Siena is a perfect base for exploring Tuscany on two wheels. Its charming streets, rolling hills, and easy access to the countryside make motorbike and scooter rentals an ideal way to see the region more intimately. We love how these tours combine the thrill of riding with authentic experiences like visiting wineries and exploring medieval villages. For example, the Vespa Tour with Lunch & Chianti Winery from Siena offers a full day of scenic riding, wine tasting, and local cuisine — all with the flexibility to ride yourself or follow behind a guide.
From guided group rides to private Vespa adventures, these options give you a taste of Tuscany’s best while letting you choose your preferred style of exploration. Whether you’re after a lively group experience or an intimate day with a personal guide, this list covers the best rides around Siena and beyond. Keep reading to find the perfect match for your travel style.
Here’s a quick overview of the different tours included: full-day Vespa excursions to Chianti’s vineyards, guided small-group rides exploring medieval towns, private tailored experiences for couples or small groups, and longer day trips from nearby San Gimignano. Now, let’s look at each tour in detail.
1. Vespa Tour with Lunch&Chianti Winery from Siena
At number 1 on our list, the Vespa Tour with Lunch & Chianti Winery from Siena is a well-rounded day trip that combines riding with wine tasting and regional cuisine. This tour lasts around 6.5 hours and offers the option to ride your own Vespa or join behind a guide, making it accessible for those with varying riding skills. The highlight is a visit to a Chianti winery, where you’ll tour vineyards and cellars, sample local wines, and enjoy a light Tuscan lunch in a stunning setting.
What makes this tour stand out is the carefully curated itinerary. You’ll start with a ride through the picturesque Chianti hills, stopping in Castellina in Chianti and Radda in Chianti — two charming medieval towns that look like postcards. The long avenue of cypress trees leading to Casale dello Sparviero is a favorite spot for photos, as guests rave about the gorgeous vineyard views. The final stop, Monteriggioni, offers free time to wander cobbled streets and soak in the medieval ambiance.
This tour is perfect for travelers who want a full-day experience, blending scenic riding with gourmet experiences. The reviews praise the guide’s expertise and the beauty of the winery visit, though passing a Vespa riding test is required. It’s a great pick for those comfortable on two wheels looking for a balanced mix of adventure and relaxation.
Bottom Line: This tour is a fantastic way to combine riding, wine, and scenery in one seamless package, perfect if you want a guided but lively day out.
2. Vespa Tour in Chianti Small Group from Florence
At number 2, the Vespa Tour in Chianti Small Group from Florence offers a similar 6.5-hour experience, but with a focus on small-group intimacy and starting from Florence. This tour provides a chance to explore the Chianti countryside in style, zipping past vineyards, olive groves, and medieval villages like Radda and Monteriggioni.
The tour includes a stop at Casale dello Sparviero, where a winery visit and tasting await, plus a traditional Tuscan lunch. The itinerary emphasizes the scenic drive along hillside roads, with unforgettable views of the Tuscan landscape. Riders can choose to drive their Vespa or join an experienced guide, making it suitable for both confident riders and those who prefer a guided experience.
Guests appreciate the opportunity to see authentic villages and enjoy regional wines in a relaxed setting. A few reviews mention initial difficulty passing the driving test — so be prepared to demonstrate your riding skills. The tour’s small group size ensures personalized attention, and the guide’s knowledge helps enhance the experience.
Bottom Line: If you’re coming from Florence and want a more intimate, guided ride through Chianti’s most picturesque spots, this tour offers excellent value and authentic immersion.
3. Private Vespa Tour in Chianti
At number 3, the Private Vespa Tour in Chianti offers a tailored experience for those seeking exclusivity. For around $365, you get about 5 hours of riding with a dedicated guide who personalizes stops at villages and viewpoints of your choosing. This is ideal for couples or small groups wanting to customize their day and focus on specific sites or scenery.
This tour provides a much deeper level of flexibility, with your guide taking care of navigation and ensuring you hit the most photogenic spots and hidden corners of Chianti. It includes a Tuscan-style lunch and wine tasting, with vineyard views that keep the camera busy. The guide’s local knowledge shines here, as they can adapt the route to your interests — whether that’s exploring archaeological sites in Radda or stopping at a viewpoint overlooking vineyards.
Guests on this tour rave about the personal attention and the chance to explore off-the-beaten-path. The main drawback is the higher price point, but the exclusivity and customization are worth it for travelers who want a unique, private experience without the constraints of a group.
Bottom Line: For a personalized day in Tuscany with maximum flexibility, this private Vespa tour delivers an intimate, tailored experience.
4. Full-Day Chianti Tour by Vespa Scooter from San Gimignano
Rounding out our list at number 4, the Full-Day Chianti Tour by Vespa Scooter from San Gimignano is a longer, 7.5-hour adventure that starts from nearby San Gimignano. This option is perfect if you’re staying in or exploring San Gimignano and want a comprehensive ride through the Chianti region.
The tour features riding through vineyards, olive groves, and medieval villages, with two key stops — Radda in Chianti and Monteriggioni — where you can explore on your own. The itinerary emphasizes scenic vistas and authentic rural landscapes, making it ideal for those who love staying on the move. The inclusion of a wine tasting and a light Tuscan lunch adds to the value, giving you a true taste of local flavors.
Guests can choose to ride as a passenger or upgrade to drive their Vespa, which is a nice flexibility. Although the reviews mention the tour’s length and some mixed ratings, most agree it’s a solid choice for those looking to combine riding with experiencing the region’s sights. The longer duration makes it suitable for travelers with a full day to spare.
Bottom Line: If you’re based near San Gimignano and want a longer, immersive ride through Chianti, this tour offers a great mix of scenery, wine, and local charm.
How to Choose the Best Motorbike and Scooter Tour in Siena
When selecting a scooter or motorbike tour in Siena, consider your budget, riding confidence, and interests. For a balanced experience that includes guided riding, wine tasting, and scenic villages, the Vespa Tour with Lunch & Chianti Winery is a top choice. If you prefer a more personalized, private experience, the Private Vespa Tour offers customization but at a higher cost.
For those traveling from Florence, the Vespa Tour in Chianti Small Group is convenient and intimate, while if you’re staying near San Gimignano, the Full-Day Chianti Tour from San Gimignano provides an extended adventure.
Practical tips include booking early, especially in high season, and confirming your riding skill level if you want to drive. Remember, some tours require a Vespa driving test, so be sure you’re comfortable on two wheels.
Siena’s surrounding countryside offers an exciting variety of motorbike and scooter experiences that suit different travel styles. Whether you want a guided group ride, a private tailored day, or a longer exploration starting from nearby towns, there’s an option for everyone. For a fun and authentic way to see Tuscany, these tours deliver a mix of scenic beauty, regional flavors, and a bit of adventure — so book early and prepare for a memorable ride.
