A Caribbean Soul: Lesser Antilles (Windward Islands)

Although the furthest Caribbean islands from Jimmy’s homes in Florida, three of the Windward Islands have managed to make it into his lyrics.

From south to north…

View Windward Islands in a larger map


The largest and most populous of the 23 islands that make up the country of Trinidad and Tobago, Trinidad is just 7 miles off the coast of Venezuela. That makes it the southernmost island in the Caribbean. An independent republic, Trinidad is colorful and lively, a fusion of many cultures and beautiful natural features. Trinidad is the birthplace of calypso, so there’s music all around.

Trinidad makes it’s first appearance in Jimmy’s music in 1978’s “Son Of A Son Of A Sailor” (from the album of the same name):

And the lady she hails from Trinidad,
Island of the spices.
Salt for your meat and cinnamon sweet,
And the rum is for all your good vices.

As is often the case, Jimmy can’t resist singing about an island’s women or food!

Five years later in “We Are the People Our Parents Warned Us About” (from the album “One Particular Harbour”) he’s still singing about the place:

You know I could have worked the rigs
When the money was big,
Or hopped a freighter south to Trinidad


In “Presents to Send You” (from the album “A1A”), Jimmy sings about Bridgetown, the capital of Barbados:

Thought I might sail down to Bridgetown.
Spend some time in the Barbados sun.
But my plans took a skid when I smoked the whole lid
And wound up where I’d begun.

Too bad he didn’t make it. Barbados is a coral island and its wonderful large beaches are made from finely ground coral. All of the island’s beaches are open to the public. Unlike Saint Martin, there is no nude sunbathing (it’s illegal), but there’s plenty more to look at. In the north, coral and sandstone cliffs rise straight out of the ocean. In the south and west parts of the island, cliffs of 50 to 100 feet rise and fall along the coast, separated by small sandy beaches and bays with coral formations. There, you’ll also find tide pools.


Martinique is an overseas region of France, so French is the language and the Euro is the currency. The culture blends French and Caribbean influences, the living standard is among the highest in the Caribbean and the island draws vacationers from France. So if you like French culture, this could be the place.

Early in his career, in 1974’s “Migration” (from the album “A1A”), Jimmy was already dreaming of retiring to Martinique,

Well now, if I ever live to be an old man,
I’m gonna sail down to Martinique.
I’m gonna buy me a sweat-stained Bogart suit
And an African parakeet.
And then I’ll sit him on my shoulder
And open up my trusty old mind.
I’m gonna teach him how to fuss,
Teach him how to cuss,
And pull the cork out of a bottle of wine.

Fifteen years later in “Off to See the Lizard” (from the album of the same name), we learn that his interest in the island may have been influenced from an early age:

I was raised by a maid who came from Martinique.
She wore geckos round her neck and bracelets on her feet.
A superstitious woman from the land of sugar cane,
She’d sing the sun to bed and dance out in the rain
Dance out dance out dance out in the rain.

Not surprisingly given the distance from Florida, Jimmy’s songs about the Windward Islands only mention others from there, or how he could have or may still visit there.

So let’s continue sailing north to the Leeward Islands, where Jimmy has definitely spent more time.

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