Picking Your Point of Departure

Part III: Caribbean-bound boats have little time to tarry, whichever route they decide to follow

With some luck, you might be among those sailors who report wonderful offshore voyages from the U.S. East Coast to the Caribbean. The weather will be so nice that you’ll hardly use your foul-weather gear. But in reality, such trips are rare. You must expect at least two blows of 25 knots, and you must be prepared to handle a blow of 30 to 40 knots. Otherwise, you shouldn’t be making the trip.

I hope you’ve read the first two articles in this series (“The Pre-Caribbean Shakedown,” June 2003, and “The Caribbean Cruiser’s Offshore Kit,” July 2003) and have taken them to heart. You’ve tested your boat and crew at least once in heavy weather, and you’ve carried out a thorough safety and equipment check. Now it’s time to look at the routing options.

When to Go
The major problem on this long passage to the islands is that the weather window is very short. Many sailors believe that October is the best time to leave and are quite happy making passages then. However, if you leave in October, there’s sufficient risk of getting caught in a late-season hurricane that I don’t recommend leaving before November 1. Even in November, you must keep an eye out for such hurricanes. And in the last 15 years, there’s been a trend toward stronger and more frequent late-season hurricanes. Navigators should note that this is the first year that the National Hurricane Center is providing five-day hurricane forecasts. Previously, the center’s forecasts extended to only three days. As with the three-day forecasts, the NHC five-day forecasts are used for planning purposes and are imprecise, so don’t forget to include an appropriate margin of error into the predicted tracks. Late-season storms are particularly difficult to predict (see “Dodging Olga, One Day at a Time,” November 2002).


Even when the Atlantic is free of late-season tropical storms, weather forecasters have their work cut out for them. As each day in November goes by, the weather conditions in the northeastern United States become more unstable and predictions less reliable. Here’s how I regard the accuracy of weather forecasts through the month: By November 1, a 72-hour forecast will be moderately accurate; by mid-November, the reliable-outlook period is down to 48 hours; by the last week in November, I’m skeptical of any forecasts beyond 36 hours.

Further, when leaving from southern New England, you can get very cold weather. I remember leaving Norwalk, Connecticut, with my wife one November with 8 inches of snow on the deck. By the time December 1 arrives, I wouldn’t consider embarking on an offshore passage to the Caribbean from the Northeast. Better to wait until next year.
Points of Departure

The departure points on the U.S. East Coast for most boats bound for the Caribbean can be grouped into four geographical sections: Beaufort, North Carolina, just south of Cape Hatteras; the Virginia capes; southern New England; and southern Florida.


From Beaufort, North Carolina: Even if you’re starting out as far north as Newport, Rhode Island, if your boat will fit under the 65-foot bridges on the Intracoastal Waterway between Norfolk, Virginia, and Beaufort, I’d recommend starting down the ICW and jumping off from Beaufort. This coastal/offshore option isn’t much longer than a route that heads directly offshore. Plus, the coastal trip from your starting point to Beaufort offers a good shakedown for boat and crew. Any deficiencies can be rectified before you take off to the islands.

Beaufort is far enough south that you avoid the really cold weather that’s encountered farther north. The Gulf Stream runs closer to shore here, so just 150 miles out of Beaufort, you’re across the Stream and almost out of the gale area. After 300 miles–except in very rare circumstances–you’re out of the gale area.

When departing from Beaufort, wait for a northwest front to come through. Take off at the top of the tide and head south, paralleling Cape Lookout shoals. Once clear of the shoals, head east/southeast (until the butter melts, as they say), then turn south to the islands. Usually the northwester will blow you across the Stream; then the wind will clock north to northeast, all favorable on your east/southeast course. Sometimes the northeast wind will carry you down to the trades, providing you with wind all the way to your destination. Early in the passage, it’s important to work your way as far east as practical before you hit the trades farther south, which in my experience tend to blow from the east, east-southeast, or southeast in November.


From the Virginia capes: If the Intracoastal Waterway isn’t an option, the next best jumping-off point is the Virginia capes. Wait in Little Creek, Virginia, for a good weather report. From here, you don’t want to take off on the face of a northwester unless you’re on a very big boat capable of making good time. To cross the Gulf Stream will require 300 to 350 miles of sailing, and if you don’t cover this stretch before the northwester clocks to northeast, the wind will be blowing directly against the Stream while you cross it. Depending on where you hit the Stream, it will be setting northeast at anywhere from 1 to 3 knots. A northeaster against this current can set up survival conditions for many small boats.

Back in the 1960s, when long-range weather forecasting was almost unknown, Hardy Wright rode a northwest front out of Little Creek on Onward III, a strong, heavy-displacement Alden staysail schooner. He thought he could cross the Stream before the wind went northeast, but he didn’t, and he was forced to heave to. Onward III rode out the storm like a duck, but the Gulf Stream was carrying the boat at about the same speed and in the same northeasterly direction that the storm was moving. Hardy had to stay hove to for two and a half days until he could set sail again. Onward III could take that sort of punishment, but I wouldn’t want to put a modern, light-displacement cruising yacht to this test.

When sailing from the capes, leave with a good weather report, steer east southeast, and get across the Stream as fast as possible. Once across the Stream, head south to get below 30 degrees north, which is pretty much the southern boundary of the gale area.


Under any circumstances, don’t start off on a southerly route, sailing inside the Gulf Stream toward Cape Hatteras, and then attempt to cross the Stream from there, where the current is narrower. In my opinion, this route (which has been suggested to some rally participants) is nuts. There’s a reason that Cape Hatteras has been called “The Graveyard of the Atlantic” for 400 years. You should avoid the stormy cape like the plague: I like to pass 300 miles east of it or 30 miles west of it–inside the ICW.

From southern New England: The passage sailed directly from southern New England presents the same problem as the Virginia-capes route: You have a long distance to sail before crossing the Gulf Stream. On this route, you’ll have to sail 400 to 450 miles to clear the Stream. But as competitors in the annual races to Bermuda have shown, you can use the features of this current to your advantage.

In years past, sailors thought that the Gulf Stream flowed steadily northeast in this region. We now know this isn’t true. Often there’s a southeasterly meander, and boats that find it usually finish near the top of the fleet in the Newport-Bermuda Race. In addition to the meander, rotating warm and cold eddies also can work in your favor. Play these eddies right and they can literally slingshot you toward your destination (see “Blasting Off for Bermuda,” June 2002).

Of course, meanders and eddies can work against you, as well. Once I was heading from Bermuda to New London, Connecticut, and instead of hitching a ride on the Gulf Stream, I hit the meander. After 24 hours of sailing in it, I’d made only 10 miles good.

To make the best use of meanders and eddies, you’ll want to obtain the latest Gulf Stream data before your day of departure and–if you have the capability–get updates every day. The U.S. Navy oceanographic-products website (www. provides excellent Gulf Stream analysis.

Unless you’re sailing a very big boat (90 feet or longer), you don’t want to leave from southern New England on the face of a northwester. Wait till the front blows through, then get across the Gulf Stream as fast as possible. If the wind is light, turn on the engine. This is the time to use your fuel. It’s important to get across the Stream and south of 30 degrees north as quickly as possible.

When leaving from this area, whether or not to stop at Bermuda is a common dilemma. One consideration is money. If you’re on a tight budget, be warned that Bermuda is so lovely and the people are so friendly that you’ll empty your wallet without even realizing it. But the main problem with Bermuda becomes clear if you look at the weather charts.
In the fall, Bermuda attracts gales like a magnet. Trying to get into St. George’s Harbour or to navigate the channel into Hamilton Harbour in a gale is a recipe for disaster. If the weather is good and you can afford it, then a stop at Bermuda will be welcome, but your boat should always be well stocked and ready to bypass Bermuda and go straight to the islands.

From southern Florida: If you’re in the Miami-Fort Lauderdale area, the fast and easy way to get to the Caribbean is to cross the Stream to Freeport, in the Bahamas, then wait there until a norther is approaching. As it arrives, take off through Northwest Providence Channel. The norther may blow hard, but since you’re starting in the lee of Grand Bahama, you may have smooth water until you exit Northeast Providence Channel, where the sea will increase.

The northerly wind will allow you to hold a course due east. Again, try to make as much easting in this wind as possible, because the wind will gradually ease and clock toward the east. When it does, go on the port tack and see what you can lay.

Some boats get lucky and make St. Thomas without tacking; others hit the eastern end of Puerto Rico; others can only lay western Puerto Rico. If you’re in the latter group, make your landfall at Mayagüez. Rest and restock before heading down the western coast of Puerto Rico and working your way east in stages along the southern coast. The only problem here is that you might enjoy cruising the southern coast of Puerto Rico and the Spanish Virgins so much that you won’t reach the Lesser Antilles before hurricane season sets in and it’s time to leave.

There is, of course, the so-called “thornless” path extolled by Bruce Van Sant in his popular cruising guide, The Gentleman’s Guide to Passages South. This route leads through the Bahamas and along the northern coast of Hispaniola. It’s based on the premise that you have plenty of time and can wait for weather windows. But as I see it, with all the stopping and waiting for weather windows, the whole winter season may be over by the time you reach the eastern Caribbean. Then you’re left with the choice of either heading back to the States or south to Grenada, Trinidad, or Venezuela to get out of the hurricane zone. I’d rather wait in Freeport and hitch a ride on a norther.

Weather Routers
The subject of weather routers often comes up these days. If you have a big boat (70 feet long or longer), a weather router is certainly worthwhile because you’ll be fast enough to position yourself on the correct side of the highs and the lows. But for the average 40-foot boat, you basically have to pick a favorable weather window for departure, then make the best of whatever weather intersects your route.

There are two types of weather routers. One merely gives you the weather and lets you make your own sailing decisions. The second type gives you the weather, tells you what course to steer, and gets very upset if you don’t follow his advice. Choose a weather router that best fits your needs. In either case, your weather router should be very familiar with the capabilities of your boat and your crew.

If you buy an all-band receiver, you can listen to both government and amateur weather forecasts as well as to the various ham nets. This will give you a very good idea of the current weather conditions in your region.
With luck and preparation, you may well enjoy one of those perfect trips to the Caribbean, and the foul-weather gear will spend most of its time in the locker. But the best way to ensure that your trip goes as expected is to prepare for the storms of the season.

For those planning to embark this fall on a passage to the Caribbean, Volume 1 of Street’s Cruising Guide to the Eastern Caribbean offers a more detailed look at the subjects covered in this three-part series. Visit Street’s website (www. for more useful seamanship and piloting lore.