No problem sailing up to virgins that time of year. First the tropical wx forecasts are very reliable for 3 days and you can make the whole trip in three days.
Only issue is when you get there you are still in the box. For marinas look at Nanny Cay on tortola or Palmas Del Mar on SE Puerto Rico. If not looking at marina go to Salinas on south coast of PR
or the island of Culebra