hi everyone - My family will be spending this spring on a sabbatical in Portugal from late Feb to late May. We are trying to decide between a few different possible rental homes as a base (Both of us will work from home with small amounts of onsite research near Linho, Sintra.) We have had some people urge us to stay in lisbon proper, and others keep suggesting Cascais, and we are having trouble determining which best suits our needs. We have a 5 year old, who likes being outside, parks, meeting other kids, and the usual 5 year old stuff. We are hoping to be car-free and able to get around easily on foot and by public transportation for entertainment and necessities. Lastly, we will take 2-3 trips during our day that involve getting to the airport and/or car rental agency. Any suggestions? Will Cascais be a resort ghost town in the spring or is there life there year-round? If Lisbon, any neighborhoods you suggest with easy access to parks/green space/family-friendly ambience? Can anyone give me a sense of what it is like to live in Cascais, as opposed to vacation? Many thanks! (I should add that we speak only a tiny amount of Portuguese, but hope to build on Spanish and learn some. That said, we will probably be most comfortable somewhere with at least some kind of Anglophone community.)

There is life in Cascais year-round but it is a rather small town with much less possibilities than Lisbon. For example eating out - the choice is much bigger, food much better and prices generally lower in Lisbon.
I lived for half a year in Campo de Ourique district in Lisbon and I think it suits your requirements well, as do nearby places (Rato, Estrela). There are several smaller and bigger parks around including the beatiful Jardim da Estrela with a big kids playground. The area is lively but not touristy. And there is even an English language amateur theatre, The Lisbon Players (http://www.lisbonplayers.com.pt/site/about-us).

Thanks so much - I really appreciate the thoughtful post. We have one possibility on rue de adelas in Principe Real. Am I right in thinking that's quite near the neighborhoods you describe?

That's also a very nice location (I know this neighbourhood) but prepare for walking up and down a lot - the neighbourhood is on a quite steep slope. Definitely for car-free living (a car is rather a nuisance in Lisbon in my opinion anyway).
Anyway, you would be a few steps from the beatiful Praca das Flores, a short walk (uphill) to Jardim do Principe Real (one of the best parks in Lisbon) and maybe 10 minutes walk (first downhill to Rua Sao Bento then very steep uphill) to the Jardim da Estrela. The area is not too touristy.
If you have no mobility issues I would accept it. If someone from your family has mobility issues, I would look for somewhere more flat.

PS. I'd also recommend you to do a virtual walk of the neighbourhood using Google Street View - it gives a good idea on what to expect.

Have stayed in both Rato (seven days last year) and Principe Real (on two occasions) and didn't have any problems apart from the slopes mentioned above - some mobility problems here, but I just shift down a gear and take the gradient in my stride!
We've usually walked around Lisbon, so we've taken good walking shoes with us and we've also used Viva Viagem rechargeable travel cards to get around on public transport via buses, trams, trains and the Metro.
No problems at all when eating out - we've visited a couple of places listed in guidebooks and also found places for ourselves that have been more than satisfactory and didn't hit us in the wallet or pursestrings too hard.
On thing we would mention is to keep some small change in a pocket or whatever as we had a couple of problems in shops etc when we first got to Lisbon last July. We only had € notes and no small change to pay for either bottles of water or ice creams - not a biggie, but it made for interesting situations as we don't speak Portugese or Spanish!
Such matters aside, we used both Preco and Pingo Doce mini markets and supermarkets last year whilst in Lisbon or on our September road trip around Northern Portugal and had no problems in sorting out food for meals in hostels or with the choice of items or fruit for snacks etc.

Yes, walking is the best way to go around in Lisbon and if you live in Principe Real you will walk through a very nice area starting right from your doorstep :)

Thanks for these wonderful suggestions. We do plan to stick to walking/transit. We have discovered that for our son, the only English-speaking school options are in Estoril or Carcavelos, so would need to be able to reach transit to those spots. We don't have any mobility issues and love walking, but do have a 5 year old who walks slower than adults! Is there a pleasant neighborhood of Lisbon that is not too hilly and fairly close to cais de sodre, where the train goes out to the schools? (If not, we may go for Cascais.... ) Thanks again!

Actually this place in Principe Real you mentioned is not so far from Cais do Sodre, maybe 20 minutes walk and never boring. A bit more on the way back, as the last stretch after the Parliament would be uphill.
I always walked to and from Cais do Sodre from my flat in Campo de Ourique which was about double the distance and much higher - took maybe 30 minutes down, 45 up.
Anyway, I simply cannot believe there are no English language schools in Lisbon proper. Maybe try to look again? Ask on this forum or other expat forums? http://www.expat.com/forum/viewforum.php?id=354

Thanks, Meczko. Your perspective is really helpful. I was surprised about the school thing, too, but have had several local parents confirm my impression that for whatever reason, the int'l/British/American schools are all in Estoril/Cascais/Sintra rather than in the city itself. More expats there, maybe? Or just more space?
Anyway, I think we will end up making Cascais the base. We would also consider Belem/Restelo, but fewer short-term rentals there. Speaking of which - do you (or anyone else) know of a good agency that does longer-term rentals? (Most websites, airbnb/homeaway, cater to shorter-term vacationers). We need a furnished rental for 3 months and so have a nice-sounding possibility in Cascais. But any and all other suggestions welcome!