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.

FAIRHOPE—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 a 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. Meredith Smith - May 8, 2019 7:06 am

    Bestill my heart Sean.

  2. Leslie in NC - May 8, 2019 9:44 am

    This story made me smile and even though I never learned to sail, being out on the water, especially the Gulf, in anything that floats makes me happy.

  3. Cathi Russell - May 8, 2019 10:12 am

    Oh Sean, thank you for making someone else’s dream come true. And with cigars….and in Fairhope…life doesn’t get much better. That just puts a button on my day!

  4. Karen - May 8, 2019 10:44 am

    God Bless you, Sean. You amaze me every day. Thank you.

  5. GaryD - May 8, 2019 11:06 am

    Ever since I read the adventures of the Kon-Tiki I had wanted to get a boat and sail . When I married and was finally able to afford one……my wife didn’t want one . So I never had that dream come true. But I still enjoy reading and hearing about others whose dreams did come true . Thanks, Sean . You made my day .

  6. Carol Heidbreder - May 8, 2019 11:18 am

    Oh my goodness! Well, I’m from Fairhope and even turned my own little boat over in a quick little squall in the Bay. Was not far off shore in front of the yatch club and was quickly rescued by power boaters much to my embarrassment. I had panicked and tried to defy some physics law and over she went. Squall past and I was right back out there having a blast. Miss it now but know this old lady needs to find more sensible ways to enjoy life. But, like you, sailing is off my bucket list and I’m glad i did it. And Fairhope? And Eastern Shore of Mobile Bay? Pretty close to heaven. What a place to grow up in! Thanks for touching my heart today! But then, you always do!

  7. Joe Patterson - May 8, 2019 12:50 pm

    Thanks again

  8. Shelton A. - May 8, 2019 1:26 pm

    Dreams are always best when you get to live them. Here’s to would-be sailors everywhere. Thanks, Sean.

  9. Sandi Gorin - May 8, 2019 1:39 pm

    This brought tears to my eyes. My late husband was a sailor; he bought a Thistle from his uncle. It needed so much work which never got finished and we hauled it through three states when his job caused us to move. I was in one regatta with him; I don’t swim! I had so many life jackets on one wouldn’t know I was a female. But when I had to “hang out” the side to help turn the boat, I bravely did. We didn’t come close to winning but I nursed a good sunburn and had a ball. The boat finally was destroyed in a Texas storm and the sailing days were over. But, oh the memories.

  10. Summer - May 8, 2019 1:41 pm

    Beautiful. Either your writing is getting better and better or my heart is getting softer and softer.

  11. Connie Havard Ryland - May 8, 2019 2:10 pm

    I’ve been sailing a few times, from Fairhope. I loved it but I love anything to do with being on the water so I’m a little biased. Thank you for the sweet story. Love and hugs.

  12. Bobbie - May 8, 2019 2:13 pm

    Ditto, the previous comment! After three posts, I’m hooked! Your writing is unique. No need for so many adjectives and exclamations. Your words in such simple terms paint a picture. I can see it as I read. Thank you, Sean, and thanks to my friend who sent me your link.

  13. Dick McNider - May 8, 2019 2:15 pm

    Sean there are more armchair sailors than real sailors glad you made yours real. But I think armchair sailors may have it right. The real beauty of armchair voyages is the freedom to sail anywhere. I have had my 27 ft sail boat for over thirty years almost as long as I’ve had my wife. We grew up going water skiing on quiet water sound at Pensacola beach but I never sailed till I was grown. My father and I took my sailboat down the Tenn Tom before he died. Remember he said you can see where you are going for next thirty minutes. But even a longtime power boat man could appreciate that it is not bad.

  14. TimRiley Circuit Judge Presiding, Marshall Co AL - May 8, 2019 3:33 pm

    Wonderful story. We are all sailing on water or land to a distant shore. We should learn to slow down with family and enjoy the trip. TimRiley Circuit Judge former submarine sailor.

  15. Chasity Davis Ritter - May 8, 2019 4:00 pm

    Dang old allergies!! You got me again Sean. You do everyday. The daily flushing of my eyes. I don’t know if you ever read the book “Th Hitchhikers Guide to the Galaxy” during all your wonderings. But it says “the ultimate answer to life, the meaning of everything is 42”. To a nerd like me that saying sticks around. Maybe this is why. Pick a copy sometime for a giggle to read when you’re sitting around a hotel room. Bet you could knock it our pretty quickly. It kinda makes sense to me now. For you at least it is the answer. There are lots of numbers that hit me for different reasons. The movie The number 23 with Jim Carrie freaked me out a little. It was making sense lol. My daughters birthday is the 23rd. Later the boy she fell for’s football number was 23. Other things. But my dads number was 68. That’s as far as he made it. 8 months yesterday. He passed on 9-7-18. 7 was always supposed to be a lucky number. In a way i guess it is. He’s journey and pain ended and he made it home to heaven on the 7th. Still hurts. 13 is supposed to be an unlucky number but it was his favorite number. At least I know that about him. Anyway thanks for sharing some more beautiful memories. You got me with that 42 though… read the book and don’t forget your towel!

  16. Sheryll Ridgway - May 8, 2019 4:44 pm

    This was so timely, cuz my 40 year old son just bought a 17ft sailboat with 3 friends. He won’t be sailing any seas in land-locked Colorado, but I’m sure they’ll still have great adventures with it.

  17. Jack Darnell - May 8, 2019 5:44 pm

    You done done it again. I was ‘forever’ gonna be a sailor. One day at Standing Indian Camp ground I announcedd to my wife, we were going to sell everything and buy a sail boat and sail around the world. For the first time in our marriage she said NO we are not, but we are gonna hike the Appalachian Trail. So naturally I hiked instead of sailing. Is it too late???
    Enjoyed MY dream with you. but I still need lessons! Sherry will be along in a few minutes and tell me I enjoyed the hike much better than sailing.
    Sherry & jack

  18. Robert Chiles - May 8, 2019 6:05 pm

    What? No artwork? I thought there would be a cigar.

  19. Edna B. - May 8, 2019 6:13 pm

    I love this story! You’re never too old to give a dream a try. I’m so glad you got to get your boat and go sailing. You have a wonderful day Sean, hugs, Edna B.

  20. Bill T - May 8, 2019 7:39 pm

    I’ve been a boater all my life, having been born and raised by the Chattahoochee. Always had a boat of some sort except for the times I was stationed overseas. After moving to toe the Panhandle my son that lived in Atlanta bought a 30′ sailboat and kept it here for me to maintain. I learned to sail it a bit by myself, not realizing how stupid that was, especially for a 50+ year old. He sold the boat and I had caught the sailing bug. “It’s not the destination but the journey” is the sailing creed. So I bought a 25′ and sailed it all over Choctowatchee bay, mostly alone, until old age and infirmities got me. Joined a Trailer Sailor group and totally enjoyed 3-4 day voyages out of Pensacola with sometimes as many as 50 sailboats.
    Sailing is one thing that can take your mind off your troubles, usually because you don’t have time to think about anything but sailing. Miss it greatly.
    Thanks for the memory.

  21. Steve Scott - May 8, 2019 7:39 pm

    I grew up in Fairhope (Class of 1961). Never got to sail much though. Some rich friends belonged to the yacht club but I was seldom invited. But the water did something to me I guess since I spent 28 yearsin the Navy. Did eventually get my B-1 certificate with the Annapolis Naval Sailing Club

  22. Mickey - May 8, 2019 10:43 pm

    When you ever decide to come up to Michigan to jabber from a stage we will get you out on the beautiful Lake Michigan.

  23. Charaleen Wright - May 9, 2019 5:42 am

  24. Estelle - May 9, 2019 6:23 am

    We once owned a boat. I quickly discovered that a boat is a hole in the water in which you POUR money. But we had a good time while we had it.

  25. Kay Keel - May 10, 2019 1:11 am

    There’s just something about a boat…sail or motor, one engine or two! Our family has had more fun on the many we’ve owned over the years than you’d ever think possible!

  26. Debbie - June 7, 2019 7:00 am


  27. Patricia - June 7, 2019 7:07 am

    I always had a dream to sail. I grew up on the shores of Lake Erie in Vermilion. When I was in my early 40s I bought my friend’s 15″ ODay. It was the kind of boat you would see on the Cape. Very durable and practically unfllppable. I took some lessons on my own and let the wind teach me. My partner in crime was my 12 year old son and sometimes if the wind was calm my husband. I was only able to sail a few years. I was diagnosed with breast cancer and that effected the use of my left arm. You know what they say about one armed sailors? Thank you for bringing back some wonderful and sweet memories. I am waiting for your book to come out.⛵

  28. Linda Black-Jones - June 8, 2019 5:54 pm

    My dad’s 89. He spent his youth sailing around Cape Cod, but never alone. His dad died when he was 15, so he earned the money for his 1st boat, WILDFIRE. He said a friend had to come & they’d take turns, “One to sail & one to bail!” He bought a J24, BLACK EAGLE many years later and taught my children to sail it. Now my 2 oldest grandchildren take sailing lessons at 7 & 5. They love it. Must be genetic!
    Thanks for making this Cape Cod girl smile every morning!
    Wishing you fair winds & following seas⚓️

  29. Lisa Lethcoe - October 22, 2019 9:53 pm

    Sean, that was a great story that brought tears to my eyes. I sail out of the Fort Walton Yacht Club and love it. I have a little Snipe that needs work, but crew on a Frers 33. Thanks so much for sharing!


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