Can't decide. I've been to St. Maarten - loved it, but would love to go to Barbados, Aruba...
Cruise-wise, it seems easier to go Western because I'm flying out of Cleveland. If I go Southern, then I'd fly into San Juan, have to get a hotel for the night then cruise the next day...I probably have to get a hotel either way since you can't seem to fly and cruise on the same day schedule-wise. I'm thinking the Southern is safer. is that true?
I did a southern cruise in December, out of Ft. Lauderdale, that went down to Aruba. Bonaire, too, plus a few other islands on the way. I'm pretty sure they've got them out of Miami, too. Southern routes usually take longer than the more common 7-day cruise, though. So if it's easier for you to get to one of those ports, you MIGHT be able to do a flight on your departure date. I did, from NH. Got into Ft. L at 12:30, was at the boat by 1. I would not have risked it on a January or early February date, though, because of the probability of a storm somewhere along the east coast holding me up. Usually I fly in the day before, and stay at one of the inexpensive motels that have both airport and cruiseport shuttles.
As for safety, I don't think any of the cruise lines go to ports where that might be a problem.
I think, the only drawback of doing a Southern route is having to flying to San Juan, the air fare can be prices...Although there are some benefits of a cruise like this, you get so see more islands, they are closer together and easy to go from one to the next with just and over night ride....It was previous mentioned of cruises out of Florida to the Southern islands, but that will be a 10-12 day cruise, so if your plans fit that, it is another option.