery
Stop 2: Casale dello Sparviero Winery
This is the main event. The drive down a long cypress-lined avenue leads to the farmhouse, where you’ll tour the vineyards and wine cellars. Guests find this part of the tour gorgeous and appreciate the informative tasting session. It’s a chance to indulge in the flavors of Chianti, paired with some local bread and snacks.
Stop 3: Radda in Chianti and Free Time
You’ll also pass by Radda in Chianti, another picturesque village, and have some free time to explore or relax. Some reviews mention that the ride includes stops in charming villages and short visits, but others felt the tour was more about the ride than in-depth exploration.
Riding the Vespas: What to Expect

This is the core of the experience. For those who love riding, it’s a fun way to traverse Tuscany’s winding roads. Expect to wear the provided helmets, listen to safety instructions, and follow the guide closely. If you’re not an experienced scooter driver, you might feel a little nervous, but the guides do their best to keep everyone safe and comfortable.
A few reviews highlight the importance of previous Vespa experience. Several guests shared that passenger riding is available, and some found the experience smooth and memorable. But a few expressed concerns about safety—so if you’re unsure or unfamiliar with scooters, this might not be the best choice.
The Challenges and Downsides
While many enjoyed the ride, others noted issues such as delays, logistical hiccups, or feeling rushed. One reviewer mentioned a late start cutting into stops, and some expressed frustration over not getting full wine tastings or more guided visits.
A recurring theme is that the tour is fast-paced, with some feeling it’s more about the ride than sightseeing. If you prefer a leisurely, more in-depth tour, this might feel a bit superficial.
Cost and Value: Is It Worth It?

Priced at around $168 per person, the tour offers quite a bit—guided riding, a vineyard visit, wine tasting, and lunch. Included are helmets, fuel, taxes, and the winery tour, which adds up to a comprehensive experience for lovers of adventure and wine.
However, several reviews suggest that the value depends heavily on expectations. For those who love the idea of riding through Tuscany on a Vespa, paying this price makes sense. But if you’re less confident on a scooter or prefer a more relaxed, guided tour with detailed sightseeing, you might find it a bit pricey. Some guests pointed out that renting a Vespa and touring independently could be more economical and flexible, especially if you’re an experienced rider.
Who Should Book This?

This tour is ideal for adventure-seeking travelers who are comfortable on a Vespa and want to combine scenic rides with wine tasting. It’s a great choice if you’re eager for a fun, physically active way to explore Tuscany’s highlights. Be prepared for a somewhat fast-paced experience and ensure your Vespa skills are up to par.
If you dislike group tours, or if you’re not confident driving a scooter, consider whether this experience is right for you. It’s not suitable for complete beginners unless you’re riding as a passenger and comfortable with the challenge. Also, if you’re looking for an in-depth cultural or historical tour, this might not satisfy that craving.
This Vespa tour from Siena offers a lively, scenic way to see Tuscany, paired with wine tasting and a light lunch. It’s a unique experience that combines adventure with a taste of local tradition, making it a memorable highlight for many travelers.
That said, it’s not perfect. The pace can feel rushed, and logistical issues have been noted, including delays and questions about safety. The experience hinges on your comfort with Vespa riding and your desire for a somewhat fast-moving adventure.
For those passionate about experiencing Italy on a scooter, enjoy wine and beautiful views, and are confident riders, this tour will likely be a highlight. But if safety, in-depth sightseeing, or a relaxed pace matter more, you might want to explore other options or consider renting a Vespa independently.
Vespa Tour with Lunch&Chianti Winery from Siena
“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…”
FAQs

Do I need previous Vespa experience to join? Yes, previous riding experience is strongly recommended. The tour requires passing a driving test, and safety is a priority.
Is the tour suitable for beginners? Not generally. If you’re inexperienced or uncomfortable on a scooter, you might prefer to ride as a passenger or choose a different tour.
What’s included in the price? Helmet, fuel, taxes, winery tour, wine tasting, and a light lunch are included. Pick-up and drop-off are optional at an extra charge.
Can I get vegetarian lunch options? Yes, vegetarian menu options are available upon request.
What happens if I don’t pass the driving test? You can ride as a passenger with the guide, or unfortunately, if you can’t drive safely, you may not participate in the Vespa riding portion.
What should I wear? Wear comfortable clothes suitable for riding, and bring sun protection and sunglasses.
Are there any age restrictions? You must be at least 18 to drive and 13 to be a passenger.
What if the weather is bad? The tour takes place rain or shine. In case of heavy rain or wind, the route may be modified, or the tour could be canceled with a full refund.
To sum it up, this Vespa tour from Siena invites you to see Tuscany in a lively, authentic way. It’s perfect for adventurous travelers who love riding, enjoy wine, and want to experience Italy’s rolling hills firsthand. Just go in with the right expectations—it’s a fun ride, but it’s not a detailed sightseeing tour. If you’re ready for some wind-in-the-hair fun and a taste of Chianti, this could be just what you’re looking for.
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