Well, plenty of people sail in the Gulf and northern Caribbean
season, but it’s a risky time to be making long east bound passages.
The conventional cruising route
from TX to VIs would be a multiday sail across the Gulf to FL. From there you sail through the Keys, jump to the Bahamas
, and island hop southeast - eventually jumping off for the Mona Passage
and the southern coast of PR where you can coastal sail east to the VIs. This takes a long time and the longer it takes, the more fun you are likely to be having.
We met a singlehander in St. Maarten who had sailed east from Jamaica
. So the southern route is possible. But even if you have good weather
all the way, you will be sailing against the prevailing trade
winds, and it will not be fun.
Given the time of your departure, I think the better idea for this summer is to head
south to the western Caribbean
via Isla Mujeres. The farther south you go, the less likely you are to get in hurricane
trouble. Don’t know about inexpensive boat work in that region, but I have heard Guatemala