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
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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

Activity 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

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.

INCLUDED

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

Of course. We aim to make your decision as easy as possible. Therefore, we crafted several selections targeted at particular groups of hikers – Best for Beginners, Best for Advanced Hikers, Mountain Hikes, Pilgrimages, Classic Treks, etc.

If you remain unsure and overwhelmed, you can fill out this form or book a call with us, and we can help you directly.

The sooner, the better! Booking in advance ensures you secure a spot, especially on popular routes where accommodations in remote areas can fill up quickly. For tours like the Tour du Mont Blanc and Alta Via, it's best to book several months ahead, as these areas have limited availability in mountain huts.

However, for some of our less-traveled tours, it's possible to book just a few weeks in advance, though availability and comfort may be more limited, particularly in remote areas with fewer options. To ensure you have the best experience, we always recommend booking early, especially during peak hiking seasons.

Our tours offer flexible starting days, allowing you to begin whenever suits you.However, for some of our most popular routes, like the Tour du Mont Blanc (TMB) and Alta Via, we have selected departure days due to high demand and pre-booked accommodations.Be sure to check the specific requirements for these tours.

We offer a variety of tours suitable for different fitness levels and technical abilities. Some of them require no prior hiking experience.

Whether you’re a beginner or an experienced hiker, we have the perfect route for you. You can find more information in our Hiking Difficulty Guide, and we also have dedicated sections for Best for Beginners and Best for Advanced Hikers to help you choose the suitable tour.

The fitness level is based on a scale determined by our hiking experts. It varies depending on the tour and defines the selected hiking tour's physical requirements in comparison to others. For a detailed overview, please refer to our Hiking Difficulty Guide.

The technical demands of each hike differ. The technical-level scale defines the technical requirements of each tour in comparison to others, ranging from basic walking to scrambling or using specialized equipment. For a more in-depth explanation of the five levels, please refer to our Hiking Difficulty Guide.

Most of our tours are self-guided, meaning you have the freedom to explore at your own pace without being tied to a group schedule. We provide detailed digital guidebooks that include maps, route notes, and GPS files to ensure a smooth experience.

You can learn more about the concept by reading Self-Guided Tours Explained. We include a guide only for the most challenging treks, like the Triglav Summit Climb.

We provide a comprehensive digital guidebook with maps, route notes, accommodation details, and emergency contacts. Our support will be available during the tour. However, you'll have all the information you need to enjoy your hike independently.

Check out how self-guided tours work in more detail and an example of our digital guidebook here.

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.

Local Experts

Our professional cycling guides in select locations know the local terrain and are trained to make this once-in-a-lifetime opportunity both safe and enjoyable.

from 1.315 € /person
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Lan Lajovic
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