One of my sons called me yesterday to ask about a rather expensive watch he was thinking of buying. Did I think it looked good? he asked.

“I don’t know,” was my reply. “How easy is it to see the hands and numbers? Is the crystal protected? Are you going to wear it in your work?” I questioned, for he’s Air Force Special Forces.

“Dad, it’s a watch; it’s got to look good! Man, are you out of date!” he said. “Gosh, Pop, when I see you on the boat, all you ever wear is cheap stuff.”

He was right. Centered on the bookshelf in Freya’s saloon is a handmade 120-plus-year-old mahogany box with dovetail joinery, a locking top lid and two drawers. Raising the top lid would expose the framed display plaques about Freya that we hang at shows, plus two pairs of sunglasses left by some long-gone guest.

In the first drawer is kept the ship’s papers, insurance info and the usual bits and pieces of life that find its way into a drawer. The bottom drawer, however, houses a rogue collection—no, a depository—of worn out timepieces of every watch or I have used or worn aboard every boat I’ve sailed in the last 30 years except for three.

In 1953, at age 13, I was softly shanghaied aboard my uncle’s fishing boat and spent the first of three summers working with him in Southeast Alaska. My mother was smart enough to realize that no watch would last long on my wrist, so she bought me a $3.95 pocket watch. Expecting something grander, I could only show disdain for the gift. After all, it was a stupid farmer’s watch. How lame could that be?

Actually, the question should have been, how ungrateful could I be? Even though the pocket watch spent most of the day and night hanging from a nail above my berth, it kept adequate time and served me well for my needs. Years later I kept it in a cigar box as a memento of the experience until it was discovered by one of my children and lost in an area behind our home known to them as the “gravel pit.”

In 1965, a beautiful 32-jewel Movado Chronograph caught my eye. The bracelet, made by Gay Freres, was itself a work of art and added much to the watch’s elegance. I saved up for a while to pay the $450 the jeweler demanded, but I reasoned I could count on the watch being very accurate. The motivation for buying it was flying, not sailing, yet when my profession took me to the Caribbean and South America in early 1969 I had the good fortune to meet and make friends with a retired navy admiral named Joe Watson.

On my free days we began to sail his 39-foot Piver Trimarian named Gemini out of Fajardo on the east coast of Puerto Rico. One day, Joe took a look at the watch on my wrist and said, “Kid, it’s beautiful, but you’re gonna break or scratch that thing and it’ll cost an arm and a leg to fix it. Go hang it from a cup hook in the galley or over your bunk.” This I did, until about a year later, when on one sweltering afternoon we launched on a supply run into St. Kitts. At a restaurant I removed the Movado to wash my hands, thoughtlessly leaving it in the washroom. By the time I remembered and ran back to the place, the watch was gone. It should have stayed on the cup hook.

Then there was the stainless steel Rolex Submariner. This purchase took several months of saving to afford. I needed it, or so I lamely reasoned, because I was flying with a group of exiled Cuban pilots. These were real men, you know—small, pencil thin mustaches, lots of gold and a Rolex or Patek Phillippe watch that was the requirement to even sit in the cockpit with them. But when I stepped onto the deck of the Gemini, wearing my new Rolex, Admiral Watson rolled his eyes and said, “Jeausus! What did you do, rob a bank? Now take that thing off and put it on a cup hook.”

I did as I was told, at least for a couple more years, until 1976, when we were crewing a friend’s 52’ Camper and Nicholson ketch from Prickly Pear Cove in the BVI bound out for Saba Island, which lies just to the west of St. Eustatius, DWI.

It had been a rough night passage and by 3 p.m., we had the boat cleaned up and organized just as we started our transit over the Saba bank, a large, shallow area 24 feet to 60 feet deep lying to the south and west of Saba proper. We were all looking forward to stopping at the island and trying out its first pier. First what, you say? You see, Saba Island was the remains of an extinct volcano that had exploded and collapsed upon itself eons ago. The sides of the island (volcano) rose steeply from the sea, so steeply the island had no beaches. None.

Before 1976, the only way onto the island was to anchor in relative shallows off a western-facing rock wall, then dingy over to the wall, tying to iron rings set in the rock. Above the rings was a narrow set of steps chiseled into the rock face that snaked up toward level ground about 200 feet above. Until the invention of the airplane, every item, including Jeeps disassembled into sack-size loads, animals or persons that came to the island, either climbed up or were carried up what they called “the ladder.”

By 1976, the Dutch government had built the islanders a short dock suitable for small island freighters and yachts. Considering the steepness of the island’s sides, the dock was thought to be a feat of engineering to simply find enough fill rock or purchase for the pilings.

On a broad reach, across the shallow bank we came, the expected taste of cheap Dutch beer (Heineken at 25 cents a bottle) or gin called us. The water—gin clear—showed every detail below. It was a picture-perfect day, other than a black growing nimbus cloud about five miles to the south of us; the sky was blue and the air sweet with the smell of salt and land. We were getting close.

While I was below, the winds switched unexpectedly and we came on another tack. Since I was going to town, I decided to put on the Rolex. Coming up to the deck, I saw that Admiral Joe was now at the winches. Would I go forward to drop and fold the genoa? the boss asked.

“Sure, for a beer,” I said.

“Hell, I’ll buy you two!”, he replied, laughing.

As we swung into the soft 15-knot trade wind, I signaled to Joe to pay out the genoa halyard slowly. As each sail shackle slid down the wire into reach, I would release the snap and work the sail into a fold between my feet. It all worked well – until that black cumulonimbus cloud passed over us. Suddenly the wind veered and piped up with a mighty gust. The boat rolled like it had been hit by a heavyweight prize fighter and the genoa beneath my legs billowed out almost simultaneously.

I reached down to keep the sail from going over the side, when one of the sail shackles closed on the bracelet of the Rolex. Another even more powerful gust slammed into us as the sail filled, lifting clear from the deck and taking me with it – hanging by my expensive wrist watch. I flailed away, trying to reach the forestay, as 15 or more feet below me churned the now surly waters of the Saba bank. While wildly reaching with my free hand for anything firm, my 185 pounds overtaxed the watch bracelet and it broke, the watch hurtling off to port, a small splash in the sea, while I fell overboard, just clearing the starboard side of the bow.

Regaining the surface, I swam, not just a little worried about the possibility of sharks, while the crew got the boat under control. Thanks to Joe keeping an eagle eye on me, I was back on deck in 10 minutes, leaving a trail of blood across the deck as I came aboard. Before the band had broken, the Rolex had scratched and gouged a chunk out of my wrist as a painful memento, and I was beside myself for losing it. We made a couple of tacks over the area to see if we could spot it, but no luck.

After my wrist was bandaged, we made fast at the pier and walked up the little road into the tiny town called the “Bottom.” While my mates laughed and talked as they played pool at Jason’s Boogaloo, the local tavern, I, in a deep blue fugue, drank—and this night, I assure you—much too much.

The next day, when I was able to keep it down, I ate breakfast with extra toast and coffee. Joe sat across from me, slowly sipping from his cup, his grey eyes boring holes into me, “Mate,” he said, “expensive jewelry is best kept in a drawer or on a cup hook. It doesn’t belong on a working vessel.” I slowly nodded my head—a lesson finally learned.

Today when I come aboard I remove the one good watch I own (a gift from my beautiful wife) and reach into the mahogany box. In there are three or four old, slightly beat-up Timex watches; none of them cost me more than $16.00. As long as the battery is good they keep excellent time (actually much better than I remember the Rolex ever did) and if lost due to my fumbling, there’s another close at hand.

Affixed to the bulkhead below the barometer and next to the wheel is a brass clock mount from an Elco PT boat, one of Joe’s commands in World War II. The clock it holds was salvaged from an odd four-engine British dinosaur I flew many years ago. Admiral Joe is gone, and the airliner, a cantankerous example of British engineering (an oxymoron if there was one), has been melted down to make Chinese bicycles. Yet when I look at the brass mount and the clock inside it ticking away, I think of my good friend and those bright days somewhere over the Caribbean, and wonder if anyone has found a Rolex lying on the bottom of the Saba Bank.

My good watch? Oh, it hangs from a cup hook above my berth—for the duration of my voyage.

Mike Oswald is a boater and retired airline pilot who lives in Tulalip, Wash.