‣ Hawaii Kai, Oahu
Oahu is a mecca of downwind paddling, and its signature run is the nine-mile Hawaii Kai. Whether your craft of choice is an outrigger canoe, surfski or standup paddleboard, Hawaii Kai is a rite of passage. Start at the vowel-laden Kuliouou Beach Park, just 20 minutes east of Waikiki off the Kalanianaole Highway (H-1). To avoid the rudder-eating reefs, head out through the channel markers to the point at Portlock where the sea crashes off the sheer cliffs. For the full monty, bash up the striated wall toward Hamauma Bay. When you turn at the entrance to the bay, it's game-on. Swift rollers will lead you ever closer to the hulking profile of Diamond Head, the extinct volcano that resembles the brow of a giant tuna. Just off the lighthouse at Black Point, the swell steepens, providing the world's warmest sleigh ride. Once around the point, stay wide of the surfers—there's a reef between them and the shore—and before you can say Duke Paoa Kahinu Mokoe Hulikohola Kahanamoku (you know, the father of modern surfing), the run ends at Kaimana Beach Park just west of the Outrigger Canoe Club.
Local Knowledge: For world-class snorkeling, head to Hamauma Bay. Farther up the coast is a great body-surfing beach called Sandy's and, farther still, the scenic lighthouse at Makapuu Point. — Joe Glickman
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