By Mark Stevens

Heading SouthYou’ve weathered COVID and you’re ready to book your charter to paradise.

You’ve done some homework, but your float plan’s also got some blank spots.

You want to discover more about the allure of specific Caribbean cruising grounds, whether in terms of the cruising itself, or in terms of shore attractions, you want to ensure that your skills and experience match the nautical demands of potential choices and you want to find the best fit when it comes to charter options.

Finally, before you book your boat and flight, you need to be aware of relevant rules and protocols. 

Now, suitably armed, you’ll be one step closer to paradise. Then it hits you.

Come winter you’re heading south.

Chasing Ye Pirates

Anguilla SunsetAnguilla doesn’t just claim one of the world’s best beach bars. Sunsets are pretty good too

Antigua and Barbuda’s history as a charter destination is unmatched in the Caribbean. Records from 1671 show a boat chartered to the governor of this region for the purpose of “chasing ye pirates.”

Nowadays pirates aren’t a concern, but you might be challenged when it comes down to choosing anchorages.

In his Cruising Guide to the Leeward Islands, Chris Doyle describes sailing here as “exceptional, with more anchorages than any other country in the Leewards.  You could cruise here for two weeks without stopping at the same anchorage twice.”

Factor in that this destination also boasts more than three hundred beaches and you get the idea.

But the beaches are just the beginning. Go ashore and catch the Sunday night party at Shirley Heights, be regaled with views of one of the Caribbean’s best sunsets, or stroll through history at Nelson’s Dockyard.

A Local VendorA local vendor helps with provisioning on the island of Antigua

Winds are generally consistent here and reefs are well-marked on the charts, so that isn’t a huge issue. Seas can get big off the south of the island, making for some slogging if you’ve chartered out of English Harbour. Navigation is primarily line-of-sight unless you head north to the sister island of Barbuda (worth the trip if you book a longer charter) and you do need a keen eye if you traverse North Sound – stay well offshore.

Make sure to build in stops at Great Bird Island, Deep Bay and Jolly Harbour. 

Then raise your sail to chase ye pirates – or one more perfect beach.

Chasing Captain Sparrow

“See that island?” I said to my friends Ed and Kim North, pointing across the water at a stand of palms spotlighted by the full moon.

The catamaran we’d booked from Horizon Yacht Charters to cruise the waters of St. Vincent and the Grenadines swung lazily on the hook in the Tobago Cays halfway down the Caribbean’s Grenadine islands.

“Filmed a scene from ‘Pirates of the Caribbean’ right over there.”  

Pigeon Point BeachWater fun off Antigua’s Pigeon Point beach

Two days later we glided past the harbour that was the set location for the first scenes in that iconic movie. Talk about chasing Captain Sparrow.

When you chose St. Vincent and the Grenadines you may encounter big seas from the east, making for occasional challenging sailing, but the appeal of this destination is so great it’s worth it.

Anchorages abound here, from the lee side of Bequia to the paradise that is Mayreau to Tobago Cays, where you can snorkel with sea turtles.

Best yet, Horizon Yacht Charters out of Grenada are focussing their energies on their base at St. Vincent.

Belize's South Water CayeThe neon aquamarine waters of Belize’s South Water Caye are just part of the allure of this delightful anchorage

According to Horizon staffer Jacqui Pascall, “we have made the decision to move all our yachts to our base in St Vincent for the winter 2021 – 22 season. This then gives all our clients the opportunity to sail in the Grenadines with ease, with a wider choice of yachts and without clearing in and out with Customs and Immigration.”

A Tale of Two (or three or four) Islands

When the French and the Dutch had to choose the borders for the bipartite oasis that is Sint Maarten/St. Martin, they reputedly chose a national from each who would hike the island from a common point. Their meeting place would form one boundary.

Belize Traffic JamTraffic jam, Belize - style

Inbibing a ration of Genever (a potent cousin to gin) while his French counterpart sipped wine on the journey, the Dutchman was slowed considerably.

The rest is history – or at least a worthy tale of “two islands.”

Best yet, cruisers here are hardly limited to this worthy duet, though the joys of exploring Sint Maarten and St. Martin are myriad.

Visit the town of Marigot on the French side and find that perfect bistro or delectable croissant to nosh in the shadow of towering Fort St. Louis, an eighteenth-century fortress. 

Venture east and drop the hook near Grand Case, considered by many to be the culinary capital of the Caribbean, or make for the Sint Maarten side and anchor at Simpson Bay, host to the Heineken, one of the Caribbean’s oldest regattas.

Snorkel The Indians with BVI CharterA chance to snorkel The Indians, a must-do for your BVI charter

Head north to nearby Anguilla, home to movie stars, to perfect beaches nuzzled by waters the colour of heaven, to watering holes that include Dune Preserve, rated the “best beach bar in the world.”

Or set your sails for St. Barth’s where you can anchor north of Gustavia and prowl cobblestone streets shopping for goods so exclusive they don’t even post their prices.

All among a cruising ground where line-of-sight navigation makes for soporific sails and consistent and thrilling winds.

A tale of two islands?

Two are just the beginning.

A Tale of Two Hundred Islands

But maybe your inner Captain Sparrow lusts for even more. 

Crossing the Drake ChannelThe fam taking over the helm while crossing Drake Channel in the BVI’s

Welcome to Belize, home to the world’s second biggest barrier reefs, a place boasting beach towns like Placentia, worthy of its name as “pleasant place”, a stretch of water sheltered by that selfsame reef so that, even when the winds are blowing, the water’s flat and manageable.

Welcome to a cornucopia of more than two hundred islands and cays.

Think deserted anchorages you share with only manatees, think overnighting in a protected cove where, in a rustic restaurant at Hideaway Caye, dinner is the catch of the day or think, come morning, some of the Caribbean’s best snorkeling.

Marigot in St. MartinDream Yacht Charters and Moorings/Sunsail maintain bases here (close to Placentia), offering fleets that include monohulls and catamarans – the latter is your best choice given two defining characteristics of this cruising ground.

First – the presence of the barrier reef and the numerous cays translates to great stretches of quite shallow waters. Second – the most common entry on your chartplotter reads: “Unsurveyed waters; use caution,” and the current cruising guide is aspirational at best.

St. Vincent and Grenadines VistaCheck out this St. Vincent and Grenadines vista then watch “Pirates of the Caribbean” again. Look familiar?

Having said that, the reasons and rewards for cruising the waters off Belize are numerous.

Better than two hundred reasons.

Eleven Thousand Virgins

Upon returning from one Caribbean excursion to report his findings to Queen Isabella, Columbus described a chain of islands with reference to a legend about Saint Ursula and eleven thousand virgins.

While this proved to be a bit of an exaggeration (the British Virgin Islands comprise only about forty members), this wealth of potential anchorages along with the appeal of those anchorages has resulted in the BVI’s reputation as one of the Caribbean’s premier charter destinations.

Visit quirky bars (Soggy Dollar and its infamous “Painkiller” cocktail), soak up some history (Drake laid in wait here before attacking the Spanish Armada and Norman Island was reputedly the inspiration for Stevenson’s masterpiece, “Treasure Island), savour delightful and surreal landscapes (the Baths at Virgin Gorda or the Indians off Norman).

Best yet, you’re talking line-of-sight navigation, the protected waters of Drake Passage and short romps from anchorage to anchorage if you’d rather laze on a mooring ball than harden the mainsheet. 

Might not be eleven thousand anchorages here despite Columbus’ hyperbole but one thing’s for sure.

There’s more than enough to go around.

Of Sails and Spice

Snorkel Tobago CaysSnorkel Tobago Cays in St. Vincent and the Grenadines and bond with some local fauna

On a lay-day during our first Grenada charter, my wife and I decide to hike a crater lake at Grand Etang. En route we are seduced by the scent of cinnamon emanating from great trays of that spice drying in the sun. Later that day we visit an herb garden, traversing paths lined with nutmeg shells.

Sail here and enjoy the aromas of “Spice Island.” 

Pick up your charter at Port Louis Marina, ensconced in the bosom of St. George’s, considered by many to be the Caribbean’s prettiest harbour. 

Now make for points south (hideaways like True Blue or Mt. Hartman Bay) or do what most cruisers do – make for Carriacou, roughly thirty nautical miles north.

Skirt an underwater volcano and glide past delightful rock outcropping as you approach Carriacou. Drop the hook in a bay aptly named “Paradise”, or join the boating fraternity moored in Tyrell Bay, dinghying ashore for dinner, or just a sunset cocktail.

Anchor off Hillsborough and dinghy out to your own Gilligan’s Island (a few hundred metres of sand and palms) or go ashore for a lesson in both history and seamanship at Windward, where you can watch them build traditional sloops.

En route back to Grenada, pick up a mooring ball in the lee of the island’s sky-reaching mountains and snorkel through an underwater sculpture gallery at Molinere. Or spend time ashore on Grenada itself, hiking to a waterfall or hanging with locals for Fish Fridays at Gouyave. 

More page-turning chapters in a saga of sails and spice.

The Shallow Seas

Grenadines SunsetJust one more perfect sunset - this one courtesy of Bequia in the Grenadines

Roughly an hour out of Marsh Harbour in the Abacos Islands of the Bahamas I’m savouring the aquamarine waters from the helm of our chartered Moorings cat when I glance at the depth sounder.

My heart leaps into my throat.

Seven nautical miles out and the depth is fifteen feet. 

Then I remember: been that way since we left the dock. 

Cruise the Bahamas and you’re sailing the shallow seas.

Yacht on Calm WatersSome historians think that’s how Bahamas got its name – a corruption of the Spanish for “shallow sea.”

Until Hurricane Dorian the Abacos were a prime Bahamas cruising destination, featuring idyllic islands and a helping of history (Hopetown and Green Turtle Cay were Loyalist colonies). After the storm the charter companies closed their bases. Until now. 

“We’ve just re-opened our Marsh Harbour base,” says Emily Turner from Dream Yacht Charter, though you should do more homework before deciding on this family of islands. 

PatioIn the interim the Exumas have gained popularity. Both Dream Yacht and Moorings offer Exumas charters from their Nassau base. With sheltered water and a year’s worth of cays and islands to visit, that reputation’s well-deserved.

Sail here and snorkel off Horseshoe Beach, act like a tourist and swim with the pigs or bond with your inner hermit on an alabaster swathe of sand. Hang with the haute monde at Staniel Cay or go for local cuisine at Lorraine’s on Great Guana.


Boating in the SouthLast night you dropped the hook of Allan’s Cay and this morning you’re making for the dunes and mangroves of Warderick Wells. 

Float plan consulted, you’re ready to sail, weighing anchor, setting the main and turning the wheel.

Velocity made good, course made good.

Today you’re heading south.

Takeout Bequia-Style



Respite for the galley crew: takeout Bequia-style

Sailing South

• Dream Yacht Charter offers catamarans and monohulls out of Abacos (recently re-opened), Exumas (out of a base at Nassau), BVI’s, Grenada, Belize, Antigua and St. Martin (along with a couple of other Caribbean destinations). Once you’ve decided on a destination you can opt to bareboat, but you can also book a skipper, crewed or charter “By the Cabin”.

• Sunsail and the The Moorings are part of the same company nowadays and frequently share docks. Options at The Moorings include all-inclusive crewed charters and powercats. Sunsail specializes in sailing charters, offering flotillas in many European destinations. Check out  or click on
• Horizon Yacht Charters maintains fleets across the Caribbean, though for the upcoming season their Grenada/SVG base is concentrating their fleet out of St. Vincent. Log on to

• CYOA is a friendly BVI charter company with a great reputation (offering Virgin Island charters since 1980) and is worth checking out. Go to

Staying Safe

• When it comes to adding COVID considerations to your float plan, things can change almost daily and the various protocols can be mind-boggling. For instance, right at this moment Bahamas merely requires proof of full vaccination with a two-week additional period while Antigua and Barbuda require a varied protocol of testing.

• The most recent information for each is generally the first “page” you see on their tourism site so that’s the best place to start:  and

• Responsive to current challenges, charter companies are proving themselves both supportive and flexible. For example, Dream Yacht Charter has cleaning protocols that match WHO guidelines while the major companies will let you change dates without penalty if affected by COVID. 

• Go to for their protocols and options


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