I write this knowing the world is filled with more accomplished and talented sailors who have completed more challenging passages. For me, this is part of the process of learning about my new boat, the good and bad. It is also about understanding how I handle this type of sailing. I don’t pretend to possess any particular insight. This is just a tale about a journey and how sailing can be transcendental – for me. 

Buying Zennora and gradually moving her around Florida to a place that puts me in striking distance of home in New York has been financially and logistically challenging. On Sunday, Jan. 24th, I put aside all those thoughts. Ahead of us was the promise of two days at sea.

Hours Zero to 24

When Robert flipped off the last dock line from a piling at Marathon Marina and Boatyard, the winds were blowing from the northeast at about 15 knots. The forecast called for the wind to hold and then rotate to the Southeast. We expected that turn in about 24 hours, around the time we were to tack north, allowing us to sail downwind in relatively calm seas up the coast. The next stop would be Port Canaveral, halfway up the Florida coast.

After discussing the weather forecast with Chris, I opted to skip Hawk Channel, a strip of navigable deep water close to the keys that avoids the sometimes treacherous Gulf Stream.

Taking the Gulf Stream means you can ride the two-to-three knot northeasterly and then northerly push as the current passes between Cuba and the Keys, and then along the east coast of Florida.

The risk, of course, is winds from the east or north, depending on where you are, pushes wind against the current, standing up the seas in steep, close waves.

We left at high tide so we had water beneath Zennora’s 7-foot-plus deep keel. (She would often settle in the mud at low tide.)

We headed west out of the marina, hugging the green-channel markers to stay in the deepest water, and then curled southwest and then south, leaving Sombrero Key about a mile to port. Just as we cleared the key, a line in the water appeared ahead of us. The water turned from a light turquoise to to a dark aquamarine. The change took place in just a few feet, certainly less than the length of the boat. And almost as quickly, the depth changed from 20 or 30 feet to 100 and then a few hundred feet. We were in the Gulf Stream.

We raised the main, the mizzen and unfurled the jib and turned east. The now stiff wind continued from the north to northeast and, as it grew, it lifted us to eight, nine knots, then ten knots and more. Zennora didn’t mind.

We kept her trimmed on a close reach during the afternoon, but powered down a wee by furling the jib to about 60 percent as the sea grew. Still, she plowed along, now in swells of about eight feet. And through it, all, we maintained 10 to 11 knots.

Liberated from the docks, Zennora celebrated.

At five, as the land to our north curled away, we entered the Atlantic portion of the Straits of Florida. The wind had been blowing from the northeast all day and the extra fetch allowed the seas to build dramatically. We tacked north, hoping the lee of Florida’s tip would allow us to sail smoother waters.

That worked for about 90 minutes but we were getting close to dropping out of the Gulf Stream and were approaching the many reefs cradling the Keys. We turned east again.

Shortly after dark, we tacked north and east a a few times, still hoping to follow the curl of the Southeast Florida coast. The winds, however, were not cooperating and we found ourselves close-hauled and inching back to the west instead of the east, despite the two-to-three knot northeast current.

Shortly before 8 pm, Robert was at the helm. I was on watch in the cockpit. Chris was below taking a nap.

We were sailing into a line of brightly-lit ships steaming southwest. One was probably a gambling boat, sitting in international waters, its passengers happily being pick-pocketed. Another, probably a cruise ship, likely out of one of Southwest Florida’s ports, its passengers happily risking dysentery.

“What the feck is that,” I asked, pointing at a burnt-rose mushroom light to the east. And for a moment, under the white-flecked black dome of our atmosphere, we were stumped.

“It’s the moon,” Robert announced after a pause.

One day removed from a full moon, it was rising behind a few clouds, distorting its shape and color.

We tacked away from the Keys and the ships, toward the Bahamas and into the moon. As is rose higher, the moon fluffed-off the scattered protons of its initial ascent and turned brilliant.  We followed a line of moonlight stretching before us, through glowing peaks of swells and twinkling wind-driven ripples.

For the next couple of hours, the waves, the trim, current and planets aligned. Zennora turned with the seas, the rudder superfluous. I leaned back and released the helm. The moon, as it rose higher in the eastern sky, moved back and forth across the bow with the swells, casting a shadow from the sails over one side of the cockpit and then the other.

Shortly before midnight, about equidistant between Key Largo and Bahamian waters, we tacked north. The wind had shifted just enough to the east that we could sail due north, running parallel with the east coast of Florida. And during the night the winds continued to build. As did the seas.

Between one and four, with Chris at the helm, they peaked, blowing from the northeast at 25 knots with gusts well into the 30s. Now the seas were sometimes over fifteen feet.

Chris and I have been together on Zennora since we left Palmetto on the first leg of a sojourn that will end this Spring in New York City. We are getting to know what Zennora can do.

And she didn’t need a reef. She wanted to fly. And she did, topping out at 12 knots.

I was below, trying to sleep.  Several times, when the winds peaked, I opened my eyes as we crashed into a trough. But she didn’t groan or shudder. She just wanted to go.

Only once did the seas reach back to the cockpit.

“Robert took the brunt of that one while sleeping in the cockpit at 3am, or so, as a wall of water broke over the bow, engulfed the deck and proceeded to dump on him before I could call it from the helm,” Chris wrote in a Facebook post. “That was surely his first wet dream in some time. But I doubt he enjoyed it as much as I did, I couldn’t help but laugh. Mo was off watch trying to get some much needed sleep below but I’m not sure how well that worked out for him given the lumpy conditions.”

When Robert relieved Chris at the helm at 4 am, the wind and seas laid down a wee bit. We passed Miami as a line of cruise ships cued up to our west, waiting to enter port after dawn.

Around 5 am, one of the last ships to arrive was on a heading toward us from the east. We hailed the skipper, who told us to maintain our course. He increased his speed, turning slightly upwind and came across our bow about a mile to the north. He didn’t have to do that and would have been within his right to ask us to tack.

The moonlight now pocked the seas with glistening patches through breaks in the clouds. I looked to the southeast and realized they were blocking our view of the unusual alignment of  Mercury, Venus, Saturn, Mars and Jupiter arcing in the southeastern sky just before dawn.

Zennora didn’t look back. She left that to us. She had a purpose and that was to carve the seas, as fast as her sails and hull would allow.

Around 6 am, a curtain of cloud briefly lifted and there it was. Even Mercury, just above the horizon, was visible

Soon, first-light appeared. I tingled. I had never felt so connected to the seas and the skies. Never was I so connected to a boat and a crew. And never so disconnected from civilization, just to our west. It was not hard to imagine myself among the ancient mariners.

By 10 am, 24 hours after we shoved off, we had traveled over 200 miles.

Hours 24 to 48

Our thrilling sail was not to last. We tacked east to west and west to east for most of the morning and well into the afternoon. We were inching forward even as the northerly winds laid down. The residual swells from the night before rolled us from side to side as the sails flogged and the booms crashed from port to starboard and back. Finally, off West Palm Beach, I decided to start the engine.

And the engine overheated.

The temperature didn’t spike, it just gradually rose to 200 degrees, 20 degrees higher than normal. Chris was at the helm and hove-to, effectively stopping and settling the boat. I went below with Robert. We checked the raw-water engine intake seacock. We checked the sea strainer for debris or a blockage. We checked the water pump and the impeller. We checked everything up to the heat exchanger (a system that uses seawater to cool the engine coolant in a similar way that a radiator uses air to cool a car engine coolant.)

We could not find anything wrong and I wasn’t ready to start tearing apart anything else.

We started the engine again and watched the temperature rise, past 180 degrees Fahrenheit, to 190 and then 200 degrees.

I told Robert if it went any higher, the engine was to be turned off. The prospect of being without power filled me with dread. I started clicking though alternatives to Port Canaveral and also how much it would cost me. We were about 25 miles offshore.

We stared at the temperature gauge. It settled at 200 degrees. And then it seemed to tick down. Moments later, the engine cooled rapidly. It settled at less than 180 degrees. We were moving again. My best-guess is the thermostat is faulty and snapped open at 200 degrees, allow sea water to flow into the exchanger.

We saw the same pattern each time we started the engine. This is a issue that must be resolved before the spring.

An hour or so later, we gave up any pretense of even motor sailing. We dropped and furled the sails and motored north for most of the afternoon and into the evening.

We were waiting for the wind to rotate from the north to the east. For some reason, Chris was convinced the forecast was now correct and it would turn at 8 pm. He wagered a quarter which Robert and I now owe him.

I awoke from a nap at 8:30 pm. The wind had shifted. We immediately raised the mizzen and unfurled the the jib. We set the “jib and jigger” and settled in for the night. The wind moved around, mostly from the east to southeast, and we found a groove heading northeast.

All night, all of us enjoyed three hours of comfortable productive sailing at the helm. When not at the helm, we all slept well.

By dawn, we had tacked and were heading northwest toward Port Canaveral.

About 15 miles from the entrance to the Port Canaveral channel, the wind died again. That was the end of sailing. We motored into the port, past a phalanx of shrimp boats, past NASA’s rocket assembly building and the launch gantries once used by the space shuttles, past the US Navy’s submarine turning basin, to the Port Canaveral Yacht Club.

Like most sailors, I am much more comfortable under sail than under power and the slips and fairway at the yacht club are not very wide. As we approached the slip, I wasn’t sure how I would make the turn or if I could squeeze Zennora’s 14-plus-foot beam between the 15 feet separating the pilings.  (Zennora does not have a bow thruster.)

But Zennora did not let me down. As we approached the slip, I goosed the throttle in reverse, using the starboard prop-walk to pivot the boat, and then gently pulled into the slip. We didn’t touch the pilings.  It was 10 am. We had traveled about 370 miles in 48 hours.

We tied up and toasted Zennora with a snort of rum. And so ended the most satisfying sail of my life.

The Crew

All of us were members of the Sarasota Sailing Squadron. Excluding occasional sailing on sunfish and similar boats as a youth, I learned to sail at the squadron in the mid 2000s. Chris Simpson sold me my first boat, a 1979 tall-rigged Catalina 27. (I eventually sold it back to him after I moved to New York.)

In addition to being a fine helmsman and sail-trimmer, Chris did all of the cooking. On this trip, the meals included Italian sausages with onions and peppers on a hoagie roll and chili. The only meal that didn’t work was Spam and eggs he served for breakfast before pulling into Port Canaveral. My tongue still feels like a salted deli meat.

Robert Hindle was also a member of the squadron when I was there but we only met a few times. Most notably, he tried to help me when I ran aground  on a sandbar on the east side of Sarasota Bay. He got stuck too. When BoatUS came out to tow me off, they also yanked Robert’s boat off – snapping his rudder.

I had largely forgotten that day until he recalled it during this trip. The fact he would sail with me after that episode is testament to his kind and forgiving nature. Under sail, he is thoughtful and careful. And a steady adviser.  

Trust is built on the water, not over drinks. I would sail anywhere with these gentlemen.