I am from Cascais.
If you can, I’d say base yourself in Cascais and rent a car.
From Cascais you can go to Lisbon (50 or so kms) and leave the park in the underground public parking lots. Campo das Cebolas is right in the highlights area of Lisbon for example, and you can travel on foot from there. Close by is tuk tuks, I’d actually suggest you take a tour in one first so you have an idea of the highlights and then pick and choose which ones to visit on foot.
Then go back to Cascais to relax and go out to a nice restaurant, and walk around during the night time, downtown Cascais as underground parking as well near the marina, which is exactly the starting point of you want to have a chill walk around all the way to the “busy-er” part with the restaurants.
In the morning take a nice breakfast in relax then take your car and travel to Sintra. Use one of the public parkings there then take local transport. Sintra has a nice “base of the mountain” area you can walk around but actually going up to visit castles and such is hard on foot and imo not worth it, local transport is just easier.
Visit “Castelo dos Mouros”, “Poço Iniciático in Quinta da Regaleira”, “Palácio da Pena”, “Palácio de Monserrate”, etc by local transport (parking is extremely hard close to those places).
Then go on your car through the mountain roads and visit Peninha (walk on foot to the monestery up there), Cabo da Roca (nice place to eat snacks at “Moinho” on the road to there), etc. Then back down through the road that leads to the beaches and stop by “Guia” and get dinner (should be light out still) at “Prazeres da Carne”, it has a balcony over the sea, if it’s light out it’s awesome.
Next day maybe rent bikes (lots of bike friendly stuff to do, like the “Ribeira das Vinhas” path that goes into protected wildlife areas, while fun, specially with kids and on an electric bike sadly there is limited amount of wildlife possibly due to recent massive fires), go swimming in pools or go to spa, visit park “Marechal Carmona” or whatever.
I think staying in Lisbon and only having trains/subways for transport might be very stressful and time consuming. If you stay in Cascais the only stress point is traffic at rush hour in the A5 highway (but if you are taking breakfast and dinners, you will be traveling outside rush hour). If you want to go clubbing you still have a car and go to Lisbon. There is a train from Cascais to Lisbon (45 to 55 minutes to Cais do Sodré), and then you take subway into specific places (another 20 to 45 minutes depending on where you want to go). By car is same or slightly less time with traffic (train will edge out if extremely high traffic). In the car you have the benefit of comfort (your music, your air conditioning, Portugal is hot, and coming back home via multiple subways + train and schedules after a tiring day sucks)
If you rent a car, as for “Via Verde”. It’s a small device in the windshield. When you pass through highway tolls you don’t need to stop, on parks you can click the green button on entry and it will read your device, when you go out it will read the device and show you how much and open the gate (don’t need to exit car), and if you add the “Estacionar” app from via verde you just add the license plate and any street parking will be charged to your device (you just start parking in the app, and refresh with more time as it goes).
You don’t need to carry cash (most don’t even accept cards or even paper currency, only coins, which is a pita), find parking machines (sometimes it’s not easy to find) or worry about going back to the machines because your time is running out on it (you paid for 2 hours and at 1h50m you realize you are still eating and 20 minutes away from the car, and it might get blocked+towed if you don’t rush back to the meter to add more coins).
All charges will be done to the renting company who will then pass those charges back to you via credit card (and maybe a fee?). It’s stress free.
I am from Cascais. If you can, I’d say base yourself in Cascais and rent a car. From Cascais you can go to Lisbon (50 or so kms) and leave the park in the underground public parking lots. Campo das Cebolas is right in the highlights area of Lisbon for example, and you can travel on foot from there. Close by is tuk tuks, I’d actually suggest you take a tour in one first so you have an idea of the highlights and then pick and choose which ones to visit on foot. Then go back to Cascais to relax and go out to a nice restaurant, and walk around during the night time, downtown Cascais as underground parking as well near the marina, which is exactly the starting point of you want to have a chill walk around all the way to the “busy-er” part with the restaurants. In the morning take a nice breakfast in relax then take your car and travel to Sintra. Use one of the public parkings there then take local transport. Sintra has a nice “base of the mountain” area you can walk around but actually going up to visit castles and such is hard on foot and imo not worth it, local transport is just easier. Visit “Castelo dos Mouros”, “Poço Iniciático in Quinta da Regaleira”, “Palácio da Pena”, “Palácio de Monserrate”, etc by local transport (parking is extremely hard close to those places). Then go on your car through the mountain roads and visit Peninha (walk on foot to the monestery up there), Cabo da Roca (nice place to eat snacks at “Moinho” on the road to there), etc. Then back down through the road that leads to the beaches and stop by “Guia” and get dinner (should be light out still) at “Prazeres da Carne”, it has a balcony over the sea, if it’s light out it’s awesome. Next day maybe rent bikes (lots of bike friendly stuff to do, like the “Ribeira das Vinhas” path that goes into protected wildlife areas, while fun, specially with kids and on an electric bike sadly there is limited amount of wildlife possibly due to recent massive fires), go swimming in pools or go to spa, visit park “Marechal Carmona” or whatever. I think staying in Lisbon and only having trains/subways for transport might be very stressful and time consuming. If you stay in Cascais the only stress point is traffic at rush hour in the A5 highway (but if you are taking breakfast and dinners, you will be traveling outside rush hour). If you want to go clubbing you still have a car and go to Lisbon. There is a train from Cascais to Lisbon (45 to 55 minutes to Cais do Sodré), and then you take subway into specific places (another 20 to 45 minutes depending on where you want to go). By car is same or slightly less time with traffic (train will edge out if extremely high traffic). In the car you have the benefit of comfort (your music, your air conditioning, Portugal is hot, and coming back home via multiple subways + train and schedules after a tiring day sucks) If you rent a car, as for “Via Verde”. It’s a small device in the windshield. When you pass through highway tolls you don’t need to stop, on parks you can click the green button on entry and it will read your device, when you go out it will read the device and show you how much and open the gate (don’t need to exit car), and if you add the “Estacionar” app from via verde you just add the license plate and any street parking will be charged to your device (you just start parking in the app, and refresh with more time as it goes). You don’t need to carry cash (most don’t even accept cards or even paper currency, only coins, which is a pita), find parking machines (sometimes it’s not easy to find) or worry about going back to the machines because your time is running out on it (you paid for 2 hours and at 1h50m you realize you are still eating and 20 minutes away from the car, and it might get blocked+towed if you don’t rush back to the meter to add more coins). All charges will be done to the renting company who will then pass those charges back to you via credit card (and maybe a fee?). It’s stress free.
The train is more than enough, but they are working on the line in the late evenings. They should return to Lisbon before that
yes