Itinerary ... Thoughts?!

Lisbon, Sintra and Cascais are easy without a car, but Mafra will be harder. I would suggest renting the car for Mafra and Tomar. If you don’t want to rent in Lisbon, Cascais has a Europcar right across the street from the train station and might be a good place to pick up your car.

That said, with only four nights in Lisbon, I doubt you will have time for three day trips. Sintra will take an entire day - and you still won’t begin to see everything. I would suggest Quinta da Reguleira in Sintra as a place your boys will love. And, your boys might enjoy Batalha more than Obidos.

Hi Julie
I agree with teenage boys you should look for an apartment. We had good luck with VRBO. The other thing you could consider is Hostels. Lisbon is reported to have some very nice ones and I believe you can get a family room. Our friends did that with teen girls.

I'm not sure I would recommend 2 nights in Tomar. My husband and I did that last April, and wished we had only stayed one. It is a pretty town, but not a lot to do other than the castle. I think I might add to Coimbra or switch to Nazare if you could get some beaching in. We did find with our teens that they always want a couple of beach days if possible.

Sintra has a lot to see, so I would not cut it short. The Quinta de Reguleira is a cool spot for kids to explore.

I would look into your Douro cruise before you decide on accommodations. We ended up not doing as it looked like a very long day to get to the prettiest parts. If we go again our plan is to hit Douro with the car first, and if possible drop somewhere there and boat in to Porto. I am not sure if this is logistically possible.

You could easily spend the whole time in Lisbon and not run out of things to do. Unless you have a burning desire to visit Coimbra, I would drop that stay and add that day to Lisbon.