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Timing for Gulf of Mexico Crossing
Calder''s guide on the Western Caribbean, while now pretty outdated, has some helpful and fairly timeless information on making passages across and up/down the Gulf. I''d recommend you start there, then review the Pilot Charts and/or Cornell''s World Cruising Routes and bounce what you see against what Calder offers up.
Also, your particular passage begs for some diligent monitoring of the main Gulf Stream branch current that runs N into the Gulf from the Yucatan Channel...as well as noting the various warm and cold water eddies, each of which can impede you or speed you on your way. Staying in that main branch can be a huge help on your passage, altho'' not as much if you steer a rhumb line course. If you use Winlink, you can even download truncated daily pics of these currents and eddies while offshore to stay current on them; they are very dynamic.