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Where to Charter a Boat to Saint Somewhere

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The choice of where to charter a boat is based on a handful of factors that begin with skill and experience. In the Caribbean, some find that the perfect places to start making memories are in the Virgin Islands. The waters are, for the most part, protected by a long reef and unless you venture to Anegada, St Croix or the south side of St. John, you can enjoy the trade winds without the added challenge of testy ocean seas. Sir Francis Drake Channel, the hub of BVI sailing, can be cantankerous enough when the wind kicks up offering plenty of challenge for those who seek it. Mostly, though, it’s as good as it gets; living up to the reputation as the best sailing spot on the planet.

Where in the Caribbean Should I Charter a Boat?


The popularity of the BVI with sailing tourists has created an industry that caters to the wants and need of boat people. Anchorages are well marked, most have rental buoys, and guest docks make shore trips a breeze.  It’s the ultimate of where to charter a boat!

Chartering out of St. Maarten requires more experience because getting pretty much anywhere means leaving the lee and biting into unprotected waters. An average itinerary includes a circumnavigation of the island, stopping on both the French and Dutch sides as well as a day sail to Anguilla, St. Barth or both. Few anchorages have buoys which means dropping and setting an anchor is not optional. Dinghy docks are scarce, compared to the BVI, so knowing how to beach land the skiff in surf might come in handy.

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Antigua is yet another step up the scale of sailing know-how, since neighboring islands are farther away and sister Barbuda is a minefield of reefs. Heading south, on down the island chain are charter bases at Guadeloupe, St. Lucia, St. Vincent and Grenada. Each presents a level of difficulty that should be taken into account by novice sailors before they consider chartering.

Another factor weighing into charter choice is the level of sailing intensity you’re looking for.


Some folks are content simply by sitting on a yacht while others can’t wait to blast off for adventure. For many, a week away from the day-to-day grind needs to be anything but work: laid back and worry free rest and relaxation, punctuated by short, perfect sails and visits to great beach bars.

Others view a week on a boat in the tropics as an opportunity to sail hard and fast. For them, swimming, snorkeling and swinging in a hammock are superfluous activates that just get in the way of long days of sailing. All points on the liming scale can be achieved throughout the Caribbean with a carefully planned itinerary.

What you will find onshore and along the journey can be a driving force of which countries you want to visit.


The Virgin Islands are full of local color but heading south you’ll find even more. Big, open markets, funky rum shops, traditional boatbuilding, indigenous cuisine, steel pans and everywhere, characters and crazies you will long remember.

Every island in the Caribbean has its own cultural flavor and quirky norms, a personality all its own. Getting to know it can be a huge piece of your tropical trip. If you think you’ve “done” the BVI because you toured Tortola, you’re just getting started. Keep sampling. Little Jost Van Dyke lies decades from the Mother Island; Anegada stretches a century away to the north. That big gal, Virgin Gorda, is a crazy combo of islands past and future.

Near the USVI, the “Spanish Virgin Islands” offer Latin flavor, via bareboat or crewed charter, and a chance to explore low key Vieques, Culebra and numerous tiny cays with quiet anchorages.

In the Leewards, St. Barth is a billion Euros from sleepy Anguilla while the buffer between them, St. Maarten, offers visitors its split personality with the Wild West Indies on the Dutch side and French country charm on the other. Antigua and Barbuda are salt and pepper. St. Kitts and Nevis, oil and water. On down the chain, Martinique, St. Lucia, the Grenadines, each has much to offer if you know what you want.

Finally, do a bit of research to see if your style of yacht is available. Not all bases have a full selection. And while you’re on the computer, check out flight schedules and costs to your destination of interest as well as nearby accommodation options. Losing a day of charter because of a red-eye flight or an inconvenient hotel is no way to start your island time.

Know Before You Go

  •  You could throw a dart at a Caribbean chart and plot your way from there but better yet, research to find your perfect charter getaway.
  • Read charter company websites and speak with agents regarding the skill and experience level recommended for a specific area.
  • Discuss with crew how eagerly you will sail, and pre-determine the level of adventure you want to undertake.
  • Once you have an area or an island, in mind, research yacht options of size, sail/power, monohulls/catamarans.
  • Investigate tourist board sites online for shore side cultural events and activities.
  • Check for ease of flight schedules and hotel accommodations.

Jan Hein and her husband, artist Bruce Smith, divide their time between the Caribbean and the Pacific Northwest with a boat and a life at each end.

How to Charter a Boat!

Congratulations! You’re on your way to one of the BEST adventures you will ever have in your life!

We’ve taken some time and spoken to many experts to bring you a collection of Tips and Tricks on “How to Charter a Boat.”  We’ve spoken to Bareboat Charter Experts as well as the Crewed Charter Companies.

The focus for this series is on “Boats” which we would categorize as anything UNDER 80′ or roughly 25 meters. When you are chartering a Yacht (Over 80 feet or > 25 Meters) the game changes.

These tips and tricks apply no matter where in the world you intend to Charter.  It doesn’t matter if you are interested in the Caribbean or Washington, North Carolina.  Hey – let’s face it…  It’s “five o’clock somewhere.”  (Thanks Jimmy Buffett)

Now…  I have to warn you…  Once you start chartering, it’s hard to stop!  There’s just too many wonderful memories and too many amazing places to visit.

Of course, we’d love to hear from some of your adventures.  Please share your story with All At Sea!  Send us your Images and send us the story of YOUR charter adventure.  Please help others learn how to charter a boat.

How to Charter a Boat – TIPS and TRICKS 


Comments and Questions are always appreciated!  We’ll be looking for new ideas to bring to you!



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So Caribbean you can almost taste the rum...

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