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.
Start your inquiryWhat 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 VenuesHandpicked private estates in Tuscany and Lake Como suitable for destination weddings: full buy-outs, 12+ guests, vetted vendor network and dedicated planner.
- Family VillasPrivate villas in Tuscany and Lake Como chosen for families: fenced pools, gentle gardens, quiet roads, child-friendly amenities and quick access to gelato.
- Honeymoon StaysIntimate properties for two in Tuscany and Lake Como: private pool or lakefront, panoramic terrace, in-house dining and total privacy.
- Large GroupsEstates in Tuscany and Lake Como that comfortably host 14 or more guests: multiple bedrooms with en-suites, vast living areas, on-site staff.