Sidecar tour in Florence and Chianti with wine tasting and lunch

Imagine exploring the enchanting streets of Florence and the rolling hills of Chianti—all from the back of a vintage sidecar. This five-hour tour, offered by De Gustibus Tours for around $240 per person, takes you on a spirited ride through some of Tuscany’s most beautiful sights. With a small group of just six travelers, you’ll get plenty of personal attention and authentic experiences, making this an ideal choice for those craving a mix of adventure, culture, and culinary delights.

What sets this tour apart? First, the combination of scenic riding and cultural visits—from riding along the historic Oltrarno district and Piazzale Michelangelo, to stopping at a family-run boutique winery where you’ll explore traditional wine-making and enjoy tastings. Second, the chance to sample a genuine Tuscan lunch, paired with local wines and products, in a relaxed setting that highlights the region’s flavors.

One small consideration is the weather dependency—an outdoor sidecar adventure is best enjoyed in clear weather, and the tour can be canceled or rescheduled if the skies turn gloomy. This experience is best suited for travelers who love a bit of adventure, enjoy wine and good food, and want a more intimate way to see Florence and Chianti beyond typical bus tours.

Key Points

• Unique Sidecar Experience: Ride through Florence and Chianti in vintage style, blending sightseeing with adventure.
• Cultural Highlights: Visit the Oltrarno district, Piazzale Michelangelo, and Impruneta, enjoying iconic views and local traditions.
• Wine & Lunch: Explore a boutique winery, taste Chianti wines, and savor a Tuscan lunch with regional products.
• Small Group Atmosphere: Maximize personal attention and authentic interactions with guides and winemakers.
• Picturesque Views: Capture stunning countryside panoramas, perfect for photos and videos.
• Weather Sensitivity: Be prepared for possible cancellations in poor weather, so check the forecast.

Exploring Florence and Chianti from a Sidecar

A Different Way to See Florence

Starting at the Café Pasticceria Gamberini, this tour kicks off at 10:00 am. From there, you’ll hop into a vintage sidecar—think classic Italian style—and cruise around Florence’s Oltrarno district and Piazzale Michelangelo.

The Oltrarno is often called Florence’s “bohemian” side—full of artisan workshops, local galleries, and lively squares. Riding through here gives you a taste of local life away from the tourist-heavy city center. The guide, likely someone like Gilberto based on reviews, makes the history lively and engaging, sharing stories as you wind through narrow streets and alleys.

Then, you’ll head out of Florence onto the Strada Statale 222 Chiantigiana, a winding road through the quintessential Tuscan countryside. Here, you’ll visit a small family-run winery, where you’ll see the cellars and learn about traditional wine-making. This authentic visit offers a behind-the-scenes look—rarely available on larger tours—and the pairing of wine and regional foods makes for a memorable tasting.

Your next stop is at Piazzale Michelangelo—a well-known viewpoint that offers sweeping vistas of Florence’s skyline, including the Duomo and Ponte Vecchio. It’s a brief but spectacular photo opportunity—don’t forget your camera!

Finally, the tour visits Impruneta, famous worldwide for its terracotta pottery. This charming town has a long-standing tradition, and a quick coffee break here is a lovely way to soak in local craftsmanship.

The Experience on a Sidecar

Riding in a sidecar isn’t just about getting from A to B; it’s about the journey. The open-air aspect means you’ll feel the breeze, hear the sounds of Tuscany, and experience everything in a more visceral way. Tour guides are often praised for their friendliness and knowledge—making this a personalized experience rather than a cookie-cutter bus trip.

The Winemaking and Tuscan Lunch

A highlight for many travelers is the wine tasting at the boutique winery. The setting is intimate and relaxed, allowing for genuine conversations with the winemakers. According to reviews, the wines—especially the Chianti—are quite good, and some even mention the delicious local food pairing that accompanies the tasting.

The Tuscan lunch includes regional products—perhaps cured meats, cheeses, bread, and local olive oil—highlighting the region’s culinary reputation. Feedback indicates that the setting is beautiful, and the food is satisfying without being overly fancy.

Group Size and Flexibility

With a maximum of six travelers, the experience feels exclusive but not pretentious. This small group size fosters conversation and allows the guides to tailor the experience to your interests. The mobile ticket system and starting point at the café make logistics straightforward, and the duration of about five hours strikes a nice balance—long enough to cover key sights and enjoy the tastings, but not so long as to cause fatigue.

The Balance of Adventure and Comfort

While riding a vintage sidecar is undeniably fun and memorable, it’s worth noting that it might not suit everyone—particularly those who dislike open-air exposure or have mobility issues. Also, since the tour depends on good weather, a rainy day could disrupt plans. Still, many travelers find that the weather conditions add to the charm, especially if you’re prepared with suitable clothing.

In-Depth Itinerary Breakdown

Oltrarno and Piazzale Michelangelo

The Oltrarno district is a favorite among those wanting a slice of local life. Its artisans, small shops, and less-touristy vibe provide a contrast to the city’s more famous sights. Riding through here allows you to see neighborhoods where locals live, work, and relax.

The Piazzale Michelangelo offers the most iconic view of Florence—its skyline with the Duomo, Palazzo Vecchio, and the Arno river. Many reviews mention taking photos here—some even say it’s the best spot for panoramic photos. The 15-minute stop is brief but worthwhile, especially in good light.

Out into the Tuscan Countryside

After leaving the city behind, your ride along Chiantigiana road is a highlight. The scenery is classic Tuscany—vineyards, olive groves, and cypress trees. This part of the drive feels like a moving postcard.

The boutique winery stop offers more than just tastings; it’s an educational peek into family-run operations that have been making wine for generations. The inclusion of a visit to the cellar and wine tasting enhances the experience, giving you context about Chianti’s reputation and the region’s tradition.

Impruneta and Local Crafts

A quick stop in Impruneta introduces you to Italy’s centuries-old terracotta-making tradition. It’s a brief visit, but many reviews highlight the town’s charm and craftsmanship. It’s a great way to see how regional artisans keep centuries-old techniques alive.

Authenticity and Value

This tour’s appeal lies in its blend of adventure, culture, and culinary delights. The price includes not only the transportation—a vintage sidecar ride that’s as much about the experience as the scenery—but also the wine tasting and Tuscan lunch.

Compared to larger, more commercial tours, the small-group format and personal interaction with local winemakers provide better value for travelers seeking genuine insight rather than just sightseeing. The reviews confirm that many find the experience well worth the cost, emphasizing the quality of the wines, the scenic vistas, and the relaxed atmosphere.

Who Should Consider This Tour?

This experience suits travelers who are adventurous and enjoy outdoor activities—particularly those comfortable in open-air vehicles. It’s perfect for wine lovers who want to combine tasting with a scenic ride, and for small groups or couples looking for something more intimate than a bus tour.

If you’re after a photo-rich, authentic experience that captures Tuscany’s spirit and offers a bit of thrill, this tour checks all those boxes. However, if you prefer indoor sightseeing or are sensitive to weather, you might want to consider the timing carefully.

The Sum Up

For those craving an authentic, fun, and scenic way to discover Florence and Chianti, this sidecar tour offers a memorable blend of sights, tastes, and adventure. The personal attention of a small group, combined with visits to local wineries and breathtaking views, makes it a standout.

It’s especially suited for travelers who value unique experiences over cookie-cutter tours—those who love wine, good food, and a bit of adrenaline. While weather-dependent, the overall experience is often praised for its relaxing pace, friendly guides, and delicious tastings.

If you’re looking to add a genuine Tuscan flavor to your trip—and enjoy a bit of fun along the way—this tour might just be the highlight you didn’t know you needed.

FAQ

Is this tour suitable for all ages?
While mainly geared toward adults, particularly those comfortable with outdoor rides, the tour is generally suitable for most travelers who enjoy adventure and sightseeing. Service animals are allowed, but check with the provider for specific needs.

How long is the ride from Florence to Chianti?
The tour includes riding through Florence’s Oltrarno district, then out into the countryside, with the total duration of about five hours, including stops.

What is included in the wine tasting?
The tour includes wine tasting at a family-run boutique winery, where you’ll explore the cellar and sample Chianti wines along with regional foods.

Can I cancel this tour?
Yes, the tour offers free cancellation up to 24 hours in advance, allowing some flexibility if your plans change or weather looks unfavorable.

What should I wear?
Comfortable clothing suitable for outdoor riding is recommended. Weather-dependent, so bring layers or rain gear if needed.

Where does the tour start and end?
It begins at Café Pasticceria Gamberini in Florence at 10:00 am and returns to the same location after the tour ends.

Is this experience worth the price?
Most reviews affirm that the combination of scenic rides, cultural visits, and tastings makes it good value—especially given its small group setting and authentic flavor.