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Caribbean Sailing

By Daria and Alex Blackwell

The Caribbean Sea is a lovely patch of warm blue water surrounded by islands that are close enough together to be within a day’s sail of each other most of the time. The Caribbean is a hop from North America and a jump from Europe. The typical routes for getting there are 1) Florida to the Bahamas, to the Caribbean 2) NE/MidAtlantic to Bermuda to the Caribbean 3) Europe to the Canaries (+maybe the Cape Verdes) to the Caribbean.  The exact time varies with the jumping off point, but basically the exodus occurs after hurricane season and before winter storms.

In early 2008, we left our carefully developed NY/NJ careers behind, got aboard our 57 foot ketch, and sailed off north and then east across the Atlantic to Europe. While we were at sea, the markets crashed globally so, along with a whole lot of other adventurous cruisers, we kept going.  In 2009, we crossed the Atlantic again back to the warm waters and blue skies of the Caribbean. We found a lot of what we thought we’d find, and lots of surprises, too. 

Cruising the Caribbean on your own boat is nothing like chartering for a week or two. There is no hurry to be anywhere in particular (unless there’s a party to get to, of course); you stop long enough to become a local in some places, and move on if you’re not overly fond of others.  New cruising friends, lush scenery, warm people, exotic wildlife, plenty of challenges, and the experience of a lifetime. ..that’s a snippet of what it means to us. Of course, there was the steering failure en route to Grenada, the dinghy swamping incident in Mayreau,  the engine repairs in Antigua, the disappearance and false arrest of a fellow cruiser by the French Coast Guard, and the physical assault in St. Martin, but hey, it’s all part of the adventure right? There was plenty of impossibly aqua water and even more rum to soothe the spirit.

Have you been dreaming of sailing off to the Caribbean? Has the cold weather gotten under your skin? Are you on the cusp of leaving all those depressing newscasts behind?  Are you yearning for a dose of armchair escapism? Let us fuel your dreams with stories of fun in the sun laced with a dose of adventure skipping along the Caribbean.  We’ll take you on a journey of the island nations that comprise the Lesser Antilles from the Windwards to the Leewards.  The Caribbean Sea occupies the territory between South and Central America and the chain of islands known as the Antilles. The Greater Antilles are the big ones between Florida and Puerto Rico. The little ones….and there are loads of them…that form the eastern perimeter of the Caribbean are the Lesser Antilles. Most of the English speaking islands are independent nations, whereas most of the French and Dutch speaking islands are part of the EU.  Like most Americans, we had been to the Caribbean on holiday, but cruising is not like being on a holiday.

There’s fantastic sailing with trade winds blowing between 15 and 25 knots most days while the sun shines seemingly forever, except over the mountains where any passing clouds get trapped against the volcanic peaks.  The sailing between the islands here can be challenging with acceleration zones where the wind veers and picks up speed between the volcanic peaks, then dies off in their shadows.

Between islands, the fishing can be very good but it’s important to take only fish that live in deep water not on the reefs and that are not too old to avoid ciguatera poisoning. Ciguatera builds up in your system and can have a cumulative effect. This barracuda was caught in deep water and very tasty. Friends of ours caught one in shallower waters and did experience a mild case of poisoning with numbness and tingling sensations in their mouth and extremities.

Cruising is a lifestyle in which you become resident of a different country every few days, weeks or months. As such, there are procedures one needs to follow…and each country’s procedures are a bit different.  Let’s talk about some of the things you need to know before you go.

Each country has slightly different procedures but most have four separate authorities, each of whom you may need to check in with: Immigration, Customs, Health, Harbormaster. The Master /Captain is responsible for checking crew in. Ship’s papers (ownership & registration), insurance, passports, vaccination certs, return tickets if not staying on, fees, licenses (captain/yacht master, radio) are all important documents to have ready.  In the French islands check in can be handled via computer at chandleries or cafes – very civilized. Traveling with pets can be challenging. You’ll need a Pet Passport, chip implant, scanner, vaccinations, etc. Still in some countries there will be restrictions.

Once checked in, you can get on with your daily activities, like reading, swimming, sleeping and fixing things. Some things that you can research before you go are the two major chandleries – Budget Marine and Island Water World.  Make a note of where their stores are because if things break down en route, you’ll need to head for an island that can get replacement parts. Check out also the Caribbean free publication All At Sea. It is available as a download in its entirety online. You’ll get schedules for all the special events so you can plan your stopovers when mardi gras, music festivals, or sailing events take place.


It helps to also familiarize yourself with the radio nets on both VHF and SSB/HAM. Many harbours have a local daily net that keeps all the sailors in touch with each other and with what’s happening ashore. You’ll also want to arm yourselves with cruising guides and chart kits before you go. Many of the chandleries run out of these essentials as soon as the cruisers start to arrive after the end of hurricane season, which is officially December 1.  There are several cruising guides but the Doyle Guides are far and away the best.  So let’s share what we learned about some of these beautiful island nations.

Perhaps we’ll arm you with enough information and inspiration to sail off yourselves.

Useful Links

 Leewards in the North

  • Guadeloupe (Fr) - Iles des Saintes & Marie Galante
  • Montserrat (UK)
  • Redonda (Kingdom)
  • Antigua (UK)
  • Barbuda (UK)
  • Anguilla (UK)
  • Nevis (UK)
  • Saint Christopher (St Kitts )
  • Sint Eustatious (Statia) (Neth)
  • Saba (Neth)
  • Saint Barthelemy (St. Barts) (Fr)
  • Saint Martin (Sint Maarten) (Fr/Neth)
  • British Virgin Islands (UK) – Jost Van Dyke, Tortola, Virgin Gorda, Anegada
  • US Virgin Islands (US) – St. Thomas, St. John, St. Croix, Water Island
  • Puerto Rican Virgin Islands (US) – Vieques, Culebra

Windwards in the South

  • Grenada & the Grenadines -– Carriacou , Petit Martinique, Ronde,Caille, Diamond, Large, Saline, Frigate
  • Saint Vincent & the Grenadines –Union Island, Tobago Cays, Mayreau, Bequia, Young Island, Petit St. Vincent, Palm Island, Canouan, Petit Canouan, Savan, Mustique, Petit Mustique, Petit Nevis, Bettowia, Balliceaux, Quatre, Moonhole Rock
  • Saint Lucia
  • Martinique (Fr)
  • Dominica


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