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Italy
Tuscany
Arezzo

Riserva naturale del Sasso di Simone

Routes
Cycling routes
Italy
Tuscany
Arezzo

Riserva naturale del Sasso di Simone

The best cycling routes around Riserva naturale del Sasso di Simone

4.4

(70)

1,793

riders

105

rides

Touring cycling routes around Riserva naturale del Sasso di Simone traverse a landscape characterized by distinctive limestone cliffs, including the flat-topped Sasso di Simone and Simoncello, and diverse forests. The region features extensive turkey oak woods and varied vegetation, providing a constantly changing backdrop for cyclists. Hilly and mountainous terrain, with Monte Carpegna as the highest summit, offers a range of cycling challenges. This area combines significant natural features with historical attractions, making it suitable for outdoor activities.

Best touring…

Last updated: June 2, 2026

5.0

(1)

19

riders

#1.

Pennabilli – Pennabilli loop from Petrella Massana

39.7km

02:52

840m

840m

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Popular around Riserva naturale del Sasso di Simone

Hiking around Riserva naturale del Sasso di Simone

MTB Trails around Riserva naturale del Sasso di Simone

Road Cycling Routes around Riserva naturale del Sasso di Simone

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Gravel biking around Riserva naturale del Sasso di Simone

Tips from the Community

Fede e Sonia
December 27, 2025, Orto dei Frutti Dimenticati

209th hike | Pennabilli loop starting from Villa Maindi ═════════════ 👇 Here's the 4K video 👇 https://youtu.be/Szbrl2NGvlQ

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Valentin
September 2, 2025, Passo Cantoniera

Very nice and flat pass!

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To infinity and beyond....

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It's the first step that our parents took us since we were little. To go on the snow or in the summer to take a walk to Sasso Simone and Simoncello. Always green, fresh. Now I come there by bike and it's always a new discovery.

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penna1973
November 18, 2024, Passo Marco Pantani

Marco Pantani pass, on Montefeltro a few steps away, view of the valley

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Iconic climb dedicated to the memory of Marco Pantani, short and intense, often above 10%.

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Here there are pretty much all difficulties between 4a and 7a. The "Rock of Orlando" is approx. 15 m high and there is even a bell to ring at the top🔔.

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Super beautiful nature at Monte Canale.

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Frequently Asked Questions

How many touring cycling routes are available in Riserva naturale del Sasso di Simone, and what are their difficulty levels?

The Riserva naturale del Sasso di Simone offers over 100 touring cycling routes. The majority, 93 routes, are classified as difficult, while 11 are moderate. There are no easy routes specifically for touring cyclists in this area, indicating a landscape generally suited for those with good fitness.

What kind of natural features can I expect to see along the touring cycling routes?

The region is defined by its distinctive limestone cliffs, Sasso Simone and Monte Simoncello, which are prominent landmarks. You'll also cycle through extensive turkey oak woods, considered among the largest in Europe, and diverse forests. Higher elevations feature upland meadows that burst with wildflowers in late spring. The varied topography includes hills and low mountains, with Monte Carpegna being the highest summit, offering a constantly changing and picturesque backdrop.

Are there any particularly challenging touring cycling routes for experienced riders?

Yes, the area is known for its challenging terrain. For instance, the Alley to Castel di Sopra – Viewpoint of Sasso di Simone loop from Petrella Massana is a difficult 47.7 km route with over 1,400 meters of elevation gain, leading through areas with prominent limestone cliffs and panoramic viewpoints. Another demanding option is the Rocca di Pietrarubbia – Ascent to Monte Carpegna loop from Carpegna, covering 55.2 km with nearly 1,700 meters of ascent.

What historical sites or landmarks can I explore while cycling in the region?

The area is rich in history. You can explore the remnants of "Città del Sole" (City of the Sun), a fortified city that Cosimo I de' Medici attempted to build in the 16th century, including the Ruins of Sasso Simone Fortress. The region also has a history of pagan cults, medieval merchants, and pilgrims. The distinctive profile of the Sassi themselves has historically served as a crucial landmark.

Are there any touring cycling routes that offer panoramic views?

Absolutely. The region is renowned for its exceptional vistas. The Alley to Castel di Sopra – Viewpoint of Sasso di Simone loop from Petrella Massana specifically highlights panoramic viewpoints. On clear days, views from Sasso di Simone can extend all the way to the Adriatic Sea. The Sella dei Sassi also offers evocative views for those traversing the region.

What is the best time of year for touring cycling in Riserva naturale del Sasso di Simone?

Late spring is particularly beautiful, as the upland meadows around Monte Carpegna transform into a vibrant carpet of orchids, crocuses, and buttercups. The diverse forests also provide a beautiful and constantly changing backdrop throughout the warmer months. Autumn offers different beauty with moss and mushroom scents. It's advisable to check for accessibility information, especially regarding the Military Range of Carpegna, which can have restrictions.

Are there any loop trails for touring cyclists in the area?

Yes, many of the touring cycling routes are designed as loops, allowing you to start and end in the same location. Examples include the Pennabilli – Pennabilli loop from Petrella Massana, a 39.6 km trail, and the Alley to Castel di Sopra – Passo della Spugna loop from Case Barboni, a difficult 36.1 km path with significant elevation gains.

What do other touring cyclists enjoy most about cycling in Riserva naturale del Sasso di Simone?

The routes in Riserva naturale del Sasso di Simone are highly rated by the komoot community, with an average score of 4.4 stars from over 60 reviews. Cyclists often praise the diverse landscapes, the challenge of the hilly and mountainous terrain, and the stunning panoramic views, especially from the distinctive limestone cliffs.

Is it possible to spot wildlife while touring cycling in the reserve?

Yes, the reserve is home to a rich variety of animal life. You might encounter wolves, foxes, deer, skunks, and various birds such as hawks, owls, and woodpeckers. The diverse forests and meadows provide habitats for these species, offering opportunities for wildlife spotting during your rides.

Are there any visitor centers or amenities available for cyclists in the region?

The Interregional Natural Park of Sasso Simone and Simoncello has visitor centers in towns like Pietrarubbia, Pennabilli, and Sestino. These centers often offer equipped areas, fauna museums, and environmental education facilities, which can serve as useful starting points or points of interest during your touring cycling adventures. There is also a Picnic Area with Tables and Barbecue available.

Are there any specific routes that are particularly famous or iconic for cyclists?

One iconic route for cyclists is the Marco Pantani Pass – Ascent to Monte Carpegna loop from Carpegna. This 20.5 km route with over 700 meters of elevation gain is a tribute to the legendary cyclist Marco Pantani and offers a challenging climb to Monte Carpegna, the highest summit in the area.

Most popular routes around Riserva naturale del Sasso di Simone

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