My first boat was a poorly maintained Thompson 21 powerboat that broke down so often I decided to try sailing. After all, having wind as the motive power and an outboard kicker when that failed would, in theory, provide the redundancy to keep me out of trouble and my family safe. The opportunity came when we moved to Miami in 1984. Soon we were the proud new owners of Watermella, an O’Day 22. The gleaming white hull set off the green stripe that had undoubtedly contributed to its name, a take from its ocean element and the owner’s wife, Carmella.

A few days later we set off from Matheson Hammock Park, south of Miami, into Biscayne Bay to learn the ropes—literally—from the previous owner. The O’Day 22 is a gentle and forgiving boat, and the basic lesson I learned that day is that if you let go of the sheets in a strong gust, the boat slows down and settles on its lines. One thing I did not learn is that this trick does not work quite as well going downwind. More on that later.

Sailing on Biscayne Bay is glorious, with the Miami skyline to look at and lots of causeways and drawbridges to negotiate—all of which made for some interesting outings for this novice sailing family.

One February weekend, we decided to head out to watch the Miami Grand Prix from the water. Part of the circuit ran along Biscayne Boulevard, making the cars visible from the water, which combined with the beautiful weather provided more than enough incentive to step the mast and sail 10 miles north on the bay to enjoy the race and admire the cruise ships.

Afterward, the plan was to sail home to Matheson Hammock around the ocean side of Key Biscayne, after which we would return to the bay via the channel marked by the lighthouse on Bill Bagg’s park on the north and Stiltsville, a collection of houses built on posts in the shallow water, to the south. The latter would require motoring out of the Port of Miami channel into the easterly wind, alongside the massive cruise ships.

As we approached Government Cut, though, the wind picked up to nearly 20 knots, creating a short, steep chop that would raise the bow to an almost 45 degree angle and then bring it down with a jarring crash into the troughs. It was nothing Watermella couldn’t handle, but it was very uncomfortable. Down below, my wife, Marisa, and then 14-year old daughter, Deanna, were being tossed into the air during each downward plunge. Out on deck, my 16-year old son, Dean, and I were hanging onto the backstay to avoid being tossed out of the cockpit.

Deciding this was no longer fun, I managed to turn around in a trough without being rolled too badly, and we started our return home the usual way: heading directly south along Biscayne Bay, throwing in a series of tacks as we approached the Rickenbacker causeway, where the drawbridge had yet to open. As I did so, I also decided to start the outboard with an eye toward motorsailing through, as the bridge blankets the sails, which could cause Watermella to lose steerage and risk hitting boats coming the opposite way. Unfortunately, no amount of pulling would start the motor, even as I frantically checked the fuel line and the spark plug wire for something wrong. Next thing I knew, it was time for the bridge to open, and as I didn’t want to wait for the next opening, I decided to get a flying start in the stiff breeze and hope the momentum would carry us through without hitting another boat or the bridge abutment. Naturally, the biggest powerboat on the bay chose to enter the bridge as we struggled to reach the other side. But we made it through unscathed, with limp sails and virtually no steerageway.

By this time, the sun was setting over the Everglades, and the wind was dying as we made our way back to Matheson Hammock, where the boat trailer was waiting. The kids took turns at the tiller as I looked for landmarks and navigation aids in what was now total darkness. This is when I discovered how daunting it can be to find a lighted buoy against a background of brightly lit shore lights.

With a sigh of relief I finally spotted the markers for the channel leading to Matheson Hammock Park and Marina. But my relief was short-lived, as I now faced the challenge of sailing up a narrow channel that curved west and then northwest, partially blanketed from the wind by shore vegetation, past a line of boats in their slips, and then finally making a 180-degree turn to take us to the boat ramps. I dropped the jib before entering the channel, relying on the main to carry us around the tortuous course in the dying easterly, and steered for the first turn. This was actually working, I thought to myself soon afterward, as we glided past the slips at a safe distance. By the time I tacked onto the southeast leg I was elated with my accomplishment.

The only thing that remained was to stop the boat at the ramp. I figured I had just enough way to make the final 90-degree turn into the ramp chute, so I positioned Dean with a dock line on the port quarter, picked one of several empty ramps and smugly and sharply pushed the tiller to port.

Of course, it was then, just as Dean slipped the dockline over the piling, that a gust of wind, a last gasp from the vanishing breeze, pinned the mainsail against the starboard spreader and sent us scooting down the chute, heading straight for the steeply angled concrete ramp. With the rope burning his hands, Dean was forced to let go of the only thing keeping us from crashing onto the ramp. But his effort slowed the boat somewhat, and three good samaritans, observing our plight, ran into the water and pushed off against Watermella’s bow, helping to slow us down and minimizing the amount of fiberglass that was removed when Watermella’s bottom struck the concrete.

Overall, it was a learning experience that made me a better, more humble sailor. More damage was done to my pride than to the boat. I found out later that the reason for the outboard not starting was a displaced “neutral” détente on the shift lever, likely caused by the pounding suffered in the Port of Miami channel.

That little O’Day 22 provided years of pleasurable sailing, both in Miami and on Lake Chautauqua, in upstate New York. It also served as a stepping stone to a Tartan 28, which we sailed on Lake Erie and later off Ft. Lauderdale and on Galveston Bay, where my wife and I now sail our Tartan 3500. Although we sail a much bigger boat now, the magic of those early sailing outings on Biscayne Bay remains a treasured memory. 

Sergio Cosso, a retired mechanical engineer, and Marisa currently sail Stella Maris, a Tartan 3500, on Galveston Bay, Texas

What I did right:

I turned back in the Port of Miami channel when the steep chop threatened to cause harm to the crew.

I had studied the chart for Biscayne Bay and was able to navigate my way back to Matheson Hammock in the dark, which I had never attempted before.

I was able to safely navigate the drawbridge under sail, in spite of heavy traffic coming the opposite way.

I correctly estimated the boat’s and my ability to get through Matheson Park and Marina under sail, to reach the ramp.

What I did wrong:

I should have taken more time to troubleshoot the non-starting outboard, but did not want to wait for the next bridge opening, thinking that we could make it back to shore before dark if the strong wind held

When approaching the Matheson Hammock channel, I should have dropped the mainsail and kept the jib up, which I could have let fly when the gust hit. This is a no-brainer, and I still agonize today over that wrong choice.

I should have had my son place a prepared loop on the stern dock line over the piling, instead of holding the line with his hands. He could have been badly hurt.

With my limited experience, I should have considered calling a tow before entering the Matheson Hammock channel. The cost of damage to slipped boats could have overshadowed the cost of the tow, should something have gone wrong.

Illustration by Jan Adkins