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Possible multigenerational trip to Portugal, where to stay, what to do.

We're trying to plan a trip in June 2023 with extended family, 2 girls (10,14), 6 twenty-thirty somethings, 2 forty somethings and 5 seniors (all healthy and able to travel, carry luggage etc). We've considered Croatia and Crete but are concerned that there's too much travel involved (connecting flights, long drives to desired areas to stay) so now we're considering Portugal. I'm just beginning to research and would be interested in any ideas or suggestions of either where to stay (areas, cities) or ideas for activities.

We'd like to all stay together either in one house/villa or in several smaller apartments within a complex for about 5-6 nights. We'd like a location that's within an hour of Lisbon airport, preferably reachable by public or reasonable taxi/uber type service. Near a beach would be good but it doesn't have to be water front. Given the wide range of ages and interests, we'd like to be in walking distance (or easy public transportation) of various activities, like shopping, hiking/walking, swimming, museums, restaurants, night time activities. Some of us may consider renting a car if it's needed, but we aren't likely to have enough cars to hold everyone at once so we'd also be interested in hiring a car/van-driver if we want to do a full-group activity/day trip.

Thanks in advance for any info.

Posted by
1826 posts

There are a number of smaller towns within an hour of Lisbon airport that might fit your wish list. Your biggest challenge might be finding a place large enough for your entire group. Vacation rentals - Airbnb, etc. - are a big thing in Portugal, so it might be possible. However, Portugal works hard to not allow several vacation rentals in the same condo complex, but finding a couple (or three) within close proximity might work.

On this side of the river, Cascais, Estoril or possibly Sintra might work. On the other side, Setubal or Sesimbra might be places to explore.

It’s very easy to find a driver with a van for transport, provided you can all fit in a large van.

You might start by researching the above cities to see if any of them sound attractive. I’m happy to give feedback on Cascais, Estoril and Sintra.