I'm travelling with my family (boys ages 9 & 12) this summer to Portugal. Currently I'm planning on spending 4 nights in Lisbon, and then was going to do 2 nights in Sintra but I'm wondering if Cascais would be a better place to stay than Sintra? We are heading to Madeira after so we don't necessarily need more beach time, but just wondering if the vibe in Cascais is more chilled and enjoyable than Sintra would be? Or would it be recommended to just stay in Lisbon the entire time and do day trips to Sintra and Cascais? TIA!
Day trips are easy by train and give you more flexibility.
Cascais is definitely a day trip. There is something to be said for a night in Sintra though, maybe on the day before you fly out to Madeira?
Several years ago we stayed in Lisbon 4 nights and took a day tour with Lisbon Riders to Sintra & Cascais. Our guide was Manuel. He was knowledgeable and engaging. It was a wonderful introduction before our time in Lisbon and tour of Portugal. This type of tour would be great for a family. I have recommended this company to others on this forum. Most recently this past year. Positive responses. https://lisbonriders.com/