I haven't been on a cruise in, 35 years. But when I did go on one, flew into PR and went to a number of small islands including Guadelope with the southern most destination being Caracas Venezuela. My parents prepared for it. One of the highlights was spending the whole day on a husband -wife run sailboat, who sailed us to coral reefs to snorkel. It was one of the most amazing experiences.
Lots of little towns, beaches. Caracas was an eye opener, with the taxi driver giving us a real tour (both of the nice areas but also other areas, with political commentary). Walked old San Juan. Also, the food on the cruise ship (Italian-run, Costa Cruise) was incredible. We had a fresh fruit basket every day in our cabin, and there was a midnight buffet that had seafood. Probably an equivalent cruise experience today would = $$.
I think I would do a regular cruise as well. It wouldn't be my first choice, but it is nice not having to worry about transportation and travel issues but get to see a number of places.