My own opinions of some places we've been lucky enough to visit!
Bermuda : Love it! Friendliest kindest people, beautiful beaches, fun shopping, so much to see and explore. Low crime rate, even the most modest house is impeccable! Not expensive if you stay away from the resorts, great restaurants. (no fast food or casinos -- I say Yay!) Wonderful British influence. Easy to get around by bus/ferry pass, mopeds in the Fall when it's quieter. Lovely foliage, unique white-roofed pastel colored houses! Have been going there for many many years.
Bahamas: Forget Nassau, Freeport -- go to the Out Islands (Abacos, Exumas)! Not much to do but enjoy the wonderful people, beautiful beaches, straw markets, rent a moped, snorkel, generally chill out!! Water like you've never seen -- you think you can reach down and touch a starfish when it's 12 feet deep! Lived there on our boat many yrs ago for a few months, later flew to Georgetown for a 10-day stay.
Puerto Rico: Had some doubts about going, can't wait to go back!! People were awesome -- friendly and helpful. Food was out of this world! (somehow I thought it would be spicy) Was worried about crime -- no problem! Sand was more like Cape Cod, water was beautifully clear, sometimes large waves. Wonderful places to explore, from Bio Bays to the Rain Forest -- could easily spend two weeks and still not see everything you wanted!
Aruba: Consistently perfect weather (this Fall was a weird exception!)!!!!
Very friendly helpful people, wonderful beaches, clean clear water (love Eagle Beach), outstanding restaurants to choose from. Not tropical, but amazingly beautiful rugged terrain to see and explore. Always feel very safe there. Many things to do, or do nothing and enjoy the beach!
St Maarten: Going for the first time in April!