Cycling the Tuscan Coast: Pisa to Grosseto, with a Ferry to Elba

Pisa is where the journey starts. Before the ride, a walk through the center is not to be missed. Piazza dei Miracoli, the Cathedral, the Baptistery, the Tower — leaning just a little more than you expected. Pisa was one of the four Maritime Republics: in the Middle Ages, it ruled the Mediterranean with its merchant and military fleets. Tomorrow the ride begins. Tonight, soak up the city.

You leave Pisa’s Tower behind and start riding. The Via dei Cavalleggeri is waiting: the road patrolled by the Grand Duke’s soldiers in the 16th century, built by the Medici to watch over every stretch of Tuscan shoreline. Long sections remain exactly as they were — original dirt track, Mediterranean scrubland on both sides, the sea glimpsed through the trees.
You pass through Livorno, then the coast narrows and steepens until you reach Castiglioncello — a village perched on a headland, dropping straight into the sea.

From Castiglioncello you ride toward one of Italy’s most celebrated wine landscapes: the vineyards of Bolgheri, where Sassicaia wine is born. You arrive through the pine forest, then the view opens onto the vines and the cypress-lined avenue leading to the village — the same road the poet Giosuè Carducci immortalized in his ode “Davanti a San Guido.” A stop in Bolgheri for a wine tasting, then back in the saddle, with the sea for company again.

The day starts on two wheels, riding to catch the ferry to the Island of Elba.
Just over an hour across the water and you reach Portoferraio, with its fortified walls — the same ones that watched Napoleon arrive in exile in 1814. You ride through the old town, up and down the narrow streets, then on to the beaches of Le Ghiaie and Biodola. In the late afternoon, the ferry brings you back to Piombino.

Before leaving the coast, there’s Follonica: the town that Leopold II of Lorraine built around the Grand Duchy’s Royal Imperial Foundries in the 19th century. Cast iron here isn’t just industrial history — it’s still in the architecture, in the doorways, in the details you notice when you slow down. Then the route stretches along the entire gulf, from Piombino to Punta Ala. In some sections, you’re back on the original Via dei Cavalleggeri. At a certain point, through the Mediterranean scrubland, the sand changes sound underfoot: you’re at Cala Violina, the beach named for the sound the sand makes when you walk on it. On the horizon: Elba, Montecristo, Cerboli, and Palmaiola. Then Castiglione della Pescaia: a fishing village ringed by medieval walls, facing the sea.

The final stage is the most Maremma of them all. Before reaching Grosseto, you ride through the Parco Regionale della Maremma: here the Butteri — Maremma cowboys — still work as they always have, on horseback, with herds of horses and Maremma cattle grazing in the wild. This isn’t a historical reenactment. It’s a vibrant present. Then the last kilometers toward Grosseto, the capital of Maremma: you enter through its 16th-century walls, still fully intact and among the best-preserved in Italy. Here, you reach the end of your incredible journey with us.

On the last day, you can head home or extend your stay.