The calçadas are slick on many walkways in Sintra. The historic center sees so many footfalls that have polished the tiles to a sheen. Take extra care—they’re treacherous in the rain.
That’s why it’s so nice to find pathways that feature encroaching moss instead. The magic of the fantastical town magnifies on these winding trails. They not only give you a way to avoid the thrust of people visiting the main attractions in town, but also an invigorating way to get to them.
Little cupid in a frame guiding our way up a forest path in Sintra 
Steps up to a shop along an alleyway in Sintra
We’d come upon the main trail leading up from town to the Castelo dos Mouros and Palácio Nacional da Pena when we were looking for a climbing wall that we’d seen from a hike near Monserrate. Back when you could easily drive through the center of town, we took the road up to the monuments, stopping at a parque de merendas, a “picnic park” where we found the trail up to the climbing area—and that continued on up to the top.
The glorious facade of the Palacio de Seteais 
You might miss the sign: A Rampa da Pena marks the path across from Seteais
I’d also heard of another trail, one of the pequenas rotas, the paths marked with yellow and red blazes that criss-cross the country. It began near the grand Tivoli Palacio de Seteais, and I went searching for it on a cloudy autumn day. The signpost pointed the way, and I hiked up about a kilometer—all that my time allowed that day. But I met only two other couples on the trail. I considered that alone to be a win, but its cool, green emeraldness enchanted me, and I vowed not to go up to the top again any other way if I could manage it.
The deeply shaded path up to Pena from Seteais keeps you out of the summer sun 
Boulders strewn along the path up to Pena from Seteais
So when friends visited in July, and wanted to see the famous Pena Palace, I met them after scaling the main path from town, which begins off of the Estrada da Pena, though you branch off of the main road at its fork with the N375, and continue to climb. I raced to the top, not wanting to have them wait—and I recommend the hike only to those ready for a stair climb, punctuated by a few easy segments through the stones and trees. There are plenty of places to stop along the way for a rest or to contemplate an old, overgrown fonte.
Graffiti brightens up one of the paths up to Pena from Seteais 
A mossy fountain on the path up to Pena in Sintra
One of these I noted on the way up, Casa das Minas, and the Paradise Art School. We caught a tuk-tuk back down, and when our chosen café, Tascatinga, was closed for vacation, we walked back up to the school to see if they had a place for us. Looking out over the Palácio Nacional de Sintra from its perch—and surrounded by funky works of art and listening to tunes on an out-of-tune piano—we had relatively pedestrian sandwiches and indifferent white wine by the carafe. But it was quiet and away from the crush we’d experience when we headed back below, to brave those shiny calçadas to find souvenirs and take pictures of the gorgeous azulejos that tile the town.
A quirky café provides a restful stop before descending into the fray of Sintra’s historic center 
Looking over the valley from above the center of Sintra, with marigolds competing with the National Palace