Vespa Tour in Chianti, Tuscany
The heart of Tuscan wine country
Chianti is the landscape that defines Tuscany in the world's imagination — a tapestry of vineyard-draped hills, cypress-lined roads, and stone farmhouses perched above valleys cultivated since Etruscan times. The Chianti Classico appellation, designated in 1716 by Grand Duke Cosimo III de' Medici, is one of the world's oldest defined wine regions. Today the black rooster (Gallo Nero) on every Chianti Classico bottle marks wines that capture the essence of this storied terroir.
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 Chianti 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 Chianti
7 handpicked properties in the area, perfect to pair with this experience.
Plan your Chianti 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 Chianti

Radda in Chianti, Siena
Borgo in Chianti
A spacious villa in the heart of Chianti, perfect for retreats

Gaiole in Chianti, Siena
San Polino
A charming borgo of three villas with infinity pool in the Chianti hills

Gaiole in Chianti, Siena
Casa all'Erta
Beautifully restored stone farmhouse with views of the Chianti hills and castle
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 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.


