Adventure Unpaved & Escape the Crowds
Val d’Orcia to Siena on gravel road
Gravel Tuscany Bike tour’s Wow Moments
- Shadow the hilly path of L’Eroica, Tuscany’s internationally recognized vintage bike race.
- ancient cellars, taste superb Tuscan wines, from Vino Nobile di Montepulciano to Brunello di Montalcino.
- Experience the serenity of the Tuscan countryside and savour the flavours of authentic pasta fresca.
- Explore the undulating white gravel roads of Tuscany—the famed strade bianche—and immerse your self in Italy’s most classic cycling local.
- Caffé espresso, cappuccino & best gelato
Most people choose to ride gravel to escape traffic and get off the beaten roads, exploring the hill town tahta made Tuscany so famous. The amount of pavement varies from destination to destination, but one thing holds true, once you are on gravel, you’ll encounter minimal traffic.
This is a short escape – 4 nights in case you do not have entire week or you want just to test gravel biking in the legendary white roads
DAY 1
Meet & Greet in Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza the “perfect town” is 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.
If you arrive in time there will be a First test bike ride to Palazzo Massaini, Montefollonico
Distance 25 km /15 miles
12 km asphalt and 13 km gravel – Easy to Moderate
DAY 2
Your tour starts with a circular ride from Pienza.
Spring brings red poppy blossoms to the vibrant green wheat fields of Tuscany, and nowhere is the bloom more brilliant than the hills of the Val d’Orcia, a UNESCO World Heritage Site. As we pedal through these corridors of proud cypress trees, the scenery may look familiar from such films as Gladiator and The English Patient. Follow the gravel tracks off the beaten path through a timeless slice of Tuscany. You’ll come to Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces. After relaxing a while, you will face a incredible breathtaking yet challenge gravel section that bring you to Monticchiello, the quintessential Tuscan hill town.
back in the valley, next destination is Bagno Vignoni, a thermal spa town that dates back to Roman times, Madonna di Vita Leta chapel is on the way back to Pienza
distance 52 km /31 miles 17 km asphalt and 34 km gravel
moderate difficulty
DAY 3
To get from Pienza to Montalcino we select the sections of Eroica called Lucignano d’asso and Pieve A Salti. You leave Pienza and after 6 km on paved road you will take with white road toward Cosona and reach the little hamlet of Lucignano – a caffe espresso at little shop emporio – is a must. Once you reach the paved road you ride only one km and start the other Eroica gravel section Pieve a Salti – so beautiful landscape. 9 km up and down in the rural countryside! arrive in Buonconvento by lunch time. Now you have to face the climb to the famed wine town of Montalcino. A total of 10 km: 5 on paved and 5 km on gravel all through vineyards and wineries. Once in town we strongly suggest to visit the fortress and admire the breath-taking view of the entire valley you’ve just biked.
At dinner tonight reward yourself with a glass of Brunello!
distance 41 km /25 miles 17 km asphalt and 24 km gravel
moderate difficulty
DAY 4
L’Eroica—meaning “The Heroic”—is a celebration of the golden age of cycling. The event takes place every October when thousands of hardened cyclists travel back in time to ride these gravel roads on primitive machines of the past. The heavy lugged-steel bikes with down-tube shifters and impossible gear ratios are no match for the red wine in the participant’s water bottles and the hardman mentality. Today, we’ll have our own taste of cycling’s heroic origins as we join one of the most beautiful gravel sections of L’Eroica. From the heart of Brunello di Montalcino, Tuscany’s most celebrated wine region, ride to the top Passo del Lume Spento. In fact starts the Castiglion del bosco gravel section. Castiglion del bosco is the biggest brunello winery & farm belonging to Ferragamo, the famous Italian fashion designer. Once in Bibbiano another section called la Piana and reach Murlo after 30 km- caffé & visit! Shortly you will face another legendary Eroica section to Radi, with some steep yet short up and down. At Ville di Corsano you deserve a light lunch. from here you have the last 12 km on secondary paved road to Siena.
Distance 56 km /35 miles 32 km asphalt and 24 km gravel
moderate to challenge
DAY 5
End of Tour after Breakfast
INFO TOUR
best period rom March 15th to November 15th
DIFFICULTY moderate to challenge
TOUR REVIEWS
Price & Inclusions
Cost: € 1190 per person – Price based on double accommodations
single room supplement € 550
Inclusions
Four nights in excellent five, four & three-star superior hotels
Four breakfasts
All Baggage transfers
RideWithGPS App: tracks, route notes, off-line navigation
Trip notes: Sightseeing & meals suggestions
Maps with elevation gain
Delivery bike at Pienza hotel & bike fitting
Pick-up of bikes and gear in Siena
Keepsake Cicloposse water bottle
Sales taxes
Not Included
Bike Rental per entire tour
Hybrid bike € 150 | E-Bike & Gravel € 180 | E-gravel € 250
Cloister is one of those places where you really feel the history of Pienza. Set in a former 15th-century convent directly on Corso Rossellino, the town’s main street, it still retains the atmosphere and character of the original building, with its beautiful cloister at the heart of the property. What we particularly love is the garden at the back, with its swimming pool and wonderful views stretching across Val d’Orcia. You are right in the center of Pienza, with cafés, restaurants and little shops just outside the door, yet once inside, the hotel feels remarkably peaceful.
For those looking for a more refined and intimate stay in Pienza, La Bandita Townhouse is our luxury upgrade. This small boutique hotel occupies a beautifully restored historic building right in the heart of town, combining the character of old Pienza with contemporary Italian design and a wonderfully relaxed atmosphere. We like it for its stylish interiors, spacious and comfortable rooms, and the personal feel that comes with a small boutique property. Step outside and you are immediately in the historic center, with Pienza’s restaurants, cafés and charming streets all within a few minutes’ walk.
Vecchia Oliviera is one of our favorite choices for a self-guided stay in Montalcino. Located just inside the historic center, next to one of the ancient town gates, it is very convenient to reach by bike while restaurants, wine bars and the lively streets of Montalcino are all within easy walking distance. We particularly like its panoramic terrace, where breakfast is served overlooking the surrounding countryside, and the lovely small outdoor pool – a very welcome treat after a day on the bike. Comfortable, friendly and perfectly located for cyclists.
For those looking for a little extra comfort, Palazzo Saloni is a wonderful upgrade in Montalcino. Set right in the historic center yet quiet and peaceful, it offers spacious suites, beautiful views over the Val d’Orcia and the convenience of having restaurants, wine bars and shops just steps away. We particularly like it for our cycling tours: you can arrive and leave directly by bike, and the hotel has a dedicated bike room. A perfect combination of comfort, location and cycling practicality.
Mastrojanni Wine Relais is a wonderful place to experience one of the things we love most about this part of Tuscany: the close connection between cycling, landscape and wine. Set within the renowned Mastrojanni Brunello estate, the relais sits in a spectacular panoramic position surrounded by vineyards and the rolling hills of the Val d’Orcia.
We particularly like the feeling of staying right where the wine is produced, while enjoying the comfort and relaxed elegance of a beautiful wine relais. Its location, not far from the Abbey of Sant’Antimo and some of our favorite cycling roads around Montalcino, makes it a very special stage!
Villa STR is a great choice for a cycling stay in Siena. Set in a 19th-century villa just outside the busiest part of the historic center, it combines a quiet setting with the convenience of being only about a 10-minute walk from Piazza del Campo.
For us, its location works particularly well: once you arrive, the bikes can be safely stored in the hotel garage and you are free to explore Siena entirely on foot. After the lively streets and squares of the city, the peaceful garden is a lovely place to come back to and relax
For those looking for a more luxurious and peaceful stay in Siena, Certosa di Maggiano is a very special upgrade. Set in a beautifully restored 14th-century monastery just outside the ancient city walls, it combines centuries of history with contemporary design, spacious surroundings and exceptional comfort.
What we particularly love is the sense of space and tranquility – you feel immersed in the Tuscan countryside while still being just minutes from the historic center of Siena. The beautiful grounds and swimming pool make it an especially welcome place to relax after a day on the bike
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Tour Reviews
This local company knows all the routes, period hotels, and local restaurants. The equipment and logistics are superb and well orchestrated. They are very responsive before and during the trip. This is our 2nd time touring with Cicloposse. We came back because the first time was a great experience. The gravel tour following l’Eroica is very special.
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