SAILING DIRECTIONS BY DON STREET
Heading South from the US, Sanely

For the past five decades I have listened to stories of boats heading south from the East Coast of the United States to the Caribbean. Some were such idyllic trips that the crew never once put on their foul weather gear. Some trips were a bit bouncy. And other times, boats ran into major storms. Some of these latter trips resulted in damage or disaster, losing boats or even crews. Many years ago I quit counting when my 39th friend or acquaintance was lost while doing this trip.

This is not a passage to be underestimated. Your boat and crew must be prepared to face heavy weather. Before you go out and put your boat to the test, make some practice runs. In your home waters when a good hard blow comes through, take your boat out and “put the bricks to her.” Ascertain any deficiencies in both boat and crew. Take your boat back in, rectify the deficiencies, then go out in a second blow. This time you will be much better prepared than you were the first time. Then go home again and rectify any deficiencies that are still not corrected from the first trial in a blow. And so forth. Then, when you eventually head offshore and run into a bad blow, both the crew and boat will have been through similar experiences before, so no major problems should be experienced.
Unfortunately, many recreational sailors fail to follow this advice; instead, they take off from the East Coast and run into their first truly bad weather at sea. The crew becomes petrified. When they arrive in St. Thomas, the boat is put on the market — and there ends their dream of an idyllic winter cruise in the Caribbean.

Also, be prepared for cold weather at the start of the trip. Make sure you have enough sleeping bags or blankets to keep the crew warm, and insist that every crewmember has plenty of really warm clothing (not just jeans and sweatshirts), hats and good foul weather gear including seaboots. Being cold is fatiguing, and as the late Jim Crawford, a seaman par excellence, stated, “Fatigue is the rust that destroys boats.” Every time in my seven-decade sailing career I have gotten my tail in a wringer, it has been because I allowed myself to get too tired and made poor decisions. A cold, wet, tired crew is a crew that makes mistakes. Keep your crew dry, warm, well rested and well fed, and the chances of them making mistakes are minimized.
This subject is covered in more detail in my book Street’s Transatlantic Crossing Guide.

JUMPING-OFF POINTS
Points from Newport to New York
I strongly advise NOT heading directly offshore from this area. It’s much better to go coastwise down to Little Creek, Virginia, near Norfolk at the mouth of the Chesapeake Bay, or, if your boat will pass under the 65-foot bridge south of Norfolk on the ICW, farther on to Morehead City/Beaufort, in North Carolina.
The reason I say this is that the autumn weather window for heading south is very small. If you leave in October or early November, there is too much danger of encountering a late-season hurricane. Data from NOAA shows that in the last 20 years or so there have been more hurricanes in late October and early November than there have been in the previous hundred years.
Unfortunately, as each week goes by in November the weather on the East Coast of the States becomes increasingly unstable, to the point that by the end of November the weather forecasts are only good for 24 to 36 hours. Boats can take off from the northeast coast of the States in the face of a northwester, with glorious sailing, clear visibility and the wind aft of the beam, but all too often the northwester then turns, swinging around to north and finally northeast. A 25- to 30-knot (and sometimes more) northeaster blowing against a two- or three-knot current in the Gulf Stream produces sea conditions varying from dangerous to disastrous.

Unless you have a megayacht that can continually knock off nine knots or more, your chances are minimal of leaving the northeast coast of the United States and getting across the Gulf Stream on a weather window, since the weather predictions are only good for 24 to 48 hours.
Thus, if you are departing from Newport, I recommend heading down the coast, through Long Island Sound. If a blow comes through, there are plenty of places to stop. If you pick up the beginning of the fair tide at South Norwalk, Connecticut, and maintain a six-knot speed through the water, you can carry that tide all the way down Long Island Sound through Hell Gate, New York Harbor, out through Sandy Hook and on down the New Jersey shore. This is where a northwester coming offshore gives a glorious sail with smooth water; it will really blow you on your way.
A good eye must be kept on the weather, because from the mouth of New York Harbor to the mouth of the Delaware River there are really no reliable harbors. Similarly from the mouth of the Delaware to the Chesapeake Bay there are no harbors. However, if you have maintained your six knots over the bottom as you approach the mouth of the Delaware, take a look. If the weather is going around to the south and you don’t like the look of it, you can head up the Delaware on a fair tide, pass through the Chesapeake & Delaware Canal, and still pick up a fair tide at the northern end of the Chesapeake.
Once in the Chesapeake you can push on south to Little Creek, Virginia, at the mouth of the bay, or stop in Annapolis or one of the wonderful little harbors in the Chesapeake and enjoy oysters, crab and other wonderful seafood.

If the weather permits, however, when you reach the mouth of the Delaware you can continue offshore to Little Creek.
If you can fit under the bridge south of Norfolk, there is only one way to go south. You should continue through the ICW to the Morehead City/Beaufort area. This is a trip of three days, but if you have the time you can easily spend a week to ten days doing some wonderful cruising, either going up the various rivers visiting the beautiful ante-bellum towns that have hardly changed in the last 150 years or, if you have a shoal-draft boat, going out to the outer banks in Kitty Hawk, where flying started.

Morehead City/Beaufort
At Morehead City/Beaufort you can sit and wait for a good clear northwester to blow through. You are far enough south so that although it may be cold, you will not have to contend with ice, sleet or snow. If you leave at the top of the tide, carry the tide down to Cape Lookout. A couple of hours after you leave Cape Lookout you will be in the Gulf Stream, the northwester will blast you across, and by the time the northwester swings around to the north you will be clear of the Stream. You can then set a course east-southeast and sail that course “until the butter melts.” (It is said the most important piece of navigation equipment on this trip is a pound of butter on a gimbaled table.) The northwester will swing north, then to northeast. If you are lucky the northeaster will continue right on down to where you pick up the Trades. Many boats in the 40-foot size range have done this route from Morehead City/Beaufort to St. Thomas in seven days.
Work your way east-southeast, until you reach the longitude of 68° to 70°W, as it must be remembered that in November and early December the Trades are still likely to be southeast or east-southeast, rather than east or northeast. This means if you have not worked your way well east, you will end up hard on the wind for the last few days of your trip if you are heading for St. Thomas.
With a favorable weather forecast, you can leave from Morehead City/Beaufort at any time from early November right up until about December first. However, if you have not left by the beginning of December, you should either delay your trip until the following year, or follow the ICW all the way down to Jacksonville or Fort Lauderdale, Florida.
In December it is not advisable to try to depart for the Caribbean from Charleston or the ports south of Charleston, as in that area the Gulf Stream is well off shore. The problem of getting across the Stream here is roughly the same as trying to get across the Stream from the northeast coast of the States.

Little Creek
If your boat will not fit under the 65-foot bridge on the waterway near Norfolk, wait in Little Creek until you obtain a favorable weather report. Then head east-southeast and try to get across the Gulf Stream as fast as you possibly can. If the wind goes light, turn on the mill and motor or motorsail. Don’t worry about running out of fuel — once you are across the Stream and south of the gale area, if you are out of fuel and get becalmed it is just a pain in the neck and a delay. But if you don’t make it across the Stream within your weather window, you can end up in disastrous circumstances. There is not enough space here to list the horror stories. Again, your course is east-southeast until the butter melts. Work your way eastward to longitude 68° to 70°W, before heading directly to St. Thomas.
The weather window from Little Creek is basically the month of November. Come December, forget about it and wait until next year.

Miami/Fort Lauderdale
If you don’t pick your weather carefully when sailing from the Miami/Fort Lauderdale area to the Caribbean, you face a dead beat to windward for 1,200 miles — a miserable trip. I have done it a couple of times, having to deliver bareboats on a schedule. We were locked into it and all we could do was put our heads down and bang away.
The proper way for the cruising yachtsman to get from the Miami/Fort Lauderdale area to St. Thomas is to go over to Grand Bahama and wait there until a norther — i.e. a northwest front — is predicted. You can take off on the face of a northwest front: it may blow hard, but the wind will be coming off the land and you will have a smooth sea. Leave the northeast Providence Channel and head east for as long as you can.

Once the norther dies out and the Trades fill in, fall off on port tack and see where you end up. Some boats have been very lucky and have laid St. Thomas in one tack. Others have fetched the eastern end of Puerto Rico, and some have only laid the western end of Puerto Rico. If you do this you can duck into Mayaguez, take a rest, recuperate and restock, then head south and east along the south coast of Puerto Rico. Make sure you have on board a copy of Street’s Guide: Puerto Rico, Spanish, US and British Virgin Islands, which describes this area in detail, complete with sailing instructions. The one problem with taking this route is that you may enjoy the south coast of Puerto Rico and the Spanish Virgin Islands so much you never get to the Eastern Caribbean!
Re: hopping along the numerous stepping stones on Bruce Van Sant’s “thornless path to windward” from Florida to the Virgins, you must have unlimited time and patience to wait for all those individual weather windows. You may spend so much time waiting for weather that by the time you arrive in St. Thomas, the hurricane season is approaching again and it will be a case of either returning to the States, or quickly getting to Grenada, Trinidad or Venezuela to be south of the hurricane zone!

I advise using the US NOAA charts appropriate to your routing, and Imray-Iolaire charts of the Caribbean depending on your landfall. (Check Imray-Iolaire chart catalogue at any major US chart supplier.) If you are going via Bermuda, use Imray-Iolaire chart E5: Bermuda; plans St. George’s, Hamilton, dockyard marina.

Visit Don Street’s website, www.street-iolaire.com, for more information.
Visit Noonsite.com for the latest Covid-related yacht entry regulations regarding your intended Caribbean landfall destination.