A hardened place of rocky outcrops, marshes and undulating hills that abut a dramatic coastline of cliffs and long windswept beaches, the Province of Grosetto is far from most people’s vision of the quaint Tuscan countryside. But for those who love to cycle, it is a landscape of plenty.

Writer Matt Phillips cycles down the road, which sits on the edge of a cliff - behind the barriers sits the Mediterranean and the forested islet of L'isolotto © Paolo Ciaberta
Cycle the Costa d'Argento to see some truly stunning coastal scenery, such as this section on the peninsula of Monte Argentario © Paolo Ciaberta

Little-trafficked roads and trails (Grosseto is one of the least densely populated areas of Italy) snake through its varied terrain, offering head-turning views, access to ancient sites and challenging climbs to historic hilltop towns whose beauty will vanquish any remaining breath. And come breakfast, lunch and dinner, your exploits in the saddle will only afford you a larger appetite to relish the famous cuisine of Tuscany. As they say, a meal earned tastes so much the sweeter – perhaps that's why so many come to the region for active holidays.

The weather in the area makes adventures on two wheels a very pleasant possibility from early March to late October. There are almost two-dozen set cycle routes through the region, but here are a couple of our favourites.

The image is looking over a green, forested gorge to the grey stone buildings of Sorano protruding from the trees and poking into a cloudy sky © Matt Phillips / Lonely Planet
The view across the gorge to Sorano from Chiesa di San Rocco © Matt Phillips / Lonely Planet

Città del Tufo: Sorano, Sovana & Pitigliano

This challenging 49km loop, with some 830m of elevation changes, winds its way through Città del Tufo and its three historic hilltop villages of Sorano, Sovana and Pitigliano. Along the way it takes in hot springs, ancient sunken roads and plenty of stunning vistas.

The route starts some 3km south of Sorano at a thermal spring that has attracted visitors since the Middle Ages. As you head north the immediate area around Sorano offers some incredible views of the town and its steep fortifications; one of the best, found at the back of the grounds of the Chiesa di San Rocco (an old Catholic church), is a slight detour west of town along the SP22. Once you’ve enjoyed Sorano itself, and perhaps downed your first espresso of the day, hop back on the bike and pedal north towards Montorio to see its castle, which was first constructed in the 12th-century by the Aldobrandeschi noble family. From there aim your handlebars south to cycle through the diminutive and charming villages of Castell’Ottieri, Elmo and Grotte Cavalieri. En route you’ll get to absorb some panoramic vistas of the valley.

 A cyclist stands atop a rock platform looking at rudamentary dwellings hewn from the rock © Mario Llorca / mariollorca.com
A cyclist admiring the ancient ruins within Città del Tufo Archaeological Park © Ciclica & Foto Mariollorca.com

Shortly after joining the SP22 and pedalling east towards Sovana, it’s worth stopping to explore one of the region’s archaeological treasures: Parco Archeologico Città del Tufo. Here you can walk or cycle (if you’re riding a mountain bike) through several steep vie cave (sunken roads) that were hewn out of the tufo rock in ancient times. These may have been part of a sacred route connecting Etruscan necropolises and other religious sites, or simply corridors for safely moving livestock and people in times of war. Also at the site is Tomba Ildebranda, a 2nd- or 3rd-century BC tomb carved into the rock that is considered to be one of the most important monuments in the region.

A cyclist stands out of the saddle and pedals up a hill with the village of Pitigliano in the background © Paolo Ciaberta
Pulling power: the hilltop village of Pitigliano lures plenty of cyclists to make the climb there © Paolo Ciaberta

From the archaeological park it’s a short climb to the idyllic village of Sovana, with its herringbone-bricked main street that dates back to Roman times. Stop for a bite to eat or drink and to check out the pair of simplistic Romanesque churches: the Duomo and Santa Maria Maggiore. Descend east from here before turning south onto the SP46. The road continues to wind down until you approach the most stunning village of the day – Pitigliano.

A cyclist leans over his handlebars onto a low wall and gazes out over a towering aqueduct with beautiful arches in the hilltop village of Pitigliano © Ciclica & Foto Mario Llorca.com
The view of Pitigliano's aqueduct and city walls is well worth stopping for © Ciclica & Foto Mariollorca.com

Early sightings of Pitigliano perched atop a towering volcanic outcrop are both inspiring and daunting, but the overwhelming need to see more keeps the pedals turning. Once inside town, you’re treated to an array of storied architecture: a beautiful 16th-century aqueduct, its arches dancing along the ramparts and down to precarious rock faces; sinuously curved staircases mysteriously climbing to and fro; some incredibly well preserved town gates and walls; and a Jewish museum and impressive synagogue dating back to 1598. Another remnant of the once considerable Jewish population here is its influence in the local cuisine.

A cyclist climbing up a steep road, with his head turned away from the camera and towards the impressive medieval skyline of Pitigliano © Ciclica & Foto Mariollorca.com
Making the climb south out of Pitigliano, where there are plenty of head-turning vistas © Ciclica & Foto Mariollorca.com

Leaving Pitigliano is a slow process, mostly due to the need to stop and take photographs of it from the opposite side of the gorge. It’s worth making the climb south along the SR74 to the first switchback, where the view can only be called stupendous. From here make a 180 and head north back towards your day’s starting point or pop back to Pitigliano for a meal and well-deserved night’s rest.

Two stark cement piers (each hosting a cyclist) reach out into the Orbetello Lagoon, which is reflecting the blue sky above © Paolo Ciaberta
Paths to nowhere, but worth the short trip: a couple of piers in Orbetello at the start of the Costa d'Argento route © Paolo Ciaberta

The Costa d’Argento: Orbetello & Capalbio

This 69km coastal loop takes in stunning coastal scenery, winds you through serene forests and still gets your heart rushing while climbing to the splendid hilltop village of Capalbio. Although 20km longer than the Città del Tufo itinerary above, the Costa d’Argento is less demanding due to far fewer hills.

Starting (and finishing) at Orbetello’s train station, this route’s access couldn’t be any easier. Located on a narrow isthmus jutting into its eponymously named lagoon, the town itself is rather laidback and low-key. Pedal west along town’s northern shore before crossing onto the rocky peninsula of Monte Argentario. The standard itinerary takes you immediately back across the southern side of the lagoon, but we’d strongly suggest making the detour up the western side of Forte Stella before looping back and descending along the jaw-dropping section of coastal road overlooking the island of L'Isolotto all the way down to the colourful harbour of Porto Ercole's old town. From there, follow the coast onto the heavily forested isthmus that separates the Mediterranean from the southern side of the Orbetello lagoon. The nicest way to cross this long, narrow section of land is to get off the road and cycle the smooth dirt trail in the forest that backs Playa del Can.

Two cyclists on foot explore the ancient Roman ruins, with the lagoon of Orbetello in the distance © Paolo Ciaberta
Ruins of the Roman city of Cosa, found within the archaeological park atop the atop the hillock of Ansedonia © Paolo Ciaberta

History calls, this time pulling you up to the summit of the nearby Ansedonia hillock – the site of an archaeological park protecting the ruins of the Roman city of Cosa. After exploring the site, its petite museum and the sweeping views over the lagoon and coast, descend on your bike northwards.

With his bike leaning against the crenulated ramparts, writer Matt Phillips looks out over the green rolling landscape to the Costa d'Argento © Ciclica & Foto Mariollorca.com
Writer Matt Phillips looks over the Costa d’Argento from the ramparts of Capalbio © Ciclica & Foto Mariollorca.com

By now you’ll have seen the lofty village of Capalbio beckoning ahead, and now is the time to make your ascent there. It’s the first substantial climb of the day, and after a flat stretch along SP Pedemontana, you’ll head up the switchbacks of SP Capalbio. There are a couple of extremely steep sections once inside the walls of the village, but keep pushing until you reach the courtyard with steps up to the top of the ramparts. Take your time catching your breath once you’ve reached the top, as you’ll have plenty to look at – vistas stretch over the green fields to the distant Costa d’Argento.

Two cyclists walk their bikes along the boardwalk that backs an endless section of beach at Chiarone Scalo © Ciclica & Foto Mariollorca.com
A short detour off the coastal road at Chiarone Scalo leads to a beautiful stretch of beach © Ciclica & Foto Mariollorca.com

After a well-earned meal in Capalbio, roll eastwards towards Pescia Fiorentina then turn south for the coast. At Chiarone Scalo you’ll find a seemingly endless stretch of beach – it’s the perfect place to lose your shoes and dip your feet in the sea. It’s now a relatively flat route back to your starting point in Orbetello via the coastal road.

Matt Phillips travelled with support from Visit Tuscany. Lonely Planet contributors do not accept freebies in exchange for positive coverage.

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