DH and I will usually hit both. We're big Jimmy Buffett fans and must always take a field trip to sit on the Porch of Indecision and swill margaritas and other assorted boat drinks. Also, Emeril's is right next door, and that's good for a fantastic dinner.
As for PI, well, the Adventurers' Club is our biggest draw. Good drinks and interactive comedy -- right up our alley! I am curious to peek in the soon-to-be opened Irish pub, too. Guinness is my friend!
Cheers,
Q
I know I do sound Bias but I rather do Pleasure Island since there are other stuff you can do prior to going to the PI ( like eating a seafood broil at the Fulton's Crab House ) we tried City Walk again in 2002 and again we did not find a good crowd. But again maybe it was just us.
Well, with the semi-new ungated policy, inside/outside doesn't mean so much anymore, you can wander around wherever (outside) for free. As someone else mentioned, it's outside, over towards the marketplace end. If you're looking for restaurants, there's also Portobello Yacht Club, a tasty Italianish kinda place.
We have been to both many times, with and without the adult children. The entire family prefers City Walk. We find the food/clubs more lively, more entertaining. Definately a better variety.