Pienza to Montepulciano Wine Bike Tour
A day of cycling, wine, and Tuscan beauty — all in one unforgettable experience. This one day bike tour takes you through the rolling vineyards of Val d’Orcia, from the Renaissance town of Pienza to the medieval streets of Montepulciano, home to some of Italy’s most celebrated wines.
What to Expect
This guided ride blends the joy of cycling with the rich flavours of Tuscany. Along the way, you’ll:
- Pedal at your own pace through vineyards, olive groves, and centuries-old stone farmhouses.
- Stop at wineries in Montepulciano, including the historic Palazzo Vecchio, for wine tastings and optional meals.
- Enjoy panoramic views of cypress-lined roads and UNESCO-protected countryside.
- Ride with full van support, so any wine purchases or “souvenirs” can travel comfortably with us.
Yes, there are a few hills (this is Tuscany!), but with the option of an e-bike, you’ll glide through the landscape with ease.
What’s Included
The Cost Includes
- Bike rental (road, gravel, or e-bike)
- Helmet and equipment
- Experienced guide
- Van service for transfers and support
- Cold water and snacks available throughout the ride
- Wine tastings (optional add-on)
- Meals
Customize This Tour
While this itinerary begins in the Pienza–Montepulciano area, we’re flexible. If your accommodation is farther away, or you’d like to tailor the route to your needs, we’ll create a custom one day bike tour just for you.
Enhance your ride with a tasting experience in Montepulciano (pay while on tour):
- 3 Wines – €15 per person
- 6 Wines – €30 per person
- Tasting Menu (3 wines & lunch or dinner) – €55 per person
- 4 Wines + Tagliere Toscano – €35 per person
Ready to Ride?
Cycle Tuscany’s most beautiful landscapes, sip world-class wines, and enjoy a perfect day between Pienza and Montepulciano. This one day bike tour is ideal for wine lovers, foodies, and anyone looking to discover the heart of Val d’Orcia in a single unforgettable experience.
Solo riders or groups of 1 or 2 — contact us for a custom quotation.
