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Italy
Lombardy
Sondrio
Tovo Di Sant'Agata

Valtellina Trail

Hard

3.7

(3)

10

hikers

Valtellina Trail

07:42

27.9km

460m

Hiking

Hike the difficult 17.3-mile Historic smugglers' route to Valgrosina valley (CAI Trail 205), gaining 1506 feet over 7h 41m.

Last updated: February 26, 2026

Tips

Your route passes through a protected area

Please check local regulations for:

Waypoints

A

Start point

Parking

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1

3.95 km

Stone Stairway

Highlight • Structure

2

7.10 km

Palazzo Pievani and Church of San Giacomo

Highlight • Religious Site

I really enjoyed it here too.

Translated by Google •

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3

7.18 km

Piazza Marinoni War Memorial

Highlight • Monument

Monument to the Caduti - Gardens of Piazza Marinoni
War memorial: Commemoration of those who fell in the First and Second World Wars.

Translated by Google •

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4

7.28 km

Sacred Heart Church

Highlight • Religious Site

That's right, the church belongs to the monastery.

Translated by Google •

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5

7.40 km

Tirano Town Center

Highlight • Settlement

The city of Tirano is the capital of the municipality of the same name in the Italian province of Sondrio, Lombardy region with almost 9,000 inhabitants.
The settlement developed on …

Translated by Google •

Tip by

6

7.58 km

Poschiavina Gate

Highlight • Historical Site

The pedestrian bridge is beautifully integrated into the old city fortifications

Translated by Google •

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7

7.77 km

Church of San Carlo Borromeo

Highlight • Religious Site

Little church dedicated to S. Carlo Borromeo
This church, part of the Palazzo Salis, is the first in Valtellina to be dedicated to this saint.

Translated by Google •

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9

9.27 km

Scenic Walking and Cycling Path

Highlight • Cycleway

With separation for cyclists

Translated by Google •

Tip by

10

9.58 km

Small Pond Rest Area

Highlight • Lake

There is a fountain where you can drink.

Translated by Google •

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B

27.9 km

End point

Parking

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Way Types & Surfaces

Way Types

12.1 km

9.75 km

3.27 km

2.58 km

108 m

< 100 m

Surfaces

16.7 km

6.37 km

3.21 km

1.06 km

522 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (720 m)

Lowest point (440 m)

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Weather

Powered by Foreca

Sunday 17 May

15°C

6°C

83 %

Additional weather tips

Max wind speed: 5.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it take to hike the Historic smugglers' route to Valgrosina valley (via CAI Trail 205)?

This challenging hike typically takes around 7 hours and 42 minutes to complete. Keep in mind this is an estimated moving time, and you should factor in additional time for breaks, enjoying the scenery, and navigating the difficult terrain.

What is the difficulty level and terrain like on this route?

This is classified as a difficult hike. The Valgrosina valley is known for its wild and rugged landscape, featuring steep climbs, mule tracks, and narrow paths with significant elevation gains. You can expect varied and strenuous terrain, including historical stone steps, making it suitable for experienced hikers.

What can I see along the Historic smugglers' route?

The route offers breathtaking natural scenery, including dense woods, watercourses, and wide alpine pastures. You'll also encounter several points of interest, such as the Stone Stairway, the Palazzo Pievani and Church of San Giacomo, and the Poschiavina Gate. The trail also passes through Tirano Town Center, where you can see historic sacred buildings.

Is the Historic smugglers' route to Valgrosina valley dog-friendly?

While the trail itself doesn't explicitly prohibit dogs, its difficult classification, rugged terrain, and significant length mean it's best suited for fit dogs accustomed to long, strenuous hikes. Always keep your dog on a leash, especially in areas with wildlife or near steep drops.

What is the best time of year to hike this trail?

Given the challenging nature and potential for snow at higher elevations, the best time to hike this route is typically from late spring through early autumn (May to October). Always check local weather conditions and trail reports before you go, as winter conditions can make the trail impassable or extremely hazardous.

Do I need a permit or pay an entrance fee for this hike?

Based on available information, there are no specific permits or entrance fees required to hike the Historic smugglers' route to Valgrosina valley (CAI Trail 205).

Where does the trail start and what are the parking options?

The tour data indicates the route starts near Tirano, passing through the Tirano Town Center. For parking, you would typically look for public parking areas within Tirano or at the nearest accessible point to the trailhead. Specific trailhead parking for CAI Trail 205 isn't detailed, so planning your start point and parking in Tirano is advisable.

Does this trail intersect with other well-known paths?

Yes, the route also passes through significant sections of the Sentiero Valtellina (covering 65% of the route) and smaller portions of the Sentiero del Sole and Sentiero Italia - Tappa D30N.

Is the Historic smugglers' route suitable for families or beginners?

No, this trail is classified as difficult and is not recommended for families with young children or beginner hikers. The rugged terrain, steep climbs, and significant length require a good level of fitness and hiking experience.

What makes this trail historically significant?

This route is notable for its historical significance as a smugglers' route. These paths were historically used for clandestine trade, often involving goods like sugar and tobacco, between Italy and the Austro-Hungarian Empire. Smugglers deliberately chose impervious and suggestive locations to evade border guards, making these trails inherently dramatic and often leading through less-traveled, wilder parts of the mountains.

Are there any amenities like cafes or accommodation near the trail?

The trail starts near Tirano Town Center, which offers various amenities including cafes, restaurants, and accommodation options. As you venture further into the Valgrosina valley, amenities become scarce, so it's essential to carry sufficient supplies.

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