31 May – 6 June 2027
Deposit €299
To stay for a shorter or longer amount of time, please contact us
Level – Expert
When you think about Tuscany, as a cycling lover you immediately picture the iconic white roads, rows of cypress trees, and those rolling green hills that seem to go on forever.
We’ve created a one-of-a-kind gravel adventure that takes you through the heart of the region—immersing you in authentic Tuscan culture, world-class food and wine, and breathtaking landscapes.
This isn’t just a cycling trip—it’s a journey through vineyards, medieval villages, and hidden trails you’d never find on your own.
With 80% off-road riding, you’ll experience the real Tuscany, far from the tourist paths and close to its soul. Whether you’re chasing gravel dreams or just want to lose yourself in stunning scenery with like-minded riders, this is your chance.
Airport transfers
31/05/27 at 14:00 from Pisa Airport (PSA)
06/06/27 at 10:00 from accommodation to Pisa Airport PSA (1h 30 min drive to the airport)
Airport Transfers
Inbound
24/05
1:40 pm from PSA (Pisa Airport)
Outbound
30/05
10:30 am from Hotel to PSA (Pisa Airport)
LEVEL: Expert
Our expert tours involve challenging distances, climbs, and technical terrain. To ensure safety and enjoyment, we reserve the right to confirm that riders meet the necessary experience, fitness, and skill levels. Booking an expert tour indicates that you understand the demands and that your participation may be reviewed.
After the airport pick up, we head straight to dinner in the town of Castagneto Carducci for our first Tuscan Meal.
After dinner, setting up the bikes for the next day, when the gravel adventure begins!
From the start, we are in Gravel, through forest by the Tyrrhenian Sea.
After 15 km we go through the beautiful Bolgheri, where we find a famous stretch of Cypress trees for some nice pictures.
Half way through the ride, we start climbing. We go through Bocelli’s hometown Lajatico for then finishing in Peccioli.
On today’s route we go by some of the most beautiful villages of Tuscany such as Volterra & San Giminiano for then finishing in Colle Val’Elsa.
Up and down through medieval villages, and stunning contryside, where everywhere you look, is a postcard!
Possible the most beautiful day.
Shortly after starting we go through the town of Monteriggioni, then in the famous Piazza Del Campo in Siena for lunch.
After lunch, we continue heading south passing through section of the popular Strade Bianche for then soak in the most beautiful countryside that you can imagine when getting close to Pienza.
We have selected the best accommodation and location to ensure that our customers have the greatest experience possible available on-site.
There are many options available, depending on your measures and budget we work with you to find the best bike for you. From standard mechanical groupset and alloy wheels to electric shifting and carbon wheels.
Gravel E-bikes are also available.
GRUPPO: Sram Rival/Force AXS, Shimano 105, Ultegra, Durace Di2 and Mechnical
Professionals, with many years of experience.
Founder & Head Coach
Since founding Cigala Cycling Travel in 2015, Matteo has been leading over 10 tours per year. A former pro and current amateur racer, Matteo is the 2022 European Champion Gran Fondo.
Guide & Gravel Expert
Piero is a passionate cyclist with a keen eye for detail, a trait shaped by his full-time profession as an architect. He began his cycling journey in downhill mountain biking before discovering his true passion for gravel riding, which he now enjoys year-round, exploring new roads and trails in every season.