≡ Menu

Five Classic Movies About Sailing in the Caribbean

Written by James Kell, founder of Sailing Virgins

Heading on a Caribbean sailing vacation and want some movies to get you in the mood?  We list six movies that capture the spirit of the area.  Even though Pirates of the Caribbean is a series (and a great one at that), for brevity we have just listed the first movie.  

Then we have a “discovery” movie followed by some classics.


1. Pirates of the Caribbean

Image result for pirates of the caribbean

A classic pirate adventure.   The first in the series starred magnificently crazy Johnny Depp as Captain Jack Sparrow.  The Curse of the Black Pearl (2003) is not only set in and around islands of the Caribbean, much of it (and later movies) is actually shot there.  There’s eccentricity, undead pirate pals, a powerful man’s daughter and more.  All the necessary ingredients for an awesome movie.  As at September 2016 the fifth movie in the franchise is about to be announced. 79% on the tomatometer. Most importantly, it instilled an interest in these types of film for a new generation.


2. 1492: Conquest of Paradise (1992)

Image result for 1492: Conquest of Paradise

The effect Christopher Columbus’ discovery had on the indigenous peoples.  With Gerard Depardieu and Signourney Weaver audiences at the time expected more.  Nevertheless, questionable plot-lines aside, this movie will make the viewer think about the effects of Columbus’ voyage and provide them with a few insights of the journey which they may not have known about before.


3. Treasure Island (1950)

Image result for treasure island 1950 movie poster

If you plan to head to the British Virgin Islands, watch this movie, especially the 1950 version, which is supposed to be the best. Adapted from Robert Louis Stevenson’s classic novel, Pirate Loyd stole treasure from the Spaniards and buried it at the lovely and very quiet Norman Island, just south of Tortola. Afterwards, it becomes a manic chase to see who can track this loot down first. Well worth a walk around while you’re there.  Don an eye patch. 100% on the tomatometer.  Serious!


4. A High Wind in Jamaica (1965)

Image result for a high wind in jamaica

You might not have heard about it but, in a away that’s what makes it so special. Set in the late 19th century, Jamaican colonial school children head to Britain when their ship is commandeered by pirates.  The spirited kids develop a relationship with the pirates.  The plot line sways in the wind; but hey it’s sailing and it’s the Caribbean.  And we love the title.  Alas no tomatometer rating.


5. The Old Man and the Sea (1958)

Image result for the old man and the sea movie

Ernest Hemingway’s classic story of an old fisherman who breaks his dry spell by landing a massive fish.  It is set in the waters of Cuba, one of Hemingway’s favourite stomping ground.  This movie enjoys 88% on the tomatometer and is often credited for being a film which goes off the beaten track.


{ 2 comments… add one }

Leave a Comment