Join Date: Jun 2005
Location: New Orleans
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The US/BVI "big four" (St Thomas, St. John, Tortola, Virgin Gorda) surrounding the Francis Drake Passage, are probably the Mecca of winter chartering.
I did it once, over 30 years ago, as (get this) 'chaperones' and skippers for a bunch of prep school kids on spring break--3 boats, 19 high-schoolers, and 5 so-called 'adults' (wife and I, at 27, were the 'old geezers').
Good steady easterlies, mostly-sheltered waters, "by eyesight" navigation, and close-by harbors make this place popular.
Those memories will last forever. i did it on the cheap, but it's worth it even if pricey.
Obviously I can't comment on the Pacific to compare, though.