Sintra Coastal Hill Circuit

A sheer endless network of lonely trails branches through the western part of the Sintra Hills. In a magical, overgrown forest, nestled between tourist hotspots on the coast and Palácio da Pena, one really gets away from it all on this short circuit. It is but one variation of many possible routes that I suggest and illustrate with additional photos. Shared running/hiking/mountain-biking trails offer excellent, moderately technical trail-running fun with steep ups and downs. High above the countryside, sweeping vistas from palace ruins take in magnificent stretches of coastline – all the way to Cascais and the Lisbon suburbs.

As usual, I started in the middle of pretty Ulgueira village, my base to explore the hills and coast on several runs. To the south a small trail tunnels underneath the main road, where it branches out in all directions through eucalyptus groves and dense forest covered in ferns. Several worthwhile, technical trails lead up towards the Santuário da Peninha getting steeper as we head trough distinctly varied layers of vegetation up the mountain side.

The famous Sintra micro climate is especially relieving on hot days up here. A layer of perpetual fog rolling in from the ocean and caught in the branches gives the forest a spooky appearance: moss-covered trees and granite rock form an intricate, otherworldly maze. I hardly met a soul before the hills finally opened up to spectacular views and a fresh breeze at the peculiar Peninha Sanctuary settlement. Perched on top of a rocky outcrop that forms one of the highest Sintra peaks, the Palace of Peninha and the ruined remains of a hermitage invite to explore (the intact buildings are closed to the public, but all outdoor areas are accessible and offer views to Cabo da Roca Lighthouse and into the hills).

Sweeping vistas open wide to Praia do Guincho in the south, one of the best surf spots near Lisbon, all the way across to the busy town of Cascais. The route continues holding the elevation gain along wide, comfortable tracks as it heads deeper into the hills.
A worthwhile, longer alternative (last four photos of the gallery above), popular with mountain bikers, heads down south and runs one level below along the mountain side with spectacular views, fields of bright wild flowers and a holy spring with crystal clear spring water – a network of trails leads back up to converge with the main route near Tholos do Monge.

The level forest track soon reaches the next peaks, Tholos do Monge, an ancient grave site adorned by a weird plinth, and a memorial cross embedded in large rocks. From the highest point of the run a new maze of trails heads downhill. Small, technical trails and beautiful tracks criss-cross dense eucalyptus forest – some bike paths are not accurately mapped, but tend to converge further on along the main tracks.

The trail emerges from the forest, with glimpses of Pena Palace in the distance, to cross the picturesque village of Penedo along steep cobble-stoned alleyways.

A hidden track through a deep creek valley leads back to Ulgueira avoiding paved roads. The delightful variety, views and technical paths that really get you away from the hustle and bustle of the tourist hotspots made this one of the best routes of the region for me – definitely worth exploring several alternatives!

An adventurous alternative route leads straight to the north from Santuário da Peninha to the stone-age megalith grave site of Anta de Adrenunes and on to Pé da Serra on the main coastal road. Through mystical forest on narrow, technical trails we come across a paved road, which marks the edge of an area badly hit by wind-thrown trees in 2025. From here on out paths blocked by trunks are common, but navigable – especially the start of the trail up to the megaliths is hidden and heavily blocked, as is the eastern downhill trail back to the road. If you don’t mind pausing the flow for some off-road adventure, it is very impressive.