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
Stay nearby — luxury villas in Siena
9 handpicked properties in the area, perfect to pair with this experience.
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.
Start your inquiryWhere to Stay
Luxury Villas in Siena
What to Do
Curated Tuscany Experiences

Full day (6–8 hours)
Private Wine Tasting & Vineyard Tour
Discover the soul of Tuscan winemaking in private cellars

Half day (4–5 hours)
Hands-On Cooking Class
Master the art of Tuscan cuisine in an authentic farmhouse

Half day (2–3 hours)
Extra Virgin Olive Oil Tasting
Learn to distinguish the liquid gold of Tuscany
From Our Journal
Tuscany Reading & Insights
- 12 min readThe Best Time to Visit Tuscany: A Month-by-Month Guide for 2026From the spring wildflowers to the autumn wine harvest, each season in Tuscany offers something magical. Here's exactly when to go based on what you want to experience.
- 15 min readTuscany Wine Regions: The Complete Guide to Chianti, Brunello & BeyondTuscany produces some of the world's finest wines. From the rolling hills of Chianti to the sun-baked slopes of Montalcino, here's your expert guide to every major wine region.
- 14 min read21 Unforgettable Things to Do in Chianti, TuscanyChianti is far more than wine country. From medieval castles and thermal springs to artisan workshops and sunrise hot air balloon rides, here are 21 experiences that make Chianti extraordinary.
Curated Collections
Plan a Trip Around a Theme
- Wedding VenuesPrivate Tuscany & Lake Como estates for destination weddings: exclusive-use buy-outs, 12+ guests on site, vetted vendors and a dedicated planner.
- Family VillasFamily villas in Tuscany & Lake Como: safe pools, gardens, quiet roads and child-friendly amenities. Cots and private chef on request — quotes on inquiry.
- Honeymoon StaysRomantic villas for two in Tuscany & Lake Como: private pool or lakefront, panoramic terrace, in-villa chef and total privacy. Quotes on inquiry.
- Large GroupsEstates in Tuscany & Lake Como for 14+ guests: en-suite bedrooms, big living spaces, pool and on-site staff. Great for family reunions — quotes on inquiry.





