re: I'm somewhat overwhelmed by the choices for the Caribbean

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I've never done the Caribbean. Help me out here. This will be next spring/summer as well.

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It really depends on where you are coming from and how long you want to spend getting to the island of your choice. I live in Houston and there are several islands I can get to quickly and directly. That is a major factor a lot of times in our trip choice b/c we rarely go for 7 days (we typically do multiple quick 4 - 5 day trips per year). Example, I can get to Grand Cayman in 2.5 hours direct, Aruba in ~ 4 hours direct, St. Thomas in ~ 4 hours direct, and sometimes you can find direct flights from IAH to Nassau (Bahamas) or Providencialies (Turks & Caicos). We've gone to each of those places at least twice.

I love some of the other islands like Antigua, St. Lucia, and Barbados but out of Houston you typically have to spend almost a full day of travel getting to them. So you'd pretty much need to block a full week for your vacation for these to work. Others that live on the East coast or Dallas (American has a ton of flights to the Caribbean) may have a different point of view.

If you want calm water, white sand beaches, a variety of food options, and relatively ease to get to, then go to Bahamas, Turks & Caicos, Aruba, or Grand Cayman.

If you want a massive all-inclusive stay at your resort the whole time type of experience then go to Dominican Republic or Jamaica.

If you want a legit Caribbean experience I'd suggest Antigua, Barbados, St. Lucia, St. Martin, or St. Vincent & Grenadines (probably the hardest to go to).

If you want the best of all of the above go to the USVI's (my personal favorite).