Sidecar tour in Florence and Chianti with wine tasting and lunch

Our review explores an engaging sidecar tour through Florence and Chianti, offered by De Gustibus Tours. For those craving a blend of adventure, culture, and of course, wine, this five-hour experience promises a lively ride—literally—through some of Tuscany’s most iconic sights and tastings. You’ll hop on vintage sidecars, explore Florence’s charming neighborhoods, and then journey into the rolling hills of Chianti for exclusive visits to boutique wineries, topped off with a relaxed Tuscan lunch.

What I really like about this tour is how it balances scenic riding with authentic, hands-on experiences. The guides, including Gilberto and Tommy, are praised for their friendly attitude and local knowledge—making even the less-known stops feel special. The small-group format, limited to six participants, ensures you won’t be lost in a crowd and can ask plenty of questions. Plus, the opportunity to stop at Piazzale Michelangelo for one of the best city views or to see Impruneta’s famous terracotta tradition adds a layer of local color few other tours provide.

A slight consideration is that the tour is weather-dependent, so if rain or adverse conditions hit, your experience might change or be canceled, but the company offers flexible rescheduling or full refunds. Also, because the tour is scheduled at 10 a.m., you should be prepared for an early start, but that means you’ll beat the crowds and enjoy the day’s best light.

Key points / Takeaways

• Unique transportation: Riding in vintage sidecars offers an intimate, fun way to explore Florence and Chianti that most visitors miss.
• Authentic wine experience: Visiting a family-run boutique winery and tasting Chianti wines makes the trip more personal and memorable.
• Scenic vistas: Stops at Piazzale Michelangelo and the Tuscan countryside offer breathtaking views perfect for photos.
• Local culture: Impruneta’s famous terracotta tradition and visits to historic districts give you a taste of true Tuscan craftsmanship.
• Gourmet lunch included: A relaxed Tuscan lunch with local products complements the wine tasting, providing a taste of real regional cuisine.
• Small group intimacy: With only six travelers max, the tour feels relaxed and personalized, encouraging genuine conversations and questions.

Exploring Florence and Chianti on a Vintage Sidecar

This tour is a delightful way to see Florence beyond the usual crowded streets and to venture into the quieter, beautiful Chianti countryside. Starting from the charming Oltrarno district, your guides, like Gilberto and Tommy, will gently take you on a scenic ride through Florence’s streets and up to Piazzale Michelangelo. Here, you’ll enjoy panoramic views over the city, a perfect opportunity for photos and soaking up Florence’s skyline. Many reviews, like Sarah’s, highlight how riding through Florence in a sidecar is both fun and revealing: “Such a fun time riding through Florence with Gilberto learning about history on the way to Luiano for our wine tour.”

The ride then takes you through the strada statale 222 Chiantigiana, a scenic route that winds through gentle hills and lush vineyards. As you leave the city behind, you’ll quickly notice the change to peaceful country roads, dotted with cypress trees and rustic farmhouses. The highlight here is the visit to a family-run boutique winery, where you can explore the wine cellar and learn about traditional Chianti production. One guest, Nancy, called this “by far the best tour my husband and I have ever been on,” emphasizing the personal touches and quality of the wine.

The Chianti Countryside and the Winery Experience

Once in Chianti, the tour slows down for a genuine hands-on experience. The winery visit is often described as relaxed and welcoming, with the chance to taste excellent Chianti wines in a cozy, historic cellar. Many reviewers mention the “beautiful setting” and “good Chianti wine,” which makes the tasting feel more authentic than a generic winery visit.

The tour includes a delicious Tuscan lunch, where regional products are served with wine, offering a chance to savor local flavors with friends or family. One guest appreciated the “laid-back and welcoming” atmosphere, which makes the experience more like visiting friends’ countryside home rather than a commercial stop.

After lunch, the journey continues with a quick stop at Impruneta, renowned for its terracotta craftsmanship. It’s a brief but memorable stop, perfect for a quick coffee or to pick up a handcrafted souvenir.

The Best Views and Final Stops

The last stop is at Piazzale Michelangelo, where you’ll get a breathtaking view of Florence as the sun begins to set or in the bright daytime, depending on timing. Many guests comment on how this spot is “the best vantage point over the city,” and it’s a perfect way to wrap up your scenic adventure.

In total, the tour lasts around five hours, leaving enough time to enjoy the sights without feeling rushed. The schedule begins at 10 a.m. from the meeting point at Café Pasticceria Gamberini, making it a great choice for travelers who want a relaxed morning with plenty of time afterward for other activities.

Who This Tour is Perfect For

This experience is ideal if you love unique transportation and want a more personal connection to local wine and culture. It suits travelers seeking an authentic Tuscan experience with stunning scenery, good food, and wine. Perfect for those who aren’t afraid of a little adventure and want to avoid large groups, thanks to the small-group format.

However, keep in mind the weather factor—if rain is forecast, it might impact your ride or tasting plans. The price, around $240 per person, reflects the exclusivity and quality of the experience, especially considering the personalized winery visit and delicious lunch included.

Practical Tips for Your Sidecar Tour in Florence and Chianti

• Book early, as the tour is popular and booked on average 110 days in advance.
• Dress comfortably and be prepared for weather changes—bring a jacket or raincoat if needed.
• Arrive early at Café Gamberini to meet your guides and settle in.
• Bring a camera or smartphone—the views and photo opportunities are fantastic.
• Small group size means personalized attention—don’t hesitate to ask questions or request specific stops.
• Make sure your camera is charged; the panoramic views and picturesque vineyards are worth capturing.
• Enjoy the relaxed pace—this isn’t a rushed tour but a chance to really soak in the sights and tastes.

FAQ about the Florence and Chianti Sidecar Tour

Is this tour suitable for children or non-drivers?
Yes, children are allowed, and the tour is ideal for those who prefer not to drive, as you’ll be riding in vintage sidecars with an experienced guide.

How long does the entire tour last?
The tour is approximately five hours, including sightseeing, winery visit, tasting, and lunch.

What is included in the price?
Your fee covers the sidecar ride, visits to Florence and Chianti sites, a wine tasting at a boutique winery, and a Tuscan lunch with local products.

Do I need to be experienced in riding or riding in a sidecar?
No experience is necessary. The guides handle the riding, and safety equipment is provided.

What if the weather is bad?
The tour is weather-dependent. If canceled due to poor weather, you’ll be offered a different date or a full refund.

Can I cancel this tour?
Yes, cancellations are free up to 24 hours before the start time, allowing flexibility if your plans change.

How many people will be on the tour?
A maximum of six travelers ensures a small, intimate experience.

Are there any special tips for making the most of this tour?
Bring your camera, dress comfortably, and arrive early. Be ready to enjoy the scenery and the company, and don’t forget to ask questions about local wines and traditions.

This sidecar adventure offers a charming, authentic peek into Tuscany’s picturesque landscapes, vibrant wine culture, and local craftsmanship. It’s perfect for curious travelers eager to combine scenic rides with genuine tasting experiences, all wrapped in a relaxed, friendly atmosphere. Whether you’re a wine lover, a lover of picturesque views, or simply seeking something different from the typical tour, this experience delivers on all fronts—plus, it’s a lot of fun.