My sailing education began with the instruction I received from Mr. Durant on his little sailboat, Blenny, during our summer vacation in Waupaca, Wisconsin in 1968. After we got our own boat the next year, my dad, who has always been good at figuring things out, helped refine some of Mr. Durant’s lessons. He bought a copy of Royce’s Sailing Illustrated, which put into words and pictures all the fundamental concepts, and we spent the next few summers working them out.
As a Boy Scout, I looked forward to spending a week each summer at Camp LeFeber near Wabeno, Wisconsin. It was a chance to work on merit badges that were almost impossible to get back home in Milwaukee, especially what were referred to as the waterfront merit badges. Over the course of three summers, from 1970 to 1972, I earned all that were offered: swimming, canoeing, rowing, lifesaving and small-boat sailing. Lifesaving was the most difficult by far, but small-boat sailing was the most fun. The camp had a couple of different sailboats of different designs. The only ones I remember now are some Sunfishes and the one they called the Yellow Submarine. It was a Flying Gunther rig, which is like a gaff rig with the shorter second mast going all the way to vertical. The trouble with the design of this boat was that the mast was situated so far forward that on a run, with the wind directly off the stern, the forward pressure on the mast would be so great that the front end of the boat would go completely underwater. Thus the name: Dive! Dive! Dive! Despite this tendency, which was terrifying the first time it happened and fun every time after that, I learned a lot from my counselor, “SS,” and finished the week with the merit badge in hand.
I didn’t receive any additional sailing instruction until almost thirty years later, in 2000. I had started looking into what it would take to charter a sailboat on vacation and was not surprised to discover that the charter companies would not rent their boats out to just anyone; the liability was too high. To be eligible, one had to have previous charter experience or a certificate from a recognized sailing school. Since I had never chartered before, other than acting as “captain” on a houseboat on Lake Powell during Columbus Day weekend in 1998, it seemed I had no choice but to enroll in some classes. The closest facility to Aspen I could find that offered approved sailing classes was The Anchorage, a sailboat dealer and chandlery incongruously located just 250 miles away in Lyons, Colorado (theanchorage.com). Fortunately, I had friends down the road in Boulder, Andy and Angie Bigford, that I could stay with during the long weekends that were required by the classes. In autumn 2000, I took three of the American Sailing Association classes in a row: Basic Keelboat Sailing, Basic Coastal Cruising and Bareboat Chartering. The on-water sections of the first two classes took place on Carter Lake, a man-made reservoir about thirty miles northeast of Boulder. Our instructor, Terry Killian, took us out in his Hunter sloop and made us demonstrate what he had taught us in the classroom above the showroom at The Anchorage. This was followed by written tests given in the cabin of the boat back at the dock. I passed the first two classes and so was eligible for the third.
The final class was more of an impromptu vacation trip than it was a sailing class. The students, Jim, Steve, Al, Doug and I, met with Terry at a restaurant near The Anchorage to plan the details, then we all met at Florida Yacht Charters in Miami about three weeks later, in mid-October. Over the next four days and three nights, we sailed a 41-foot Hunter named “Grande Child” from the yacht harbor in South Beach to Key Largo and back. Along the way, we experienced many of the joys and terrors of ocean sailing.
The first day out, we motored past the freight docks and Fisher Island, then hoisted sails and sailed south down the Intracoastal Waterway on a course we plotted carefully with our charts and compass to our anchorage in the lee of a small island, Pumpkin Key. Doug, Al and I went snorkeling, only to find there was nothing to see but sea grass. The bottom was muddy—not good holding ground—so when the wind picked up during the night, a warning horn from a nearby sailboat alerted us that we were dragging anchor. It took us three more tries to get it reset and get back to bed.
The next day, we motored out of the Intracoastal between two mangrove-covered keys and out into the open ocean. The wind that day was brisk, so we spent the morning working on sail trim, trying to coax maximum performance from the boat. At one point, we were heeled over so far that a stack of plates in the galley fell over and broke, scattering shards everywhere. We made such good time that we arrived at Key Largo just after lunchtime. Terry took advantage by making us practice our heaving to and man overboard drills.
The idea behind the man overboard drill is to get the person who has fallen overboard back on board as quickly as possible. The recommended way to do this is to throw the person a life buoy and have a crew member keep an undisturbed eye on them while the rest of the crew puts the boat into a beam reach to build speed quickly, then comes about and heads back toward the person, leaving plenty of room to round back up into the wind and approach the person to windward. As the boat slows, crew members use a boat hook and muscle power to wrestle the person and the life buoy back into the boat. This figure-8 maneuver becomes second nature with practice, and Terry had each of us man the helm while we repeated it over and over using a boat fender as our overboard man. I managed to garner Terry’s wrath twice: once by throwing a life buoy at our floating fender ("Now we have TWO things to rescue!"); and once by going too far forward with the boat hook, only to have a flapping jib sheet whip off my ball cap and sunglasses. The sunglasses I managed to recover but the cap, a treasured souvenir from a trip to the British Virgin Islands, was lost.
We arrived at Key Largo about mid-afternoon. After showers and clean clothes, we headed to the Coconuts bar for happy hour, then to the Fish House for dinner. Just two days into the trip, tensions were starting to run high between some of the crew members, so when we returned to Coconuts to watch Monday Night Football, Steve and Doug almost got into a fight. Steve had been openly critical of Doug a couple of times on the boat, and alcohol just added to the emotion. Doug said to hell with Steve and the rest of us, he was jumping ship. I tried to explain to him that if he did that, he wouldn’t pass the course and get his bareboat chartering certificate. The anger he was feeling would pass, but the resentment of failing the course would last a long time and prevent him from doing what he really wanted to do, which was to charter a sailboat on his own. He said he would think about it and stumbled off to spend the night on a poolside chaise lounge under a beach towel.
The next morning, everyone was not only nursing hangovers but also on edge over the conflict the night before. Doug had grudgingly returned in time for our departure. The return north was a quiet, uneventful one, with most of the crew working on their navigation skills or helping at the helm or sails. Our destination that afternoon was Boca Chica, a tiny island once owned by the Honeywell family and featuring one of the only lighthouses in the area. Rumor had it that during prohibition, Mr. Honeywell would boat over to the mainland to tie one on and then find his way home by way of his little lighthouse. Now the island is abandoned, but it’s still a popular overnight spot for the Miami boating crowd. We spent the afternoon practicing our docking and backing down skills at the concrete-lined harbor, until Terry had used up all his available patience. Since this would be our final night out, we were planning something special, a steak and baked potato barbecue. But as darkness descended, the mosquitoes came out in force, so instead of eating at the picnic tables near our grill, we retreated to the boat. After dinner, it was time for our final exam. It was harder than we expected but everyone passed it. A couple of celebratory beers later, we were all ready for bed.
The final stretch back to Miami the next morning started early because Jim had an early flight to catch back to Colorado. We departed at dawn, with me at the helm. There was a light fog on the water, so the navigation buoys that would normally keep us on track in sufficiently deep water as we departed the island were difficult to see. Even with two crew members at the bow with binoculars, we still managed to get off track and run the boat’s wing keel firmly into the mud on the bottom. Terry took charge and ordered all of us forward on the lee side of the boat to heel it over in an attempt to lever the keel out of the mud. It took the addition of having Terry gun the engine and swing the wheel back and forth to finally get us free, but we managed it. The fog had burned off by then, so we were able to navigate smoothly back to deeper water in Biscayne Bay, then on to our starting point four days earlier at Florida Yacht Charters. It seemed more like a month since we had started out, the experience of those few days was so compressed. Jim took off in a taxi to catch his flight while Terry debriefed the rest of us and signed our log books. The trip was over.
Looking back on it now, I think we all learned a great deal not only about sailing, but also about each other, and about ourselves. I think this is probably true of every experience where we intentionally remove ourselves from our daily routines. Adventure is the surest path to self-knowledge and also to being truly alive.
This blog is an account of the pursuit of a dream, to sail around the world. It is named after the sailboat that will fulfill that dream one day, Whispering Jesse. If you share the dream, please join me and we'll take the journey together.
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