I sat on the docks in the late afternoon and watched the sailboats do figure eights. It made me smile.

I once had this crazy idea that I wanted to take up sailing. And when I get ideas I can’t be stopped. I don’t want to say that I’m stubborn. So I’m not going to say it.

I had always wanted to sail. I started looking in the classifieds for boats. I visited everywhere from Mobile to Panama City looking at them.

I finally found a twenty-six footer in Fairhope. It was old, and ugly, but seaworthy.

It was a big step for me. I’d never done anything notable except once, when I slid down a bannister with the wood grain facing the wrong way.

This does not give you the same exhilaration as sailing.

The man on the sailboat was waiting for me. I waltzed along the dock and I declared that I would buy his boat. Then, I handed him a check.

“But you haven’t even seen it yet,” he said.

“No, but I’ve seen enough bad boats to know when I’ve seen a mediocre one.”

That man took me on my first voyage. I sort of discovered myself on that Fairhope water. I didn’t think it would be that easy to find yourself, but sometimes it is.

For three months, that kindhearted man gave me lessons. He taught me to raise the main, to trim the jib, and he taught me to sail single handed.

And after my first successful solo sail, he handed me a cigar and said, “I bought these for celebration.”

“No thanks,” I said. “I don’t smoke.”

“You do today.”

In the following years, I would use the boat with my wife, my dog, or some unfortunate friend. And I would demonstrate my newly acquired knowledge by sniffing my nose and saying things like:

“All hands on deck, secure the scuttlebutt on the starboard side! Prepare for portside tack!”

Sometimes a man just needs to get it out of his system.

When I was a boy, my father told me he had always wanted to be a fighter pilot.

“Why didn’t you ever become a pilot?” I once asked him.

“Because,” he said. “Your old man’s eighty-percent deaf in this ear. I walked into that Navy exam room, the doc took one look at my bad ear and said, ‘Sorry, son. You’ll never be a pilot.’”

And that, by God, was that.

My father promised himself he wasn’t going to give up on his dream. He swore that when he turned fifty he would take flying lessons.

For the rest of his life he collected jet calendars, fighter plane posters, and aviation wrist watches. Sometimes, he’d sit in his workshop and stare at a poster of Cessna 172.

“Fifty’s getting closer every day,” he’d say. “Wouldn’t it be fun? You and me, flying to Texas, or Tennessee, or anywhere in the world, then smoking a few cigars to celebrate?”

“You don’t smoke,” I said.

“Well, maybe when I’m fifty I will.”

He never made it past forty-two.

For some reason, that particular memory is burned into my mind. The night of a forty-two-year-olds funeral, I replayed it until I wore out the record.

With my new boat, I participated in sailing races. I raced on weekends against other day sailors. I am not a good seafarer—actually, I’m god-awful—but I am an expert when it comes to fun. I did my undergraduate studies in fun.

But over the years, I found myself getting busier and sailing less. So, I finally sold the boat because it costs money to keep a boat. Especially a crummy one.

A man from Panama City came to look at it along with his nineteen-year-old son. The man announced that he wanted the boat before even stepping aboard.

“Don’t you wanna inspect it first?” I asked.

“Nope. I’ve wanted to learn to sail since I was a little kid. I’m ready to finally do it.”

I gave the man and his son a few lessons. They were naturals.

On the day they sailed home, I was emotional. The man had brought his three boys with him. They took pictures of each other. They laughed. They looked happy.

They were about to shove off when his oldest son started the others singing “Happy Birthday.”

The father blushed, then shook my hand and said, “Forty-two sounds so old, doesn’t it?”

No, it doesn’t. To me it’s an age that will always seem too young.

They hit the open water, and I watched them do figure eights in the water until the sun went down. It was magnificent to see.

I smiled about it then, and I’m smiling about it now.

I hope they found the cigars.


  1. Lita - May 23, 2020 7:34 am

    Hugs. There’s more but, right now, hugs.

  2. Meredith Smith - May 23, 2020 9:01 am

    Sean, your stories have a way of warming my heart when it needs warming the most. ❤️

  3. Don Simms - May 23, 2020 10:24 am

    One of your best. You’re always very good. I learned to fly fish at 42. I became good enough to be a part time guide. My lungs crapped out about 8 years ago, and I miss that gentle art more than anything I’ve ever done. I still tie a few flies for my daughter, because I was lucky enough that she came to love it, also. We learn so much from loss, and when the pain turns to acceptance, a gentle peace happens. Some scars are beautiful. Anyway,,, thanks for what you do. I’m not sure you know how valuable it is. You need a tip jar

  4. Curtis Lee Zeitelhack - May 23, 2020 11:52 am

    Sailing is alluring and exhilarating. I caught the bug back in the 70’s and craved a 42-footer. Alas, my paycheck and the cost of sailing (even a modest 16-footer) had no intersection. But I had some grand times sailing with a friend for a few years. Those times are long gone, but the memories are fresh. Fresher today, after reading your story. Thanks, mate!

  5. Cynthia Harmon - May 23, 2020 12:52 pm

    When I was 9 my dad bought a sailboat the size of yours. I became his 1st mate. We sailed on Lake Ontario from Rochester. He didn’t sail in races. I think it was too stressful and the whole point of the boat was to relax. When I was in high school he bought a 32 ft. and sailed for many years into his 70s. Now my brother has it. He races often. Last June we were all home for our dad’s service and my brother took my kids out but I just couldn’t do it.

  6. Susan A. Royal - May 23, 2020 1:21 pm

    You’ve made me laugh, and now you’ve made me cry. And you’ve reminded me to never give up my dreams.

  7. aucat76 - May 23, 2020 1:24 pm

    I don’t see how your stories can get any better. But they do. ❤️❤️

  8. Berryman Mary M - May 23, 2020 1:52 pm

    Today is my birthday, Sean. And I feel that you wrote this for me. My late brother was a Navy pilot. Thanks from the bottom of my heart. My eyes are leaking.

  9. Steve - May 23, 2020 2:12 pm

    I jumped out of a plane at 54 for the same reason. Always wanted to. My kids pushed me to do it. Never too late.

  10. Ann - May 23, 2020 2:16 pm

    Very deep….⛵️🤗

  11. Billie - May 23, 2020 3:20 pm

    Oh, Sean, my eyes leaked on this one. I’m approaching a birthday…one that’s way past 42. And there’s a couple of things on “the list.” Sailing isn’t one of them…

  12. Charles Mathers - May 23, 2020 3:32 pm

    And the string that wraps you and I together just pulled a little tighter. 2 nd saddest day in my life was the day I donated my sailboat to the GA Lighthouse for the Blind. I laugh out loud at the concept of blind people feeling the wind in their faces! 👍👍

  13. Susie, as well - May 23, 2020 3:39 pm

    Beautiful story! I love the way you always write, so thoughtful and straight from the heart.

  14. Cindy B. Stevens - May 23, 2020 3:40 pm

    Thanks for this.

  15. Ann Everett - May 23, 2020 3:49 pm

    I had to stop and cry before I could finish this. That’s what great storytelling does to me.

  16. Linda Moon - May 23, 2020 4:23 pm

    I smiled just now as I visualized the sailboats. Stubborn AND Fun…..are you related to people I know and love in my family?? (I’m not going to say who). There’s not much “ugly” to be found in Fairhope, so I’m glad you found a seaworthy boat there. Fairhope itself is exhilarating for me. Forty-two is too young. So was thirty-seven. Both of them. So, sail away with some more smiles, Sean. I’ll be smiling with you and my stubborn fun family like I’m doing right now, even with remembrance and reminders of two too-young men we each loved.

  17. Brenda - May 23, 2020 11:08 pm

    Sweet memory!

  18. Steve Winfield [Lifer] - May 24, 2020 6:58 am

    I second the tip jar.

  19. Dawn Bratcher - July 3, 2020 6:57 pm

    Oh, the memories that boat could share! What a lovely story of lost dreams & dreams fulfilled.

  20. Joe Patterson - July 3, 2020 10:00 pm

    Thanks for sharing another beautiful story

  21. Latrelle Grayson. - July 16, 2021 10:42 am

    A pirate told me in Key West that the happiest days are when a man buys a boat and the second day is when he sails it.


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