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

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  • 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 3/4* 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
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 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 image 1

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

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.

Ratings & Reviews

Google Reviews

5.0 average rating

Greg Martin's profile photo
Diane Flynn's profile photo
Em Milly's profile photo
Jensie Weygers's profile photo
Gašper Kolenc's profile photo
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Top Rated Brand
Greg Martin's profile photo

Greg Martin

Verified customer · 10 months ago

Great holiday. Really easy to follow routes, good choice of hotels and the en route places to eat and visit was really helpful. Super responsive to questions during my holiday. Would definitely use them again.

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Diane Flynn

Verified customer · 2 years ago

We had a wonderful cycling trip, starting in Trieste, then onto Slovenia and Croatia. Before the trip, Klemen was extremely patient with our many questions and addressed our concerns very satisfactorily- even changing the original bike route to meet our needs. The bikes we used ( e-bikes) were in great condition, and easy to use. The hotels were very satisfactory- and included big breakfasts to start our days. The towns we visited were charming. All in all- a first class experience!!

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Em Milly

Verified customer · 9 days ago

Great trip: excellent customer service, great route, excellent hotel stays during the tour. The bike rental company that they use is the best I've ever experienced in Europe. I am even planning to buy the same bike for myself at home that I had on the trip! We had this service also book our stay for after the tour, and that is the only thing I would do differently next time, since the hotel for the several days after the tour was not very good, had mediocre service and not a good location. But for the tour, I would definitely recommend DenmarkBikeTours.

Jensie Weygers's profile photo

Jensie Weygers

Verified customer · 2 months ago

Gašper Kolenc's profile photo

Gašper Kolenc

Verified customer · 2 months ago

Exploring Tuscany on a self-guided cycling holiday was pure joy. The carefully curated routes took me through vineyards, olive groves, and picturesque towns like Siena and Pienza. I loved being able to stop whenever I wanted to soak in the views or enjoy a cappuccino in a quaint café. The GPS and route notes were spot-on, and the logistics, from luggage transfers to charming accommodations, were seamless. Tuscany’s beauty is best experienced on two wheels, and the freedom to set my own pace made it unforgettable.

Andrija V.'s profile photo

Andrija V.

Verified customer · 4 months ago

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

Hassle-Free

We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy a carefree holiday.

Completely Customizable

Completely Customizable

Flexibility is our middle name — whether you want more or less, or just beyond ordinary, we’ll make it happen.

Book with confidence

Book with confidence

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

Unbeatable support

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.

from 1.349 € /person