Just out of Ala Wai Harbor, in the shadow of Diamond Head is the world famous Waikiki Beach. Not everyone realizes but this is a perfect place for a casual day sail or sunset cruise. With Diamond Head sheltering from the Trade Winds, the water is usually calm here. Lots of charter sailing cruises operate in this area, with a few catamaran cruises picking up passengers for booze cruises from beach.
At one point in the middle of Waikiki, the "bight" you can get close enough to shore to anchor in 15 ft of water and sandy bottom, just outside of the surf break. You probably wont be alone though, since this popular anchorage is the happening place to have a boat party. Aloha!
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