Article written by Mark Stevens. Photos by Sharon Matthews-Stevens.
Come winter Canadian sailors look to the Caribbean.
Come winter we dream of raising our sails in paradise.
Sound like a recipe for happiness? Then add these Caribbean sailing must-dos to your float plan.
WHERE IT ALL BEGAN (British Virgin Islands)
No coincidence the self-chartered sailboat industry (called ‘bareboating’) began in the British Virgin Islands.
This roughly forty island archipelago offers some of the Caribbean’s best sailing. Think constant winds, sheltered waters and short passages between postcard-worthy anchorages.
Visit an island boasting nothing but sand and a duet of palms; an island decorated by surreal granite landforms; an island that reportedly inspired “Treasure Island.”
Get the appeal?
Fifty-plus years ago Charlie Cary came up with the idea of bareboating charters, giving birth to The Moorings, one of the world’s biggest charter companies.
Nowadays North American sailors universally recognize a BVI charter as a nautical rite of passage.
Here is where it all began.
CHASING CAPTAIN SPARROW (St. Vincent and the Grenadines)
For a sense of déjà-vu go sailing here then watch “Pirates of the Caribbean”.
Explore a St. Vincent harbour, film location for the movie’s beginning; anchor in Tobago Cays and look east: it’ll seem strangely familiar.
But chasing Captain Sparrow (AKA Johnny Depp) is hardly the only appeal. Furthermore, you should add Dominica and Grand Bahama to your Caribbean bucket list to visit other film locations if you’re a fan of that movie franchise.
Although St. Vincent and the Grenadines are popular with more advanced sailors due to sometimes challenging conditions and greater distances than those in the BVI’s, its unspoiled vibe does make this chain a must-do.
Sip a cocktail on Bequia, claim your very own anchorage off Mayreau, hang out with the haute monde at Mustique or snorkel with sea turtles in Tobago Cays.
Just watch for the ghost of Captain Sparrow.
SAILING INTO HISTORY (Antigua and Barbuda)

Nelson’s Dockyard in Antigua and Barbuda is just one attraction that makes this destination a history-lover’s must do.
Sailing Antigua and Barbuda is a must-do for history-lovers.
Climb a trail ashore leading to the ruins of a nineteenth-century fort; cast off from a historic dockyard once commanded by Admiral Nelson; go ashore and visit the ruins of a plantation.
But history’s hardly the only appeal.
A wealth of perfect coves to anchor overnight and a year’s worth of beaches make Antigua and Barbuda an irresistible cruising ground for any sailor.
Make the passage to nearby Barbuda, an island worthy of Robinson Crusoe, an idyllic oasis boasting a pink sand beach stretching for miles.
Or just explore Antigua itself.
Antigua and Barbuda boast more anchorages than almost any other Leewards cruising ground and winds are always cooperative.
SAILING THE SHALLOW SEA (The Bahamas)

Go far from the madding crowd in The Exumas in The Bahamas, but be ready for some interesting neighbours.
While water depths off The Bahamas demand situational awareness (many attribute the name ‘Bahamas’ to a corruption of the Spanish for ‘shallow seas’) those conditions are responsible for those delightful sea colours unique to this archipelago laying claim to a multitude of islands and cays.
Two cruising grounds here are popular.
History-lovers are smitten by the Abacos. Think sleepy cays boasting Loyalist architecture, a picturesque candy-cane-painted lighthouse and pink beaches.
Want to go far from the madding crowd? Book the Exumas.
Anchor off an island with more iguanas than people. Go ashore and dine in rustic restaurants ashore or dine aboard. Share your anchorage with only one or two other boats.
Or raise your sails on the shallow sea.
A WEALTH OF POSSIBILITIES

Sail the Abacos in The Islands of the Bahamas to find a beach to call your own. You’ll never want to leave.
You don’t have to be an expert for a unique adventure in paradise.
Go bareboating (where you’re skipper and crew), book a skipper, add a cook to the crew or simply book your own cabin and bond with other like-minded adventurers.
No shortage of possibilities if you want to raise your sails in the Caribbean.
Just remember to ship your sea legs.
Article written by Mark Stevens. Photography by Sharon Matthews-StevensFor twenty-five years the writing/photography team of Mark Stevens and Sharon Matthews-Stevens has provided editorial and photographic Caribbean content to a multitude of publications.
They’ve worked with newspapers from The Washington Post to The Globe and Mail, magazines from Travellife to Caribbean Business and Travel, and online publications from ATasteforTravel.ca to VacayNetwork.com. They have hiked the rainforests of St. Vincent in search of the Vinci parrot, sailed the waters off countless islands and traversed Jamaica in search of the world’s best jerk.
In addition to numerous other writing and photography awards, they have been recognized for their writing and photography fifteen times by the Caribbean Tourism Organization during their Canadian Media Awards events. Mark and Sharon are true Caribbean specialists.






