Sunset over the Keys

My Week Out of the Channel

Lessons Learned Sailing on the Deep Blue Sea

Recently I had the great fortune of spending a week on an offshore sailing adventure. My goal was to improve my offshore sailing skills in hopes of getting a crew slot on the Carib 1500, an annual cruising rally from Virginia to the British Virgin Islands. I’d sailed overnight before, but this was going to be 7 days and nights of sailing out of sight of land, without any stops. I actually hoped we’d have some good storms to take me out of my comfort zone and help me learn how to handle adverse conditions. It was an incredible trip and, as is often the case, what I learned was much, much more.

A ship in harbor is safe, but that is not what ships are built for.— J. A. Shedd.

Know where you’re going, but be flexible in how you get there

Our adventure started in Ft. Myers, FL on a 51’ Beneteau sloop with 5 guys I’d never met before, including Captain John and 5 other crew. Our final destination: Beaufort, SC. The plan was to sail south to Key West and then catch the Gulf Stream north to Beaufort, with an estimated time frame of 7 to 10 days depending on the weather. Before heading out, we got to know the boat and learned about offshore safety and what to do when the unexpected happens…which is almost a misnomer as the unexpected is always expected to happen when sailing.

As soon as we were out of the harbor and in the Gulf of Mexico, we raised the sails, turned off the engine, and began the peaceful bliss of sailing. We put out several hand fishing lines and caught our first Wahoo before noon. Soon we were zigging and zagging to avoid the endless procession of crab pots that can snag your keel, as we soon learned. After a beautiful sunset, it was clear that the wind coming out of the South was making Key West a difficult destination without a lot of tacks. We decided to change our plans and headed towards the Dry Tortugas, about 20 miles west of Key West. That was the plan, at least when I went to bed after my 8pm to Midnight watch. When I woke up the next morning for my 8am to noon watch, the wind had shifted again and we were headed towards Marathon, about 10 miles East of Key West. No worries; when sailing you have to learn to make adjustments.

Get to know your team and play to their strengths

One of the best parts of the trip was sailing with a crew I’d never met before. Captain John is a very experienced and competent sailor who knows his boat inside and out. An electronics buff, he had all the latest gear and taught us how to use it. My favorite, in addition to the autopilot, radar, and GPS, was the AIS (Automatic Identification System). One of the biggest concerns when sailing offshore, especially at night, is colliding with another vessel. AIS is new collision avoidance system that gives you an early warning of any boat passing anywhere near your boat, with details on the boat’s speed, course heading, and how close it will come to your boat and when. And if that boat has registered with AIS, it tells you the boat name, length, beam, and draft. Sailing off the coast of Miami at night, we knew a Disney cruise ship was heading towards us long before we could see the lights.

Our crew consisted of Don, Tom, and Dennis – all 3 Vietnam vets; Doug, a Canadian and a survivor of the 2004 tsunami in Thailand; and Kyle, a first-time sailor. Don crewed on a minesweeper during the war and then went on to become an air traffic controller at Miramar, the Top Gun training base. He kept us all in stitches with stories of his endless pranks on his crew-mates and superiors. Tom, a helicopter mechanic in Vietnam, had recently retired and was in the middle of acquiring a sailboat that he intends to sail across the Atlantic. Since Dennis was an army cook, you’d guess he did all the cooking. He probably would have if we’d let him, but Doug and I enjoyed cooking so much we only let Dennis do one or two meals. Doug hailed from Ontario, had an amazing memory for songs and jokes, and was infinitely curious of everything. Thanks to Doug’s questions, we all learned a lot more from Captain John about the boat and sailing. Kyle was our newbie. He fell in love with sailing after watching the documentary “Maiden Trip” about the 14 year old Dutch girl, Laura Dekker, who sailed alone around the world.

Who is the happier man; he who has braved the storm of life and lived, or he who has stayed onshore and merely existed? — Hunter S. Thompson

When everything is working against you, don’t fight it

After sailing under the 7 Mile Bridge in Marathon, we entered the Atlantic ocean and headed for the Gulf Stream.  This powerful current starts in the Gulf of Mexico, passes by the southern tip of Florida, and flows north along the east coast at an average speed of 4 knots. Our plan was to sail in the Gulf Stream to take advantage of the current, but also to gain some sailing skills in the notoriously fickle patch of the Atlantic. With a wind that was now coming out of the North against the current coming from the South, we knew we were in for some rough seas – just what we wanted to test our mettle. By our second day in the Stream, the winds had picked up to a steady 25 knots, with gusts in the 30’s. The sailing was exhilarating.

Coming on my watch at 8pm, we were already sailing with a double reefed mainsail and about 30% of our foresail. Our wind gauge was showing 30 knots plus and the waves were getting bigger. It was soon dark out and you couldn’t see the waves, but you could hear them coming. If it weren’t for the canvas enclosing the cockpit, we would have been drenched by the waves hitting the side of our boat. Even though I was taking Bonine every day to avoid seasickness, I have to admit I was a bit queasy. Fortunately I could see lights from the South Florida coast that helped me keep a fix on the horizon and avoid full-blown seasickness.

Later that night, after my watch, I tried sleeping in the forward berth (the aft berths, where there’s less motion, were already taken). I was tossed around for several hours before the boat finally calmed down. I wondered if the wind had died down, but it turned out the Captain “hove to” in order to ride out the storm for the night. “Heaving to” is a great tactic where you can position the boat and the sails in such a way that the only headway you make is due to the current. Rather than fighting the wind and the waves, we bobbed gently along. The next day we sailed west to exit the Gulf Stream and immediately had much calmer seas.

When you’re not getting the expected results, keeping asking “why?”

We snagged our first crab pot late afternoon on our first day out of Ft. Myers. We could see the line that connects the crab pot to a small buoy trailing behind the boat and knew it was caught on our keel. Fortunately we were able to free it simply by turning the boat sharply to the right and back again to the left (sailing downwind, we “gybed” left, then right). Worst case scenario is having to send someone overboard with goggles and a knife to cut it free. (Been there, done that!) Later that evening, back on my 8pm to midnight watch, the wind started picking up again after a few hours of almost no breeze. With a 20 knot wind, we should have been able to sail at a speed of at least 7 knots. But despite all our attempts at different sail angles, we just couldn’t seem to go any faster.

Our Captain came up to the cockpit after I’d gone to bed to investigate. Suspecting we’d snagged another pot, he had the crew do the same gybe right, gybe left maneuvers. Sure enough, the boat suddenly surged forward and we were quickly sailing South at 7 knots. Clearly we didn’t question our slow speed long enough while on my watch.

Every day we used the manual bilge pump and counted how many pumps of water it took to clear the bilge. After several days with a dry bilge, we started pumping out more and more water as the seas got bigger. It was time again to ask why. Captain John had us heave to, then began looking for the leak. He checked all the through-hull fittings, the transom locker, all the lockers in the cabin, but no sign of a leak. He then went to the bow compartment where the generator was stored and found 2 bolts missing from the flange where the exhaust goes through the hull. Not big holes, but big enough to let the water through. After replacing the bolts, we were back on our way.

And most importantly: Enjoy the ride!

One of the greatest benefits to offshore sailing is the amazing sunrises and sunsets over the ocean. And when the skies are clear, the stars are unbelievably bright. We had fun picking out the constellations, marveled at the Milky Way, and even got to see the Southern Cross.

Another big plus is the fishing. The first time we entered the stream where the water temperature climbed to 80 degrees and we almost immediately caught a Mahi Mahi. Several days later we caught another as we were exiting the stream. Mahi Mahi is known for great eating, but unfortunately we never successfully landed one on the boat. Sailing north along the Georgia coast we started catching “Little Tunnies”, a type of Mackerel. They were easier to get on the boat, but are not known for good eating, so we threw them all back. Earlier in our trip, while still in the Gulf of Mexico, we spotted a beautiful hammerhead shark, about 8 feet long, which swam right by our boat. And on our last day spotted a giant sea turtle.

Our final night was another rough one, with following seas that made sailing downwind a challenge. I was tossed around again in the forward berth as the crew on watch did their best to keep things under control. I was awoken by a very loud bang. While reefing the main we did an accidental gybe – a very dangerous event where the wind gets behind the wrong side of the mainsail and swings the boom violently across the boat. We were getting close to Beaufort, South Carolina, our final destination, and Caption John decided it was time to take the helm.

We’d sailed over 750 miles non-stop in a wide variety of conditions and learned a ton. While it took us out of our comfort zones, Captain John’s calm confidence during the heavy weather set the tone and spread throughout the crew. Pulling up to the dock, we were ready for a hot shower and a good night’s sleep. As I write this I’m flying 36,000 feet over the Atlantic Ocean at 569 miles per hour. I look down at the deep blue sea and can’t wait for my next sailing adventure – hopefully as crew on the Carib 1500!