Sintra & Cascais: Private Day Trip with Hotel Pickup

4.97

(412 reviews)

What’s the experience like?

“Here, the fog is like a blanket,” said João as we wound up the road into Sintra. I could smell wet moss and something sweet from the pastry shop we’d just passed — honestly, I was still half asleep but that woke me up. João didn’t rush us; he pointed out tiny details on the Pena Palace tiles that I’d have missed (some are chipped from when kids used to play here, apparently). The colors of the palace looked brighter than I expected against all that mist. My shoes got a bit muddy — should’ve worn boots — but it felt right for this place.

We ducked into Quinta da Regaleira next. The tunnels were colder than outside, and my friend tried to spook me by whispering “initiation” as we climbed down the spiral well (I laughed but also gripped the rail tighter). João told us stories about secret societies with this glint in his eye — not sure how much was true, but it made everything feel more alive. At Monserrate Palace, the mix of Arab and Indian patterns was almost dizzying. There was this old gardener who waved at us while pruning roses; his hands looked stained from years of work.

Cascais surprised me — it’s busier than I thought but has this relaxed air. We stopped for lunch at a place João likes (he knows everyone there), and the grilled fish tasted like it had just come off a boat. I tried to order in Portuguese and got a big smile from our server, though I probably mangled it. Afterward, standing at Cabo da Roca with wind whipping around us, João said quietly, “This is where land ends.” It hit different hearing it out loud; you really do feel small looking out over all that water. The day trip from Lisbon to Sintra and Cascais wasn’t what I pictured — somehow messier and better. I still think about that view sometimes.