Hotel in Siena









Tuscany Gravel Cycling Tour
6 days / 5 nights
|
Starting point
Siena
Finish point
Siena
Fitness level
3/5
Season
From April to October
Starting point
Siena
Finish point
Siena
Fitness level
3/5
Season
From April to October
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
NOT INCLUDED
OPTIONAL EXTRAS
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
Ratings & Reviews


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.
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!


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.

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.


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.
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.

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!


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.


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.




























