Hotel in San Quirico d’Orcia









Tuscany Road Bike Tour
7 days / 6 nights
|
Starting point
San Quirico d’Orcia
Finish point
San Gimignano
Fitness level
3/5
Season
From March to November


Starting point
San Quirico d’Orcia
Finish point
San Gimignano
Fitness level
3/5
Season
From March to November
Highlights
- 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
FREE ITINERARY
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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!
Top Places You’ll See
From natural wonders to authentic local culture, the route is packed with memorable sights—these are our absolute favorites.

Val d’Orcia
A UNESCO World Heritage landscape, Val d’Orcia embodies the quintessential image of Tuscany — soft rolling hills, cypress-lined lanes, and medieval towns perched above golden fields. The valley, shaped by centuries of harmonious farming, has inspired painters since the Renaissance. Today, it remains one of Italy’s most photographed regions, where light, color, and human craftsmanship merge into a scene of perfect balance.

Montalcino
Crowned by a medieval fortress and encircled by vineyards, Montalcino is synonymous with the celebrated Brunello wine. Its cobbled streets and honey-colored stone buildings tell stories of prosperity and pride. From the fortress ramparts, sweeping views extend across olive groves and the rolling Val d’Orcia.

Chianti
Between Florence and Siena, the Chianti region is a rolling tapestry of vineyards, cypress avenues, and hilltop villages. For centuries, its landscape has been shaped by winemakers whose craft is as refined as the land is beautiful. Medieval castles, rustic farmhouses, and the scent of grapes ripening in the sun create an atmosphere of harmony and abundance.

Crete Senesi
South of Siena, the Crete Senesi unfold in a surreal landscape of clay hills, eroded gullies, and silver-gray soil. Often compared to a lunar terrain, this area changes color with the seasons — golden in summer, green in spring, and violet under stormy skies.

Siena
Siena’s medieval heart beats in the shell-shaped Piazza del Campo, where the famous Palio horse race takes place each summer. Once a rival to Florence, the city flourished in art, architecture, and civic life during the Middle Ages. Its striped cathedral, Gothic town hall, and frescoes by Lorenzetti reveal the depth of its cultural heritage.
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.
Frequently Asked Questions
Ratings & Reviews

5.0 average rating






I would highly recommend anyone doing this tour take the e-bike option. There were only 3 of us on our tour who completed this on regular bikes. Four others who started out on regular bikes swapped over to e-bikes after the first day. The climbs are long and steep. There is pretty much only up or down, not much flat or undulating road. It is doable, but very challenging. If you are on an e-bike then this also helps with the group staying together and no-one having to wait too long for others to catch up. The bikes were really good and had great gearing that was capable of handling the steeper climbs. When we booked we were unaware that we would be riding in a group of 20plus at all time. Thankfully our group had prior group riding experience but we did observe other large groups with less than desirable riding behaviours.Others in our group were extremely understanding and supportive. Our guide, David, was very adamant about staying safe on the road. He was flexible with the itinerary and made changes to suit the weather conditions and to ensure we got in as much riding as possible. He was vey knowledgeable about Croatian history and agriculture and taught us lots about the country he is so passionate about. Our captain, Tolma, was also amazing and along with his awesome crew, made our cruise an enjoyable experience.


Just back from enjoying a long weekend cycling in Slovenia, the company arranged transfers to and from the airport, hotels, bikes, bike routes, including what to see and where, and even transportation of bags between hotels. The only thing we needed to worry about was where to eat; the whole trip was painless, and I would highly recommend them.


Wow! What an awesome tour! We did a self-guided cycling tour on gravel bikes and it could not have been more enjoyable! Such a beautiful country and such an intimate travel experience. We biked through mountain valleys, over mountain passes, along rivers, through small villages, through wooded hills, through vineyards, and along the Adriatic coast. Kudos to everyone that put this trip together! The hotel accommodations were perfect and the bikes we rented were high quality! Thank you!


Just back from enjoying a long weekend cycling in Slovenia, the company arranged transfers to and from the airport, hotels, bikes, bike routes, including what to see and where, and even transportation of bags between hotels. The only thing we needed to worry about was where to eat; the whole trip was painless, and I would highly recommend them.


I would highly recommend anyone doing this tour take the e-bike option. There were only 3 of us on our tour who completed this on regular bikes. Four others who started out on regular bikes swapped over to e-bikes after the first day. The climbs are long and steep. There is pretty much only up or down, not much flat or undulating road. It is doable, but very challenging. If you are on an e-bike then this also helps with the group staying together and no-one having to wait too long for others to catch up. The bikes were really good and had great gearing that was capable of handling the steeper climbs. When we booked we were unaware that we would be riding in a group of 20plus at all time. Thankfully our group had prior group riding experience but we did observe other large groups with less than desirable riding behaviours.Others in our group were extremely understanding and supportive. Our guide, David, was very adamant about staying safe on the road. He was flexible with the itinerary and made changes to suit the weather conditions and to ensure we got in as much riding as possible. He was vey knowledgeable about Croatian history and agriculture and taught us lots about the country he is so passionate about. Our captain, Tolma, was also amazing and along with his awesome crew, made our cruise an enjoyable experience.


Wow! What an awesome tour! We did a self-guided cycling tour on gravel bikes and it could not have been more enjoyable! Such a beautiful country and such an intimate travel experience. We biked through mountain valleys, over mountain passes, along rivers, through small villages, through wooded hills, through vineyards, and along the Adriatic coast. Kudos to everyone that put this trip together! The hotel accommodations were perfect and the bikes we rented were high quality! Thank you!


All available guidance options
Self-guided
Those who like good adventure and limitless flexibility should go on a self-guided cycling holiday. It offers complete freedom, multiple detour opportunities, and exploration at your own pace without having to adapt to a group.
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.






































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