WB: C-street and Mase and Sweetwater and all sorts of chill places around WB. Its rad.
Out front, or c-street, is without a doubt the best spot on the island. Its a reef/pointbreak and the wind always blows offshore. There is always at least a 1-2 foot overhead wave breaking there. It's pretty much always spitting, glassy barrels. It's almost never crowded either. No one ever surfs there. You can basically jump out into the lineup with dry hair and pull right into the wave of your life without having to dodge any other surfers or swimmers. Nowhere else on the island is even worth a try, just pull right up to the gravel lot behind sweetwater, grab yourself a spot, wax up your stick while macking on the plentiful womenfolk, then mosey on down to the best shred spot on the planet and post up for the day. When you get done with your always perfect, unstressful sesh, you can go chill with the boyz at sw and talk about the shacks you scored while the ladies oooooed and ahhhed on the beach. Don't even bother looking elsewhere because its pretty much the onpy spot worth going.
Grab a 10 ft soft top and head right to the south end. Park in any driveway down there you like, the residents don't mind. Stroll out to the surf zone and paddle right out in the middle of the 100 or so guys packed in there. Everyone is very friendly, so just strike up a conversation if you like or just enjoy all the waves they will share with you. Grab a shower under the house that you parked at - cause the residents don't mind that either...then you're on your way. That's what locals do, so you will fit right in.