D. M. Street Jr – Fall Migration to the Caribbean

Published on November 12th, 2012

Fall migration to the Caribbean

D. M. Street Jr is a very opinionated 82 year old WOPF (well preserved old fart) that is still writing, racing a 74-year old Dragon and drinking Heineken. He is also passionate about seamanship, particularly navigating between the U.S. and the Caribbean, and he hopes his advice saves lives.


Reflecting on the loss of the Bounty, and given the fact that the fall migration to the Caribbean is about to start, a migration that I have followed in print and in bar room conversations for sixty years, I feel compelled to bring to everyone’s attention the first article I ever wrote, Going South, Yachting September 1964.
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If sailors had followed the advice written in that article there would be a lot more sailors alive today and following the advice would have saved the underwriters many millions of dollars. That original article has been updated, re-written and republished about six times in Cruising World and Sail. In some cases the editors editing of my re-write did not properly express my views.

The re-writes are a result of my personal experience of almost 40 trips between the states and the Caribbean or the reverse in the period 1960 to 1980, plus reading everything published about going south and many hours in various bars hearing of trips south, trips that varied from being excellent, good, bad to disastrous. Added to all this was the information gathered in 49 years in the marine insurance business.

Some years no boats are lost, other years one, sometimes two, and once in a while three boats are lost in a single year. On a long term average I would estimate, over the last 60 years, one boat a year has been lost. Many lives have been lost. About 1980 I stopped counting when my 30th friend or acquaintance was lost on this route. Because of the improvements in life raft design, ELT/EPIRBS, the magnificent work of the USCG search and rescue helicopters, and the spectacular work of the swimmers that drop from the helicopters to help sailors into the basket, in the last 20 years relatively few sailors are lost, but sailors are still lost, one last November.

The following is a condensation of my seven articles on going south and what I have learned about going south in the last 60 years.

In 1964 I pointed out that as fall approaches, weather on the east coast of the states and between the states and Bermuda, the weather gets more and more unstable. But in September weather is relatively stable. I recommended checking that there were no hurricanes brewing, and if no hurricanes brewing, head south to Bermuda in September, leave the boat in Bermuda and fly back, pick up the boat in December and head south to the islands. This I still feel is an excellent way to get a boat to the Caribbean.

Sailors will say that Bermuda is in the so-called hurricane box 12 to 35 north, which it is. But Bermuda is like a person standing on the median divider of a high way. Hurricane whistle by Bermuda fairly regularly but if one checks the NOAA hurricane book that gives the track of every hurricane from 1878 to the present, you will see that Bermuda has been hit butt end first by only eight hurricanes. That number is no greater than the number of hurricanes that have hit the northeast coast of the states in a similar period.

Unless a boat is fast and at least 55-feet, and has an experienced tough crew on board, I strongly advise not going south via the Bermuda route. On boats smaller than 55-feet, it takes three days to cross the Gulf Stream and be safely out the other side. In the fall weather gets more and more unstable as winter approaches. By November it is impossible to give a reliable three of four day long term weather forecast.

About thirty years ago discussing long term weather forecasts on the phone with Bob Rice, his words were approximately as follows: “in the beginning of November the weather is so unstable that weather forecast are good for 48 hours and possibly a bit more. Mid-November they are good for 36 hours and by the end of the month and early December they are good for 24 hours”. Through the years many boats have left the northeast coast of the states with what they thought was a “weather window” and have been caught in the Gulf Stream by an unforecasted blow, and gotten their tails kicked, sometimes disastrously so.

2011 is an excellent example where a large group of boats took off on what they were told was a good weather window but they got their tails kicked in. One boat was lost, crew saved by a passing freighter, while another boat lost a crew overboard never to be found. Many boats arrived in Bermuda with busted gear and/or torn sails.

As a result of this I sent an email to a couple of the leading weather routers. In the email I said that since it is all but impossible to obtain a RELIABLE four day weather forecast in November, I felt that weather routers, when working with boats other than boats over 55-foot with a tough off shore crew on board, should instead of giving them routing directions to Bermuda they should recommend that they sail coast-wise to Norfolk.

Boats that can not fit under the 64-foot bridge south of Norfolk will have to depart from Norfolk (actually Little Creek, Hampton, or Norfolk) direct to the eastern Caribbean. This routing is only about 100 miles longer than the route Newport, Bermuda, and on to the islands. Leaving from the mouth of the Chesapeake puts the route to the islands on the bottom edge of the gale area whereas heading direct to Bermuda from Newport means the boat is in the gale area the entire time. They should recommend that those boats that can fit under the 64-foot’ bridge should spend three days in the waterway, then take off from Beaufort.

I received no replies to my email.

Taking off from either Norfolk or Beaufort has a number of advantages. The trip from Newport to Norfolk, inside via Long Island Sound, NY harbor, down the Jersey shore, up the Delaware, through the CandD canal and on to Norfolk, will take about a week but will give both the crew and boat a good shake down. Any deficiencies in crew or boat can be rectified before taking off from Norfolk or Beaufort. With a good 48 hour weather forecast a boat can take a straight shot 300 miles, two days from Newport to Norfolk.

One of the great advantages of sailing direct from Norfolk or Beaufort to the islands is that the crew cannot jump off! Frequently when boats arrive in Bermuda after a rough trip down some or sometimes all of the crew depart on the first plane north. The skipper is then searching for crew in Bermuda. This happens so frequently that some Bermudians take their vacation in late November or early December, knowing that boats will be needing crew, to get a nice sail to the Caribbean and air ticket back to Bermuda. Often if the trips down have been rough, there is a shortage of crew, the Bermudians will be paid to sail to the Caribbean, and so they have double income their normal pay plus the payment as crew.

When departing from the Norfolk area it is essential to have a good 48 hour weather forecast as it will take 48 hours to cross the stream and get out the other side. If the wind is light, turn on the mill and get across the stream. From Beaufort the stream is right up on the beach, you are across the stream in 24 hours. In both cases, once across the stream the sailing directions have been the same for 400 or more years, “east south east until the butter melts, then head south”.

Look at ImrayIolaire North Atlantic passage chart 100 which show the recommended courses to and from the Caribbean from the east coast of the states. On the back of the chart one finds routing directions and weather charts for every month of the year except January, February and March, months that yachts should not be in the north Atlantic.

If you are not out of Norfolk by mid December, and you can not fit under the 64-foot bridge, forget about heading to the Caribbean for the winter. If you can fit under the bridge but cannot leave Beaufort by mid December, continue through the ICWC to Charleston. Do not try to head directly to the Caribbean from Charleston as the Gulf Stream is well off shore. It will take you two and a half to three days to cross the stream and get out the other side. To obtain a reliable three day forecast in mid December…forget it.

Also sailing direct to the islands from Charleston in late December or early January puts you into the gale area for a fair bit of the trip. From Charleston, head south along the coast right up on the beach INSIDE the Gulf Stream and on to St Augustine, Jacksonville, or Cape Canaveral. Wait there for a norther which in the winter months come through Florida two or three times a month. Thirty-six hours before the norther is to hit, take off get across the stream. Once the norther arrives you should be able to due east. Head due east as long as you can, trim sheets as the wind veers, and see where you end up.

You may reach all the way to St. Thomas on port tack, or the Spanish Virgins. If you can only lay the western end of Puerto Rico, it is no longer a problem. There is now a modern marina, Marina Pescedoria in Puerto Real. There is a buoyed channel leading to the marina, 18-feet at the outer end gradually shoaling to 9-feet at the marina. Stop there for R and R, then work your way eastwards along the south coast of Puerto Rico, taking advantage of the land sea breeze phenomena. This area is well described with sailing and piloting directions and in Street’s Guide to Puerto Rico, Spanish, US and British Virgin Islands – the only guide that covers all the island groups in one volume.

Regarding crew and the number that should be on board for the off shore passage, until the fiberglass boom in yacht construction caused a yearly exponential expansion of the number of boats looking for insurance, Chubb and Son/Federal insurance was the major US yacht insurer. For boats looking for Lloyds insurance, the leading US broker was CA Hansen. Both companies were headed by long term experienced sailors. Chubb and Son Percy Chubb, who owned Laughing Gull, then Antilles – boats that sailed north and south each year. CA Hansen was headed by the oldest of the five Rodstrom brothers, all of whom were excellent sailors.

Chubb and Son basically set the terms and conditions that boats would have to comply with if they wanted insurance. The other US companies pretty much followed Chubb and Sons lead. CA Hansen pretty much did the same thing for a number of leading Lloyds syndicates; the other syndicates tended to follow the terms and conditions set by the leading syndicates. Both Chubb and Son, and CA Hansen required FOUR CREW on board for all off shore passages.

When yachting exploded with the fiberglass age, all sorts of companies jumped into the yachting market and the four person requirement disappeared. However, even if a couple wants to cruise the Caribbean as a couple with no one else on board, for the trip down I and many others feel that two extra crew should be taken on board for the trip to the islands.

Following the directions for leaving from Norfolk and the directions from Beauport does not guarantee that everything will go as planned as is illustrated by the following two stories.

Back in the middle 60’s, Onward 111, a 63-foot heavy displacement, low freeboard Alden schooner was heading south with skipper Hardy Wright. He was an excellent sailor, but needless to say, the jokesters had fun with his name. He was often referred to as Hardly, or ‘Hardly Ever Right’. He sailed from New York to Norfolk where he waited for a good break in the weather. He left Norfolk with what he thought was a good weather report.

Onward was half way across the stream when the wind went from North West to North East and was blowing a solid 25 to 30 knots against a north east going stream of three knots. Sea conditions quickly built up to the point that Hardy was afraid of getting rolled if he continued on his south east course with the breaking seas on the beam. He was a good seaman, so he hove-to under double reefed main, reefed main staysail, and reefed staysail. All was well, no one was sea sick, his wife was putting out three meals a day, being a wooden boat Onward was leaking but the pumps kept the bilge level down with no problems.

But the storm was moving northeast at the same speed as the Gulf Stream was pushing him northeast. He was stuck in the stream for three days before he was able to set sail and head to the Caribbean. By this time he was all the way back up to the New York area that he had left two weeks before.

Another trip south that did not go according to plan was my delivery of Cantellena, a 40-foot double headsail rigged Casey ketch. In the 60’s, I was committed in spring and fall to navigate Antilles owned by Percy Chubb of Chubb/Federal insurance. She was 46-foot S&S designed Direcktor built keel center board ketch. This was before the days of loran units small enough to fit on medium sized sail boats, Satnav, GPS weather satellites, long term weather forecasts, or weather routers. Navigation was strictly by sextant, DR and hand bearing compass. Weather was looking at the weather map, calling the airport, and hoping to find a cooperative weather man that would talk to sailboats instead of the usual pilot inquiries.

Because October is too soon to head south, December too late, the window of opportunity to head south is so short that it is extremely difficult to make two trips south the same year. The only ones that do two trips south in one year are skippers overconfident in their abilities, or broke and need money, or owed a good friend a favor.

All these three things fell in place in the fall of 1963 (year of the Cuban crises) and I agreed to take Cantellena south. We sailed in company with Antilles from Annapolis to Morehead City. I left Cantellena in Morehead City yacht basin and took off on Antilles as navigator on a perfect trip.

We left Morehead on the top of the tide with a good strong northwester that blew us across the stream and out the other side before the wind veered to northeast where it stayed and blew 20 knots. Antilles really flew. We did 980 miles in five days, 196 miles a day (but we never broke 200!). Immediately upon arrival in St. Thomas, I flew to NY, then plane and bus to Morehead where my crew of three had already assembled.

However, the weather was god awful. Every night at 0200 I called the tower in Norfolk airport and explained we were a sail boat heading for the Caribbean. The man on duty gave me the official weather report, but said call back at 0400 and he would have looked at the charts and would give me his personal report. I did this for a week until he finally said go. We went.

All was well for the first 48 hours but in the afternoon of the second day out, we saw a big black cloud in the north west stretching across the full horizon. We started shortening down as the wind increased so by the time it started to blow we were down to the small staysail. How hard it blew, I do not know, nor do I know how big were the waves, but I do know that periodically as we surfed down the largest of the waves the 40 HP gasoline engine was turning over against compression! Also periodically, we would get pooped, the cockpit would fill to the top.

If we had had a Reiser and Raymond “sea brake” we certainly would have streamed it to slow us down, but it had not yet been invented! The cockpit had two 2 1/2″ drains but there were locker doors in the sides of the cockpit that we discovered were less than watertight. Whenever the cockpit filled, the water draining through the locker door filled the boat up to the floor boards.

We had a big 2 1/2″ navy piston pump. It threw a lot of water, but being an upper and downer piston pump it required a lot of effort. The crew was young and fit so all was well until, with the handle all the way up, the pumper lost his footing, fell against the pump shaft and bent the shaft. End of pump. We were saved by an on-center sink with a 2″ drain and a half gallon coffee pot that just fitted between the floor timbers.

We got through the gale, the wind died, we started the engine only to have the water pump give up. Our solution of that problem was ingenious but space does not permit describing the solution. The MBLU master of the bastard lashup, a degree I learned while serving on a submarine during the Korean War came through. The MBLU is to the sailor more useful than an engineering degree!

The Cuban crisis was on, every morning a plane would fly over and wiggle his wings and in the afternoon the same would happen. We arrived in St. Thomas amid cheering, the men shoving beers in our hands and clapping us on the back, the gals kissing us. We had come back from the dead. They showed us the last newspaper that went to press before the big newspaper strike. It had an announcement from the USCG that yacht Cantellena was missing with all hands and all were presumed dead! When I showed up at the New York boat show that year my friends thought they were seeing a ghost.

Upon checking I discovered that boats had stacked up waiting for a break in the weather, the break came, about a dozen boats departed on the same day. All were hit by the same storm that hit Cantellena. Every other boat either sank, had the Coast Guard flying out and dropping pumps to them or had ships standing by.

Since we did not call for help they presumed we sank. They never checked with the Navy! This was the second time the Coast Guard reported that I was missing at sea and presumed lost despite the fact that in neither case did I send a distress message.

I had learned my lesson about pumps.

On the next three deliveries I felt the pumps were inadequate and made the owner allow me to buy a Edson 25 gpm single acting diaphragm pump and a long length of hose. I mounted the pump on a board, cut the hoses so one would reach to the bilge and the other one over side. Thus I had a good big reliable pump to use in an emergency.

When I bought the third pump, Henry Keane, the father of the two men that now run Edson, asked me what I was doing buying three pumps in three years. I explained to him what I had done. The next year the Edson catalog had the Edson pump mounted on a varnished mahogany board.

I say nuts… a varnished mahogany board will slip and slide. The pump should be mounted on an unvarnished, unpainted board that has on the bottom, secured with copper tacks, a piece of indoor/outdoor carpeting so that it will not slip or slide.

I say anyone going off shore without a 25 gpm single acting diaphram pump, either permanently mounted or the above mentioned Edson emergency pump, is NUTS! Fifty-seven years of offshore sailing and 49 years in the insurance business has proved to me the most easily avoidable claim is flooding and sometimes sinking because of inadequate bilge pumps.

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