Not too sure what it's like now, but I have stayed twice at the Estoril Eden with my wife and kids.
It's a wee bit soulless, but they have/had comfortable self catering apartments as well as more traditional rooms.
Close by Monte Estoril station but also walkable to Tamariz Beach in Estoril and Praia da Rainha etc at Cascais. Taxi rank outside.
The only problem I ever experienced there was down to its use as a conferencing facility. NATO were hosting a multi-national confreence. Families of attendees were invited and spent their days lazing by the pool.
My wife and I got to know a few of the senior officers - Dutch mainly, and lovely people.
The behaviour/attitude of the "British wives" towards hotel staff and other guests was embarrassing.
Sorry - off topic but just a memory which flooded back as I thought about this.
We are a similar family and I have been looking at this area for our summer week.
The only concern I have is that it is too quiet and there would not be enough to do.
Is Cascais too quiet?
This might be abit late but as you said you are going at the end of June/Summer thought I'd reply.
Have just returned from Cascais from 1 week spent at Vila Bicuda. Late Rooms website offered a good deal on the accomodation. That was absolutely lovely, just perfect, if not a little bit out of the town centre / beaches for what you are looking for, although if you have a car its no problem at all in the day, then just get a taxi at night (4.5 euros to Cascais town).
It generally is a laid back town with lots of nice restaraunts and cafes you can sit out in. However, if you have teenagers there are a few bars in the centre of Cascais that are quite lively, including O'Neills, Palm Tree and the Bally Bally pub. They would be good for definately a couple of nights.
If they want more of a club, there is Coconuts which is the large dance club which is meant to be really good, although I didnt get chance to go. This is on the other side of the Marina from Cascais town but in easy walking distance.
Then there is always the train into Lisbon which is really cheap and safe. It takes at most half an hour with absolutely no hassle. Takes you right into the centre of Lison really easily and safely, where there is so many bars and so much nightlife you are spoilt for choice.
Trains runs every 15 mins until around 1 am. Worst scenario you miss that, there is always a taxi from Lisbon which was around 25/30 euros.
I would recommend accompanying them into Lisbon and you can split up and they can have their night out and you could go to a traditional Fado night (no earlier than 8.30pm though) and have some lovely traditional portugese food while listening to the beautiful music, just meeting up when time to go home everyone happy.
Never got chance to go to Estoril so much else to do so can't help there.
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