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It is difficult to find a fair weather window that will stay open long enough to sail to Bermuda from the US East Coast in the late fall. Your prospects tend to worsen the longer you wait. Typically you will end up departing on the tail end of a strong cold front, ride it to the Gulf Stream, and then hope for moderate west to southwest winds to get you the rest of the way to Bermuda before the next big system runs you down.
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THE BOAT: Design: Gilmer 31; LOD 31', LWL 25', Beam 9.5', Draft 4.5', Displ. 13,600lbs.