Beautiful sailing spot

Sail the Caribbean: The Top 4 Sailing Spots

With more than 7000 tropical islands dotted over 1 million square miles of crystal-clear waters, it’s easy to see why the Caribbean Sea is so popular with yachting and catamaran enthusiasts. The region takes prime position on just about every sailing aficionado’s bucket list of ultimate sailing destinations. Sail the Caribbean and explore the most beautiful part of the world freely. 

Add the allure of a calm, warm ocean, secluded white beaches, coral reefs teeming with marine life – and you might find your inner pirate reluctant ever to set sail from this azure ocean paradise.

close up on a turtle

The Caribbean is a region of the Americas, made up of the Caribbean Sea, its islands and surrounding coasts. To the north, it is bordered by the Gulf of Mexico, the Straits of Florida and the Northern Atlantic Ocean. To the south lies the coastline of South America. The Caribbean islands include the Greater Antilles (north) and the Lesser Antilles (south and east). The Greater and Lesser Antilles form part of the larger West Indies group of islands.

Coral reefs, rainforests and a pirates’ legacy

A known pirates’ playground during the 1600s – 1800s, the Caribbean Sea has warm, moist trade winds blowing from the east, creating rainforests and semi-desert conditions on the mountainous islands.

It is also home to a stunning array of marine life, including several species of turtles, large schools of migratory fish, marine flora and pristine coral reef formations.

The Caribbean Sea is a region steeped in history, with many of the island nations being former European colonies. Hurricanes batter the area from time to time, so you’ll be wise to visit between November and May, outside of its rainy season.

Think calm, turquoise waters. Abundant coral reefs and lagoons. Volcanoes, tropical rainforests, mischievous monkeys, rum, grapefruit and turtles.

And, did we mention perfect sailing conditions?

Read on for our list of the top 4 Caribbean yachting destinations you’ll definitely want to include on your sailing itinerary.


Sail the Caribbean:  Barbados

Originally named Los Barbados, Portuguese for “the bearded ones”, after its fig trees’ beard-like appearance. Barbados is the easternmost island in the Lesser Antilles group of islands.

Barbados palm trees

With a plethora of idyllic beaches, bays and coves to explore by yacht or catamaran, the island, affectionately named “Bim” by the local Bajans, is known for its warm breezes, sheltered harbours and tranquil seas. It also has a well-earned reputation for offering near-perfect sailing conditions for novice and seasoned sailors.

Drop anchor in Port St Charles, a luxury marina development off the island’s north coast for a day of exploration. Then sail southwards to Carlisle Bay to swim with green turtles or dive some shipwrecks.

Other activities to enjoy in Barbados include; windsurfing, kitesurfing, cave exploration, rum tours or exploring historic Bridgetown.


Sail The Caribbean: St Lucia

Part of Lesser Antilles, this breathtaking volcanic island is known as the jewel of the Windwards. Covered in tropical rainforest, it not only epitomises Caribbean sailing perfection but is a bird watchers’ paradise as well.

Woman in St Lucia

With year-round sunshine and varied seasonal winds, St Lucia offers superb sailing conditions throughout the year. Think powder-white, palm-fringed beaches, warm, turquoise waters, world-class diving and an ocean teeming with turtles and other marine life.

St Lucia is famous for its impressive array of underwater flora, including massive sea fans, gorgonians and barrel sponges. It is the ideal location to set out to explore the islands of St Vincent, the Grenadines and Martinique.

When you are in the region, be sure to sail past St Lucia’s most famous landmark, the Pitons. It consists of two stunning, towering mountains located between the towns of Soufrière and Choiseul on the western side of the island.


Sail The Caribbean: St Vincent

The lush, green island of St Vincent lies west of Barbados and south of St Lucia. Nicknamed “the gateway to the Grenadines”, it’s extremely mountainous with dense rainforest covering most of the island.

St_Vincent island mountains

St Vincent is the capital of St Vincent and the Grenadines, an island nation comprising a cluster of 32 enchanting islands and cays. Island-hopping in azure waters, visiting secluded bays and palm-fringed beaches make this piece of sailing heaven perfect for exploration by yacht or catamaran.

When sailing this region, be sure to explore the stunning Tobago Cays, an archipelago consisting of five pristine uninhabited cays and reefs. In the national marine park, you can dive with turtles, stingrays, lobsters and schools of colourful fish. The park is also known for its enchanting mangrove ecosystems and seagrass beds.


Sail The Caribbean:  Port St Charles

One of Barbados’ two official ports of entry, Port St Charles is a stunningly beautiful luxury marina located on the northwest tip of the island.

Port St Charles

Dotted year-round with yachts, catamarans and other sailing vessels, the exclusive marine resort is situated on a vast stretch of beach facing the Caribbean Sea.

Sunset Island is where it's all happening in Port St Charles. The man-made island is surrounded by the azure lagoon and home to the Port St Charles Yacht Club. The yacht club boasts a restaurant, swim-up bar, pool and a vast dock area, ideal for relaxing with a rum cocktail while enjoying a perfect, pink-and-orange Caribbean sunset.

Port St Charles is located within walking distance of the restaurants and markets of charming, historic Speightstown, established in 1653. Just off the coast of Port St Charles, lies Tom Snooch reef, where you can enjoy a day of snorkelling or scuba diving around the pristine coral reef.

Laid-back, sailing heaven

Sailing the beautiful Caribbean, you’ll have the chance to swim with stingrays, see flying fish, dive shipwrecks, discover quaint harbours and explore historic towns and bustling villages.

Like many other sailing enthusiasts, you’ll probably never want to leave – or at least return to this tropical paradise as soon as possible.

Be sure to include the Caribbean on your list of must-see sailing spots and find out for yourself why this region is so often named one of the most popular sailing destinations on the planet.

The beautiful Knysna views

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