Hello Scott,
This past summer, I did a country club beach party theme event and here is a list of tunes that seemed to work:
A couple of Belefonte songs;
Banana Boat
Maryanne
Jamaica Farewell
Jimmy Buffet;
Cheeseburger in Paradise
Changes in Latitude
Come Monday
Fins
Margaritaville
Brown Eyed Girl
Pencil Thin Mustache
Also;
Jump in Line
Limbo Rock
No Woman No Cry
Rum and CocaCola
Two Pina Coladas
Mambo No 5
Escape-Rupert Holmes
Summertime
And you could do some tunes that you usually do but with calypso and Raggae styles. I also used a couple of cumbias and bachatas. Good luck.
Ciao,
Jerry