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Italy
Tuscany
Arezzo

Sestino

The best walks and hikes around Sestino

4.5

(852)

3,416

hikers

17

hikes

Hiking around Sestino offers diverse natural landscapes within the Tuscan-Romagnolo Apennines, characterized by impressive limestone formations and extensive woodlands. The region features the Sasso di Simone and Simoncello Nature Reserve, known for its dramatic flat-topped calcareous rocks. Nearby, the Alpe della Luna Nature Reserve adds to the varied terrain with wooded ridges and stream-carved slopes. This area provides a range of trails suitable for various skill levels, set against a backdrop of significant geological features.

Best hiking trails around Sestino

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Last updated: June 30, 2026

4.6

(11)

42

hikers

#1.

Cliffs of Sasso Simone – View of Sasso Simone loop from Case Barboni

7.10km

02:34

330m

330m

Moderate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.

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Moderate

Moderate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.

Moderate
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Hard hike. Very good fitness required. Mostly accessible paths. Sure-footedness required.

Hard

Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Tips from the Community

Ale Ferri
September 1, 2025, Sasso Simone

Handsome

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Highly recommended, watch out for cows with ticks and those that stand in front of the gate without moving

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Beautiful, well kept

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Hi, roughly how far is Sasso Simone from Sella dei Sassi? I mean without climbing up πŸ˜…. Thanks!

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area equipped with tables and barbecue, shaded, excellent for a break

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at the bivouac when there was snow ═══════════════════ 152nd excursion and 9th time at 2 Sassi | from Passo Cantoniera to Sasso Simone and Monte Simoncello with snow | Carpegna ══════════════════ πŸ‘‡ here is the video in Full HD (1080p) πŸ‘‡ https://youtu.be/2XEAFGqqrEs

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Conceived by Cosimo I de' Medici in the spring of 1554, on the borders of the Marche on one of the most inaccessible peaks of the Apennines, the fortress city of Sasso Simone was an expression of the ambitious policy of the grand dukes of Tuscany But the daring project soon failed: defeated by the hardships and terrible climatic conditions, the inhabitants fled after just 10 years. The structures began to deteriorate more and more, until, in 1674, the city was already totally ruined and its dismantling was ordered to recover reusable materials.

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Sestino is an Italian municipality located in the province of Arezzo, Tuscany. With 1,210 inhabitants, it is the easternmost municipality in the region and is located 79 km from the provincial capital. Geographically, Sestino is part of the Foglia valley, which mainly belongs to the Marche, but administratively it is part of Tuscany. This road center connecting the Adriatic lands and the Tiber Valley is located on the slopes of the Umbria-Marche Apennines, on the border with the Marche and Emilia-Romagna. Its altitude is 496 meters above sea level. The history of Sestino dates back to Roman times. In the 1st century BC, the Romans began the construction of a large city with a forum, curia and baths, which today we can admire in the National Antiquarium. Over the centuries, Sestino changed ownership and status, belonging to the Malatesta family of Rimini and subsequently becoming an autonomous vicariate established by Pope Paul II. In 1520, it was assigned to Florence by Pope Leo In addition to its history, Sestino also offers other attractions, such as the Visitor Center and the Antiquarium Museum, which tell the story of the evolution of the Sasso Simone Reserve, a natural area of great interest.

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Frequently Asked Questions

What kind of hiking trails can I expect in Sestino?

Sestino offers a diverse range of hiking trails within the Tuscan-Romagnolo Apennines. You'll find routes characterized by impressive limestone formations, extensive woodlands, and varied terrain. The region is home to the Sasso di Simone and Simoncello Nature Reserve, known for its dramatic flat-topped calcareous rocks, and the Alpe della Luna Nature Reserve with its wooded ridges and stream-carved slopes.

How many hiking routes are available in Sestino?

There are 17 hiking routes available around Sestino. These include 2 easy trails, 11 moderate trails, and 4 difficult trails, catering to various skill levels.

Are there any easy hiking options for beginners or casual walkers?

Yes, Sestino offers easy hiking options. There are 2 routes specifically rated as easy, perfect for beginners or those looking for a more relaxed walk. The majority of trails are moderate, providing a good balance of challenge and accessibility.

What are some notable natural features or landmarks to look out for on the trails?

Hikers can explore several significant natural features. The most prominent are the Sasso di Simone and Simoncello, impressive limestone boulders that form the core of a nature park. You can also find the Sasso Simone itself, a large flat-topped rock. The nearby Alpe della Luna Nature Reserve features wooded ridges, rock spurs, and slopes carved by streams and springs, including the distinctive crescent-shaped Ripa della Luna.

Can I find circular hiking routes in Sestino?

Yes, many of the popular routes in Sestino are circular. For example, the Cliffs of Sasso Simone – View of Sasso Simone loop from Case Barboni is a moderate 7.1 km loop, and the Cliffs of Sasso Simone – View of Sasso Simone loop from Petrella Massana offers a 8.5 km moderate circular path.

What do other hikers say about the trails in Sestino?

The hiking routes in Sestino are highly regarded by the komoot community, with an average rating of 4.5 stars from over 600 reviews. Hikers often praise the varied terrain, the stunning views of the Sasso Simone rock formation, and the immersive experience within the nature reserves.

Are there any historical or cultural points of interest along the hiking trails?

Beyond natural beauty, Sestino's region offers historical sites. Hikers can visit the Hermitage of Saint Alberico, a religious site nestled in a deep gorge, offering both natural beauty and a sense of solitude. Additionally, the area includes the Passo Marco Pantani (Cippo di Carpegna), a historic cycling climb that also appeals to hikers interested in its legacy.

What is the best time of year to go hiking in Sestino?

Hiking in Sestino is enjoyable across seasons, but autumn is particularly recommended for its beautiful views and vibrant foliage, though trails can be muddy. Spring offers pleasant temperatures and blooming nature. Summers are generally warm, while winter can bring colder conditions, especially at higher elevations.

Are there any castles or ancient villages to explore near the hiking routes?

Yes, the area around Sestino features several historical sites. You can explore the Petrella Guidi Medieval Village, or discover structures like the Monteboaggine Tower and Castello della Pieve, which add a historical dimension to your outdoor adventures.

Are the hiking trails in Sestino suitable for families with children?

Many of the moderate and easy trails in Sestino are suitable for families. The diverse landscapes and natural features like the Sasso di Simone offer engaging experiences for children. It's advisable to check the specific route details for distance and elevation to ensure it matches your family's fitness level.

Can I bring my dog on the hiking trails in Sestino?

Generally, dogs are welcome on many hiking trails in the Sestino area, especially within the natural reserves. However, it's always recommended to keep them on a leash, especially in protected areas or near wildlife, and to check for any specific local regulations or signage on individual trails.

Where can I find parking for the hiking trails in Sestino?

Parking is typically available near common starting points for trails. For routes around the Sasso di Simone, you can often find parking in villages like Case Barboni, Petrella Massana, or Carpegna, which serve as access points for various loops.

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