Vespa Tour in Val d'Orcia, Tuscany
UNESCO landscapes, Brunello wines and hilltop towns
The Val d'Orcia is the UNESCO-protected valley that postcards have made famous — a perfectly composed landscape of solitary cypresses, undulating golden hills, and Renaissance villages. This is Brunello di Montalcino country, home to some of Italy's most prized red wines, and the birthplace of Pecorino di Pienza. Pope Pius II rebuilt his hometown of Pienza in 1462 as the first 'ideal city' of the Renaissance — and the surrounding countryside has been protected ever since.
There is no better way to feel Tuscany than from the saddle of a vintage Vespa, cypress-lined road unrolling in front of you, the cooling air of Val d'Orcia in your face. Our half-day tour pairs you with a local guide who knows every shortcut, viewpoint and family-run trattoria off the SS222.
Routes are tailored to your group's confidence — beginners practise on quiet back roads first; experienced riders explore deeper into the back country. Stops include a hilltop village for espresso, a panoramic photo point, and (optionally) a small winery for a tasting. A back-up van follows for luggage and for non-riding companions.
What's included
- •Vintage Vespas (automatic or manual)
- •Local guide-rider in front
- •Quiet back-road routes
- •Hilltop village + viewpoint stops
- •Optional winery tasting + chase van
Plan your Val d'Orcia stay
Our concierge designs every vespa tour around your group's pace, dietary preferences and travel dates. One email is all it takes to start.
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