Strade Bianche Bike Tour
Val d’Orcia to Gaiole in Chianti — Tuscany’s famed white gravel roads
Ride the legendary strade bianche—the white gravel roads that made Tuscany iconic in modern cycling.
This self-guided gravel tour blends the best unpaved sectors inspired by the Strade Bianche pro race and the Permanent Route of L’Eroica, connecting Val d’Orcia, Siena’s countryside, and the heart of Chianti.
Expect rolling panoramas, cypress-lined climbs, historic villages, and well-earned Tuscan food and wine along the way.
“Strade bianche” literally means white roads—named after the pale limestone gravel that turns to fine dust in dry conditions.
This is a private self-guided tour: ride at your pace with GPS routes and local support.
Wow Moments
- Ride handpicked Strade Bianche sectors through Val d’Orcia and the Siena countryside
- Follow parts of L’Eroica’s legendary route toward Gaiole in Chianti
- Hill towns, castles, and vineyards—Chianti Classico landscapes at their best
- Tuscan flavors: authentic pasta fresca, cellar visits, and tastings—Brunello & Nobile highlights
- Espresso stops, cappuccino breaks, and the kind of gelato you’ll remember
The Famed White Roads of Tuscany
The Permanent Route of L’Eroica lets you experience the spirit of L’Eroica all year round—an iconic journey through the rolling hills of Chianti and the Siena countryside. We run this self-guided tour from March to November, when Tuscany’s white roads are at their best.
The classic Eroica route begins in Gaiole in Chianti and follows some of the region’s most beautiful backroads: historic vineyards, quiet hilltop lanes, and unforgettable landmarks such as the cypress-lined approach to Castello di Brolio.
The idea is simple and timeless: embrace the joy of effort, ride with respect for cycling’s heritage, and let the past inspire the future.
New to Strade Bianche? Read our guide: “What are the white roads in Tuscany”
Bikes: choose between a premium carbon gravel bike, an e-gravel option, or a trekking-style e-bike—depending on your riding style and the tour setup.
Options typically include the Scott Addict Gravel 20, Cannondale Synapse e-gravel or a trekking e-bike.
Strade Bianche Tour FAQs
What makes Tuscany perfect for gravel riding?
Tuscany is made for gravel: rolling hills, quiet backroads, and a unique mix of white gravel lanes (strade bianche) and smooth secondary roads. The scenery is constantly changing—cypress avenues, hilltop villages, vineyards, and open countryside—so every climb feels rewarded. Many white roads are well maintained, especially in spring and autumn, when the region hosts major cycling events—making the ride even more enjoyable.
What are the Strade Bianche—and where are the best sections to ride?
Strade bianche literally means “white roads”: pale limestone gravel roads that can turn into a fine white dust in dry conditions. On this tour we focus on the most scenic and rideable sectors across Val d’Orcia, the Siena countryside, and Chianti/Gaiole—choosing stretches that are beautiful and safe, and avoiding the most “leg-breaker” gradients when there’s a smarter alternative. Highlights can include classic segments around Cosona, Vagliagli, and the lanes near Castiglion del Bosco.
Is this Strade Bianche tour self-guided—and how does support work?
Yes—this is a private self-guided tour. You ride at your own pace with GPS routes and ride notes. We meet you in person at the start for bike delivery and fitting, and during the tour we handle the logistics (including luggage transfers). An emergency number is always available for support.
How much gravel vs paved riding should I expect?
Most days are a well-balanced mix—roughly 50% gravel and 50% paved roads. The final loop typically includes less gravel than the other days, for a smoother finish and a nice change of rhythm.
Which bike is best for the white roads—gravel, e-bike, or e-gravel?
All three work beautifully on Tuscany’s white roads—we set each bike up with appropriate tires and gearing. The best choice depends on what you normally ride at home and the feel you want: a classic gravel bike for performance, an e-gravel/all-road option for extra support while keeping a sporty feel, or a trekking-style e-bike for comfort and an upright position.
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 +558 m / -565 m
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 an incredible breathtaking yet challenge gravel section that brings 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 51 km +872 m / -875 m
17 km asphalt and 34 km gravel
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.
Tonight at dinner you can reward yourself at least a glass of Brunello – we have a list of our favorite.
Distance 41 km +855 m / -807 m
17 km asphalt and 24 km gravel
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 58 km +1,015 m /-1,229 m
32 km asphalt and 24 km gravel
DAY 5
Today the destination is the town where the Eroica starts.
After your gourmet breakfast, head out into magical Chianti.
You will exit form Siena via a eroica gravel section Pieve a Bozzone, Vico d’Arbia making your way through wheat fields before we hit the vineyards of this celebrated wine region. Reach Pianella after 15 km. From here you will take a long glorious section to Canonica A Cerreto, Vagliagli. All riding through chianti classico vineyards, counting castles and old hilltop hamlets!
Get in Radda in Chianti for lunch time after 38 km ride – mostly gravel.
relax .. you have only 8 km to Gaiole following still the Eroica itineray. Last gravel stage: San Donato in Perano and Vertine are amazing, enjoy the breathtaking landscape.
distance 46 km +923 m / -874 m
12 km asphalt and 34 km gravel
DAY 6
Today is dedicated to explore all the villages and hamlet of Chianti Senese.
Start from your “castle di Spaltenna” in Gaiole and reach Castello di Brolio after 10 km. Here the caffe at agribar in front of winery is a must: all cyclists, locals and visitors seems to meet there.
After you can ride into the gravel section of Eroica, is short and then you will ride on very secondary scenery roads until Castelnuovo Berardenga. It worth a visit and if you are there for lunch time offer many options. Back to the saddle and encounter other small borgo: San Gusmé and villa a Sesta. Back to Brolio: to return to Gaiole you have 2 options, one road downhill and flat so somewhat easy, or challenge uphill to Castagnoli, downhill to castello di Meleto.
distance 54 km +1013 m / -1012 m
44 km asphalt and 10 km gravel
DAY 7
If you still have energy and feel your legs stronger you can have a short ride to Badia a Coltibuono a loop of 20 km
Back to Gaiole where you will leave bikes.
Departure: bus available to reach Siena where you can take fast train to other town
INFO TOUR
best period : from end of March to end of October
DIFFICULTY : medium to challenge
TOTAL DISTANCE : 275 km/ 172 miles in 5 stages
TOUR REVIEWS
Price
Cost: € 1790 per person – Price based on double accommodations
single room supplement € 790
What’s included
- Six nights in excellent five, four & three-star superior hotels
- Six breakfasts
- All Baggage transfer
- RideWithGPS App: tracks, route notes, off-line navigation
- Trip notes: Sightseeing & meals suggestions
- Delivery bike at Pienza hotel & bike fitting
- Pick-up of bikes and gear in Gaiole
- Keepsake Cicloposse water bottle
- Sales taxes
Not Included
Bike Rental per entire tour
Gravel bike, E-Bike € 260 | E-Gravel € 350
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.
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
Castello di Spaltenna is a beautiful 5-star hotel and one of those places that has a real “wow” effect from the moment you arrive – and it has long been a favorite with our guests. Set on a hill just above Gaiole in Chianti, it feels wonderfully peaceful and immersed in the Tuscan countryside, yet the village square is only about 600 meters away.
The historic castle combines traditional Tuscan character with a refined, elegant atmosphere, beautiful valley views, a swimming pool and spa. After a day on the bike, it is a wonderful place to slow down and enjoy the setting. For a special dinner, the property is also home to the fine-dining restaurant Il Pievano.
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Tour Reviews
Hello Giuliana,
Rick and I just arrived back in the USA and wanted to take a moment to let you know that we had a wonderful Gravel Bike Trip. We thank you for the extraordinary job organizing, responding and planning the tour. The hotels were lovely and everyone was so helpful. Your Bike Trip Handbook was very helpful and will be a treasured souvenir from our trips. We will definitely look into taking another bike tour with your company and have already passed the word on to many of our friends and relatives. Maybe Sardinia! We do not have Instagram but will share our five star rating on sites listed.
It was great working with you and I wish you the best with your tours this Summer.
Thanks Again,
Hi Giuliana,
We had such a wonderful week biking through Tuscany and were so pleased with you and your Cicloposse family. It was very enjoyable working with you and your company’s expertise allowed us to have a stress free week. We will certainly recommend you to everyone who inquires.
Thank you,
Hello Giuliana
Thank you for arranging a very fun and successful trip for all of us. We loved every day of biking and it was really just what we needed. The accommodations were also excellent and so was the gear.
we had no problems at all, … thank you again for all your coordination. We will definitely let others know about Cicloposse and will be in touch again if we want to travel elsewhere through Italy, or to have you connect us with a “partner” company in a different country who does similar tour organizing.
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