Tuscan Maremma Grand Detour

Arrive independently · hotel check-in
Our Tuscan Maremma Grand Detour begins in the city that serves as both the start and end of the tour. After dropping your bags at the hotel, a walk through the old town alleyways is a must. You’ll feel a calm, relaxed atmosphere — a pace far removed from any big city.

Before leaving the historic center of Grosseto, we recommend a visit to the Medici Walls — a green, fully pedestrian walkway that wraps around the oldest part of the city. A stroll here before you set off should not be missed.
And then you get in the saddle.
Before leaving the plains, we make a stop at Roselle: here, you’ll walk among the ruins of a city that was first Etruscan, then Roman. A small journey back in time that continues in Vetulonia.

The climb to Vetulonia is the first real test for your legs. At the top, a small village of just over a hundred inhabitants will greet you, but you’ll quickly see there’s more to this place than just the wonderful sea views. (like Roselle, Vetulonia was one of the most powerful city-states of ancient Etruria). The descent brings us back to sea level through the Diaccia Botrona Natural Reserve, where flamingos move slowly through the shallow waters. The day ends in Castiglione della Pescaia.

There’s a beach in Tuscany where the sand sounds like a violin. It’s not a legend: it’s called Cala Violina, and it’s our third stage. We’ll arrive by bike along a road immersed in Mediterranean scrubland — the same road Grand Duke’s soldiers marched in the sixteenth century, which is why it’s called Via dei Cavalleggeri (the Cavalrymen’s Road).
55 kilometers with the scent of rosemary and salt blending together as you gradually approach the sea, all the way to Cala Violina, one of the most famous beaches in Tuscany. A unique sensory experience before heading back.

You leave the sea behind and climb inland. Before the grand finale, a stop that’s worth the entire ride: Lake Accesa, where you can swim and rest. Even here, only a few steps from the lakeshore, Etruscan ruins are waiting to be explored. The archaeological area is free to enter.
From here it’s time to head toward the day’s destination: Massa Marittima. A one-of-a-kind village where Piazza Garibaldi and the Duomo with its iconic staircase open up suddenly after the climb — one of those moments that no photo can capture.

On this fifth stage we’ll reach a place where the earth breathes. The Biancane Natural Park, at the gates of Monterotondo Marittimo, is a landscape unlike anything you’ve seen so far: white steam rising from the ground, bubbling mud pools, a sulfur smell that cuts through the air. Geothermal energy in its purest form. The place is so unusual it’s also known as the Iceland of Maremma. Don’t miss the Mubia Museum and, on the way back, Monterotondo Marittimo: a village powered entirely by geothermal energy.

64 kilometers, nearly 1,200 meters of elevation gain: the kind of day on the bike you’ll remember for years. We’ll ride toward villages that over tourism hasn’t reached yet. Prata is one of them: a small, quiet village tied to the story of Pia de’ Tolomei — the woman Dante Alighieri mentions in Canto V of the Purgatory, the second book of his Divine Comedy, with one of its most celebrated verses: “Remember me, who am La Pia.” From Prata we move on to Tatti, a village where a walk through its narrow lanes and alleys feels like stepping back into the Middle Ages.
Roccatederighi opens with a panorama over Maremma that alone is worth the climb. Then Casal di Pari: birthplace of Aurelio Galleppini, the illustrator who gave a face to Tex Willer — the cowboy hero of Italy’s longest-running and best-selling comic book series, in print since 1948 and translated into dozens of languages worldwide. A hamlet of a few houses that shaped the Western imagination of millions of Italian readers. The day ends in Pari, overlooking the Farma and Ombrone valleys.

The day begins downhill, toward the Petriolo Hot Springs. The sulfurous water at 43°C — perfect for a soak — flows all the way into the Farma river. The route then crosses Paganico, a walled village with a Sienese fortress still perfectly legible in the stone. The stage culminates in Campagnatico, on a hilltop overlooking the valley — a village that Dante mentioned in the Purgatorio, proof that some things endure.

The climb toward Mount Amiata begins. But first, we cross Cinigiano: we’re in the heart of the Montecucco wine region, home to one of the three wines that define Maremma, all Sangiovese-based. Then Monticello Amiata and Arcidosso, where the legend of Davide Lazzaretti still lingers — a self-proclaimed prophet who in the late nineteenth century gathered thousands of followers around him and founded a spiritual order called the Giurisdavidici.
The stage ends in Santa Fiora, a medieval village built around a fish pond fed by the springs of the Fiora river. Don’t miss the Chiesa della Madonna della Neve, right next to the pond, where you can see water flowing beneath the church floor. Inside the Pieve delle Sante Flora e Lucilla, you’ll find the Robbiane — glazed terracotta works by the Della Robbia family, one of the great artistic dynasties of the Italian Renaissance.

The highest stage of the entire tour: 1,531 meters of cumulative climbing over 44 kilometers. The ascent to the summit of Mount Amiata — an extinct volcano — is demanding. What you’ll find at the top is a view that takes in Grosseto, the sea, and Lazio all at once. Every meter of climbing is repaid by the panorama and the peacefulness.
The route continues toward Merigar, one of Europe’s most important international centers for Tibetan Buddhism, set among the woods of Amiata. Then Monte Labbro, where Davide Lazzaretti’s Giurisdavidica Tower still marks the skyline.

From the fire mountain you descend into what is known as the Tufa Area. The landscape changes completely: colors, scents, even the type of rock. The route leads to Sorano, built on a tufa outcrop much like Matera in southern Italy — which is why it’s known as the Matera of Maremma. And then the Vie Cave: paths carved by hand by the Etruscans into the tufa, up to ten meters deep, connecting settlements like hidden arteries beneath the countryside.
The stage ends in Pitigliano, the Little Jerusalem — a village built on a tufa cliff that seems to rise from the earth itself. For centuries it was home to one of Tuscany’s most established Jewish communities: synagogues, ovens for unleavened bread, and ritual wells, all still open to visitors.

From Pitigliano we pass through Sovana, one of Italy’s officially recognised “Most Beautiful Villages,” with its iconic Piazza del Pretorio. A walk here is a must. Then back in the saddle — and before reaching the Cascate del Mulino, we arrive at the Muro del Pirata, an ascent dedicated to the late Marco Pantani, one of the greatest professional cyclists of all time and the last rider to win both the Tour de France and the Giro d’Italia in the same year (1998). Pantani used to train in this very area.
After the Muro, we reach the Cascate del Mulino at the Saturnia Hot Springs: water at 37°C cascading over a series of natural rock pools. You stop, you soak. The stage ends in Montemerano, a heart-shaped medieval village, perfect for those who love places suspended in time.

A stage that keeps changing. We ride through Manciano, nicknamed the Spy of Maremma for its panorama that stretches across most of the horizon, and then reach Capalbio, also known as the Little Athens, with its charming old town and the unmissable walk along its walls.
Along the route you’ll see enormous colorful sculptures emerging from the Mediterranean scrubland. These are the works of the Tarot Garden by Niki de Saint Phalle — a magical place reminiscent of Parc Guell in Barcelona, but here the sculptures are inspired by tarot cards. Riding on, we pass the Burano Lake Oasis, the first WWF-managed nature reserve ever established in Italy. We cycle further past the ruins of the Roman city of Cosa before reaching the Orbetello Lagoon, where flamingos keep us company once again.

The Argentario is no ordinary promontory. The panoramic road that circles it runs right on the edge between sea and sky: to the left, the islands of the Tuscan Archipelago; to the right, the lagoons. We ride with the wind in our faces and the feeling of being exactly where we’re meant to be.
The route leads to Porto Ercole, a fishing village built when the Spanish ruled this coast. It was here, in July 1610, that Caravaggio died — the revolutionary painter whose dramatic use of light and shadow transformed Western art, and whose masterpieces hang in major museums around the world. After Porto Ercole we continue to Porto Santo Stefano, then head back to Orbetello.

Day 14 takes us to Giglio Island, departing from Porto Santo Stefano. Once on the island, we immediately begin the climb to Giglio Castello: the medieval village perched on top of the island, with narrow alleys and views that embrace the sea in every direction. 940 meters of cumulative climbing over 44 kilometers on an island leaves no room for half measures, but what you’ll find at the top is worth every switchback.
The route then descends toward the Capel Rosso Lighthouse, on the southern tip: cliffs plunging into the sea, nothing but the wind and the waves. Before heading back to the port, take a break at Cannelle Beach.

One of the sharpest transitions of the entire trip: you leave the blue of the sea and climb toward the green hills of Morellino. The ascent is constant, the views over the Argentario grow with every switchback. Along the route, you’ll pass the remarkably well-preserved walls of Magliano in Toscana, and then the ruins of the Abbey of San Bruzio, where legend has it that fate itself dwells. The stage ends in Scansano, capital of Morellino di Scansano, a wine whose origins date back to the time of the Etruscans.

The last day begins with a descent toward the sea. From the Morellino hills you ride down to Talamone, a seaside village tied to Giuseppe Garibaldi — the nineteenth-century general who led the unification of Italy. It was here that his legendary expedition of the Thousand stopped to load weapons and ammunition before sailing to Sicily.
The route then runs alongside the Maremma Natural Park — pine forests, scrubland, beaches with no umbrellas, where wildlife goes undisturbed and protected. The final stretch follows the bike path along the Ombrone river, until Grosseto reappears with its Medici Walls. The loop is complete.