Vespa Tour in Siena, Tuscany

Medieval Tuscany and the rolling Crete Senesi

Siena is the great medieval rival of Florence — a city frozen in the 14th century, with its shell-shaped Piazza del Campo, the twice-yearly Palio horse race, and a Gothic cathedral whose striped marble façade is one of Italy's most striking sights. The surrounding countryside — the Crete Senesi to the south and the Chianti hills to the north — is a landscape of clay hills, isolated abbeys, and farmhouses that have been the model for Tuscan rural life for centuries.

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 Siena 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 Siena 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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