Barbados ~ we had such a blast here!! Beautiful Island filled with lovely people, places, and spaces to explore...
ABC Islands - Aruba, Bonaire, Curacao. Spent a week in Bonaire though July 1990. Snorkle right off the beach, biked around the island, loved the flamigos and how they put cucumbers on their sandwiches.
St. Maarten - great place to base yourself from if you like Anguilla or St Barth's
How to choose a Caribbean island - Lonely Planet
Carribean Cruise from Puerto Rico to St Thomas, St. John, St Lucia, Guadeloupe, Antigua, St Croix then sail back to San Juan.