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If you go counterclockwise the upwind stretch is in the channel and waves are much lower as the long fetch is broken by the outer islands. The winds are milder (but more variable). I just did the downwind JVD stretch from the North Sound a couple of days ago in 30+ knots and waves higher than 7 feet but it was a comfortable and easy downwind run and I pitied the few boats (under power, nobody was sailing) when I saw them pound against the Atlantic swells (I gather that the waters north of JVD and Anegada are considered Atlantic and not Caribbean).
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Zanshin - 残心
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