I can’t rank them; they were all amazing. Here are some of my best days ever, as I begin one that has the potential for being added to the list.

1999. Georgetown, Bahamas. In a crowded anchorage, my tiny sailboat, Xerxes, swayed on the wake of a passing yacht. It was sundown. I stood naked on the bow pulpit with a conch shell in my hands, my body sore from a day spent in the sun playing volleyball, eating a burger on the beach, and snorkeling for hours. The sunset tradition of horn blasts spreading through the harbor had not yet begun. Raising the conch shell to my lips, I blew through the end I’d hacked off with a rusty saw and filled my lungs with crisp island air.

The blast from the shell resonated across the water. I blew until I was dizzy and saw stars. Leaning back against my furled jib, I waited a heartbeat or two. And then the reply from my fellow boaters, a blast here, a toot there, a long roar from a powerboat. It was all for the sunset, but it felt like an answer for my little shell. I dropped the conch into the water with a splash, leaned forward, and dove into the cool sea to retrieve it, staying down for as long as I could.

July 2002. The Tongue of the Ocean, Bahamas.

“Are you sure those are dolphin?” she asked. “Those look too big to be dolphin.”

I peered over the windshield at the fins, beginning to doubt myself. Amber and I were on a 74′ yacht. We’d left Antigua the week before, island-hopping out way through the Caribbean toward Ft. Lauderdale. I’d just taken the boat down to Barbados with the owners, who had introduced us to each other months prior. When we’d met, I knew I was leaving on this long trip. It felt safe to date for a few weeks. Last month, we celebrated ten years together.

“I think those are whales,” I told her. “These are dolphin, here, but those are whales.”

“What kind of whales?” she asked. “Do you think they’re eatin’-people whales?”

Before I could answer, she was grabbing her snorkel gear. The boat drifted toward the pod. I killed the engines and allowed it to coast silently. There was no land in sight, the boat moving across a sheet of windless glass in thousands of feet of water. We were abandoning ship, sliding from the swim platform into an ocean teeming with life.

Whales. Thirty feet away. Twenty feet. Babies with curious eyes and mothers with wary ones. They circled us, Amber and I laughing through our snorkels, swimming around with soft motions, me thinking about a sudden breeze blowing the yacht further and further away.

The water does strange things to the light when it’s that deep and that calm. It glittered in rays deep below, creating this panic of heights even as you bob on the surface. We were a mountaintop away from the seafloor. All that held us were our bellies full of awed breath, the splash of fin and flipper, holding hands and perfectly aware that this would never be topped.

The summer of 1987.

My first sailboat, a tiny sunfish on a rusty trailer with flat tires. When we arrived at the beach house every year, this was the first thing I went to. Straight out of a stuffy van and to the garage, throw off the wooden beam that holds the doors from the inside like a castle keep, then pull that trailer through loose sand toward the sound at the back of Figure Eight Island.

I was twelve, and assembling the small craft took the full measure of my wiry strength. It took a long year of remembering where lines went. I would push away from the shore, pale and frightened. A few days later, I would be tacking in a stiff breeze, riding the keel dangerously out of the water, on the edge of recklessness, my skin brown and my confidence soaring.

One day, while stalking the beach with a five-pointed gig like little Poseidon himself, I heard the screams. The laughing girls flapping across the sound in their own sunfish were tipping. Screams turned to shrieks, the sail crashing into the water, three teens flailing as the craft’s keel pointed up through the waves like a shark’s fin.

I remember running, feeling swift as a crane, packed sand putting a spring in my step. They were hundreds of yards away, out in the middle of the sound. I took the beach as far as I could and dove into the still waters, long strokes, turning my head to the side, no plan for my heroics.

“Easy,” I gasped, as I arrived to the upside-down craft. Two of them were clinging to the hull. Another was trying to swim it toward the distant shore, tugging on a halyard, the submerged sail making it arduous.

I knew what Superman felt like, seeing their reaction to my sudden arrival. They were so much older than me, at least two years. Teenagers. I dove down to survey the damage.

The mast pointed down into the dark depths, the tip invisible. I’d never turned one all the way over like that. Had always jumped off in time and held the keel, scampering up like a pirate’s plank. I knew it wouldn’t right itself with the weight of the sail. Up for a deep breath, the girls fearfully quiet, waiting. I went back down and planted my feet on either side of the mast, upside down, sea water tickling my nostrils. I pulled on the mast, yanking it out of the hull, gravity helping.

The thing was heavy. I kicked for the surface, an elbow under the end of the mast, the tip trying to float now, the boat rocking more with the drag gone. With a halyard in hand so I didn’t lose the mast, I climbed up and leaned back on the keel. The girls squealed as the boat flipped over. Water sloshed in the hull as they scampered up on the deck.

I handed them the end of the mast. With the three working together, they lugged it up on the deck, waterfalls sliding off the sail. I was out of breath and numb from the adrenaline, but teenagers were watching, expecting me to know what to do.

“Just relax,” I told them. I was not really this brave. It was the effects of too much sun, too many days sailing around the sound daydreaming of adventures, nights spent trying to spear wily fish. It was the effects of watching three bikini-clad girls sail around all afternoon, giggling, no notice of me at all. I would drown gladly before I did anything rational.

So I tied a bowline in a halyard, stuck my foot through the loop, and swam for shore. Long and slow pulls, a gentle pace, turning my head for gulps of air. And as my muscles broke down, some mystique grew on the deck of the dismasted ship. And an afternoon of lying on the dock of three teenagers I didn’t know, my back rubbed by way of thanks, a tiny legend, for only a day, and perhaps only in my own mind…

1999. Isla de Providencia.

The day started at five in the morning. An outboard motor puttered to the back of the M/V Billy, a steel-hulled expedition yacht we were supposed to be taking to Hong Kong. It was the proverbial slow boat to China, and now it looked like it would never make it at all.

We spent Christmas in Cuba, met Hemingway’s old fishing boat captain in a bar, toured Havana, watched the locals dance in a bar. I told the owner we shouldn’t leave. She preferred to trust a weatherman back in the states who couldn’t see the two fronts colliding to the West of us. This had been the pattern of our trip so far, the owner making foolish decisions, Douglas and I shrugging and going along for the ride.

South of Cuba, during our straight shot to Panama, I made an off-hand comment that continues to haunt me. “You know, Douglas, our existence is pretty tenuous out here.”

Douglas surveyed the empty horizon. “Yup,” he said. Douglas was a man of few words, and we were in the middle of nowhere. The seas were building, the tops white-capped and breaking.

“All it would take is losing a handful of systems, and we’d be screwed.”

“Yup.”

“Think about it.” I ticked them off with my fingers. “Get rid of our sat phone, the generator, our watermaker, and the main engine, and we would be toast.”

Douglas sipped his instant coffee. “Yup.”

Within 24 hours, those four systems were all gone. The seas were in the 10-12 foot range. At one point, heading out on the back deck to take a picture, Douglas and I were swept off our feet by one of the waves breaking over the steel coaming, which was a good ten feet off the water.

This day was not one of the best in my life. It was one of the worst. Sick and dry-heaving, the boat choking with black fumes from a ruined main engine, we slid in complete darkness into a treacherous inlet for an island we had no chart of.

We woke up in paradise. It got even better when the owner flew out with her four adopted children. Over the next few weeks, we merged with the island, getting to know the locals, hanging a new rope swing for the kids, hiking to mountaintops, going to a cock fight, lobstering at night, diving off of cliffs, and then . . . the day a boat was named after me.

The day started at 5 with the puttering of an outboard. I jumped on the bow, joining the two fisherman. We laughed and joked as the powerful outboard took us away from the island and near the breakers. For the next hour or two, we pulled up traps and spilled fish into the bottom of the boat. We made repairs on the traps with bits of wire and tossed them back in. My legs and back were sore when we returned to Billy, a half dozen fish in exchange for the work.

After breakfast, we spent a day on the beach. A local we knew well by now, I think his name was Michael, but I’m shitty with names, comes up to us. He explains the significance of the regatta that day, the race between these spectacular hand-built boats that take place every week and end right in the harbor in which we were anchored.

The same boat had won every one of these races for many years. Michael and some friends had just completed a brand new boat, months in the making, and it was to compete that day for the title. It’s maiden voyage. He wanted us to participate.

I had no idea what this meant, but I told him I’d love to. Douglas, who had a nifty new digital camera and who loved puttering around in our diesel-outboard dingy, volunteered to film. We sipped on our beers, enjoyed the sun and the waves, no idea what we were about to witness.

I had a meeting spot, pretty close to the beach we were on. When I got there, the new and nameless sailboat was being tugged into place by a Boston Whaler. The unbeaten ringer of a ship bobbed nearby, a gaggle of fierce men sitting proud in the hull. The crew I was joining was a ragged bunch. An overweight skipper, a man so tall he had to stoop to avoid the lazing boom, terrified and nervous glances cast like weak cannonballs toward the neighboring boat, where glares gleamed like cutlasses.

We were outmatched. Someone told me, as I got aboard, that I was the first white man to participate in one of these regattas. It was not said with clear kindness, I didn’t think. People looked to Michael, who looked to the skipper, who looked to me. I looked away. The race was about to start.

With a tightening of the mainsheet and a flap of canvas, we were off to the sort of tense and dreadfully slow beginning that sailboat races were known for. A lot of sitting there, staring up at your sail and that of your enemy’s, wondering who the wind gods would favor.

The two boats were evenly matched rounding the island. Women and children waved from the shore. Dozens of small boats motored alongside and around us, cheering. Douglas sat back and steered our dingy with his feet, recording the entire thing. I waved. I felt conspicuously as though I did not belong.

By the time we got to the mouth of the harbor, the other boat had taken a slight lead. Isla de Providencia sits in a pocket of eternal wind which blows straight through the harbor. Our boat, Billy, never deviated on her anchor. We nearly lost our tender one day to these winds, and one night, stuck without the keys, I allowed the stiff breeze to blow me from the docks, hundreds of yards, all the way to the boat. It was a formidable test for the last leg of the race. Directly upwind into a steady 15-20 knot torrent of air. Our competition tacked immediately. The portly man at the helm of our unnamed craft did not budge.

There was much yelling and complaint among our crew of eight or nine men. We were mostly ballast, changing from one side of the hull to the other, clinging and leaning out over the lapping sea, trying to pull the said up into the breeze. Now we were all captains, barking suggestions. Except for Michael and me. As our foe began a series of sharp tacks into the harbor, we kept on a long reach, racing across the wide mouth of the bay, speeding on a tangent, parallel to the finish line, not getting any closer to victory.

But Michael and I counseled patience. We sat nearest our skipper, and understood his argument, heard it best. All that time wasted tacking. It was the same distance, however you got around a square. The speed was killed in the tacking.

We raced across the mouth of the bay, the fleet of john boats and whalers splitting and confused, yelling and waving. Finally, after much silence and chewing our thoughts, the captain told us to come about.

We did. And picked up a wind unbroken by the mountainous peaks of Providencia. It roared over our sails as we beat into the bay. The other boat seemed far ahead, but it was tacking in an unfavorable direction. The sea foamed and screamed against our hull.

The end was more climactic than anything I’ve ever seen on film. Two boats with different routes, different histories, different crews. An island of habitual gamblers gathered at the cargo dock, waving their pretty currency, dying for an end to a streak.

With a last tack and a nice reach found, the captain ordered the ballast to begone. To my amazement, members of my crew began spilling over the rails, throwing themselves into the sea. We were no longer needed. No more beating directly into the wind. We were on the home stretch, amazingly ahead, but the swifter boat gaining on us.

I looked back to see members of the fleet picking up these men who had been strangers to me a few hours ago and now were like comrades in a military unit. I turned to dive over the rail.

“You stay!” Michael said, grabbing my arm.

The captain nodded. I didn’t appreciate the superstition filling our sails at the time. I gripped the gunwale and watched our competition close. Our tactics had been superior, our captain brilliant, but our ship was not the fastest. We willed our nameless craft forward, the edge of the crowded cargo dock the finish line, and as the other ship caught up to our stern, we passed through, victorious in less than a hull’s length.

The island went mad. Dozens of locals dove off the dock and swam out toward us. The rest of our crew was deposited in the hip-deep water. Somehow, the towering mast was pulled from the deck by a dozen of men and waved like a flag for a brief moment, before all came splashing down around us.

Douglas motored on the outskirts, grinning through his red beard, a small silver camera aimed at the spectacle.

I had done nothing but watch, but sit there. And yet, superstition filled those sails. And the nameless craft was dubbed “The Lucky Gringo.”

May 9th, 2012…