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North Island
New Zealand's insider take:

It's no coincidence that Auckland is nicknamed "the City of Sails." Hundreds of schooners, sailboats, yachts, and megayachts dot the harbor year-round, and its Westhaven marina, with more than 1,400 dockings, is one of the biggest in the Southern Hemisphere. The fervor of Auckland's yachties has only grown since New Zealand's two consecutive America's Cup victories, in 1995 and 2000 (the city hosted the regatta in 2000 and 2003). Sail NZ runs two-hour sails around Auckland Harbour on retired 12-meter America's Cup yachts. those who want to get a real taste of the Cup experience can try match racing along a course similar to the one used in the 2000 and 2003 regattas. Prices start at NZ$135—about US$100 per person (64-9-359-5987;

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