Heart Tuscany self guided bike


Cycling  in the middle heart of Tuscany 

Are you ready to take a ride in the heart Tuscany self guided bike tour?

Heart Tuscany self guided bike tour is the right way for discorver all the province of Siena. If you like gravel bike this self guided tour is available also by gravel roads.

Be aware there are many hills to climb but your efforts will be very well rewarded.

The route we have selected in this self guided tour, takes you along quite country lanes passing through  farmland and small  villages, vineyards, golden fields, rolling hills, ancient monasteries and medieval forts.

Visiting Pienza, Montalcino, Siena and the Chianti area. The Heart of Tuscany.

You will experience the true essence of Tuscany, where history and nature fill the heart as water fills a well.

But Tuscany nourishes your appetite too … After all your cycling you can not miss to savour the pecorino cheese, homemade pasta and “pici”, organic olive oils and sip Tuscan wines like Brunello and Nobile of Montepulciano o il Chianti red wine.

The Heart Tuscany self guided bike tour is all this and something more that you have to discover!!


Journey into the heart of Chianti – Siena and Castellina in Chianti

Follow the path of  l’Eroica – one of the best international  bike rides in the world

In ancient cellars, taste super Tuscan wines, from Vino Nobile di Montepulciano to Brunello di Montalcino and red Chianti wine.

Day by Day

Day 1 – Rapolano Terme – hot spring Town

We meet in Rapolano Terme for the bike fitting.
Rapolano Terme is a small renaissance town located  in the valley of Ombrone, in the heart of Tuscany,  Crete Senesi, 30 km from Siena.
In the province of Siena rise 10 spas, for this reason the area is also called “land of waters”: the thermal spa here have  ancient origins, Etruscan and Roman.
Rapolano Terme is a unique nature resort, with two thermal sources (Terme Antica Querciolaia e Terme San Giovanni).

Day 2 – San Giovanni D’asso town of white truffle

The tour starts with a long loop. We follow the street to Asciano in the middle of the the Crete Senesi area where the distinctive colouration of the soil gives the landscape of sculpted curves an appearance described as lunar.
Soon we start uphill one of the most scenic roads we have in Tuscany and reach San Giovanni d’Asso the town of the white truffle.
After a short break we keep on going up and down until we reach Trequanda and take our way back to Rapolano Terme.
Total Distance: 55 km/75km

Day 3 – Pienza – the perfect town

From Rapolano we ride to Pienza across the Crete Senesi via San Quirico d’Orcia.
You will pass through the Parco naturale della Val d’orcia – an Unesco site, cycling up and down in a painting scenery until you reach the town of Pienza  a remarkable example of Renaissance-era town planning.
If you have even the least appreciation for beautiful architecture, it is a treat to stroll around its cobblestone streets.
Total distance :50km/70km

Day 4 – Montalcino Brunello Wine Land

Ride from Pienza to the wine town of Montalcino, with a pause in fairy-tale Bagno Vignoni, a unique miniature spa .
Before the day is over we’ll be in  Montalcino, ending up at the Fortress for one long last look at the beautiful countryside.
Here you can  reward yourself with dinner at  your  favourite wine cellar.
Total Distance: 55km

Day 5 – Siena & Monte Oliveto Maggiore Abbey

From Montalcino to Siena.
Following a picturesque crest road you’ll ride by Monte Oliveto Maggiore Abbey, a large Benedictine monastery built in the 13th century: Its buildings, which are mostly of red brick, are conspicuous against the grey clayey and sandy soil—the Crete senesi which give this area of Tuscany its name.
From here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity, an unusual, almost lunar landscape of chalk cliffs .
Finally we reach Siena , famed for the “Palio”, one of the most beautiful cities of Tuscany.
Set on three hills, the city is drawn together by winding alleyways and steep steps, whilst the Piazza del Campo stands at its heart, and the Duomo and St Maria della Scala serve as additional cultural landmarks.
Total Distance: 65km

Day 6 – Castellina in Chianti 

From Siena we take direction to Castellini in Chianti .
This is the best route for the serious wine lovers. It wends through the vineyards, past abandoned and renovated farmhouses on the way to one of Tuscany’s most renowned castles, Brolio.  
This is the heart of the Ricasoli empire, family headquarters since 1067 and center of countless battles between Florence and Siena during the Middle Ages.
Many people consider that the wine we now know as Chianti was born inside its hallowed cellars, which we can visit.
In Brolio we can have a break in the Agribar Eroica caffè. 
From here we continue on to reach Castellini in Chianti .
Total Distance: 55km

Day 7 – Arrivederci! 

Enjoy the  breakfast and wander in Castellini in Chianti.
Departures: trains and buses available to reach Firenze where extension of vacation is suggested or where you can take fast train to other towns.

Extra stage on request: from Castellina in Chianti to San Gimignano

More vineyards await us today, but you’ll be amazed at how different they look once we get into the district of San Gimignano. Pretty soon you pass Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around.
Also seen in the distance are the seventeen towers of San Gimignano.
You’ll have plenty of time to wander through the cobblestoned streets, window shop and buy a few last-minute Tuscan mementos for our friends and…why not, for ourselves too!
Distance: 60km

Price & Inclusions


Cost: € 1590 per person in double occupancy

Single room supplement € 350


Six nights in excellent four & three-star superior hotels

Six breakfasts, maps, elevation gain and city map and Garmin Edge GPS

Sightseeing, restaurant and shopping suggestions

All Baggage transfers

Pick-up of bikes and gear in Castellina


water bottle

Sales taxes

Not Included

Bike Rental per entire tour

Hybrid bike euro 280

Race bike euro 350

E-Bike euro 315

City Tax  each village charges a tax per day between euro 0,70 to euro 4,00


We will upload all the route notes and you will have really no problems in finding your way to the next town



Self Guided


Moderate Challenge

Best Time

Any time from March to October


Rapolano Terme





Castellina in Chianti

San Gimignano


Rapolano Terme


Any time from March to October


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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