Sidecar tour in Florence and Chianti with wine tasting and lunch

A Detailed Look at the Sidecar Tour in Florence and Chianti with Wine Tasting and Lunch

If you’re dreaming of combining sightseeing, wine, and a touch of adventure in Italy, this sidecar tour in Florence and Chianti might catch your eye. It’s a small-group experience that promises a distinct way to explore some of Tuscany’s most beautiful spots — from the lively city streets to rolling vineyards and charming towns. But as with all experiences, it’s worth digging into what makes it special, and what might be less ideal for certain travelers.

Two things we genuinely appreciate about this tour are the personalized, intimate feel thanks to the small group size—only six travelers max—and the chance to see Florence’s highlights from a unique perspective atop a vintage sidecar. Plus, the inclusion of a wine tasting and a traditional Tuscan lunch makes it not just a sightseeing ride, but a true taste of the region’s culture and flavors.

One thing to keep in mind is that this is a half-day adventure lasting around 5 hours — perfect if you want a manageable experience without feeling overwhelmed. However, it does involve a fair amount of riding on open-air vehicles, which might not suit those who prefer a more relaxed, indoor experience or are sensitive to weather conditions. Still, if you’re after a memorable, active way to explore Tuscany, then this could be just right.

This tour is especially suited for adventurous travelers, wine lovers, and those wanting a more personal, off-the-beaten-path experience. It’s not likely a fit for anyone looking for a more relaxed, traditional bus tour or those with mobility concerns, but for most open-minded visitors, it offers a fun, engaging way to see Florence and Chianti.

<h3 id="section-0">Key Points

• Unique Transportation: Riding a vintage sidecar adds a memorable twist to sightseeing.
• Small Group: A maximum of 6 travelers means more personalized attention.
• Active Experience: Combines scenic riding with cultural and culinary stops.
• Wine & Food: Includes tastings at a boutique winery and a Tuscan lunch with local products.
• Stunning Views: Stops at Piazzale Michelangelo and Impruneta offer great photo opportunities.
• Weather Dependent: As an outdoor experience, weather can influence the quality of your ride.

Why Choose This Sidecar Tour?

Imagine starting your day in Florence’s bustling Oltrarno district, feeling the cool breeze as you cruise on a vintage sidecar, taking in the city’s rooftops and iconic sights. That’s exactly what this tour offers from the very first moment. The guide will take you up and down the Oltrarno neighborhood, known for its artisan shops and vibrant atmosphere, then to Piazzale Michelangelo, which gives you one of the best panoramic views over Florence.

From there, the journey shifts gears from city streets to the tranquil landscape of Chianti. Riding along the Strada Statale 222 Chiantigiana, you’ll leave behind the hustle of Florence and dive into the lush Tuscan countryside. This part of the tour is where the adventure really unfolds, as the open-air sidecar allows you to soak in the fresh air and expansive vistas.

Exploring Florence’s Highlights

The Oltrarno district is a lively, authentic part of Florence, less touristy but rich in character. The guide will escort you through its charming streets, sharing stories and history along the way. Then, after a quick stop at Piazzale Michelangelo, you’ll get a chance to snap some memorable photos of Florence’s skyline — a must-do for any first-time visitor.

The Chianti Experience: Wineries and Lunch

The real highlight for many travelers is the visit to a small family-run boutique winery in Chianti. Here, you’ll explore the winemaker’s cellar and learn about the local Chianti Classico production process. According to reviews, this part of the tour is particularly well-received — one reviewer called it a “beautiful setting” with “good Chianti wine.”

The tasting experience is relaxed, giving you the chance to sample different wines and chat with the winemakers. Afterward, there’s a traditional Tuscan lunch featuring local products, which complements the wines perfectly. The combination of good food, great wine, and stunning vineyard views makes this stop memorable.

Impruneta and Its Artisan Tradition

Before heading back to Florence, you’ll stop in Impruneta, a town renowned for its terracotta production. The brief visit offers a taste of local craftsmanship, and usually, visitors enjoy a quick coffee break here. It’s a nice touch that adds cultural depth to the experience without taking up too much time.

What’s Included and How It Works

• Meeting Point: Starts at Café Pasticceria Gamberini in Florence at 10 am, making it easy to plan your morning.
• Duration: Around 5 hours, including city stops, countryside riding, winery visit, and lunch.
• Group Size: Small-group with a maximum of 6 travelers, fostering a friendly, personalized atmosphere.
• Pricing: At about $240 per person, it’s a fair price considering the unique mode of transportation, guided experience, winery visit, tastings, and lunch.

The tour operates with confirmation at booking, and free cancellation is available up to 24 hours beforehand, which is handy if you’re unsure about the weather or your schedule.

What Travelers Say

Reviews paint a very positive picture. One traveler, Sarah, called it an “amazing sidecar wine tasting tour,” praising the laid-back vibe, beautiful setting, and quality Chianti. Nancy described it as “the best tour I’ve ever been on,” mentioning how Tommy, the guide, went out of his way to make the day special. Stacey highlighted the “fantastic experience” — blending sightseeing, learning, and tasting all in one.

People also appreciated the stunning views and the opportunity to learn about local wines and culture in a relaxed environment. The small group size means you’ll get more attention and a chance to ask questions, making it an educational yet fun experience.

Practical Details and Tips

• Weather: Because it’s an outdoor activity, check the forecast. The tour can be canceled in case of bad weather, with options for a different date or full refund.
• Clothing: Dress comfortably and appropriately for riding and weather conditions. Layers are a good idea.
• Accessibility: The tour involves riding on open vehicles, which might not be suitable for everyone.
• Booking in Advance: Since the tour is popular and booked on average 110 days in advance, plan ahead to secure your spot.
• Photography: Bring a camera or smartphone to capture the scenic vistas and charming towns along the way.

In The Sum Up: Is It Right for You?

If you’re someone who appreciates discovering Italy from a different vantage point, this sidecar adventure blends sightseeing, wine, and local culture into a compact experience. It’s especially suited for those who enjoy a bit of thrill, great conversation, and beautiful scenery — all while tasting some of Tuscany’s finest wines. With its small group size and personal touches, it’s perfect for travelers who want to avoid the crowds and have meaningful interactions.

However, if you’re looking for a leisurely, indoor experience or are concerned about riding in open-air vehicles in uncertain weather, this might not be your best fit. Still, for most adventurous spirits and wine lovers, this tour offers a memorable way to explore Florence and Chianti—something you’ll likely be talking about long after the day ends.

FAQ

Is this tour suitable for children?
The tour is designed for adults and involves riding in open-sided sidecars, which may not be suitable for young children or those with mobility concerns.

How long is the entire experience?
The tour lasts approximately 5 hours from start to finish, including all stops and activities.

What’s included in the price?
You get guided rides in a vintage sidecar, visits to Oltrarno, Piazzale Michelangelo, and Impruneta, a stop at a boutique winery with wine tastings, and a Tuscan lunch with local products.

Do I need to bring anything?
Comfortable clothing, weather-appropriate gear, and a camera are recommended. The experience is outdoors, so check the weather forecast.

Can I cancel if my plans change?
Yes, you can cancel for free up to 24 hours before the tour begins, receiving a full refund.

Is this tour available year-round?
The description doesn’t specify seasonal restrictions, but weather conditions can impact the experience. Confirm at booking for current availability.

This sidecar tour combines the thrill of riding with scenic views, cultural stops, and tasty wine — a distinctive way to see Tuscany that many travelers find well worth the price. It’s a small, engaging adventure that offers more than just the usual sightseeing, making it a fantastic addition to your Florence and Chianti itinerary.