Short, but very useful related answer here: So what is the deal with tiki culture? by /u/Ragleur

More detail on the exoticism of tiki bars in particular: What was the general sentiment of Pacific Islanders towards the 'tiki' aesthetic that emerged after world war II's pacific theater by /u/khudgins

Hey there. Thanks for linking my earlier post. Jimmy Buffett's inclusion comes from a different place, too: he's authentically Caribbean-based. His grandfather was a sailor, eventually putting roots in Mobile, Alabama, which is a gulf coastal city. There's a shared culture across the Caribbean which includes a lot of the coastal cities in the southern US.

The "boat drinks" that he sings about are derived from the same sources as tiki drinks, only without the Pacific faux-Polynesian escapism but filtered through an American's experience growing up on the rim of a region steeped in a rich culture that can only happen when you have a melting pot of colonialism literally importing cultures on top of each other. That "beaches and rum drinks" crowd of parrotheads is pretty much the modern take of American tourism in the Caribbean islands. There's a long history there, too - You can see another pop culture reference from the 1930s with the song "Rum and Coca-Cola," which is referring to the drink Cuba Libré which is unaged Spanish-style light (Cuban) rum, a little lime juice, and Coca-Cola. The drink is definitively the crossroads of American culture and Caribbean drink culture in a glass. The song's narration is from the viewpoint of a Trinidadian local getting excited about the "exotic" Americans coming in as garrisoned soldiers in WW2 and throwing around cash like the locals can't do, which fascinates local girls. Super escapist, from the same influences as the Tiki culture, only Caribbean influenced. That song's based on a traditional Trini melody, written by Lord Invader (Rupert Grant) and was stolen for the American market. It's interesting to me that it's a Cuban drink, and from that I infer that Americans insisted on drinking in Trinidad. The Cuba Libré dates back to pre-Prohibition era - near 1900 or so, and was made popular with Americans when they descended on Havana during Prohibition as a very close place to visit with free-flowing alcohol.

The history of the Cuba Libré, like a lot of traditional cocktails invented pre-prohibition, is shady and overlaid with marketing as alcohol brands used the cocktail to sell their liquor. Reference on that below.

It's all escapist, all catered to the "Yanqui Dolla", and in many cases it's locals taking advantage of what the Americans wanted and giving them a curated take on what the tourists wanted to see. Same reason you can now go to Jamaica and spend thousands on an all-inclusive resort and never actually see a single lick of local Jamaican culture.

A few references:

Jimmy Buffett's own site with some of his background: https://www.jimmybuffett.com/about

More original Trini-style of Rum and Coca Cola, by calypso musician Lord Invader: https://open.spotify.com/track/7AfFaJORQCRpFHc9aRfWI2

One reference I could find on the history of that song: https://secondhandsongs.com/work/149881

Wayne Curtis' book "... And a Bottle of Rum" covers the Cuba Libré: https://books.google.com/books?id=TrExKFNmKFcC&pg=PA200#v=onepage&q&f=false

Note: I am NOT a historian. I'm a tikiphile who absolutely recognizes the cultural appropriation roots of the genre and wanted to learn more about where all this came from, and I'm also a nerd who reads everything he can get his hands on. I'm also a southerner whose family lives on the gulf coast, and got quite a few of the same experiences Jimmy Buffet had as a kid, so I can also somewhat speak to that. Jimmy's capitalizing on the romanticization of that "island life" deliberately. He knows what he's doing.