A Classic Caribbean Vacation Playlist


Heading off the to the Caribbean? Here’s a classic, island-inspired playlist to put you in a sunshine frame of mind. (Listener Advisory: Most of these picks are kinda corny – but you won’t be able to stop singing them anyway.)

> Kokomo - The Beach Boys

Although the eponymous island doesn’t exist, the soundtrack it’s included on is real enough: Port Antonio, Jamaica, was the setting for parts of the 1988 Tom Cruise movie, Cocktail, which spawned this hit.

Sailing – Christopher Cross

It may be cheesy, but when you’re cruising the Caribbean with the wind in your hair, salt spray on your skin and the sun in your eyes, you’ll find this old chestnut to be the perfect soundtrack.

Dreadlock Holiday – 10cc

Undeniably kitschy but oh-so-catchy, apparently this tale of a tourist lost in Jamaica was inspired by was inspired by band members’ unpleasant experiences in Barbados. Talk about turning lemons into lemonade: it became a number one hit in the UK in 1978.

Could You Be Loved – Bob Marley

What would a Caribbean playlist be without at least one Bob Marley song? This is one of my faves, and reminds me of days spent on Negril’s sands every time I hear it.

Hot, Hot, Hot - Arrow

Forget the 1987 Buster Poindexter version; Caribbean aficionados prefer the original party jam, released five years earlier by the Montserratian singer.

Escape - Rupert Holmes

Popularly known as “the Pina Colada song,” this bored lover’s 1979 ode to the Caribbean cocktail caused a worldwide rum shortage and a rush on pineapple. (Just kidding.)

Montego Bay – Amazulu

This tune was originally recorded back in 1970 by Bobby Bloom, but I first heard it in 1986, when Brit band Amazulu made it a top-20 hit on the UK the charts. I never really thought about the lyrics beyond the chorus, but a Google search reveals that the song’s really all about getting high in Montego Bay. ‘Nuff said.