Gravel Bike Tours in Tuscany

When we talk about gravel, Tuscany has definitely lots to offer. Single track trails, “strade bianche”, dusty roads, and rolling hills are what we are most proud of. Here below, we offer a wide variety of one-day guided tours that you can book around different parts of our breathtaking region.

Each cycling spot is about one hour away from the other, so you might want to consider combining some of them during your time in Tuscany.

Other than guiding you along these routes and offering photographic service, we can also help and advise you about where to stay and how to make the most of your time here.

Additional wine tasting tours can be arranged in advance to make your bike tour even more magic!

Whether this is something you would like to do on your own, as a couple, family, or group, we are happy to design a route that will suit your skills and expectations.

At Asimismo we believe enjoying the journey is what matters the most, and this is what makes us and our tours so unique.

As well as one-day guided tours, we also offer a full week dedicated to gravel cycling (in collaboration with a bio Agriturismo near Montaione). Every day we will take you exploring a different route diving into unique places.

Go to the gravel week

Before you ask. For any doubts or questions about tours and the way we work, please check our Frequently Asked Questions page. There is where we have tried to cover all the points.

FAQs

To book one of the tours in offer please use the matrix underneath. According to the length, number of participants and Tour name the price will change accordingly.

Gravel Bike Daily Tours

Tour Name:

Tour Length:

Number of Participants:

- Free Asimismo T-shirt.
- Certified Guide with recognition at European level GAE (you will be guided to the best spots and the best routes, you will also get a botanical and historical insides of each place).
- Professional photographic service during the ride.
- Sport gels and energy bars.
- Food or refreshment expenses
- Travel insurance
- Rental
We refund 50% of the price you paid if you cancel a tour up to 30 days in advance. After that term we will keep the total sum.
- If you have any questions please visit our FAQ page then get in touch.
- Price for groups bigger than 5 persons on request (as we might have to add an extra guide)
- Drone footages and support vehicle during the tour at extra cost.

In case we are booked already in the date you want to ride we will refund you in full.
After purchasing a tour we will be able to put you in touch directly with the best rentals in the area you are in, in case you need to rent a bike.
In the cost of each tour is calculated also the time for the editing of the photos taken along each ride.

To discover what our previous client said about us, click here

Chianti

Discover the untamed beauty of Chianti on two wheels, where pristine gravel paths wind through ancient oak forests and iconic cypress groves. This challenging guided tour takes you beyond the typical wine routes, connecting hidden dirt roads that reveal breathtaking vineyard panoramas from elevated vantage points.

Prepare for significant elevation gain as we tackle rolling hills and sustained climbs that reward your effort with sweeping views across the legendary Chianti landscape. From shaded forest single tracks to open ridgelines overlooking endless rows of vines, this gravel adventure showcases the region's diverse terrain and natural beauty.

Perfect for experienced gravel riders seeking both physical challenge and scenic rewards in one of Tuscany's most celebrated wine regions.

cyclist riding in the Chianti area along a guided gravel tour with Asimismo

cyclist enjoying a break during a gravel tour

riding in the Chianti area of Tuscany with Asimismo

Val d’Orcia

One of the most fascinating areas here in Tuscany, where history blends with breathtaking landscapes, making the perfect combo for this tour. Starting from Torrenieri, you will get to know places and cross through old towns such as Pienza, Bagno Vignoni and San Quirico d’Orcia, feeling like in movie set, but better.

cyclist riding in Val d'Orcia area along a guided gravel tour with Asimismo

The view of the Madonna di Vitaleta chapel in Val d'Orcia area along a guided gravel tour with Asimismo

Vignoni Alto with Asimismo and its bike tour

the chapel of Madonna di Vitaleta, along an Asimismo bike tour

Cypresses in Val d'Orcia with Asimismo and his bike tour

Scenic landscape of rolling hills with a castle or fortress on top, distant mountains, and cloudy sky.

Old stone buildings with tiled roofs by a calm body of water in a European village

Stone buildings along a canal with reflections in the water, trees, and a blue sky.

A stone building on a hill viewed from a winding dirt road lined with trees.

A street in a historic European town with stone buildings, tall cypress trees, a church tower in the background, and clear blue skies.

A scenic view of rolling hills with a distant town and a cloudy sky, foregrounded by yellow wildflowers in a field.

Two cyclists riding on a dirt trail surrounded by trees, under a partly cloudy sky.

A person cycling on a rural road with tall cypress trees and a partly cloudy sky.

Two cyclists riding on a dirt road through a hilly landscape under a cloudy sky.

Two cyclists, a man and a woman, stand near a stone wall by a canal with historic buildings in the background. The man is smiling and holding a bicycle, while the woman looks away, wearing helmets and cycling gear.

Two cyclists riding on a gravel dirt road through open fields with a few trees and a partly cloudy sky.

Two women and one man riding bicycles on a gravel road through rural countryside with fields and hills under a partly cloudy sky.

Cyclists riding on a dirt trail through a rural landscape with fields, a large tree, and a partly cloudy sky.

Etruria

This gravel bike tour will take you all around the beautiful roads of Volterra. This land has seen pilgrims passing by and during the Bronze Age was a settlement for the ancient Etruscan population. The tour finishes at the old town, at 555 m. Along mostly all the segments, you will be able to appreciate the incredible vastity of this territory and a geological peculiarity called “Balze & Calanchi”, typical of this area.

Terre di Siena

When we think about gravel bike tours and riding offroad in Tuscany, the first thing that appears in our mind is Siena. With this tour, you will admire stunning landscapes, ride endless dusty white roads & relive the atmosphere of the "Strade Bianche": the classic Pro Race which takes place around this area. Forget about any sort of traffic and stress: you will enjoy Tuscany surrounded by scenic views, fully immersed in nature.

Santa Luce

A gravel tour to discover the South Western part of the province of Pisa in the area of Santa Luce. Vast wheat fields, lines of cypresses, twisty white dusty roads and the famous lavender fields are waiting for you here. This part of Tuscany not as advertised as many others is still very typical and great for riding bikes benefitting from a unique quietness and silence.

Vie del Tartufo

This gravel bike tour starts in San Miniato and will take you along the best trails famous for the Truffle Hunting. Riding along roads surrounded by cypresses and green hills, and pedaling along stunning vineyards will bring you back in time to when pilgrims were crossing these lands heading south towards Rome.

Tuscany Gravel Bike Tour Vie del Tartufo

Monteriggioni

In this gravel bike tour, you will ride around the area of Monteriggioni ending at the fortified medieval Castle. A great mix of wide dusty roads and trails through vineyards and more forestry hidden gems. You will be able to see how the landscape has been shaped and has changed during the centuries since the introduction of agriculture. In the past years, indeed, the whole central part of Tuscany was an untouched forest of oak trees.

I Colli Medicei

This area near the well-known Cerreto Guidi is the perfect spot if you want to ride surrounded by vineyards where our Chianti wine is made. These amazing quiet trails will make you discover the best views of the area. From these hills, you will be able to take a look at the ancient city of Vinci where Leonardo - the great genius - was born. Landscapes like these ones are exactly what make Tuscany so unique.

Le Colline Pisane

This gravel bike tour will take you exploring the best gravel roads of Valdera in the province of Pisa, riding predominantly between Ponsacco and Terricciola and passing through iconic spots a bit more south like the famous “Teatro del Silenzio”. You will travel back in time by riding through old medieval villages, such as Morrona, while admiring endless views and breathtaking hills

People riding bicycles on a dirt path through rolling green hills with a small flock of sheep, a farm, and a hillside with trees and buildings in the background under a partly cloudy sky.

Two men riding mountain bikes on a rugged dirt trail in a rural landscape with hills and cloudy sky.

A rural dirt road winding through grassy fields with a large tree on the right, rolling hills in the background under a partly cloudy sky.

I Calanchi

Starting from Iano, you will embark on a gravel ride that will take you close to the local “Calanchi”, where you will be able to admire clay hills eroded by wind and rain forming a unique landscape. Afterward, you will move south near Peccioli, descending through some dusty roads surrounded by a lunar scenery, and back from Castelfalfi, where cypresses define the route and shape the view.

A person riding a mountain bike on a dirt trail through a dry, grassy landscape with hills in the background under a clear sky.

A cyclist riding on a dirt trail through a hilly, rural landscape with dry grass and plants, under a clear blue sky.

A person biking on a dirt trail through a rural landscape with rolling hills and tall, thin trees under a clear blue sky.

A cyclist riding on a dirt path through barren, rolling fields with distant hills and a clear sky.

A man riding a mountain bike on a dirt trail in a desert landscape during daytime.

Val d’Elsa

Starting from Castelfiorentino you will abandon traffic and noises to fully immerse yourself in nature. The perfect mix of "Strade Bianche" and more forestry trails with plenty of climbing and picturesque views. The quietness you can experience on these trails is difficult to describe in words, but the best part is definitely a stop at the old town of Certaldo, home of the well-known poet and writer Boccaccio.

A cyclist riding a mountain bike on a winding dirt road through rural countryside with rolling hills, dry grass, and trees under a clear blue sky.

A person wearing a helmet and athletic clothing standing outdoors near a picnic table and chairs, looking at a sky lantern hanging from a tree in a scenic countryside landscape.

A person riding a mountain bike on a dusty forest trail surrounded by tall trees, with sunlight filtering through the foliage.

Person in cycling gear and helmet leaning on a water fountain with a bicycle beside them, in front of a weathered brick wall.

A person riding a bicycle on a dirt path through a vineyard landscape with a hilltop castle in the background during daytime.

A person riding a bicycle in a vineyard during daytime with rolling hills in the background.

Val di Chiana

This gravel tour will take you exploring all the eastern part of the province of Siena and the area near Chiusi and Montepulciano. Away from the industrial parts of Tuscany here the Italian slow living life it is still something you might be able to experience. You will be riding at time through trails along vineyards but also through some forested parts and aside cultivated fields of corn. Quiet roads and stunning little villages are what you should expect to find along your way if you decide to book this tour.

Two cyclists wearing helmets and sunglasses talking on a sunny street corner with buildings, a fountain, and a bicycle in the background.

Two cyclists with helmets and biking gear standing on a sidewalk next to a large historical stone building with a dome and a steeple, under a partly cloudy sky.

Two children riding bicycles on a narrow, cobblestone street in a historic European town, with pastel-colored buildings, vintage street lamps, and a view of rolling countryside in the background.

Cyclists ride along a sunny street in a European town, with colorful buildings, a clock tower, and outdoor cafes under umbrellas.

A cyclist riding on a gravel country road past an abandoned brick house with boarded windows and walls covered in weathered plaster, with rolling fields and cloudy sky in the distance.

Two people biking on a gravel dirt path through a rural landscape under a clear blue sky.

Two people riding bicycles on a narrow street with a brick wall on the right and old buildings on the left, under a clear blue sky.

Two people riding bicycles on a gravel trail in a rural outdoor setting with clear skies, trees, and open fields.

Monti Pisani

Starting from San Giuliano Terme we will explore the nicest gravel trails around Pisa and the mountain behind it. The course of this gravel bike tour is modulable. Meaning that according to your fitness and bike skills we will chose the best trails for you to enjoy the ride. We can vary between flat off road segment, b roads but also trails up in the mountain to gain perspective and admire the coast from up above. At the starting point you will also be able to rent a gravel bike in case you need one.

A silhouette of a person wearing a helmet and cycling gear, stretching with one foot on a sidewalk ledge, with a mountain bike parked nearby against a wooden fence, under a blue sky with wispy clouds.

Old orange building with arched and rectangular windows and a red-tiled roof, surrounded by a gravel driveway and green lawn with decorative stone posts.

Purple bicycle leaning against a rusty fence along a gravel country road with trees on the right and open fields on the left under a cloudy sky.

A male cyclist wearing a helmet and cycling gear sitting on a stone wall along a canal in a city with colorful buildings, blue sky, and mountains in the background.

A cityscape showing a river running through a European city with colorful buildings along the riverbank, under a blue sky with scattered clouds and distant mountains.

Person biking on a dirt trail through a forest with tall trees and sunlight filtering through.

Two mountain bikers riding on a dirt trail through a mountainous landscape with green and brown foliage, under a blue sky.

A person riding a mountain bike up a green, forested hillside with a village in the background.

A person riding a mountain bike on a rocky trail through a forested hillside, with some trees burned and others green, overlooking a distant landscape and blue sky.

A person wearing a helmet standing with a mountain bike on a rocky trail in a natural landscape with trees, shrubs, and a distant view of farmland on a bright day with clear skies.

A muddy dirt road with puddles, green fields, leafless trees, hills, and a cloudy sky.

A dirt path winding through a rural area with leafless trees and bushes on either side, under a cloudy sky.

A dirt trail winding through a forest of tall pine trees with green foliage and some shrubs on the side.

A person riding a mountain bike on a dirt trail with rocky terrain, surrounded by bushes and pine trees, with a mountain in the background under a clear blue sky.

Frequent Answered Questions - FAQs

What is the typical length of a guided bike tour?

Typically our guided tours are from 50 to 90 km in length. During the booking phase we typically have a chat with our client to understand his level of fitness. Depending on the area of the region and which tour you pick, in less than 90 km we can do up to 2000m of elevation gained, that is why the range of Km can vary quite a lot according to many factors. Every tour will be suited to match clients need and expectation.

Why on the matrix is it possible to choose only full day and not half day?

We believe that a certain minimum of km is necessary to explore an area and even though we will be able to customize each tour according to the client's needs, desire for riding and time available, for us it will still be a full day of work, with the impossibility of accommodating any other client on the same day.

Is there a specific location for the starting point of each guided bike tour?

Our guided bike tours are completely bespoke. We have divided them into areas for you to better understand where each of them will take place. Sometimes the tours can overlap in the sense that by starting in one area we could also get to see places that features on another tour that we have in offer.

Which factors influence the cost of a bike tour?

The number of participants and distance of the selected tour from where we are based determine the cost of each of them. When you contact us, please make sure to specify exactly where you will be staying, which tour you have in mind to do and the total number of people that will be riding to get an exact quote and price.

Are these bike tours family friendly and suitable for kids?

During the years we have taken on our guided tours families with teens or younger riders. It is important to specify the age of each participant at the beginning of the booking so we can organize the tour taking those important factors into account.

Is it possible to combine a visit to a winery during a bike tour?

Yes it is possible to stop or visit a winery during one of our tours, according to what is available and the location. Our suggestion will still be to start and finish the tour at the selected winery so we will avoid riding under the effect of alcohol.

Is lunch included in the price of the tour?

Any food stops along the route or during the length of the tour are not included in the displayed price. Any costs in relation to that need to be covered by the client also for the part of the guide.

What makes these bike tours unique?

Our knowledge of the territory combined with the level of customization of each tour according to your needs are key factors to make the tours with Asimismo something unique to find here in Tuscany. As well as that we are the only ones that offer a professional photographic service included with any tour. Something very nice for you to remember the time spent riding along our idyllic countryside.

If I decide to join one of these tours will I be riding with other people?

We consider our tours bespoke and private, so you will only be riding along with the people from your group or with the guide in the case you book it as a single person. Here at Asimismo we really believe in offering a bespoke service and each of you will ride an itinerary designed according to your needs.

How fit should I be for embarking on one of these guided bike tours?

During the phase of booking you will be telling us your level of fitness. You could share with us your Strava profile so we can best guess how to structure the length of the ride according to your skills. Our gravel tours never get very technical in fact we aim to do them with gravel bikes so no single track or sketchy segments in the forest.

What is the level of experience required to join a bike tour?

There is not a predetermined level of experience for joining one of our guided bike tours. During the booking process we will try to understand which type of itinerary and amount of elevation gained is most suited for you.

What if I am in need of renting a bike for the tour?

The price of the guided bike tour you find on this page does not include the fee for the rental of a bike, but feel free to get in touch with us via email in case you need to rent a bike for one of our tours. We will surely be able to help with it and with the transport of the bike to the place where you will be staying.

From where we ride