Tuscany on Two Wheels: A Four to 6 Days Ride Through Landscapes, Wine, and Timeless Italian Charm
- Mauro Clerici
- 3 days ago
- 3 min read
There are places in the world that feel like they were designed for slow travel — where every curve of the road, every hill, every scent and sound invites you to take a breath, look around, and savor the moment. Tuscany is one of those rare places. And exploring it by Vespa transforms it from a destination into a living, breathing experience.
Our 4-day, 4-night Tuscany “Chianti” Vespa Vacation begins the moment you arrive at our boutique 4-star basecamp: Palazzo San Lorenzo Hotel & Spa in Colle di Val d’Elsa, a beautifully restored 13th-century building blending historic charm with modern comfort. From its rooftop views to its spa and gourmet dining, this becomes your home, your gathering place, and the backdrop of the stories you’ll collect throughout the week.
Day 1 — Settling In & First Ride Into the Hills
After check-in, we take our first gentle ride through the surrounding countryside — a perfect warm-up to get comfortable with your Vespa and to take in the soft, cinematic hills of Tuscany. That evening, we sit together for a welcome dinner, sharing wine, laughter, and the excitement of the week ahead. Chianti Ride Vacation.pdf
Day 2 — Monteriggioni, San Gimignano & Vineyard Aperitivo
The next morning begins with breakfast and a ride to Monteriggioni, one of Tuscany’s most intact medieval walled towns, followed by a visit to San Gimignano, the “Manhattan of the Middle Ages.” We enjoy lunch at an authentic trattoria, savoring Tuscan dishes just steps away from where the ingredients were grown. The day winds down with an aperitivo in a local vineyard — the perfect pairing of rolling hills, a golden sunset, and a glass of Chianti.
Day 3 — Cooking Class & Hidden Gem Exploration
On Day 3, Tuscany shifts from being a place you visit to a place you live. We spend the day in a countryside farmhouse with a local cook learning how to prepare ravioli, tiramisu, and other specialties from scratch — a hands-on experience travelers rave about long after returning home. Then we ride to Certaldo Alto, a small medieval village perched above the valley, known for its peaceful charm and excellent gelato.
Day 4 — The Legendary 100 km Chianti Ride
This is the day riders dream of: a leisure and slow 100-kilometer journey through the iconic Chianti Valley. Smooth roads, vineyards, stone villages, espresso stops, panoramic views — it’s Tuscany as you imagine it in a film. The ride concludes with a dinner in a local trattoria, celebrating the miles conquered and the memories created.
Optional Day 5 — Choose Your Adventure
Travelers can extend their stay with two unforgettable options (both can be added to the itinerary):
Val d’Orcia: Pienza, a UNESCO World Heritage landscape, organic farm lunch, and vineyard aperitivo.
Peccioli & Piaggio Museum: A cultural + Vespa-themed day featuring contemporary art and a private museum tour with discounts.
💜 What Travelers Love Most
Our small-group format and warm, human-centered approach means you don’t just see Tuscany — you feel part of it. Past travelers speak of deep connections, slow mornings, long dinners, and a sense of wonder that stays long after the trip ends.
🚀 Interested?
Travel & Itinerary Disclaimer
While the core format, quality, and spirit of the Vesping Around experience remain consistent across all departures, please note that the specific itinerary described above — and on the booking page — represents a close approximation of the planned journey.
Certain elements may shift as we approach the departure date due to local events, seasonality, partner availability, weather, or other logistical considerations.
Any adjustments will be made with the intention of preserving (and often enhancing) your overall experience. All confirmed travelers will be promptly informed of any updates or changes.
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