Siena is one of Italy’s most charming cities, famous for its medieval architecture, lively piazzas, and surrounding rolling hills. It’s a place that begs to be explored on two wheels, and luckily, there are plenty of motorbike and scooter rental options that put the countryside at your fingertips. Whether you want a guided experience that takes care of the logistics or a private ride to discover hidden corners at your own pace, Siena offers something for every type of traveler. One standout is the Vespa Tour with Lunch & Chianti Winery from Siena, which combines the thrill of riding through Tuscany’s vineyards with the comfort of a guided tour. Throughout this list, you’ll find different options tailored to various interests and budgets, all promising a memorable way to see the region.
If you’re seeking a full immersion into the Chianti wine region with a sense of adventure, these tours are well worth considering. But if privacy and personalized stops are more your style, the Private Vespa Tour in Chianti offers a more tailored experience. Read on to see which ride suits your style best.
1. Vespa Tour with Lunch&Chianti Winery from Siena
At number 1, this Vespa Tour with Lunch & Chianti Winery from Siena is a full-day experience that combines riding, wine tasting, and sightseeing. For around $168, you get about 6.5 hours of Tuscany on a Vespa, with the option to ride yourself or hop on behind a guide. The tour kicks off from Siena itself, taking you through the famous Chianti hills on a convoy led by experienced guides, which means you don’t have to worry about navigation.
What makes this tour stand out is the carefully curated itinerary. You’ll stop in Castellina in Chianti for free time, then visit Casale dello Sparviero for a wine tasting amid cypress-lined avenues—perfect for photos. The tour also includes time in Monteriggioni, a small fortress town that looks straight out of a fairytale. The highlight? The winery visit, where you’ll tour vineyards and cellars, and sample Tuscan wines paired with a light lunch. Reviewers love the mix of riding and relaxing, with one calling it “epic and fun.” The only caveat: participants must pass a Vespa driving test, so be prepared to show your skills.
Bottom line: Great for those who want a guided, all-inclusive day in Tuscany, with a mix of riding, wine, and picturesque towns.
2. Vespa Tour in Chianti Small Group from Florence
Number 2 is the Vespa Tour in Chianti Small Group from Florence, perfect if you’re based in Florence but want to experience Siena’s nearby countryside on a Vespa. For roughly $168, this 6.5-hour adventure is ideal for those who enjoy a more intimate small-group setting. The tour begins with a scenic drive out of Florence, reaching the Chianti hills in about an hour, where you can choose to drive your own Vespa or ride with an experienced guide.
The route takes you through Radda in Chianti and past historic villas and vineyards, with plenty of chances to stop for photos and explore. The highlight is the visit to Casale dello Sparviero, where you’ll enjoy a wine tasting and a chance to learn about local production. You’ll then have time in Monteriggioni, this time free to wander on your own. Reviewers praise Sveva, their guide, for her safety instructions and friendly attitude, making the experience accessible even for newcomers. One note: some travelers have noted the challenge of passing the Vespa driving test, especially if they haven’t ridden recently.
Bottom line: A good choice for small groups wanting a guided, scenic ride starting from Florence, with wine and town stops.
3. Private Vespa Tour in Chianti
Number 3 offers a more exclusive experience with the Private Vespa Tour in Chianti. For about $365, you get approximately 5 hours of personalized riding tailored to your interests. The private option is perfect if you want flexibility in choosing stops or prefer a leisurely pace. Your guide will ensure the best viewpoints and photo stops along the way, making this a more curated experience.
The itinerary includes stops in Radda in Chianti, with archaeological sites dating back to 2000 BC, and Panzano in Chianti, a village with Etruscan roots. Your guide’s local knowledge guarantees a bespoke tour, whether you want to visit small villages, scenic viewpoints, or vineyard estates. The tour also includes an authentic Tuscan lunch and wine tasting at a vineyard with beautiful vineyard views. Reviewers note the high level of personalization and the guide’s expertise, with one saying, “Took us through some beautiful countryside and small towns that offered great history and fabulous views.”
Bottom line: Ideal for travelers seeking a private, curated experience with the flexibility to explore at your own pace.
4. Full-Day Chianti Tour by Vespa Scooter from San Gimignano
Last on our list is the Full-Day Chianti Tour by Vespa Scooter from San Gimignano. Priced at around $168, this 7.5-hour tour is a solid choice for those based in San Gimignano wanting to explore Chianti’s vineyards and villages. Starting from San Gimignano, you’ll ride through the rolling hills, with stops in Radda in Chianti and Monteriggioni, similar to other tours but with a longer duration.
This tour includes a wine tasting, a light Tuscan lunch, and the flexibility to ride as a passenger or upgrade to drive the Vespa. Reviewers mention the scenic route and the well-organized itinerary, making it a good value for a full-day outing. Some note that the group size and pace are comfortable, allowing time to soak in the views.
Bottom line: Best for travelers based near San Gimignano wanting a longer, more relaxed day exploring Chianti’s vineyards and villages.
$168.00 per person
How to Choose the Right Motorbike or Scooter Tour in Siena
When selecting your ideal tour, consider factors like budget, time available, and your level of comfort with riding. Guided tours like the Vespa Tour with Lunch&Chianti Winery are perfect if you prefer all logistics handled and want to focus on the experience. In contrast, the Private Vespa Tour offers a tailored route, ideal for those seeking flexibility.
If you’re based in Florence or San Gimignano, the Vespa Tour in Chianti Small Group or the full-day San Gimignano option might suit your schedule better. Always check if you need to pass a driving test and consider your comfort level on a scooter.
Booking early, especially in peak season (spring to early fall), ensures you get your preferred date and vehicle. Each tour offers a different balance of adventure, comfort, and customization—think about what matters most to your trip.
In summary, Siena and its surroundings offer many exciting ways to see Tuscany on two wheels. For an all-in-one guided experience with wine and sightseeing, the Vespa Tour with Lunch is a winner. For a more personalized adventure, opt for the Private Vespa Tour. And if you’re based outside Siena, the Chianti tours starting from Florence or San Gimignano are excellent options. No matter your choice, renting a motorbike or scooter makes for an authentic, liberating way to explore Tuscany’s stunning landscapes—so book early and get ready to ride!