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Assuming that your boat is "ocean ready" and you are experienced in big waves and strong winds - it takes from one to three months to get from Florida to the USVI. The normal route is from Miami to Bahamas (Grand Banks) to the Exumas to Mayaguana to Turks & Caicos to Luperon, Dominican Republic to Samana to Mayaguez/Boqueron, Puerto Rico then along the south shore to Salinas and finally east and up into the Virgin Islands. Weather is the big limiting factor along with the speed that your boat can motor into the wind. After the Exumas you will be going dead to weather unless you plan the weather windows carefully. Some of the most nasty water is from T&C to Luperon and from Luperon to Puerto Rico and along the south shore of Puerto Rico. Get the Gentlemen's Guide South by VanSant and memorize it.
The main time frame is in March/April to head south.
When you get to the Virgins/eastern Puerto Rico you will need to have a Hurricane haul-out plan. The main problem is that all the hurricane proof-boatyards are totally booked by February so you better plan ahead.
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