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For casual upscale dining with an island flair, try Fish House at Bluewater Point or Turtle Island.
Pop over to Southport and check out Provision Company for burgers, fish
sanwiches and steam shrimp. It's an outside restaurant right on the
boat harbor, so you can drive up by boat.
Oak Island Sub shop is a great place to pick up sandwiches for the beach.
Good cheap calabash (fried) seafood, try Captain Stanley's
For Ice Cream, try the homemade ice cream at the Tiki Hut and they have family karaoke for the kids.
Good cheap burgers, Little Bits, cheap and huge. Don't get the large unless you are really, really hungry.
Fine Dining choices include Chagall's, Mr.P's, or Live Oak Cafe. Call ahead to see if they are taking reservations.
For nightlife, realize that at any bar on the island, there is a mix of every type of person you can think of so the idea of nice nightclub versus dive really doesn't apply. Choices include Chaser's Beach Club, Pirate's Deck, Island Music, and 49th Street Station. These are private clubs so you must be a member, but memberships are cheap and you can often find someone to sign you in. And they usually don't get a crowd til late (10-11 pm)
Many of the restaurant's on the island have bar areas that are nice for an earlier evening out. There is a restaurant with an outside bar right on the ocean at the Oak Island pier.