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You’ve been at sea for days. You knees feel weak and you long for solid ground. You look out towards the horizon and you see it, land. You’re ready to go ashore, spend your loot, find some “company” and drink rum until you smile crooked.

This is what the pirates did back in the golden age of the Caribbean. If you think about it, it really isn’t that far off from what the modern day cruiser does. Yes I am a pirate, 200 years to late.

The Caribbean is full of beautiful harbors and ports of call, some more beautiful than others though. These harbors/harbours act as hubs for the islands, a place where first time seafaring visitors first fall in love with the island. A love that will surely have them coming back time and time again. A mistress is never satisfied.

7 Most Beautiful Caribbean Harbors

1. Willemstad, Curaçao





This lively port is one of six UNESCO World Heritage sites in the Caribbean, joining the ranks of Old Havana, Old San Juan, and Colonial Santo Domingo.

The Punda District – once fortified and walled – along with its neighboring districts of Otrobanda, Pietermaai, Scharloo, preserve some 765 buildings as national monuments. Chief among these are Fort Amsterdam, the Governor’s Palace, Mikve Israel-Emanuel Synagogue and the colorful Penha building on the waterfront.

2. Charlotte Amalie, St. Thomas

St. Thomas

St Thomas

St Thomas

Charlotte Amalie on the island of St Thomas in the US Virgin Islands, is nestled on the mountainous slopes of a large natural harbor that accommodates several large cruise ships each day. The city has been declared as the shopping mecca of the Caribbean.

3. Gustavia, St. Bart/St. Barths

Gustavia St Barths

St Barths

Most cruise ships anchor outside sheltered Gustavia Harbour and tender guests to Port de Pleasance, past all the mega-yachts. Gustavia, the island’s charming capital city is a slice of France in the Caribbean. Surrounded by elegant designer boutiques, topless beaches, vibrant nightlife and waterfront bistros, the French vibe wraps around you like the warm blue sea.

4. English Harbour, Antigua

English Harbour Antigua


English Harbour is a center of boating, especially yachting. There are two sheltered deepwater harbours nearby; English Harbour itself and Falmouth Harbour.

English Harbour is best known for Nelson’s Dockyard, which occupies the site of the British Navy base. It displays restored buildings and other historical artifacts from the colonial period of the dockyard, especially the time it was commanded by Horatio Nelson. (Info from wikipedia)

5. St. Georges Harbour, Grenada

Grenada st georges

Grenada st georges

Grenada st georges

St. Georges is the capital of Grenada and it’s also the largest harbor and city on the island. The city extends for miles in every direction from St. George’s Harbor, and ashore are more facilities than most can ever see in a single visit. Entering the harbor is easy, as the approaches from north or south are deep, wide, and easy to navigate, even for deep-draft boats.

6. San Juan Harbor, Puerto Rico

San Juan Puerto Rico

San Juan Puerto Rico

Shoehorned onto a tiny islet that guards the entrance to San Juan harbor, the atmospheric ‘Old San Juan‘, with its historical authenticity and pulsating modern energy, this seven-square-block grid of streets that was inaugurated almost a century before the Mayflower laid anchor in present day Massachusetts. Surreal sounds and exotic sights resonate everywhere.

7. Havana Harbor, Cuba

Havana Cuba

Havana Cuba

Havana Cuba

Havana Harbor

A view across the harbor in Havana, with a monument to Jose Marti in the Plaza de la Revolucion visible centre right. The monument was constructed between 1953 and 1959, just in time for the more recent revolution.

Which harbor is your favorite? Did I leave any off the list? Leave a comment below if you think you have a more beautiful Caribbean Harbor. My favorite? Going off of these photos, I’d have to say…St. Georges, Grenada. Simple, beautiful and old school Caribbean.



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About the Author: RumShopRyan

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty. To learn more, visit our About Us Page.