Next time I will stay in Cascais longer and day trip to Lisbon.
I had been worried reading that Cascais was over-developed and resorty. Well, it is not tacky at all and is very upscale. Think Capri, Cannes or Mykonos. Lots of tourists, but there is a reason for that.
Charming old town, with cobblestone winding streets to get lost in. Old buildings, outdoor restaurants around open squares, lots of beaches, a marina, museums,,,, So what if on the way to town you pass a macdonalds? and, there are some designer boutiques on the outskirts.
Overall, the town retains its charm, and doesnt have loads of tacky cheap t-shirt and postcard stores (has some, not overrun with them).
Great base to visit Sintra as well.
If you own or manage Cascais Old Town, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.