Gravel road through rolling hills with cypress trees, farm buildings, and hazy mountains in Tuscany.
Cyclist on gravel path under pine trees in sunny Tuscan landscape
Winding road lined with cypress trees through rolling green hills at sunset in Tuscany
Mountain biking past a stone hut on a gravel path in Tuscany.
Cyclist on gravel road with olive trees and forested hill with ruins in Tuscany
Siena cityscape with Duomo cathedral dome and striped bell tower under bright blue sky
1/6
Authentic adventure

Tuscany Gravel Cycling Tour

6 days / 5 nights

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Discover the beauty of Tuscany like never before, as you cycle through pristine gravel roads, taste world-renowned wine and cheese, and embrace the countryside.

Starting point

Siena

Finish point

Siena

Fitness level

3/5

Season

From April to October

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Highlights

  • Cycling through some of Tuscany's most pristine and picturesque gravel roads
  • Visiting famous Tuscan destinations such as L'Eroice and Chianti
  • Sampling world-renowned wine and cheese, including the famous Pecorino cheese
  • Experiencing Tuscany's natural beauty up close and personal, from rolling hills to vineyards and olive groves

What’s included in the price?

Self-guided

Tour design and organization
Booklet with detailed itinerary and route instructions
5 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
Gravel bike
Hotel upgrades
Single supplement

Starting in the charming city of Siena, you’ll embark on a journey that will take you through some of the most breathtaking landscapes that Italy has to offer.

Along the way, you’ll visit some of Tuscany’s most famous destinations, including L’Eroice, Chianti, and the surrounding area where the Strade Bianche race is held every year.

As you travel along the winding gravel roads that crisscross the region, you’ll be immersed in Tuscany’s natural beauty. You’ll pass through rolling hills dotted with olive groves and vineyards, and enjoy sweeping vistas of the countryside. And because you’re cycling, you’ll be able to experience it all up close and personal.

Of course, no visit to Tuscany is complete without sampling some of the region’s famous wine and cheese. You’ll have plenty of opportunities to indulge in both, as you pass through the heart of the Chianti wine region and visit charming towns and villages that are famous for their artisanal cheeses, such as Pecorino.

But beyond the food and drink, what truly sets this Tuscan cycling experience apart is the opportunity to travel on some of the region’s most pristine and picturesque gravel roads. These roads wind through some of the most remote and unspoiled corners of Tuscany, taking you off the beaten path and providing you with a truly unique and unforgettable cycling experience.

From the challenging climbs to the exhilarating descents, every mile of this six-day journey is packed with excitement and adventure. And when you reach the end of your journey, you’ll not only have unforgettable memories to cherish, but you’ll also have a deeper appreciation for the beauty and history of Tuscany.

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
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World discovery Top Rated Brand

Gašper Kolenc

Verified customer · 9 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.

Mystie Pineda

Verified customer · 3 months ago

I found this place with a simple Google search, and I never could’ve expected the custom experience I received. They provided options to help my husband and I hone in on exactly what we wanted to do for our honeymoon. We had perfectly curated GPS-lead rides all across the country, they booked all of our hotels, and planned all of our transportation. Every place that we went was so beautiful. I’m so grateful that we found this company to help us plan our honeymoon, couldn’t have asked for a better experience!

Mountain bikes parked near blue and white crosswalk in European alpine village street
Wet, narrow street in a European town leading to a church spire, backed by a forested mountain.
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Bill Wright

Verified customer · 3 months ago

I was able to tailor a bike tour itinerary along the Adriatic coast that suited our group during the shoulder season. We added individual pre and post-trip activities which went smoothly. Our trip included stops in Italy, Slovenia and Croatia. The trip planner, guide and support team were great.

Group posing in front of Pula Arena with a stone wall and parked car.

barney barnhart

Verified customer · 3 months ago

Brilliant planning, great communication, terrific hotels and accommodations, interesting cities and beautiful scenery plus amazing routes.

Black and white cat with green eyes looking up from light gray tiled floor
Maroon gravel bike resting against a low stone wall in grassy terrain
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John Woeste

Verified customer · 4 months ago

Highly recommend the bike trip from Bled to Pula. It was well planned. We did a small group self-supported. Big fun. Bikes, hotels, route selection and communication with the company was great.

Cyclist riding on dirt path under green leafy archway toward open field
Cyclist with panniers riding up a narrow cobblestone street in a historic town.
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Alison Booth

Verified customer · 4 months ago

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.

View from sailboat bow approaching coastal town with white buildings and green hills under blue sky.
Sailboat on the water during a vibrant orange and yellow sunset over the sea.
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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 995 € /person