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Chartering 101: Newbie Tips on WHERE to Charter a Yacht

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So you’ve finally decided to cast off, tired of prowling Caribbean docks with a bad case of nautical envy. You haven’t sold the house to sail into the sunset but at least you’ve committed both time and budget to a charter.

Now where do you go? Who do you book it with? Do you have the necessary skills?

Fear not intrepid mariner, for the answers, like Blackbeard’s Treasure, lay herein.

At the end of my first bareboat charter we pulled into the dock shaken and humbled. My wife was now convinced that, safely ashore, she’d live to see her children again. A crusty salt standing nearby grinned and said “it’s not the BVIs, is it?”

So You Want to Work on a Yacht in the Caribbean

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Forget about hotels or shore-bound inns. When you charter you get your own room with a view - like this sunset over Tortola. Photo: www.sherryspix.com
Forget about hotels or shore-bound inns. When you charter you get your own room with a view – like this sunset over Tortola. Photo: www.sherryspix.com

Grenada is unspeakably beautiful – mountainous and lush with steep slopes blanketed by vibrant orange and red flamboyant trees. And although Grenada is spectacular and a must-do charter destination, the robust sailing conditions of the southern Caribbean are perhaps not the place for your first charter.

If you’ve never done blue water sailing, start with the British Virgin Islands. The two big advantages here are (1) with forty-plus islands in this picturesque archipelago you can get from one overnight spot to the next in just a couple of hours and (2)  Drake Passage is protected from most of the big waves of the open sea.

But you can also encounter kindly conditions in The Abacos in the Bahamas. While depths can be a factor here (you have to have solid chart-reading skills), the islands ringing Abaco Sound make for both sheltered waters and a variety of anchorages with short passages. Charming, too: Hope Town is like a pastel-painted New England, only with perfect pink sand beaches.

Three Days, Three Boats, No Watch

If you’re a solid skipper with a seaworthy crew, consider the Grenadines. Wind and waves are challenging and passages between islands are longer, but once you arrive and drop the hook in Tobago Cays – with their brown sugar sand, a thousand shades of green, and waters the color of heaven – you may never weigh anchor again.

Some of the Leewards are great compromises, rich in history and nautical traditions, offering secluded anchorages or great nightlife.

If you cast off from St. Martin’s popular charter base at Oyster Pond you’ll be taken aback by the serious waves lashing the harbor opening. But once out there you can head south and round the island, with some great sheltered passages up the west side. Not to mention the fact that this island with the split personality boasts some of the Caribbean’s best nightlife and shore-bound dining.

From here you can also explore the idyllic island of Anguilla or pull up at Gustavia in St. Barths and fancy yourself a member of the haute monde.

Lots of options if you cast off from Antigua too: protected waters in North Sound, a year’s worth of beaches, a great selection of anchorages and a nautical tradition without equal. In addition, St. Kitt’s and Nevis are fairly painless downwind passages from there.  And your reward is an anchorage off Nevis at one of the most beautiful of Caribbean beaches.

But you don’t have to be dissuaded from a destination like Grenada because you lack confidence. All the charter companies offer skippered charters. With outfits like Moorings or Sunsail you can go for the royal treatment: have them provision the boat and book a skipper and a chef. Would that I had that kind of budget!

Yachting 101

You can also ship some help for part of your trip – arrange a skipper for the first day or two then head out on your own. Another great compromise is to sign up for a flotilla. I’ve never done this in the Caribbean but I did it last year in Croatia and loved it. No undue hand-holding – just daily briefings from a local expert that include hazards to navigation and perfect lunch stops and some downright fabulous nightly get-togethers.

When it comes to choosing a charterer you look at your budget and needs and the kind of service you want – sometimes it’s a matter of which charterers serve which destination.

In my experience, Moorings is sort of the Cadillac of charters while Sunsail’s brand position leans more toward performance boats. A company like Horizon offers friendly service because they’re smaller than the first two although they do offer a comprehensive fleet in several locations.

So, now you’ve had the two-minute primer there’s just one more task at hand … It’s time to cast off.

Top Caribbean Destinations to Charter a Yacht

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Mark Stevens is an award-winning travel writer whose specialties include Canada, the Caribbean and boating. Credits range from Sailing magazine and Canadian Yachting to the Washington Post.

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