FL to the Caymans - which route?
Jonathan, either route can be made to work but they are quite different in terms of the time it would take and the diversity of cruising it would offer; I think your choice is more a function of what you want from the trip than about the destination. As you probably know, Passages South by VanSant would be your best reference for understanding wx patterns and monitoring wx, while Rauscher''s guide is the best for the W Carribean and Calder''s now dated guide gives a useful overview of wx systems, seasonal variations,routings, etc. I would strongly recommend against a summer/fall cruise due to the frequency (and destructive strength) of the storms that frequent the area.
If it were my choice to make, I''d definitely use the clockwise routing. IMO the advantages are:
1. the chance to cruise and enjoy the Bahamas, shake down the boat, and decent provisioning in Georgetown, Great Exuma
2. departure via the Ragged Keys or via Crooked/Acklins when leaving (I would probably not be tempted to stop at Great Inagua)
3. sail south thru the Windward Passage, expecting the perfunctory USCG boarding since that''s a choke point for drug deliveries into Haiti
4. if we were doing this in the early Spring or late Fall and prevailing conditions were moderate, I''d be eager to sail along Haiti''s S coast and revisit Ile a Vache, a wonderful experience that''s akin to walking thru the front cover of a 1930''s Nat''l Geographic and also very safe; short stays involve no officials or clearance efforts, and I''d be sure to catch Market Day at Madame Bernard, too
5. with/without Ile a Vache, I''d enjoy cruising the N coast of Jamaica; no clearance fees and a free transire make it simple/easy; John Lethbridge''s dated but still helpful guide well worth carrying
6. with a good f''cast for extended stable wx, I''d leave the anchorage at the far W end of Jamaica for Cayman Brac and be very careful about where I anchored on arrival, as the anchorage isn''t ideal and usually fairly active in prevailing conditions
7. continue on to G''town, GC (free moorings but don''t clear in on a weekend; very expensive) and take a breather by then entering North Sound and resting in the totally protected anchorages adjacent to the yacht club
8. begin heading back to FL with many cruising options open to me, and with this routing never requiring you to revisit places you''ve already seen nor needing to deal with the Cuban dilemma that, as U.S. citizens, we currently face