Life Aboard LULU

Brian Hancock on the Caribbean 1500
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This article was written by Brian Hancock about his experiences as captain aboard Lulu during the Caribbean 1500 rally in November 1999.  If you like his writing, I recommend his book, "Spindrift" which can be purchased at: .  You can email Brian at .


It’s a recurring question I get when talking about offshore sailing. "What’s the hardest part," they ask, expecting me to elaborate on the storms and vagaries of tropical weather systems, and when I answer, a blank look of disbelief crosses their faces. They don’t get it, but I can assure you that the hardest part of sailing offshore is actually leaving the dock. This is where most wannabe’s falter. Where most dreamers fumble on their dream. Where the trip of a lifetime ends with the boat of your dreams still tied stern-to in the marina two years past your scheduled departure date. It’s true – take a look at the statistics. At least half of those who plan to set sail, fall to the convenience of procrastination. It’s easier to postpone your departure until next spring or fall, than it is to toss the lines ashore and head out into the unknown. That was until Steve Black, the originator of the Caribbean 1500, came along. His idea of "cruising-in-company" struck a chord, and legions of sailors have since been able to make that leap from land-locked lubbers, to offshore sailors. Thousands have gone from cruising wannabe’s to water gypsies, and it’s because there was someone there to apply pressure and expertise when the fingers of self-doubt started to creep into their sailing plans. The Caribbean 1500 has come of age and it’s future looks certain. I am now a graduate, and firm believer.

Last fall I received a call, and the soft voice on the other end introduced herself as Lulu. She was looking for a captain, a man of strong mind (as Jimmy Buffett once sang.) She was looking for someone to skipper her Oyster 61 (also named Lulu) in the upcoming Caribbean 1500 and wondered if I might be interested. I was. I had followed the fortunes of the past few 1500’s, and thought it was a great event. I was also interested in the Oyster. Their legendary reputation for speed and comfort was enticing, and a race headed for the Caribbean with a New England winter fast approaching, was more than I could resist. Lulu and I came to a mutual agreement, and I struck two weeks from my calendar in early November. My next call was to Steve Black, and a day later the race instructions arrived in the mail. There was a fleet of fifty-two boats entered, some sleek, some not so, but behind all of them a common desire to set sail for a warmer climate, and common misgivings about their ability to cope on their own. The idea of company "out there" was appealing, and so they filled in the application forms and mailed in the entry fee, the first step towards setting sail on an adventure of a lifetime.

Steve Black has that rumpled look of someone who has seen many sea miles, but behind his casual exterior is a competent seaman and a seasoned race organizer. He first came up with the idea of a US based rally in 1988 after noting the success of Jimmy Cornell’s Atlantic Rally for Cruisers. The ARC was rapidly becoming the way for cruisers to sail "in company" from Europe to the Caribbean, and Black reasoned it would catch on in the US if only someone would organize it. The job fell to him and it has been a full time occupation since. Initially there were two separate races to the Caribbean, one originating in Newport RI, and the other in Virginia, however the shorter course from Virginia proved more popular and Steve plans to stick with a single race in the future. "It’s hard to predict weather and to find a weather window that late in the year, especially if the fleet has to cross the Gulf Stream en route to Bermuda," he told me. "Hampton has proved to be a popular place for departing and crossing the stream is a much simpler matter, plus," Steve added, "it gives the cruiser time to enjoy the fall in the Chesapeake." I think he is onto something there and many of the participants agree.

Gary Strutin and Louise "Lulu" Wollman are typical of most Caribbean 1500 entrants. Their dream of "giving it all up and setting sail" had lurked just beneath the surface for many years waiting for a catalyst to galvanize their hidden hopes. They knew of the 1500 and were sure that is was what they needed to get them going, but it was only when the entry fee was paid that they knew for sure that they would actually do it. "Signing and sending the check was a turning point in our plans," Louise later told me. "Once it was gone and we inked in the start date on our calendar, everything changed for us. Suddenly there was a deadline, a date by which time we had to be ready to head offshore. All of our focus was on October 31. I think that without it we might have waited another season before heading off. It’s easy to find things to do that will keep you tied to the dock." It’s a recurring theme among entrants – the date set and the check mailed quickly altered the focus of their plans. They were now committed. It was that single act that propelled them from wannabe’s to blue water sailors. It’s also a key ingredient in the success of the event.

Gary and Louise like comfort and saw no need to compromise for the sake of a sailing trip. They bought one of the most comfortable yachts on the market and set about modifying it to suit their lifestyle. Among other changes, the galley was enlarged and modernized, and a washer and dryer were added. I made Louise promise that none of my sailing friends would ever hear about the washer and dryer – my reputation as an offshore racer would be in jeopardy if anyone found out about them. When I first stepped on board a month before the start for a quick "look around," I was delighted by their attention to detail, both in decorating and in preparation for the trip. Gary was writing checks by the dozen and I quickly dubbed him the "Checkbook Captain." Louise was stocking food enough for a crew of fifteen for two seasons in the islands. We would not go hungry. I named the entire affair "Lulu’s Plastic Fantastic Traveling Road Show," and that was exactly what it was. We would later be joined by two very competent women, both great sailors, and both lesbians (I add that only for color and not for criticism – they were fantastic crew mates.) Our final crew member arrived with a chip on his shoulder, and left in Virgin Gorda two weeks later with a chip on both shoulders, proving, I guess, that it is still very hard to find the perfect crew. We came damn close however.

All boats were required to assemble in Hampton, Virginia a week before the start. Race organizers were offering both compulsory and voluntary seminars for all participants. It was also a time for the different crews to meet and to get to know each other, also an essential aspect of the Rally. The marina is right downtown Hampton and the colorful flags and bustling scene did not go unnoticed by the locals. Many of them came to look at the boats and offer comments, and I heard one admirer say to her friend, "Man dat would be some fun to one day sail over the horizon and never be back." She echoed the sentiments of most of the crews who were leaving behind their life on land, and heading for a new one on the water. I skipped the seminars and arrived in Hampton two days before the start.

I knew that I had joined the right event when during the pre-race briefings Steve Black commented on the starting procedure, and warned that the penalty for being over the start line early would require the guilty party to buy a round of rum drinks for the entire fleet in Virgin Gorda. It’s a fitting penalty that should be adopted by more race organizers. While last minute preparations were taking place, we watched the weather carefully since it was still officially hurricane season, and the sting of the previous years encounter was still evident. As to happened, a disturbance in the Gulf of Mexico and a strong front in Texas combined to cause the race organizers to postpone the start three days. It turned out to be a great move despite grumblings by some that they could not face another party. I had some partying catching up to do, and enjoyed the festivities while rain and strong winds lashed the fleet and yachts tugged at their dock lines. I, for one, was very happy to be on land and not at sea.

When the front eventually passed, we set out for the start in a brisk clearing northerly. I was expecting the bulk of the fleet to take a relaxed approach, but as soon as the ten minute gun fired it became obvious that this was no rum run to the Caribbean. There were some very determined skippers looking for victory. We were just happy to be pointing in the right direction when the gun fired and followed the procession down the Chesapeake Bay and into the Atlantic. It would be a cold wild night as we hugged the coast, staying out of the adverse current of the Gulf Stream, and settled the boat and crew in to a routine that would last another seven days. There were a couple of green looks aboard Lulu, but nothing serious. The relief of leaving the dock and eventually getting underway was palpable. Everyone was glad to be away.

Over the years I have railed against the tendency for modern sailboats to closer resemble bungalows in House Beautiful, than seaworthy sailing vessels, and so I was anxious to see how the Oyster fared once away from the dock. The warm, well-appointed interior had every conceivable convenience, and the climate control dutifully switched from heat to air conditioning right on cue just as we entered the warm waters of the Gulf Stream. Right off Cape Hatteras we hung a sharp left aiming to cross the north-bound stream as quickly as possible. It was bumpy and a bit wild, but the turquoise water was a welcome change from the cold slate-blue of the Chesapeake. My strategy was to ride the northerly wind down the rhumb-line, and wait for the trades to kick in as we sailed further south. Delivery skippers will tell you that you need to head for a well worn turning point in the north Atlantic at 25 degrees north and 60 degrees west, before heading for your destination in the Caribbean. If you do not make enough easting early, you will find yourself hard on the wind at the end as the trades fill in and blow strong from the south-east. Aboard Lulu we favored the east side of the fleet, all the while keeping the speed on and sails trimmed. Everything was working perfectly and continued to do so all the way to Virgin Gorda. The galley produced fabulous meals to accompany ice laden cocktails, and the hot showers each morning were a welcome change from my usual routine of a bucket of salt water and dishwashing liquid for lather. I was even careful to neatly fold my fluffy towel after each use. On the one occasion that I actually got wet (outside of the shower), I dried my clothes in the dryer and when I put them back on, they were warm and soft. I am starting to get used to this kind of sailing and will tone down my remarks about going offshore on "floating furniture."

The 1500 fleet followed a variety of strategies for their passage south. One wonderful rule for the race is that you are allowed to use your engine. You keep an honor log, and add the time spent motoring to your overall elapsed time. This unique allowance throws a tactical curve-ball to each navigator as they try to determine whether or not to motor. We were lucky, and only had to use the engine for a few hours. Some boats, not far from us at the beginning, fell into a windless zone and ended up motoring for days. In fact, it was a case of the rich getting richer as the front boats kept the wind and stretched their lead on the tail-enders. I carefully plotted all the boat positions on a chart, and it was evident that those to the south and east were making out. We romped down the rhumb line until just after half way, and then started a slow ease to the east. The weather had been great since crossing the Stream, and the crew aboard Lulu’s "Plastic Fantastic Traveling Road Show" were living the high life in near perfect sailing conditions. Our only complaint was that we were going too fast to catch any fish and the sushi supplies remained untouched for the trip.

We crossed the finish line off Virgin Gorda a few hours after the line-honors winner Aquila who had set a new course record of six days, ten hours and forty-two minutes. The sun tans and seasoned looks of my fellow crewmembers told it all. They had completed not only an offshore passage, but they had made a successful transformation from blue water wannabe’s, to blue water sailors. It’s a badge many of them wear with pride, and the Caribbean 1500 fraternity is as solid as ever. Many competitors from previous years were on hand to welcome the latest arrivals, and it was more than a bottle of champagne that was handed out to each yacht as they tied up alongside. It was that knowing tip of the hat to a fellow passage maker that made it all worthwhile. I was proud to be included among them.


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