I could say that if you've been there a number of times, you should probably know how to get there. But.... that would be snarky and the hollidays are upon us...my wife tells me that if I'm not good Santa will leave coal in my stocking, so.....
Okay! First to Florida; then, a choice. If you have time and don't mind an extra mile or two head north in the ICW (mast height?) to enjoy spring in the Carolinas before heading offshore in late April or May direct Tortola / St. Martin....OR, from Florida cross the GS at or above Miami, transit the Bahamas (draft?) to the Thorny Path to DR, PR
, USVI, BVI and St. Martin. Then steer S by SE to the Windwards before shaping a course direct Hugo-land.
Now, if a contrarian spirit lives in you, try this: from Galveston steer for the Yucatan Channel, then to Jamaica and then direct to the Socialist Paradise. It's much shorter and you'll get to experience the joys of contrary currents, headwinds everyday, and lots of bumps -- all before arriving totally exhausted just in time to have some nice local fella rob you of your last gringo dollar.
PS -- send us a post card!
PPS -- in your OP you said you were "considering" the trip. The guys were just providing a little info for you to "consider".