Hotel in San Quirico d’Orcia
Tuscany Road Bike Tour
7 days / 6 nights
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Starting point
San Quirico d’Orcia
Finish point
San Gimignano
Fitness level
3/5


Starting point
San Quirico d’Orcia
Finish point
San Gimignano
Fitness level
3/5
- Explore the breathtaking landscapes of Tuscany
- Visit charming medieval towns and villages such as Montepulciano, Monticchiello, and San Gimignano
- Savor world-renowned Tuscan cuisine and wine through tasting tours and lunches at local wineries
- Discover the rich history and culture of the region with visits to iconic landmarks
Itinerary of the trip
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What’s included in the price?
Self-guided
NOT INCLUDED
OPTIONAL EXTRAS
Embark on an unforgettable cycling journey through the heart of Tuscany, where every turn of the wheel reveals breathtaking landscapes, rich cultural heritage, and exquisite culinary delights. This 7-day tour will take you on a magical adventure through the iconic Val d’Orcia region, where the rolling hills, winding roads, and medieval towns are a true feast for the senses.
From the “ideal” city of Renaissance time, Pienza, to the charming and picturesque towns of Montepulciano and Monticchiello, every stop along the way is an opportunity to immerse yourself in the history and beauty of Tuscany. Experience the warmth of the Italian culture through the local cuisine, such as the Pecorino cheese and Brunello wines, which are produced in this region and are renowned worldwide.
As you cycle through the scenic routes of the Crete Senesi and Chianti regions, you will discover a landscape of unparalleled beauty, with vineyards, olive groves, and ancient forests. Marvel at the impressive medieval castles and the well-preserved walls of Monteriggioni, and explore the charming narrow streets of San Gimignano, known as the “City of Beautiful Towers.”
The tour also includes visits to world-renowned wineries, where you can indulge in the tastes and aromas of the finest Italian wines. From the Abbey of Sant’Antimo to the Castle of Brolio, every landmark is a testament to the rich and fascinating history of Tuscany. The journey ends with a visit to the enchanting city of Siena, with its majestic medieval center and iconic landmarks, such as the Duomo and Piazza del Campo.
This tour is E-Bike friendly! This tour can be booked with e-bikes for a more leisureful experience. Explore the great Tuscany without breaking a sweat!
Our Bikes
To ensure the best possible experience on your cycling adventure, we offer top-quality bikes for rent. Our fleet features the latest models, meticulously maintained for both performance and comfort.
To match each rider with the right equipment, our team will also assist you in selecting the most suitable bike based on your physical profile, personal preferences, and the technical requirements of the tour.

Road Bikes
Best for: Paved routes, longer distances, and climbs
Our road bikes are lightweight, fast, and built for endurance. They typically feature carbon or high-quality aluminium frames, smooth gearing, and reliable components—often Shimano 105 or similar. Well-suited for long days in the saddle, they’re perfect for climbs, steady cruising, and covering serious distance on tarmac.
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All available guidance options
Self-guided
Those who like a good adventure and limitless flexibility should go on a self-guided cycling holiday. We prepare the itinerary and book your accommodations; You enjoy the journey without our guide, being fully in charge of all the daily decisions. While you’ll have the full support of our team in case of any emergencies or concerns, a certain level of self-reliance is required.
Hassle-Free
We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy carefree walking holidays.
Trusted by many
We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.
Handpicked Adventures
Only the best hut to hut hikes in Europe, cherry-picked by our local team with an in-depth knowledge of the region.
Unbeatable support
Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.