For a sailing experience in Oahu, you need go no farther than the beach in front of your hotel in Waikiki. Strung along the sand are seven beach catamarans that will provide you with one-hour rides during the day and 90-minute sunset sails. Pricewise look for $12 to $15 for day sails and $15 to $20 for sunset rides. They all have their little perks and they're known for bargaining so feel free to haggle, especially with the smaller boats. Some provide drinks for free, some charge for them, and some let you pack your own, so keep that in mind when pricing the ride.
Mai Tai Catamaran. Taking off from in front of the Sheraton Hotel, this cat is the fastest and sleekest on the beach. If you have a need for speed and enjoy a slightly more upscale experience, this is the boat for you. 808/922-5665.
Na Hoku II Catamaran. The diametric opposite of Mai'Tai, this is the Animal House of catamarans with reggae music and cheap booze. Their motto is "Cheap drinks, Easy Crew." They're beached right out in front of Duke's Barefoot Bar at the Outrigger Waikiki Hotel and sail five times daily. 808/239-3900. www.nahokuii.com.
Pirate Bar Hawaii. A true pirate vacation where the grog is always flowing and your "black jack" is always full (that's a drinking mug to you land lubbers), adventures abound once you set foot on their 80-foot Maxi, the only one of its kind in the Islands. Setting sail out of Kewalo Basin, they will teach you the real meaning of the "No Rules" cruise while sailing into the sunset with their all-pirate crew. It maxes out at 60 people so it's good to get reservations, ask for Captain Rabbit. 808/227-3556.