I can’t remember the exact date or even the year. I believe it was in the late 1980s when I got a call from Dan Look, a good friend living in Atlanta and who had his own consulting company specializing in providing technical assistance, mainly on food service, to senior living communities. He knew I was a sailor like him and asked me if I would like to be first mate on a week-long, “bareboat,” charter cruise in the BVIs that he was planning. He was going to invite seven or eight friends, all guys, mainly in the not-for-profit, senior living world though without much previous sailing experience. I enthusiastically accepted, had a terrific time, and volunteered to skipper a second boat the following year. It was not long before others learned enough about sailing to able to skipper a boat themselves. The event became an annual happening, and the fleet grew to four or five boats, occasionally even more. These cruises, which were almost always in the late winter or early spring, happened almost every year and went on for at least a decade. I made almost every one of them.
It did not hurt that the BVIs are widely considered to be among the best sailing waters in the world especially during the winter and spring when trade winds from the northeast are steady and consistent at 15-20 knots every day and it hardly ever rains.
A typical Dan Look BVI cruise would go something like this: Eager sailors, all men, from various locations in the United States would arrive on a Saturday. Many were executive staff of not-for-profit, continuing care retirement communities or consultants, bankers, or other professionals in the senior living industry though there also were usually some members of the Atlanta Rowing Club where Dan was a member. A week’s supply of food, which Dan had purchased and packaged the week before in Atlanta, would arrive there about the same time, and with help Dan would distribute the food (mainly for lunches and breakfasts) equally among the boats in the fleet. He would also distribute golf-type shirts for each participant with a special logo on the pocket showing the date of the cruise. The boats were chartered from Sunsail, at the time the world’s largest sailing charter company, and they were mostly identical 40-45 foot Jeanneau boats from France, each equipped with a large dinghy.
Dan would decide which men sailed on which boat; and while I usually already knew at least one or two people who were assigned to my boat, occasionally I would be assigned three of four guys I had never met. Everyone usually ate out together at the restaurant in the marina the first night. The next morning there would be a skipper’s meeting required by Sunsail for all charter captains and first mates. By late morning we would cast off to sail the islands. The big question was whether to sail the islands in a clockwise or counter clockwise fashion. Most of the time we cruised counter clockwise sailing first to Peter Island to the east, then Beef Island farther north a dozen miles away upwind, then Virgin Gorda, Anegada, Josh van Dyke, Norman Island and back to Tortola. My favorite was Anegada, which was situated by itself to the north, almost 20 miles away from all the other islands and the least populated. Each leg, of course, would often involve a race though those in the boats who arrived well behind the winner would usually argue that they were not racing. But my boat was and we often won.
The boats did not raft up in the BVIs the way they do in the Chesapeake Bay because of the strong winds and crowded anchorages, but at the end of the day, after anchoring or tying up to a mooring everyone would jump in their dinghies and motor over to Dan’s boat for drinks and dinner. Dan was a professional food service consultant, loved to cook for the 15 or so hungry guys, and on many of the cruises was assisted by the owner of a popular steak house chain in Atlanta. I don’t know how he did it, but the dinners were always delicious and always fun. My self-appointed job was bartender, and I got pretty good at making pain killers (black rum, orange and pineapple juice, with coconut milk and spices.) The participants for the most part were not heavy drinkers and anyone who wanted booze was responsible for bringing it on board themselves. As bar tender, however, I was careful to buy enough black rum to mix a pain killer for anyone who wanted one, and there were always takers. On one of the cruises someone presented me with a tee shirt which said, “Drinking Team with a Sailing Problem.”
There was always laughter, storytelling, and never a word about politics. Many of the crew came from faith-based, continuing care retirement communities and were from the South or Midwest so it was understood that we did not want to go there, unsure of their politics. Regardless from where the guys were from or what their politics were, I liked every person who ended up as crew on my boat; and making new friends with people who were not like me was one of the best things about these cruises.
One of the biggest thrills on these cruises was spotting whales. Over the decade that we cruised on the Dan Look cruises we saw several whales, mainly Humpbacks and some up close and personal. Our boat was once cruising alone when we saw a giant whale come out of the water about a hundred yards away, then disappear below the surface. We were all oohing and aahing, then looked down and saw the giant creature swimming just below the surface next to our boat, close enough that we could touch it. The creature, probably an immature Humpback someone said, was longer than our 40-foot boat. Then the animal suddenly disappeared not to be seen again.
The strangest experience that happened was on an overnight crossing from Saint Martins Island to Tortola, the only cruise that we had that did not originate in the BVIs. Four boats were motoring together in a flotilla on a moonless night and calm seas with no sign of any other boats except an occasional large cruise ship passing in the distance. Then around 3:00 AM three large, bright lights in a triangle appeared from nowhere and for a few minutes followed the first boat in our flotilla. The lights were so bright that you could not tell if there was a vessel associated with them or not or how far they were away from us. They appeared to be about six or seven feet above the water. Were they on another boat or on a helicopter?
The strange lights followed the first boat for a few minutes, then moved to the second and the third and finally to our boat. I was asleep at the beginning and awakened by a nervous crew when the lights got closer to our boat. I tried to figure out what might be going on but was stumped. Then suddenly the lights went out, and whatever they were, they were never to be seen again.
As you can imagine, we were all spooked. When we reached the BVIs around eight the next morning we anchored near the customs house; and after the skippers all motored their dinghies into the marina to do the paperwork, we compared notes. No one had a clue. For the next few days, I was haunted by the experience but eventually put it out of my mind though it seems as real today as I write about the account as it did at the time. Go figure.
And those were the days. I am not sure exactly why but after about a decade of these annual BVI cruises, they started to peter out. I always will be grateful to Dan for inviting me to join him that first cruise and for all the cruises that followed. I do not think I missed more than one or two.
But I was hooked and for me the closing of the Dan Look BVI cruises marked the beginning of my sailing experience in exotic waters, not the end. And these ventures included sailing in oceans all around the world. Stay tuned for the next post on the “Second Wind Days and More Sailing in Exotic Seas.”
(Visit my substack site for photos.)
1 Like
Discussion about this post