Pirate Express

Some places carry so much historical significance that movies will simply steal their names at will. The pirates of the Caribbean pillaged freely from the early 17th to 18th centuries. Places that are now bucket-list destinations were once pirate strongholds. Sailing the Caribbean Sea offers swashbuckling explorers the opportunity to retrace the courses oft sailed by some of the most notorious pirates.

Port Royal, Jamaica

Nowadays, Port Royal is known for having its fair share of British naval bases that date back to the mid-17th century, when the British used it as their economic base. A jaunt around the island will put you en route to the city’s six fortresses. of which St Charles is the most impressive on the island. Before becoming the British naval headquarters of Jamaica, it was widely referred to as the “wickedest city on Earth”, due to the flagrant displays of pirate pleasures such as prostitution, gambling, drinking, and general marauding. Yacht ownership by European powers was more of an ephemeral experience when sailing around Port Royal.

Nassau, Bahamas

Nassau is by all accounts one of the most prized gems of the Caribbean. It’s home to The Retreat of Nassau National Park which boasts a host of exotic plants along with an incomparable palm tree collection. As a tribute to the past it has an attraction dedicated to Nassau’s history of privacy, which includes interactive exhibitions and a museum. Cable Beach is the most tourist-driven beach in the city; if you’re looking to dock up and want to experience the touristy side of the Bahamas this spot is highly recommended. The Franco-Spanish fleet that attacked Nassau in 1703 and 1706 led inhabitants to abandon the island. This left a vacuum to be filled by pirates of English descent. The Republic of Pirates, which lasted for about 12 years, was then formed in 1706.


From 1500-1763 Dominica came to be ruled by many nations. It was constant battleground for colonial powers wishing to flex their muscles in the Caribbean. Since gaining their independence from the UK in 1978, Dominica has become a key Caribbean tourist destination. Dominica has some of the most robust national parks that the Caribbean has to offer. The Boiling Lake is a World Heritage site, just six miles east of the capitol, Roseau. The lake is only approximately 200 feet wide but contains the enigmatic quality of bubbling water that is permanently veiled in a thick billow of vapour. Dominica’s forests are so lush they were used as the setting for the most recent Pirates of the Caribbean film, On Stranger Tides.

So whether you’re a Caribbean pirate history buff or just an avid sailor looking for an unforgettable sailing vacation, the Caribbean has got you covered.


The author myfavouritetrips

Leave a Response