If you like sailing, the sail to St Croix (and back) is about as good as it gets - about 32nm easy reach both ways. I would go even if the only thing on ST Croix was a bum on a beach selling warm beer and stale Fritos.
Absolutely! But pretty lumpy when the sea forecast is more than 3 to 5ft. I'd do it anyway but my crew would have to be doped up. Only done the trip twice but both times the trip back north was smoother and nicer than the trip south.