Help planning beach vacation carribean vs Bahamas

Please let me know if I should repost tomorrow in the low effort weekly post but I am trying to plan a beach vacation for me and my husband this spring/summer and need some recommendations! We have 2 kids under 2 and haven’t taken a vacation that was just the two of us in years. We desperately need some romantic alone time. I care most about a beautiful beach setting, but it would also be nice to travel to a place where if we wanted to go off resort for dinner or excursions there was a town or something else to see/do. I don’t want to be somewhere so isolated that we can’t leave the resort.

We used to live on the west coast and would often travel to Hawaii but we are now on the east coast and it is so far away we are looking for other closer options. I am thinking maybe Caribbean or Bahamas but have traveled to neither.

Some of our favorite stays have been at the Andaz Wilea, Four Seasons Hualalai, and RC Turtle bay so looking for something of that caliber.

Hoping $1000-2000 a night or less.

I have seen recs in this sub for Anguilla and St. Barths but I haven’t explored the Caribbean or Bahamas at all. Some of the beaches I have seen don’t look that different from the Florida keys so I would like something that seems worth the trip. Also open to Florida recommendations as well!

Edited to add: We are hoping to go around May or June. Is that a terrible time to go to this area? Our youngest is a tiny baby and I’d feel more comfortable traveling without them when they are a little older. Also open to other nice costal areas that time of year (although I really craving something tropical).