Many sailors make the trip to windward from Florida on to the Bahamas, Dominican Republic, Turks and Caicos, Puerto Rico and The Virgin Islands. Here are some tips to make the trip easier.
No sailor enjoys beating to windward. The constant slogging of your boat's bow against the oncoming waves can make even the patient weary. Aside from the discomfort you will be constantly tacking to achieve your waypoint. I recently made the trip from Key West to the US Virgin Islands.
Step2
We paid particular attention to NOAA weather radio as we left Key West for our Gulf Stream Crossing to Bimini. Once you are past Bimini you loose US weather radio and have to rely on SSB and the weather "nets" on marine VHF. An onboard weather fax was also available to us and we found it very handy. One tool that was indispensables to us was Bruce Van Sant's "A Gentleman's Guide To Passages South, The Thornless Path To Windward"
Step3
In Mr. Van Sant's book he describes the best times of the year to make the crossings from island to island, what time of day to leave and navigational hazards to look for that are not described on marine charts. Once past Georgetown Exuma the guide really proves its worth. He lists the best ports of call in the Dominican Republic and other stops along the way, customs procedures, anchoring tips for certain harbors and even SSB and VHF frequencies where "nets" meet to discuss cruising conditions. Try and avoid the early spring when strong cold fronts can can sneak up on you and try to be out of below Grenada for Hurricane Season or have a backup plan on where the hurricane holes are if you decide to stay north of Grenada for the summer. Getting "A Gentleman's Guide To Passages South" will make the sail much easier.