EXCLUSIVE: Read Best Sailing Destinations in Caribbean

Caribbean boasts some of the best sailing conditions on earth and consists some of the region’s best sailing spots.

EXCLUSIVE: Read Best Sailing Destinations in Caribbean
EXCLUSIVE: Read Best Sailing Destinations in Caribbean

Caribbean: Caribbean boasts some of the best sailing conditions on earth and consists some of the region’s best sailing spots. Palm trees rustle gently in the breeze, the clear blue sky above the head mirrored by the shallow turquoise water below is something a tourists can find in the region.

The sun warms your back as an endless white-sand beach curves like the crescent of the moon before you; does it get any better than this? With islands like a string of emeralds, a steady 15 to 20 knots of easterly wind and year-round warm weather, the Caribbean boasts some of the best sailing conditions on earth.

A plethora of charter companies, all keenly competitive and eager to please, means that whether you’re an old salt or just learning the ropes, they’ll be able to find something to fit the bill.

While some specialise in watersports like kitesurfing or scuba diving and provide everything from equipment to training, others offer bareboat experiences with just the basics. For those truly looking to relax, fully crewed and catered options are almost always available.

While the Caribbean islands might look similar on a map, each has something unique to offer. From the powdery white beaches of Grenada to the busy duty-free shopping streets of Sint Maarten, read on to explore some of the region’s best sailing spots.


The tri-island nation of Grenada, Carriacou and Petite Martinique is a beach lover’s dream. Carriacou in particular has secluded white-sand beaches that are simply unmatched in number and beauty. In fact, Paradise Beach on the island’s west coast was recently voted #1 in USA Today’s 10 best beaches in the Caribbean.

On the main island of Grenada, an international airport and thriving yachting industry make getting there and setting sail easy. A lush and mountainous interior, quaint downtown harbour and great wreck and reef scuba diving sites tempt sailors from across the globe.

The sister islands of Carriacou and Petite Martinique are just a day’s sail away and are geographically part of the Grenadine Islands. They are flatter and drier than Grenada, where shallow bays of clear azure water sit quietly around almost every corner.

An added bonus of sailing in Grenada, Carriacou and Petite Martinique is that they’re south of the hurricane belt, making it the best choice for sailing during the shoulder seasons.

Chart the course

True Blue or Prickly Bay to Grand Anse

Grenada’s largest anchorages are on the southeast coast, so you’ll likely start by sailing south around Point Saline to the island’s most picturesque beach area-Grand Anse. The capital of St George’s is also a short dinghy ride away, and the best place to get supplies.

Molinaire and Black Bay Snorkel in the world’s first

underwater sculpture park, where there are dozens of concrete sculptures to be discovered among the fish and coral. Anchor a bit further north in Black Bay for the night, shortening the passage to Carriacou the next day.

Tyrell Bay (Carriacou)

As the yachting centre of Carriacou, Tyrell Bay is a good place to have a meal ashore and experience the local rum shop culture.

Sandy Island, Paradise Beach and Anse La Roche

All within a few hours’ sail of each other, these are three of the most beautiful and easily accessible beaches in the area.

Petite Martinique

Try to spend a few hours exploring ashore here. The short but steep hike up the piton provides far-reaching views of the surrounding coral reef and islands.

White Island and Isle De Ronde

White Island’s one-boat anchorage is a great place to stop for lunch and a swim on your way south. If you’re not in a hurry to get back, spend the night at Isle de Ronde, halfway between Carriacou and Grenada, for some snorkelling or diving.

Mourne Rouge

This shallow, sandy bay is a great place to spend your last night aboard. Keep an eye out for green sea turtles, which often frequent the area to feed on the seagrass meadows


Sint Maarten is an island of two nations: the northern half French, and the southern half Dutch. Combined they create an interesting mix of Caribbean and European cultures where the culinary delights range from French wine and pastries and Dutch cheeses to French Creole accras.

Plus, the whole island is duty-free, making it a shopper’s paradise. Anchor in Philipsburg. the Dutch capital, and wander the bustling brickwork streets where you can find everything from electronics to the famed Guavaberry liqueur.

In Marigot, the French capital, charming cafés and open-air markets enchant passers-by. But it’s not all hustle and bustle; a few offshore islands and secluded anchorages make for a relaxing escape from the crowds.

For fine French dining, don’t miss Anse Marcel on the northern coast, where they can take their time strolling along the waterfront, browsing the daily menus and enjoying the view.

Chart the course

Marigot to Grand Case or Anse Marcel

Stock up on fine French wines, cheese and baguettes and set sail for Grand Case or Anse Marcel.


The sandy bay of this uninhabited offshore island is backed by copper-red cliffs, creating a vibrant backdrop.

lle Pinel and Orient Bay

A lively holiday area, where lounge chairs, beach bars and watersports line the beach at Orient Bay. Ile Pinel is usually a quieter escape.

Isle Forchue

Much further off the beaten path, this secluded island is a great place to get in the water and explore the seascape and marine life.

Anse de Colombier (St Barths)

This deep bay at the northern tip of St Barths is surrounded by rocky hills, and is great for hiking and taking in the interesting rock formations and views of the anchorage below.


Wander ashore and shop till they drop.

Simpson Bay

This popular anchorage is surrounded by beachfront restaurants and hotels, with no shortage of entertainment. For some interesting snorkelling check out the wreck just north of the bridge.


One of the more remote cruising destinations in the Caribbean, the steep tropical mountains of the main island of St Vincent are contrasted with the gently rolling hills and low sandy atolls of the Grenadines, a series of 30 islands that extend south from the mainland.

They hold endless island-hopping potential, and the most picturesque and sought-after destination within them is the Tobago Cays. A series of four uninhabited islands encompassed by a Marine Protected Area, a sweeping barrier reef creates a large central anchorage frequented by turtles and other marine life.

Snorkelling here and throughout the Grenadines is always rewarding. Bright tropical fish dart between coral heads while sea turtles munch on seagrass nearby. The Tobago Cays and surrounding islands are also an ideal location for kitesurfing and windsurfing.

Beginners wanting to take kitesurf lessons shouldn’t miss Union Island, where multiple schools will be happy to show you their favourite spots.

Scuba divers should get in touch with Glenroy at Grenadines Dive, also in Union, who will meet them in the Cays to take you diving

Chart the course

Blue Lagoon to Mustique

Sail south to Mustique, a private island fit for royalty. Mick Jagger and Bryan Adams have homes here.

Tobago Cays

Plan to spend two nights here exploring the islands and snorkelling with turtles in the sanctuary. In lobster season, the lobster beach BBQ can’t be beat.

Petite St Vincent

This private island resort is a great place to lounge with a cold rum punch.

Chatham Bay (Union Island)

Snorkel and swim, or spend an extra night to kitesurf or kayak around Frigate Island and Ashton Lagoon.


Barhop your way along the beach in Salt Whistle Bay.


The largest of the Grenadines, enjoy some live entertainment and a meal ashore at one of the many waterfront restaurants.


Along With St Maarten, Antigua is one of the major yachting centres of the Caribbean. Experience history come to life in Nelson’s Dockyard, the oldest harbour in the western hemisphere and a UNESCO World Heritage Site.

Stroll the cobblestone streets, wander among the old sail loft pillars, and follow the paths among the ruins to spectacular views and sandy beachfronts. Hundreds of boats gather here each May mile upon mile of white- sand beach and shallow turquoise water.

Sailing between the scenic sheltered bays provides ample opportunity to appreciate the underwater life too. If you have more than a week, seriously consider making the passage and spending at least a few nights in Barbuda.

A stark contrast to Antigua, Barbuda has a large interior lagoon that is home to one of the largest frigatebird nesting colonies in the world, plus

The long sandy beach or post up under a beach umbrella with a cocktail Great Bird Island for the Heineken Regatta.

Chart the course

English or Falmouth to Mamora Bay

Enjoy the beachfront, watersports and restaurant at the St James Club Marina in Mamora Bay.

Green Island and Nonsuch Bay

With anchorages only large enough for a boat or two, these idyllic bays are the perfect getaway.


From luxury resorts to sleepy fishing villages, the dramatic twin peaks of St Lucia’s Pitons dominate the landscape almost anywhere you go. Wild and untamed, their precipitous cliffs afford incredible views from both the anchorages below and the lush, jungle interior within.

From almost every harbour there is an opportunity to hike or adventure ashore. The passive explorer will enjoy the island’s towering waterfalls, winding rivers and sulphur springs, while adrenaline junkies will head for the zipline and ATV tours.

Many of the hiking trails are marked and can be hiked without needing a guide. The sheer dramatic beauty of the Pitons paired with the sandy shores and calm coastal waters make sailing here some of the most alluring in the Caribbean.

Chart the course

Rodney Bay

After provisioning, explore Pigeon Island and hike to the peak for views of the anchorage below.

Marigot Bay

Kayak among the mangroves in the bay, or south along the coastline and up the Roseau River.

Soufrière (Petit Piton)

Hike, snorkel, dive or simply lounge under the serene beauty of the Pitons.


Wander ashore to experience the quiet rural life of this seaside village.

Between the pitons

Another night with a magnificent view of the Pitons.

Anse Cochon

Stroll the white sands and enjoy a sophisticated dinner ashore.

Rodney Bay

Tuck into Trou Gascon for one last secluded beach before returning to port.