+1 for Settlers of Catan. The only downside is that it requires at least three players so if you and your son want to play alone, you can't do it. There is a card-based version of the game for two players though it's a bit hard to find. I think we picked up ours on Ebay.
DH and I played endless 2-player games of Settlers of Catan, including the island version, over the summer. My only recommendation is to not use the robber for 2 players.
Edit:
OK, now I've read through the thread, these are the games some of my friends and I play (in a largish group of 6 to 8, not sure how well they work for 2-3 players):
- Alhambra
- Tsuro
- 7 Wonders
- Dominion (might not be suitable for younger kids - I found the strategy/learning curve harder than for most other games I've played, but I do love playing it)
- Pairs (card game)
- Pandemic
- Carcosonne (only played this as a 2 player)
Card games with a normal deck of cards
- Whist (simpler form of bridge, I loved it as a kid but find it tedious now)
- 500 (was seriously addicted to this at university, played endless games)
- Gin rummy (there are many variants, some more fun than others)
-
HeartsSome people have mentioned Fluxx. I hate Fluxx cos I find it so tedious with zero strategy. I usually play one game to be social and then drop out.
For adults, Cards Against Humanity is hilarious fun, but generally utterly inappropriate for kids.