The classical "Thorny Path" can be rushed and done in 2 or 3 months. Or you can do the I-65 route which is head
east/northeast staying in the westerlies until you get to Longitude 65 west and then turn south to the Virgins. Reportedly that is a week to 10 days on average.
- - The classical path through the Bahamas
, T& C, D.R. P.R. to the Virgins is extremely variable due to weather
and your ability to motor-sail up wind
and up current
- - Doing it in May is not too late although you are crowding the probability curve of Tropical Storms. Historically the majority of the storms start the season - Jun-Aug in the western Caribbean
Basin and then switch to the Atlantic storms Aug-Nov. Some years the Caribbean
gets clobbered and other years few if any storms threaten the islands. Mother Nature does as Mother Nature wants. You can go to: Unisys Weather
and look up the Atlantic Storms for the last 160 years or last 15 years for detailed information. After that you "place your bet and take your chances."