Caribbean Dreaming

Photo David Lyman

Sitting in my home in Maine watching the snow fall in early December made it easy to understand why many sailors pack up and head south to the Caribbean during the winter. There’s an idyllic element to the notion of fleeing the cold on your own boat and lazily cruising in the crystal-clear waters as the mellow breezes guide you and your crew from island to island.

“If you want to sail to the Caribbean, you’re going to need a year to prepare,” said David Lyman, a contributor to Ocean Navigator, has logged more than 60-000 deep-water miles at sea. He has made in excess of 12 round-trip deliveries from his home in Camden, Maine, to the Caribbean including trips via Bermuda, down the Intracoastal Waterway to Florida, the Bahamas and back. “You need to work on your boat over the summertime and you’re going to work on your crew and then when they decide not to go, you’re going to need to find more crew.”

To familiarize yourself with the Caribbean Sea, first let’s understand the region we’re discussing. To the south, it is bounded by Venezuela, Colombia and Panama; to the west lie Costa Rica, Nicaragua, Honduras, Guatemala, Belize and the Yucatan Peninsula of Mexico; to the north are the Greater Antilles islands of Cuba, Hispaniola, Jamaica and Puerto Rico; and to the east by the north-south chain of the Lesser Antilles that consists of the Virgin Islands in the northeast to Trinidad. Within the boundaries of the Caribbean, Cuba is the largest island.

The best way to learn about the region is to read the Caribbean Compass, a local monthly sailing magazine, that also produces online newsletters. “You also need to get the cruising guides by Doyle of the windward and Leeward islands,” said Lyman.

Doyleguides.com makes available downloadable cruising guides and subscriptions for the Virgin Islands, the Leeward Islands, the Windward Islands and Trinidad and Tobago. For old-school types who like things printed on paper, the guides are also available as books.

There are different boats for different purposes. An offshore boat is OK in the Caribbean, but you need to watch depths. Lyman says the ideal boat for the Caribbean would be a catamaran.

Lyman also says that a boatowner should download Navionics to a mobile phone or tablet to help with planning stops and to learn distances between harbors. A captain will need to learn where reputable yards, chandleries and stores with provisions are located.

One of the more involved tasks for captain and crew will be filling out the paperwork to clear customs at every port when you arrive and depart. “BVI, St. Marten, at the French and Dutch sides and at every island, you have to clear in and out,” said Lyman.

If you’re looking for crew, SailOPO.com is a great resource. OPO stands for Offshore Passage Opportunities is a networking service that offers experienced and potential crew members the chance to get aboard a yacht heading south. With a paid membership, experienced crew sail for free. Some voyages require crew to provide proof of experience with solo, night watches and other abilities.

Sailors seeking additional offshore experience would be interested in the Swan Program that was designed to help knowledgeable sailors gain the blue water miles needed to join crews on longer passages. SailOPO is also a proven resource for captains seeking experienced crew to help on a delivery or long passage. Another site offering similar services is saltydawgsailing.org. The crew service is free benefit for paying members who are seeking positions on boats. Opportunities for participation in longer rallies and local cruises and races can be found here.

Lyman says the best way to learn about sailing the Caribbean is to go on a two-person crewed charter. “If you haven’t bare-boated, they know where to go, how to anchor and where,” he said. Plan to spend up to $10,000 for four people for 10 days including food, but not alcohol. You can find charters at websites including charterworld.com.

Lyman says an experienced sailor could also charter a boat and take the helm or if the money is right, “You buy two boats, one up here and one down there.” Sounds idyllic doesn’t it?

By Eric Colby