Caribbean sailing on a bareboat

October 27, 4:48 AMLA Islands ExaminerMaggie Dobbins

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Tranquillity in the quiet of Barbuda

Photo by Maggie Dobbins

Sailing the Caribbean islands can be magical.  There are so many beautiful islands that are distinctly different from each other.  You can be in French, Spanish, English, American, Dutch or independent islands. 

Each has their own culture, food and rhythm. The more you explore them, the more you realize how different they are from each other.  And sailing amongst them is a wonderfully paced and independent adventure.

I have written previously about some favorite islands to explore and also made recommendations on crewed charter boats that make for a fabulous adventure without the hassle.

But if you know how to sail and anchor, you may well want the freedom of chartering your own boat without a crew. Both monohulls and catamarans are widely available on most islands or within an easy sail of others.

There are a lot of charter companies that offer sailboats, from the major companies to smaller Caribbean companies. The larger companies generally have newer boats, the smaller companies boats tend to be a bit older, but well maintained and usually a little less money.

The sailing is great in the spring and generally less money.  Christmas/New Years is the busiest time of year on most islands.  Then there is a quiet period in mid-January, before it picks up again in early February.

Barefoot Yacht Charters is in St. Vincent and the Grenadines.  They have a great reputation for support and friendliness. Since they are there in the Grenadines, you don't waste anytime trying to get to those islands from a more distant island.

Barefoot also offers a 6 day liveaboard class for three different levels of sailing certification by the American Sailing Association. (ASA) What a great place to get your sailing certifications!

Horizon Yacht Charters has the usual locations of the British Virgin Islands and the Grenadines, but they also offer charter bases out of Antigua & Barbuda, which is one of our favorite combination of islands for exploring by boat.  Antigua offers the old English harbor with buildings and fort intact from the 1700's to an 11 mile stretch of sand on Barbuda where there are few boats and only one hotel.

They also offer boats out of the half French/half Dutch island of St. Martin.  This opens up a whole lot of other islands in the Leewards to explore such as Anguilla and St. Barths. If you really hurry, you can hear Jimmy Buffet play for free in St. Barths on November 7th!

TMM Yacht Charters is a smaller company that charters boats out of the British Virgin Islands, the Grenadines and Belize. We are headed up to Belize this season and understand it is gorgeous.

Sunsail and Moorings are owned by the same company now.  They are well established and have a large fleet of boats to choose from.  They have smaller boats for two people and boats with 5 or more staterooms for a group.

Have fun deciding which islands to visit, then pick the charter company that meets your needs at the best price.

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