✓ 2026: Free cancellation up to 7 days before (travel credits) · ✓ 2027: Book with just 10% deposit✓ 2026: Free cancellation up to 7 days before (travel credits) · ✓ 2027: Book with just 10% deposit
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
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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

4/5

Season

From April to October

Bike Type

Gravel Bike / E-Bike

Accommodation Level

Comfort

Daily Distance

31 – 44 mi

Daily Elevation

1969 – 4429 ft

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
Accommodation levelComfort

Carefully selected 3- and 4-star hotels, guesthouses, and B&Bs, all with private en-suite rooms and breakfast included. Expect comfortable, well-appointed rooms with attentive hospitality, typically in convenient and scenic locations — some properties also offer on-site dining.

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

The best time for cycling in Europe depends on where you're headed. Here's a quick breakdown by season:

  • Spring (April–May) is ideal for Southern Europe — moderate temperatures, quiet roads, and the countryside in full bloom. Great for Portugal or Italy

  • Early summer (June) is the sweet spot across most of Central Europe — Austria and Slovenia are all at their best, with long daylight hours and alpine passes fully open.

  • Late summer to early autumn (August–September) suits places like Norway and Denmark — cooler temperatures, plenty of daylight, and far fewer tourists than peak season.

  • Winter is generally off-season for most European cycling destinations. The exception is warmer regions like the Canary Islands and southern Spain — all rideable year-round.

Still a hard choice? See our tour choosing guide that will answer any questions or doubts you still might have.

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 Europe.

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.

Europe is a very diverse continent and there is something for every cyclist. Whichever bike you choose, we will find the perfect route for you.

We offer four types of cycling holidays, each suited to a different kind of rider — and it's worth noting that most of our tours are compatible with more than one bike type, so you're rarely locked into a single option.

  • Road cycling — best for avid cyclists with the endurance to handle multiple long days in a row. Expect high daily distances, paved roads, and a pace that rewards fitness.

  • Gravel cycling — suitable for anyone comfortable spending multiple days in the saddle with some moderate climbing. Terrain is mostly tarmac and gravel, stages are manageable, and the pace is flexible. Our most popular format.

  • E-bike holidays — ideal for those who want to cover the same scenic routes with less physical strain. Electric assistance makes longer distances and hillier terrain accessible to a much wider range of riders.

  • Mountain biking — suited to riders comfortable on technical terrain. Our MTB holidays tackle rougher trails, steeper descents, and more demanding surfaces. Adjustable to your skill level, but not recommended for complete beginners.

Absolutely — and in fact, most of our tours are designed with solo travellers in mind.

Our self-guided tours mean you cycle at your own pace, on your own schedule, without being tied to a group. You're independent on the road, but fully supported behind the scenes — we handle your accommodation, luggage transfers, and route planning, and our team is reachable throughout your trip.

If you're travelling alone, just let us know when booking. We'll advise you on the single supplement and flag which tours are most popular with solo travellers.

If you want to, sure! We are well aware that some people love to stay in groups while others prefer some more alone time on their trip. We wanted to give you the opportunity to do things your way — it is your holiday, after all!

As long as you respect the group timings and locations designated by your guide, please feel free to customise your itinerary by scheduling a free meeting with our specialists and we will see what we can do at the chosen destination!

On a self-guided cycling tour, you're in charge of your own pace and schedule — no group to keep up with, no fixed departure times, no guide leading the way.

Before your trip, we take care of everything behind the scenes. We plan your route, book all your accommodation, arrange daily luggage transfers, and load your GPS with turn-by-turn navigation. You receive a detailed digital guidebook covering each stage, what to expect on the road, and recommendations along the way.

On the day, you simply check out, drop your bags at reception, and ride. Your luggage arrives at the next hotel before you do.

Throughout the trip, our team is reachable if anything comes up — a question, a change of plan, or something unexpected. You're independent, but never on your own.

If you'd like to know more about how it all fits together, visit our self-guided tours manual.

On our guided tours, you will have professional local guides. Our guides will make sure that you will have expert guidance combined with great fun and a memorable experience.

Some of our Slovenian tours are also also available as group guided tours.

Every day starts with breakfast at your hotel. From there, the day is yours.

Your luggage is collected from reception and transported to your next hotel — so you set off with just a daypack. Your GPS route and daily notes are ready in the app.

Most stages take between 4–7 hours of cycling depending on the tour, with plenty of stops along the way.

You decide the pace, when to take breaks, and whether to linger somewhere that catches your eye.

By the time you arrive at your next hotel, your bags are already waiting. The evening is entirely free.

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