Last week I spent five days at sea. My father and I crammed enough food, water and other necessities aboard our 30-foot wooden sailboat and headed out to a distant harbor to meet a fleet of similarly rigged boats for a seasonal regatta. It was the third time we had participated in the event, the second time we had registered for the races. The first year – wanting to discover how competitive or cutthroat the other crews were – we opted simply to sail leisurely around the course while other boats raced. I had raced smaller boats in college, and knew how intense the competition could be. I didn’t want to be subjected to that kind of stress on my vacation. We ate, drank and were merry for the entire three-day event, and we often share stories from that year with friends and family at the dinner table. 

We had such a good time the first year, and it appeared the racing was somewhat relaxed, so last year we made the fateful decision to participate in every race. We talked about it all winter, and once the boat was in the water we tweaked the rigging and devised the perfect plan to come home with a gigantic trophy. 

Three times our boat crossed the finish line dead last, and Dad and I were at each other’s throats. Our 30-footer wasn’t big enough for two captains who each thought they could sail the boat faster than the other, and by the end of the weekend my mother and wife were ready to throw us overboard. We didn’t come home empty handed, however; we received an award for the numerous repairs we had done to the boat the year before. 

Despite hopes of having fun and relaxing and being OK with whatever place we were ranked this year, I turned into a hellacious captain – barking orders, ridiculing crewmembers and cursing at the race committee – once the gun announced the start of a race. My father and passengers insisted on having a good time onboard with squirt guns, water balloons and all sorts of food and drink, which only annoyed me more – I felt like a race car driver at the wheel of a clown car – as I tried to turn our seven-ton sailboat into a speed machine. One by one the other boats slipped past us, pelted with balloons and streams of salt water from my crew as they went by. 

We were ranked dead last once again. We were so slow the race committee began to remove race buoys from the course before we were finished, and we had to remind them we were still under way.

The sail back to our home waters was rainy and devoid of wind, and despite bad weather I was able to transform into the jovial sailor I had once been. Is it the promise of a glittering trophy, or an attempt to assert a superior sailing ability that brings out my aggressive racing streak? As soon as the gun goes off, I feel like a greyhound fixated on some mechanical rabbit I’ll never get, ignoring the natural beauty of the sea and the other gorgeous boats all around me. 

I’m beginning to think we had it right the first year; coming home empty handed and happy is a better reward than even the greatest trophy bestowed upon a miserable skipper. 

- Nate Jones