My family (8 adults, 2 toddlers) is planning a trip to Portugal in May. We have never been and are looking for some recommendations about where to stay/visit. We are thinking that we want to start in Lisbon for maybe 2 days and then move to another town/village for the rest of the time. We are looking for a charming town that is walkable and central to other day trips. Something that would be a good base for our family with enough to do in town for the days that we don't want to get in the car. Also hope to find something that is not too touristy. We have started looking around and are interested in towns like: Obidos, Averio, Evora, and Monsaraz. Again, we have never been so if there are better towns that we haven't found please recommend!

Two days is very short for Lisbon, which is also a base for good day trips - Belem, Sintra and Cascais/Estoril.

Obidos is irredeemably touristy. Evora is OK, but you would need a car for day trips, which could be a problem with that many people. Have you considered Coimbra?

Where are you arriving from?

For such a large group, you'd be best off with an apartment in Lisbon, but with only two nights, you would end up loosing to much time and energy waiting to check in and get settled in the apartment (no services), so go with a hotel.

Anyway, finding a 4 bedroom apartment anywhere will be a challenge. Villas are a better bet.

Obidos would be best as a day trip from Lisbon.

Aveiro is much larger with more to see. Monsaraz is nice, but a little isolated if you have any interest in seeing things, but then again one week doesn't give you much time to do anything challenging, like exploring the region.

Evora would be good for a few days, but you will need transportation if you want to get out and see things, explore the countryside and visit an Adega or two.

In May, you might want to consider Foz do Douro, the upscale coastal residential part of Porto. There are a decent number of apartments to choose from, it's walkable and only a few minutes from the center of Porto. No need for a car. Publich transportation is good and taxis cheap.

Thank you for the input! As I said, we have never been to Portugal before and know very little about the region so we're kind of doing this blind. If you were to plan a week long trip with a family what would be your itinerary? Lisbon is more cost effective to fly in and out of so we will have to start and end there. We don't want to move around too much so a good base to day trip from is ideal. The towns I suggested earlier were simply ideas. If there is anything better that we don't know of, please let me know!

If you have to fly in and out of Lisbon, I would just stay there. Moving ten people around will be a big hassle. Rent a couple of apartments and do day trips from Lisbon. You can do Evora and Obidos as day trips, in addition to the ones I mentioned already. If you do those you will barely have enough time for Lisbon itself.

My TR on Lisbon is old, but the sights haven't changed:

https://www.fodors.com/community/eur...ing-lisbon.cfm

There is a castle and parks and an aquarium for the toddlers, plus you can take a boat across the river.

Would you have a recommendation for a town just outside the city where we could possibly find a villa to rent?

Cascais area could be it - old seaside resort.