Tip-Top Tips for First-Time Caribbean Cruisers

Heading out for your first Caribbean cruise? One of the best things you’ll find is the willingness of the Caribbean cruising community to give advice! We asked a wide selection of experienced Caribbean “old salts” for their top tips, just for you. (One correspondent remarked, however, “I object to the term old salt! I’m not an old salt, I’m a person of mature years and saline disposition!’)

We received a wealth of information, ranging from the objective and practical to the subjective and offbeat. Thanks to everyone who so generously shared the wisdom of their experience. We hope all you first-time Caribbean cruisers will find many helpful hints here to enhance your experience.

Plan ahead (but not too much)!

Writer, photographer and sailor David Lyman says, “Research before you leave home. Build a library. Develop basic knowledge of the various islands, their cultures, topography, harbors and marine facilities. Buy and read through Chris Doyle’s cruising guides to the Leeward and Windward Islands, take them with you. Subscribe to Caribbean Compass by sending a request to sally@caribbeancompass.com — it’s free and full of useful and entertaining information, and you’ll get a link each month to the current issue. The Back Issues Archive at www.caribbeancompass.com/ backissues.html is another great resource. Read some of the classics to get a historical point of view on the islands. Michener’s Caribbean, and Don’t Stop the Carnival by Herman Wouk are two that come to mind; there are a hundred others. Books and guides not only provide practical information, they fuel the dream.

“Get NGA Nautical chart - 108, Southeast Coast of North America. It covers the Western Atlantic from Canada to Antigua (US$25). Stick it up on the wall and look at it each day. It’ll get you into the immensity of the two-week offshore voyage to get to the islands. I bring one with me on each delivery and add fixes twice daily, make notes, add drawings — create a visual record of the voyage. I have two dozen of these now, plus the logbooks and journals.

“Buy Imray Nautical Chart - Imray-1 Eastern Caribbean (US$25). Stick that on the wall as well. More dream fuel. Bring it with you. Get Navionics on your smartphone and iPad. For less than US$100 you have all the detailed charts you’ll need, and a navigation tool to plan voyages, stow routes, and calculate time-rate-distance problems. I used my iPhone and Navionics to navigate from Maine to Martinique two years ago. Didn’t look at the chart plotter once.

“Destination? Have you figured that out yet? You could spend two weeks or an entire season exploring the US and BVI. I’ve spent years. But, once there, it’s a headwind bash to get east and south. You could head south-southeast on an east- northeast breeze from the BVI all the way offshore to Grenada, then work your way north back up the island chain, but that would take a full season. If you’re planning to spend just a few weeks or a month on your own boat, head for St. Martin/St. Maarten or Antigua. Both have marinas with slips to park your boat while you are back home. There are marine services, provisioning and frequent flights home. From either destination, there are nearby islands to visit, cultures to explore, hiking trails, waterfalls, open-air farmers’ markets. Antigua is perhaps a better jumping-off spot, as the French islands of Guadeloupe and Martinique are a day sail away and the wind will be on the beam down and back.

“We’ve made the leap from the BVI to Guadeloupe in 30 hours, with the east- northeast wind. A delightful jaunt. We worked our way all the way down to Bequia and spent a month, then sailed on to Grenada and spent a month, then worked our way back north to Antigua for the Classic Regatta and Race Week, then sailed offshore back to Maine. That was six months.”

Cruising guide author Chris Doyle says, “You'll be changing countries (and the Caribbean has a lot of them) and the procesd of cl;ering in and out will  probably remain complicated, with the necessity of filling in and submitting forms.

“Several countries in the Eastern Caribbean, once entered, have many anchorages that allow for a week or two of cruising without having to clear Customs again. These include the USVI and BVI, Antigua & Barbuda, Guadeloupe, Martinique, St. Vincent & the Grenadines and Grenada, Carriacou & Petite Martinique. Most other islands have enough going on ashore to make lengthy visits worthwhile. An investment of significant planning time to get the most out of your cruise, to allow for thoroughly exploring countries one by one, rather than flitting up and down the chain, will be rewarding.

John and Darcy Dillon on S/V Kindred Spirit can attest to that strategy, saying, “We began our passage south in 2018 and have spent the last three seasons between St. Vincent & the Grenadines and Grenada.”

John and Darcy add, “As the old cruising saying goes, ‘You can pick a day or a place — just not both.’ Make sure you have an open agenda on your passages from North America. Having to be in a specific port on a specific date rarely works, as you’ll be pounding into the tradewinds and having a miserable time. Weather windows for pleasant passages always arrive. You may have to wait for two weeks, but that’s why you give yourself plenty of time to reach your Caribbean destination.

“Spend some time and develop a hurricane plan; chances are your insurance company is going to ask for one anyway. As to specifics on tropical events we’ve found Don Street’s information invaluable in understanding and preparing for the tropical season in the Caribbean. See www.street-iolaire.com.”

Lynn and Ken on Silverheels III remind us, however, “Be flexible. Cruising plans are best written in the sand. So many variable factors such weather, boat problems and the general wellbeing of your crew may necessitate last-minute changes to one’s long anticipated cruising itinerary. And get your head out of those screens. Planning a cruise by asking on Facebook questions such as ‘What are the must-do things in Caribbean?’ takes the spontaneity out of your cruise.”

Anchor tips

John and Darcy say, “You want to sleep well, so come down with a proper anchor and chain that will suit your long-term needs. Our suggestion is to read Capt. Fatty Goodlander’s book Creative Anchoring, as it has time-tested information to keep you safe at anchor, along with anchor etiquette. It’s well worth the read.”

Cruising guide author Don Street goes further: “As an absolute minimum, have two anchors in the bow rollers so that in crowded anchorages they can be dropped in a V formation in what Americans call a ‘Bahamian moor’ or what the British call a ‘proper moor’ to minimize swinging space. This is well illustrated by drawing and text in the booklets that accompany Imray Iolaire charts.

“A third anchor should be stowed aft, preferably with its chain and rode attached, to be used as a stern anchor when mooring bow and stern close to shore. Again this is illustrated with drawing and text in the booklet that accompanies Imray Iolaire charts. Note in the drawing that, when bow in, the stern anchor is pulling uphill so large amounts of rode do not have to be used.

“If the boat is going to be in commission during hurricane season it is essential that at least two other anchors with chain and rode be carried in case the boat is unfortunate enough to be caught by the hurricane or strong winds on the edges. A big Danforth with the cross-arm removed takes up very little space. The aluminum Fortress anchor disassembles. Stow two Danforths or Fortresses in the lazarette so you have a total of five anchors — and hope you never need all five.” (Read the story of how Iolaire survived Hurricane Klaus using seven anchors at www.street-iolaire.com.)

Click here to see the next page . . . .

Click here to see David Lyman’s anchoring tips

Caribbean Contributors chime in for the October 2021 issue     .