I’ll put in a recommendation for Dominica as a place everybody needs to visit in the region. We went early this year. Beautiful and lush, the “nature island” and still a little under the radar. Secret Bay is one of the best resorts in the world.
We’ve been to about 20 different countries / islands in the Caribbean. YMMV, and not a bad time on any of the trips, but the ones that stood out the most to us included:
St. Barts: Incredible hotels and beaches. Great food scene. Can be a party.
Mustique: Been over a decade, but a lovely tiny little island. All villas except for a couple hotels. When we were there no cars allowed to drive on roads so we took golf carts everywhere.
Dominican Republic: Best golf in the Caribbean. Eden Rock is a fantastic resort. Tortuga Bay another good one, little more quiet.
St. Lucia: Sugar Beach Resort has an all-time setting between the Pitons.
St. Kitts: Belle Mont Farm