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altIt hits me as hard as the waves crashing into our bow just outside the shelter of Sunsail’s St. Vincent base, strong as the thirty-knot winds gusting out of the east, that I have not planned this trip as well as I should have.

We ship two good friends as crew – both relatively experienced sailors – but they aren’t ready for this. Nor am I.

Supposed to be a bucket list adventure but it starts as a romp from hell.

And it’s my fault.

We weren’t ready to bareboat the Grenadines. While we all eventually got our sea legs and the voyage turned out to be a rousing success we could have done things differently. We could have shipped a skipper, we could have gone with a flotilla, and we could have done more research on local sailing conditions.

For pre-departure planning is the biggest factor in determining whether your Caribbean charter is a question of sailing into the sunset or holding on for dear life as you watch your life pass before you. Do your homework, though, and you’ll have filed in your memory bank the stuff of every boater’s dream.

A Beam Reach for Paradise

So what’s your assignment? Choosing a charterer, a boat, a cruising option. And finding the destination that sets you on a beam reach for paradise.

The Abacos in the Bahamas features 'Champagne Cruising' on aquamarine waters protected by a delightful necklace of islands where Cape Cod architecture meets tropical surroundings. Depths are an average of twenty feet and the only decisions you have to make are whether to find a pink coral beach and stretch out or sample the ambiance of Hope Town. Nice winds, gentle waters and a wealth of anchorages close together.

No accident that Moorings got its start in the British Virgin Islands – a chain of roughly forty lush mountainous islands ringing Drake Passage.

Sail all day. Sail for an hour or two. It doesn’t matter: you’ll still end up in a postcard-perfect anchorage off a nearly deserted beach.

If you’re new to bareboating, your crew manifest includes landlubbers or you just want to relax, Abacos and BVI’s are both excellent choices.

Way to the south is an equally gorgeous chain of islands beginning with Grenada and stretching north to St. Vincent.

Do dinner at an upscale resort on a private island (Petit St. Vincent) or swim with the sea turtles at Tobago Cays – one of the most beautiful anchorages in the Caribbean. Make passage north to Mustique, the playground of the rich and famous, or drop the hook in Bequia’s Admiralty Bay, with a pastel-painted waterfront and almost as many yachter-friendly bars ashore as there are sunset-gazing cruising boats anchored in the bay.

One of the most beautiful of the Caribbean charter destinations.

But it is not for beginners. You need to be able to sail in moderate to heavy seas and winds and you need strong navigational skills.

Sint Maarten and Antigua are both prime destinations. The former is home to one of the biggest Caribbean regattas and a yachting infrastructure matched only by Antigua.

Sint Maarten cruising offers a variety of anchorages and marinas in sheltered waters and you can go further afield. St. Barth’s is a half-day sail away, while there’s no more exhilarating sailing than Anguilla Passage with a pit stop at Anguilla’s Road Bay, a perfect anchorage on an A-List island that regularly hosts the likes of Uma Thurman and Robin Williams.

If you like history with your heeling – and a wide selection of anchorages – Antigua is for you.

The island is dotted with fortifications that compete in vain with the plethora of beaches – many just off the beam of your boat in a protected little cranny. Best yet, the west coast offers more anchorages on the lee side than most Caribbean islands.

And Barbuda is the ultimate island getaway if you’re shipping a solid crew and want to drop the hook off the most deserted beach in the West Indies.

One lesser known Caribbean gem is St. Lucia. While many charterers book here and use it as a jumping-off point for either St. Vincent and the Grenadines to the south and Martinique to the north, that’s a mistake.

It’s no accident St. Lucia’s called the 'Helen of the Caribbean.' The French and English fought over her for decades – both testament to her strategic importance and her sheer beauty. Plenty of anchorages along the west coast – the one at the Pitons makes the short list for most beautiful Caribbean anchorages – and a growing and dynamic infrastructure.

"We are really working on being yacht-friendly," says St. Lucia’s director of yachting, Cuthbert Didier. "From being the ARC (Atlantic Rally Cruisers) destination to training many of our youth in the marine trades, we think you’ll love sailing here. And we will make sure the experience is a great one."

Think your only problem was choosing a flight? Think again.

And the only thing you’ve decided so far is what landform reclines abeam of your broad reach to paradise.

Decisions, Decisions

One day off Grenada’s west coast line squalls fly across the green mountains like steel curtains. A wind line makes for our boat like a school of hungry piranha.

But we’re worried. In fact, it’s downright exhilarating. On this trip, we ship a skipper.

The boat goes way over and the water hisses along the hull. But I just hold on while my wife admires the spectacle. And Andell David, our skipper, who knows the weather inside out and knows the hazards to navigation like the back of his hand, yells out in glee. "I love to race."

We’ve made the right choice – one of a multitude of decisions that comprise your pre-departure checklist.

Book a skipper for your entire vacation (generally provisions and $125-175 daily). Sail as much or as little as you want. Add a chef to the manifest and you’ll feel more like an admiral than a sailor.

Most of the charter companies down here offer a comparable range of options.

Hire skipper and chef together and choose your own provisions. Or let them do it. Festiva Sailing Vacations offers a sample menu from fillet of Mahi Mahi to stuffed chicken - with welcome appetizers so you get the royal treatment the moment you step aboard.

Flotillas offer a perfect compromise: skipper your own boat but cruise with other vessels and a lead skipper.

Or learn to sail while you’re down here: Offshore Sailing School offers certification in keelboat cruising in partnership with Moorings.

Decisions, decisions. And you haven’t even chosen your vessel or charterer.

The emphasis at Footloose is on value. Both Moorings and Sunsail provide a full fleet of both monohulls and catamarans. Festiva’s fleet consists exclusively of catamarans while companies like Mango Yacht Charters or Canadian-owned Conch Charters offer both exceptional service and a wide range of monohull and cats.

So choose your boat, choose your option, choose your charterer. Then get ready for the royal treatment.

The Royal Treatment

It’s a hot afternoon in a gentle bay decorated by swaying palm trees. The peaks of Tortola recline voluptuously to the south.

We take a swim in bath-tub-warm waters then recline in the aft cockpit sipping on a rum concoction. The smell of grilled salmon wafts over us from the galley and then we head topside for a feast fit for royalty.

Our hostess opens a bottle of wine, our skipper sits back and grins at us. "It doesn’t get much better than this, does it?" he says.

It may get better but I can’t imagine how.

We may not actually be sailing into the sunset – our boat is a Moorings Powercat – but we’re no less ecstatic.

With Moorings, you can power cruise in either the BVI’s or the Sea of Abaco. They maintain a fleet of Powercat 474’s out of Marsh Harbour and 393’s, 372’s and 474’s at their Tortola base. CYOA Charters maintains several trawlers out of their USVI St. Thomas port.

Something for every boater down here in paradise.

You don’t have to sail into the sunset to sail into the sunset.

Cruising Into the Sunset

We’re swinging on the hook at the end of January in the shadow of the Pitons off St. Lucia’s southwest coast. It is an anchorage of breathtaking beauty, a vista framed by two towering peaks – the most photographed place in the Caribbean, in the top five of Oprah’s list of places to see before you die.

An icing sugar beach lounges off our starboard beam. Flying fish break the water’s surface, glittering in the late day sun like coins of the realm.

The sun falls in the west, spotlighting the craggy face of Gros Piton.

We see the green flash.

We’ve chosen our destination; we’ve picked a charter company and a boat. We’ve booked a skipper for his local knowledge.

And now we’ve cruised into the sunset.

By Mark Stevens Photographs by Sharon Matthews-Stevens