Make it the Pacific. From May to September, it's downwind all the way from California to Hawaii. It'll get warmer every day, phosphorescent plankton will light up the rolling seas at night, and the hula music keeps getting louder on the radio. Before you cash in the house to buy your own boat, go with some pros. Joining a crew isn't easy—it's every sailor's dream trip—but J World Sailing School offers up to six spots a year for either the Transpac (L.A.–Hawaii) or the Pacific Cup (San Francisco–Hawaii) on a Santa Cruz 50, a boat designed for offshore racing. You won't sleep much over the eight to ten days, but isn't that the point? (Approximately $10,000; sailing-jworld.com)
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