San Quirico to Pienza Self-Guided Bike Tour
Explore the rolling landscapes of southern Tuscany on a self-guided cycling journey that links the medieval villages, vineyards, and hill towns of Val d’Orcia, Siena, and Chianti. From the thermal waters of Rapolano Terme to the towers of San Gimignano, this ride offers the true essence of Tuscany—history, landscapes, and flavours all at your pace.
Bike Tour Itinerary
This itinerary takes you into the very heart of Tuscany. Ride through vineyards and olive groves, stop in Renaissance towns, and climb rolling ridgelines that open to sweeping views.
- Best time: March to October
- Cycling routes through Val d’Orcia, Siena, and Chianti
- UNESCO sites including Pienza and San Gimignano
- Thermal spa towns, medieval abbeys, and fortress villages
- Daily luggage transfers and boutique hotel stays
- Ride your way – bring your own bike or choose from premium rental options
- Level: Moderate to challenging
Arrive in Rapolano Terme, a Renaissance spa town famous for its thermal baths with ancient Etruscan and Roman roots. Bike fitting and orientation.
Ride through the sculpted curves of the Crete Senesi to the white truffle capital, San Giovanni d’Asso. Continue via Trequanda before returning to Rapolano Terme.
Follow quiet roads through Val d’Orcia, an UNESCO World Heritage site, before reaching Renaissance Pienza—a perfect town both in design and gastronomy.
Pass the thermal spa town of Bagno Vignoni, visit Sant’Antimo Abbey, then ride through Brunello vineyards into Montalcino, a fortress town with sweeping valley views.
Ride along a crest road past Monte Oliveto Maggiore Abbey, with its striking red-brick façade against grey clay hills. Finish in Siena, home to the Palio horse race and Piazza del Campo.
Cycle north into Chianti, past castles, vineyards, and the historic Brolio Castle, birthplace of Chianti Classico wine. Pause at Eroica Caffè before arriving in Castellina in Chianti.
Optional extension to San Gimignano, famous for its towers. En route, pass Monteriggioni, a perfectly preserved medieval castle town.
Breakfast and departure, with easy connections via Florence.
What’s Included
The Cost Includes
- 6 nights in beautiful boutique hotels
- Daily breakfasts
- Luggage transfers between hotels
- Daily route briefings (orientation + daily notes)
- Garmin GPS device with preloaded routes
- Sightseeing, restaurant & shopping suggestions
- Pick-up of bikes and gear in Castellina in Chianti at tour end
- Keepsake Bikeriding Tuscany water bottle
- Keepsake Bikeriding Tuscany jersey
- Sales taxes
Not Included
- Bike rental (see Bike Rental Options below)
- Local city taxes (typically €2–€4 per person per night)
- Wine tastings and meals unless specified
Bike Rental Options
Our tours do not include the price of a bike rental. You are welcome to bring your own bike, or we have the following options for the duration of the tour:
- Hybrid bicycle rental €280
- Carbon road bike rental €315
- E-bike rental €350
Payable at checkout.
Map
Ready to Ride?
From the thermal waters of Rapolano Terme to the fortress walls of Siena and the towers of San Gimignano, this self-guided Tuscany cycling tour reveals the true heart of the region. If you have any questions about this trip before you book, feel free to email us or send a quick message on WhatsApp.
