A new destination from The Vespa Trip
Everyone knows Tuscany, but Chianti is where you truly find the very best: fewer tourists, more wine, more tranquillity and even stronger road-trip vibes. Welcome to Chianti!
The newest destination of The Vespa Trip and one of the most extraordinary places to explore by Vespa.
While our Tuscany Il Giro Classico is known for its iconic postcard highlights, Chianti feels like the elegant, lesser-known sister: quieter, more intimate, more authentic… and perfect to discover at your own pace during a Vespa tour through Italy’s most scenic wine region.
The heart of Tuscany’s wine region
Chianti is the beating heart of the Chianti Classico wine region. Riding here means travelling through the birthplace of one of the world’s most iconic wines. Everywhere you look, you’ll see vineyards, small wineries and centuries-old estates that have produced wine for generations.
During this Vespa trip, you naturally pass places you would never reach otherwise: a wine tasting among the vineyards, lunch at an agriturismo, or a stop at a family-run winery that still works in the most traditional way. These authentic moments are exactly what make this route so unique.
Who is the Chianti Vespa trip for?
The Chianti route is perfect for anyone who wants to experience Tuscany in a unique and more authentic way. This Vespa trip is ideal for:
- 🍷 Wine lovers who want to taste Chianti Classico right where it’s produced
- 💑 Couples looking for a romantic Italian road trip
- 📸 Photography enthusiasts eager to capture dreamlike Tuscan landscapes
- 🛵 First-time Vespa riders who prefer a calm, beginner-friendly route
- 🌿 Travelers seeking authentic Italy, far away from mass tourism
The real difference compared to our classic Tuscany route
The Tuscany Il Giro Classico is beloved and for good reason. It’s an iconic route filled with famous highlights and postcard-perfect cities. But that popularity also means: more crowds, less space and fewer hidden gems.
Chianti offers the exact opposite:
- Less traffic → more peace on the road and at every stop
- Smaller villages → a more intimate, authentic Italian atmosphere
- More wine experiences → Chianti is the heart of Chianti Classico
- Quieter roads → ideal for a relaxing Vespa road trip
- More nature and panoramas → endless hills, forests and vineyards
- Unique stops → family farms, agriturismi and wineries you won’t find on the classic route
Where Tuscany is the well-known classic, Chianti feels like a hidden gem, the kind you discover before the rest of the world does. If you’re torn between the two, choose Chianti if you want more tranquility, deeper wine experiences and a more authentic Italian charm.
The Chianti route
During The Vespa Trip Chianti, you’ll discover the very best of the region in just four days. These are the top spots, carefully selected by our team, to give you the perfect Vespa experience through Chianti and Tuscany’s iconic wine region.
Montespertoli: Tuscany at its purest
Montespertoli is the ideal first introduction to the Tuscan landscape. Quiet roads, panoramic hills and endless vineyards immediately show why this region is made for exploring by Vespa. It’s the place where you naturally slip into the relaxed rhythm of the trip.
San Gimignano: The ‘Medieval Manhattan’
You can spot the skyline of San Gimignano from miles away: towering medieval structures, narrow alleyways, and a historic center that feels like an open-air museum. It’s no surprise this town is known as the “Medieval Manhattan.” Wander through its atmospheric streets and enjoy one of the most iconic places in Tuscany.
Lucolena: Hidden in the hills
Lucolena is one of those villages you only find when you drive there yourself, which is exactly what makes it special. Here, you’ll find silence, nature and the feeling of being truly in the heart of Chianti. Perfect for a short break and breathtaking views.
Radda in Chianti: The historic capital of the wine region
Charming, intimate and unmistakably Chianti. Radda is full of small squares, wine bars and steep streets that invite you to wander. Order an espresso on a terrace and watch daily Tuscan life unfold.
Greve in Chianti: The heart of Chianti Classico
Greve always has a lively buzz. Its central square is lined with arcades, local shops and wine merchants. Don’t miss the famous Macelleria Falorni, one of the oldest butcheries in the world and perfect for tastings or something delicious to take with you.
Fiesole: Views over Florence
Just above Florence lies Fiesole, a peaceful hilltop town with a spectacular panoramic view of the city. With its Roman amphitheater and tranquil atmosphere, it’s an ideal stop before descending into Florence.
Florence: The renaissance capital of Italy
Florence never fails to impress. Art, culture, fashion, sunlit terraces and the buzz of scooters. You’ll have plenty of time to explore at your own pace: museums, shopping, long lunches or simply getting lost in the streets.
Top team recommendations for your Chianti Vespa trip
Beyond the beautiful route itself, there are a few experiences you absolutely shouldn’t miss during your Vespa trip through Chianti. These insider tips make your journey even more unforgettable:
- San Gimignano = gelato time: Don’t skip the famous gelateria on the main piazza. In our opinion, it’s the perfect treat after riding up into the iconic hilltop town.
- Taste at least one Chianti Classico at a local winery: Many small wineries along the route offer spontaneous tastings. A quick stop is always a good idea.
- Save some battery for Piazzale Michelangelo: That panoramic view over Florence is next level. Photos, videos, sunset moments… all guaranteed magic.
- Take the cable car up to Certaldo: Affordable, fun and within minutes you’re standing in the medieval upper town, well worth the detour.
- Start your mornings a little earlier: Chianti’s early hours are incredibly peaceful and the soft morning light makes the roads and vineyards even more stunning.
- Picnic? Absolutely. In Greve or Radda you can pick up the perfect Tuscan picnic with salumi, cheese, fresh bread and stop anywhere along the way for a scenic lunch break.
- Leave space in your backpack: Trust us: you’ll want to bring home something local, delicious, or wine-related. It’s inevitable.
Chianti: A new Vespa trip and maybe your new favorite
Chianti has everything that makes Tuscany iconic, but in a quieter, more elegant and intimate version. That’s why this might just be the perfect Vespa trip for you. It doesn’t get much better than this. Discover this new Chianti Vespa trip and experience Tuscany at your own pace.