Tuscany Road Bike Tour
Vineyard rows with yellow autumn leaves, olive groves, and a villa on a hill in Chianti.
Cyclist on dirt road through rolling green hills toward Tuscan hilltop town under dramatic clouds.
Historic stone wall and brick buildings in Buonconvento under a dramatic sunset sky.
Rolling golden hills of Crete Senesi with a farmhouse, cypress trees, and hay bales.
Rolling hills of Val d'Orcia with cypress trees, vineyards, and farmhouse in morning light.
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Tuscany Road Bike Tour

7 days / 6 nights

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Experience the breathtaking beauty, rich history, and exquisite flavors of Tuscany on a 7-day cycling tour, and explore the heart of this beautiful region.

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

What’s included in the price?

Self-guided

Tour design and organization
Booklet with detailed itinerary and route instructions
6 nights in a 3* hotels with breakfast
Service and support during your tour
GPS navigation with an easy-to-use app
Luggage transfer

NOT INCLUDED

Tourist tax

OPTIONAL EXTRAS

Airport transfer
E-road bike
Hotel upgrades
Road bike
Single supplement

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 leisurely 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.

Frequently Asked Questions

Our priority is to find the ideal accommodation that suits your needs. We collaborate with several lodging providers that meet our criteria, but please note that availability can be limited, particularly during peak seasons. Furthermore, we can tailor your holiday to align with your preferences and budget, and are committed to finding a more suitable alternative that matches your taste.

Our tours are categorized into three difficulty levels: leisurely, moderate, and challenging. Although each may include both easier and more demanding days, our rating system reflects the average difficulty level for a typical day.


Leisurely tours take place primarily on flat, paved cycling paths, asphalt roads, or easy gravel tracks, and they are suitable for all fitness levels.


Moderate tours may include some uphill climbs or technically more demanding terrain, but they are manageable for individuals of average fitness.


Challenging tours entail either long distances and numerous climbs or technical terrain, possibly featuring downhill sections requiring proficiency with a mountain bike.

Our tours can be adapted to any bike type, whether road, gravel, or mountain bike. We are in constant communication with you to find the optimal conditions for your cycling holidays in Italy.


The most versatile option is a gravel bike, even if you are coming on a road cycling holiday. It does not really affect your road performance while allowing you to take some scenic backroads that can be in a slightly worse state than the main ones. A gravel bike is usually more comfortable as well.

If you are not bringing your own bike and equipment, we can certainly arrange that for you. We have a wide selection of bikes at our disposal and we will choose the ones that best fit your tour. All we need from you is your usual bike size and any other relevant information or preferences so we can make sure you will be comfortable throughout your trip.

The availability of food options in Italy depends on the extent of your dietary restrictions. While it is relatively easy to find vegetarian dishes, locating vegan meals can be challenging, particularly in smaller towns and rural areas. Additionally, the traditional lunch stops we make may have limited ability to accommodate special requests beyond their standard menu. We recommend considering this when planning your meals.

Absolutely, the choice is yours! We understand that some travelers enjoy group activities while others prefer a more solitary experience. Therefore, we want to offer you the flexibility to personalize your trip to suit your preferences. After all, it is your holiday! As long as you adhere to the designated group timings and locations outlined by your guide, please feel free to customize your itinerary and embark on your own adventure.


If you want to have a completely independent holiday, you can always opt for a self-guided tour, which is possible on most of our tours!

The optimal time for our tours varies depending on the specific trip. However, typically late spring (May) and early autumn (September) are ideal. Of course, summer is also an excellent time to travel. Additionally, some of our holidays can be enjoyed in winter too!

With proper attire, most of our tours can still be enjoyed even in light rain. During the summer months, afternoon thunderstorms are not uncommon, so it’s recommended to start your day early. If inclement weather is forecasted, we will do our best to modify the tour or arrange for shuttle transportation to skip a particular stage.

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 take care of route planning, accommodations, luggage transfers, and all logistics, so you can focus purely on enjoying your ride.

Tried & Tested Adventures

Our cycling routes are hand-picked & tested, to ensure breathtaking landscapes, smooth roads, and maximum safety - giving you the perfect ride every day.

Unbeatable Support

Our 24/7 customer support is where we show our passion, ensuring your cycling holiday runs smoothly and your well-being is always our top priority.

Book with Confidence

We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.

from 1.349 € /person
Discover Italy on two wheels with our cycling holidays! Choose from a variety of available cycling tours in Italy's most beautiful and picturesque regions.

Have questions? Talk to us.

Lan Lajovic
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