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Seacrets is the big bar down there...it's this multiplex sort of thing, they usually have several bands playing, there are tons of different rooms that have different kinds of music, it backs right up to the bay...it's pretty cool. It's on 53rd street, I highly recommend it.
Fager's Island is another good one, their big night is Monday when they have a deck party, but my friends and I went on a Friday and there was still a good crowd, and they had live music. It's on 60th street, bayside.
Macky's on 45th (I think) is another cool place, they have a back yard beach on the bay side that has a bunch of long tables and solo cups on them so you can play beer pong or flip cup if you so desire.
The boardwalk is pretty long, there are tons of stores and places to eat, but then again there are tons of stores and places to eat all up and down Coastal Highway. Also, in Rehoboth Beach (in Delaware, about 20 mins away) there are a TON of outlet stores and DE shopping is tax-free so if you have bad weather one day or you're sick of the beach, it's a good place to go.
Have fun!
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