The sailing weather is absolutely lovely around these parts this time of year. Wind has been blowing 10 ~ 15 knots for the past two weeks.
Culabrita and the entire south coast of Vieques should not be missed. Be aware that popular anchorages can get a bit crowded on weekends, as the entire "Puerto Rican Navy" seems to come out on their sport fishing boats enmasse to party Party PARTY!
And, to the best of my knowledge, regulations for fishing in the manner you mention are non-existent. Lobsters are in season right now, too!
Are you flying into San Juan or St Thomas? If time allows - spend a day and a night in Old San Juan, one of the most vibrant and historic cities in all of the Caribbean.