Are You Sailing South to the Caribbean?
Story and images by David H. Lyman
Well — are you?
Getting your boat to the Caribbean and back will cost you less than your winter storage bill at a stateside yard. Besides sailing your boat, exploring the world, and visiting islands, isn’t that why you bought the boat in the first place? Letting it sit idle for seven months on the hard is a waste of your investment.
So, how do you do it? Let’s take it one step at a time.
While Lin and the late Larry Pardey sailed around the world, twice, on two wooden sloops, both less than 30 feet in length, the preferable seagoing boat these days is now 40 feet and longer, if not 50-plus feet.
What constitutes a seaworthy, offshore boat, one prepared for a year in the tropics?
Books have been written about the proper offshore yacht. Don Street’s The Ocean Sailing Yacht was published in 1973. Handbook of Offshore Cruising by Jim Howard was revised by offshore expert and noted marine author Charles J. Doane in 2009. Ocean Sailing: The Offshore Cruising Experience with Real-life Practical Advice by Paul Heiney, was published in 2019.
Remember: Hands-on experience and sailing a variety of OPBs (Other Peoples’ Boats) beats reading every time.
Also, preferably, a year or more before you intend to depart, answer these:
Has your boat been designed and built for offshore voyaging? Is it ready for a winter in the tropics? There are a few people who can tell you. The first is your insurance agent. Call and ask. He will probably get back to you with some requests.
Your insurer will want a full survey, out of and in the water. He will also ask for the skipper and crew resumes, and your itinerary or cruising plans. If you’ve not been offshore before, they may insist you take along a professional delivery skipper or experienced mentor who can teach you the ropes and keep you and the boat out of trouble.
If the boat’s never been offshore or it’s been a while, a survey is a good idea. The surveyor will help you determine what’s amiss and needs attention. A professional rigger and an experienced diesel mechanic should inspect. Someone who has spent a season or two in the Caribbean can tell you about awnings, anchors, dinghy security, port clearance, marines, radio nets, anchorages and guidebooks.
Have three VHF radios, one stationary and two handheld, and redundant navigation systems: a chart plotter and a GPS iPad or an iPhone with Navionics. Doyle Guides, as well as the newly-released mobile app, are a must. Subscribe to the Caribbean Compass online to keep up with what’s happening in the islands.
Check the steering system, find and test the emergency tiller. Get the life raft inspected. This is just the short list.
Check List: Boat, Crew, Rallies
Every airplane pilot consults a check list before take-off and landing. Sailors need them as well. My pre-departure list is eight pages long. Savvy sailors will have begun checking these items months before departure.
Was the boat designed and built for extended voyaging offshore, coastal cruising, or racing?
Racing hulls, with fin keels, need a lot of steering, tiring out the crew or overtaxing the autopilot. Long keel boats maybe slower, but they track better, and are more comfortable. Is the rig set up for offshore? Is there an inner stay on which to hoist a staysail? Can the boat be reefed and hove-to, easily?
Are lifelines at least 30 inches high? Can you rig a jackline from the mast back to near the cockpit, on either side? Jacklines along the deck may keep you from becoming a man overboard, but center line jacklines keep you from falling overboard.
Coastal cruisers seldom carry enough fuel to make a two-week offshore voyage, or water sufficient for a crew of three or four. You’ll need stowage and refrigeration to keep food to feed a crew for as long as three weeks.
Accommodation: Are there enough berths and lee cloths to keep them tucked in?
I want at least two experienced offshore sailors along with me for a total of three. Four is better. And I want sailors who don’t get seasick, can hand steer, know navigational lights and will not panic if things get dicey. With four in the crew, we each stand a three-hour watch twice each day, giving each six hours on and 18 hours off. I don’t like a rotating watch schedule. My body can get used to a late-night watch, if it’s consistent.
If this is your first time offshore as skipper, hire a pro to mentor you and the crew underway. Friends are nice to have along, but perhaps not for an offshore voyage, unless they are experienced. You can post your crew request on various websites, read resumes, and choose who you want (SailOPO.com, CrewFinder.com, Coboaters.com).
There are two major rallies that depart the U.S. East Coast each fall for the Caribbean. The NARC (The North American Rally to the Caribbean) departs in late October from Newport, Rhode Island, with a stop in Bermuda, and ends in St. Martin. It’s the oldest of the rallies, professionally run, primarily for delivery skippers, but experienced offshore owners are welcome. Hank Schmitt, who started NARC, is retiring after this year, and turning NARC’s Newport departure over to the Salty Dawg Association, a nonprofit amateur organization which has been departing from Hampton, Virginia, and the Chesapeake for the past ten years. The Salty Dawg was initially organized by cruisers who had made the offshore voyage before, but in recent years it has welcomed the first timer, swelling numbers to nearly 100 boats.
Or you can just take off when the conditions are right and go it alone.
Routes to the Caribbean
The voyage itself is 1,500 nautical miles, no matter which route you take, and there are a dozen. Research your departure point, the route, weather systems and offshore communications.
Being from Maine, I used to sail down to Newport for the boat show in September, then leave for Bermuda when the forecast was favorable. At that time of year, the weather windows are usually wide open. I do keep an eye on the weather in the tropics and if there are no storms brewing, I’ll leave, knowing I’ll get to Bermuda in four or five days, before a hurricane forms and beats me there. Bermuda Yacht Services will watch your boat if you need to fly home and resume the trip south in November. Hurricanes usually skirt around Bermuda, but I rode out a direct hit in September 1987, when Hurricane Emily swept through. The island has seen more activity recently, so beware.
More recently I’ve taken to joining Hank Schmitt and the other delivery captains on the NARC. That means it’s cold — for the first two days. Wait for an advancing cold front, bringing northwest winds, 18 to 25 knots. With the wind astern, it’s 200 nautical miles, 33 hours to the Gulf Stream. Pick a waypoint on the north wall of the stream, west of the rhumb line. By the time you exit the stream ten hours later, the 3-knot current will have swept you 30 miles east, putting you back on the rhumb line. With the stream behind you, it’s time for T-shirts and shorts.
Bermuda is just 360 nautical miles ahead, two and a half days away. When the front peters out, another may catch up with you just north of Bermuda. With the wind astern it’ll blow 30 knots with 50 knots in gusts. It’ll rain. Seas will build to 12 to 15 feet, cresting. If you, your boat and crew are prepared, this can be a thrilling ride.
The front passes in a few hours, and the loom of Bermuda’s lights appear hours before landfall. Last time I made this trip, in 2021, we made it in 3 days 20 hours, with winds no stronger than 25 knots all the way. Wait in Bermuda a few days fixing stuff, re-provisioning, sightseeing, swapping stories with others at the bar and resting. The next leg is 850 miles to St. Martin or 950 miles to Antigua; figure five to eight days. This second leg will be a great deal more comfortable.
Leaving from the Chesapeake means the Gulf Stream is only 100 miles offshore. You’ll be across within 24 hours. Leave on a northwest cold front and you’ll have the wind aft of the beam for two, perhaps three days. This popular route is a 1,500-nautical mile arc out into the Atlantic before turning south. It’s a seven to 12-day non-stop voyage, with a few days motoring through the Bermuda Triangle. While this route bypasses Bermuda itself, each year half a dozen boats from the Salty Dawg Rally stop off for fuel, rig or sail repair or to just break up the long voyage — and to visit a most charming island. It’s a long voyage and boats need to be adequately prepared with sufficient fuel for at least five days of motoring plus food and water for three weeks. Each year, some boats run into problems with steering, the rig, fuel, seasick crew and retreat. Be prepared.
I prefer to stop in Bermuda, even if I’m departing from the Chesapeake. Getting to Bermuda gets you far enough east so the last 800 miles will have the wind on the beam. Those Chesapeake boats that attempt a straight shoot to the islands often find the southeast trade winds on the nose for the last three days. Slow and uncomfortable going.
Heading down the ICW gets you around Cape Hatteras, with the rule “63/6” in mind (63-foot mast height to get under the bridges and 6-foot draft so you don’t run aground). In three days, you’ll be in Beaufort, North Carolina, a wonderful town with three marinas. From here the Gulf Stream is only 50 miles offshore. You’ll be across and into warmer weather in 15 hours — then it’s a similar course to those departing from the Chesapeake.
From Beaufort you can also meander farther down the ICW, or sail slightly offshore, inside the Gulf Stream, ducking into ports when necessary, all the way to Florida.
Once in Florida you have your pick of departure ports: Fernandina, Palm Beach, Ft. Lauderdale. In late November and December, watch the weather carefully. When a good hard norther threatens, leave 24 hours before and steer east-southeast “until the butter melts,” to quote Don Street, then southeast, and you may actually arrive in St. Thomas on track.
If the winds in the Bermuda Triangle are unfavorable or non-existent, the Thornless Path along the Bahamian islands is yet another option.
I begin studying the weather patterns a month before departure. This gets me intuitively familiar with what to expect on departure and en route. Climate change has thrown a monkey wrench into the works, so study up and stay alert.
Weather Router Services
• Commanders’ Weather (commandersweather.com)
• Weather Routing Inc. (wriwx.com)
• Locus Weather (locusweather.com)
• Marine Weather Center Services (mwxc.com)
Online Weather Sites
Look for Part Two: “Caribbean Landfall and Island Cruising,” in an upcoming issue. David H. Lyman is an author, award-winning marine journalist, photographer, and offshore sailor. He writes from his home in Camden, Maine, when he’s not in the Caribbean. Read more of his stories at DHLyman.com.