Maremma Challenge: 500km of pure wonder in the heart of Tuscany

Starting in the main square of Massa Marittima, ‘Piazza San Cerbone’, considered one of the most beautiful late-medieval squares in Italy, the tour will continue through rolling, hilly landscapes and along singletrack for several kilometers. We’ll ride through the amazing beech woods of Mount Amiata, finishing the day in Castel del Piano for a lovely dinner and overnight stay.

From Castel del Piano we’ll ride towards the wonderful medieval town of Roccalbegna and on to Sorano, Pitigliano and Sovana, the world-famous towns perched on a cliff of local turf stone. A 100-km ride immersed in the most enchanting landscapes, with the chance to discover the stunning local historical heritage.

The best panoramic views are yet to come, as we ride from Sorano towards the beautiful Tyrrenean coast. We’ll cycle through Manciano, where the wind blows from every direction and captivating views surround you, from the Amiata to the Argentario, to the islands in the Tuscan Archipelago. En route, we’ll take a relaxing break at the thermal hotsprings and waterfalls, Cascate del Mulino, located a few kilometers from Manciano.

Today we’ll will ride through vineyards, olive groves, nature reserves and dense pine forests. The route is varied with minimal elevation gain and includes gravel and asphalt roads.

Our ride starts with a sweeping panoramic view of Porto Santo Stefano bay, its old port and exclusive marina. We’ll cycle in the shade of the evergreen maritime pine forest that stretches along the coast before reaching the breathtaking Diaccia Botrona Nature Reserve, considered the most important wetland in Italy and a real paradise for birdwatchers.

We’ll end the ride in Castiglione della Pescaia, an enchanting medieval town and fishing village nestled between blue sea and green hills. The destination is renowned for its crystal-clear waters, sandy beaches, wonderful panoramic views of the coastline and culture.

The final day on the route promises breathtaking panoramic views and truly unspoiled natural landscapes. We will cycle through nature reserves and medieval villages that hug the seashore, making several stops along the way to enjoy the glorious views along the coastline, including towards the islands of Elba and Montecristo. The Maremma Challenge reaches its finale as we return to Massa Marittima.

The Maremma Challenge experience isn’t complete without a final day off the bike to relax and enjoy a local wine tasting, guided tour and exquisite dinner in one of the best wineries of the region.