Crete Senesi gravel Tuscany bike tour


Cycling gravel Tuscany Eroica & Strade Bianche tour

Crete Senesi gravel Tuscany Eroica & Strade Bianche bike tour is an ideal option for cycling enthusiasts of all levels.

Whether you’re looking to pedal calmly along the gentle lanes of this beautiful region, or challenge yourself on the same hills that cycling legends have trained on—including Bartali, Cipollini and Bettini— Tuscany can truly be said to be a land of cyclists, and much, much more.

In the Crete Tuscany gravel bike tour  you’ll be able to enjoy a diverse array of Tuscany cycling routes.

There are bike routes going to the UNESCO World Heritage site Val d’Orcia, tracks across the stark but gentle landscape of Crete Senesi, or lanes cutting through the vineyards of Chianti and Montalcino, and last but not least on the Eroica and Strade Bianche roads.

You’ll also get a chance to walk the hallowed halls where the Chianti wine was born, or to stroll in such renowned and beautiful towns as Siena and Pienza.

You will be warmly welcomed for all 7 nights of your Crete Senesi gravel Tuscany bike tour in Rapolano Terme. This is an excellent way to discover Tuscany at its most real and authentic. As well as being in a nice Hotel with Spa, with premium accommodation options with luxury trappings—perfect for couples, solo travelers, and families alike.

Ecological sensibilities are also fully respected on this greenest of Tuscan bike tour vacations. And a complete cultural immersion into the Tuscan lifestyle—together with a warm hospitality—is guaranteed from Michele and Silva.


DAY 1: Asciano Warm-Up

Welcome to Tuscany! Our meeting point is at the Terme in Rapolano Terme. In the afternoon after the bike fitting, we’ll ride around Asciano.
km 28   mt 375 altitude increase
mi 18 ft 1230

DAY 2: Val Di Chiana

Today we’ll ride along the Val di Chiana reaching Cortona nice town famus for the movie “UNDER THE TUSCAN SUN”.
The Val di Chiana is a huge fertile plain bordering Lazio, Umbria and Tuscany. It has an esteemed agricultural production, becoming the symbol of the Terre di Siena and of entire region.
km 106  mt 1268 altitude increase
mi 66 ft 4133

DAY 3: Orcia Valley

Today we’ll plunge into Val d’Orcia, considered one of Italy’s wonders and a UNESCO World Heritage Site.
Medieval castles, sunny rolling hills, isolated hill top towns, charming isolated rural homes, avenues of cypresses, and golden wheat fields are just some of the elements of the fantastic and harmonious landscapes of this area.
We’ll stop in Pienza, another UNESCO World Heritage site, for a stroll through town.
km 93  mt 1581 altitude increase
mi 58  ft 5187

DAY 4: Rapolano Terme, Siena and Crete Senesi Loop

Today is a rest day! There will be an optional loop ride along the Crete Senesi, the world’s most photographed panorama!
Those who don’t want to ride, can spend the morning at the Spa and natural hot spring San Giovanni in Rapolano Terme.
Hot springs are naturally produced by the emergence of geothermal heated groundwater from the earth’s crust.
The Terme di San Giovanni is a natural terrace overlooking the sea of hills that is the Crete Senesi, so while relaxing in the pools or having lunch, you can enjoy a breathtaking view on this gorgeous landscape.
km 73mt  1408 mt altitude increase
mi 45,5  ft 4619

DAY 5: Chianti Classico

Today we’ll ride through the famous Chianti Classico region.
We’ll ride along Castello di Brolio, built around 1,000 AD and owned since 1141 by the Ricasoli family, the oldest winery in Italy and the second oldest in the world.
Afterwards, we’ll stop for lunch in Gaiole in Chianti, the starting point of L’Eroica, and we’ll visit the vintage “White Roads” to browse a selection of artisanal products.
In the late afternoon, we’ll return to the hotel and we can enjoy the oil testing.
km 95  mt 2071 altitude increase
mi 59  ft 6794

DAY 6: Montalcino

Our last ride will lead you to Montalcino, the city of the famous wine Brunello di Montalcino DOCG.
We will ride along the Pecorile road in the heart of Crete Senesi and the Asso Valley.
Montalcino, renowned all over the world for the production of its precious Brunello red wine, has scarcely changed in appearance since the 16th century.
Once you get up to the town, a magnificent spectacle unfolds for your eyes.
km 91  mt 1506 altitude increase
mi 57  ft 4940

DAY 7: Monte San Savino

Today will have a short ride to Monte San Savino was one of the first urban settlements in TuscanyItaly.
It originated around 1100, but a further century had to pass before Monte San Savino could be considered a centre of a certain social, political and cultural importance of Tuscany in those times.
But it is no longer now.
The last past of the ride is mostly down hill!!
km 58  mt 851 altitude increase
mi 36 ft  2673

DAY 8: Arrivederci!

After breakfast at 9 am, is possible, on request,  have one group shuttle to Siena train station from where you can connect to Florence and Rome.

Price & Inclusions


Cost €3150 per person in double occupancy

single room supplement € 450


Informative tour leaders throughout the program

Van support

Guide bike

All Dinners and breakfast

Lenght: 8 days / 7 nights

Not Included

Use of a carbon road bike or gravel bike

Shuttle at the beginning and end of your bicycle tour in Tuscany, as well as for certain specified activities mentioned in the program.

Bike Rent Tour

Road bike 270€

Gravel Bike 270€

Ebike 270€

Trip Details


Guided Gravel or road Tour



Daily Average 78km/49mi

Total Mileage 544lm/340mi

Terrain Rolling hills

Best Time







Go Private

Custom groups any time


Hotel due mari

Breakfasts inspired by the localism movement for sustainable food

Relax at the spa and thermal springs in  Rapolano Terme we have discount for Therme.


Rapolano Terme



Rapolano Terme



March 19/26

April 02/09-16/23

June 21/28

July 11/18

August 23/30

September 11/18

October 15/22

Maybe also you can like: Ride and cook

contact us and book the tour

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Based on 96 reviews
Manuel König
Manuel König
I rented the Canyon Gravel bike for the Strade Bianche and felt I had made the optimal choice. The booking process was very easy, Luigi is extremely kind, knowledgeable and helpful, the bikes are beautiful, perfectly maintained and adjusted to your needs and the price is more than fair compared to competitors. 5/5 stars. I would come back any time.
Silvia Dagnoli
Silvia Dagnoli
Top! Professionalità e disponibilità al 100%. Ho preso una Canyon Gravel a noleggio, mi sono trovata molto bene.
Very friendly, speaks good english. The bikes themselves are great. The bikes are nog insured by default.
Matthew Ng
Matthew Ng
We had 5 excellent days of gravel riding (self guided Tuscany tour). The routes that Luigi provided us were a good mix of paved and gravel, and of course hills! The bikes (Canyon Grizl) were very nice and the luggage was always waiting for us at the next hotel. Luigi was accomodating, modifying the routes based on my requests. I would definitely recommend doing a trip with this company.
Robert Head
Robert Head
The route was wonderful, with amazing scenery and history at every turn. Our guides, Sarah and Gigi were the best. They are both very accomplished and personable riders, provided interesting history of Tuscany during the tour, and emphasied safe riding while keeping everyone within sight. They are also great dinner companions!
James Twidale
James Twidale
Luigi and BikeRiding Tuscany were an absolute pleasure to deal with. The bike was in incredible condition, delivered to my hotel and Luigi even arranged for a local mechanic to help with a small mechanical issue after my first ride. The experience from start to finish was brilliant. The communication friendly and quick. Simona was equally helpful on collection of the bicycle. I would love to join Luigi for a cycle tour as he seems very knowledgeable about the area and a good rider. I would recommend this company to anyone looking to explore Tuscany or Siena.
Mark Gatha
Mark Gatha
Exceptional self guided tour. I highly recommend for all levels (but especially for a road cyclist). This is the tour company to book with! Bikes - excellent high end bikes. I rode a Canyon Ultimate CF SL Ultegra - light and fast and we'll tuned with new tires. My wife road the e-mountain bike which she really enjoyed. Routes - beautiful. We did 50-60km a day. Rapolano de Terme, Pienza, Montalcino, Siena and Castellini in Chianti. Varied terrain, vineyards, great climbs and beautiful medieval towns. Extremely well thought out. All on quiet roads. Hotels - all 3 and 4 stars with loads of character. The ones with pools were our favourites. All of the hotels were able to let us check in very early (it was hot so we rode as early as we could manage). Hotels all came with breakfast. Really great. Service - Luigi was a gem. Easy to contact, quick to communicate (before we came and during the tour) and passionate about cycling. He gave us a lot of great recommendations to help maximize our tour. I cannot say enough positive things about this trip and Bike Riding Tuscany. This was truly memorable. Highly recommended.
Bruce Jenkins
Bruce Jenkins
I was on a trip around the world and stopped in Italy. A friend recommended BikeRidingTuscany to me for an unforgettable experience and it didn’t let down. They planned a custom 1 day gravel ride for me that took us from Rapolano Terme to Sienna and back. The pace was perfect and they were gracious with any requests for breaks or stops for water/food. I enjoyed myself so much that I extended my stay to do a run on the gravel amongst the beautiful sunflowers. If you’re adventurous, and seeking some safe fun riding, this is your team
greg luckos
greg luckos
Great rental service! Nothing is a problem for Luigi. All bikes are set up tubless. Thank you

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