Tall 3-masted ship at sunset anchored with decorative flags

Taking the Helm of a Tall Ship: One Magical Night

UPDATED: August 12, 2021

And all I ask is a tall ship, and a star to sail her by. – John Masefield, Sea Fever

Minutes slipped away as midnight approached. Like Cinderella, it seemed I would soon turn into a pumpkin.


The place was St. Kitts, a whale-shaped islet in the Leeward Islands. Our ship, the Polynesia, was docked in the harbor town of Basseterre.


For years, I had dreamed of taking a trip aboard a Windjammer. Unlike the mega-ships that dominate today’s cruise industry, this company boasted a collection of historic vessels catering to more laid-back, barefoot vacationers. I was one of them.

EDITED Mandaly at St Kitts BETTER
The Windjammer ship Mandalay in St. Kitts harbor, as seen from the Polynesia

In Jimmy Buffett’s ballad “A Pirate Looks at 40,” the wistful buccaneer-wannabe laments that he was born 200 years too late. Like him, I’ve sometimes wished I lived in an earlier era, the age of steam trains and sailing ships.

Trying to reason with hurricane season, I had come to the Caribbean to celebrate my 30th birthday, hoping for decent weather, a bit of rest, and the chance to turn back time by sailing aboard a tall ship. To my delight, the captain posted a sign-up sheet for would-be helmsmen, meaning I could actually pilot the ship!  I grabbed the midnight slot on September 21st to be at the wheel sailing into my thirtieth year. It seemed an ideal setting to capture some nostalgia as a new decade dawned.

Alas, it appeared my dream would die in port that night. Filling the ship’s fresh water tanks was taking longer than expected. At least there was a steel-drum band plonking away on deck. As the music wrapped up, I dejectedly glanced at my watch as the hands mockingly signaled midnight. Hooray, I was thirty years old. Boo-hoo, I was going nowhere.

Canceled plans are hard for me. Though I’m more patient now, having to miss something I’ve anticipated still stings. I also struggle with brooding, replaying an event in my mind and stewing over how I wished it had turned out. Would this birthday be another one of those times spent moping over a missed opportunity?

Tall sailing ship Polynesia rests at anchor

The captain, strolling toward the ship’s stern, noticed my crestfallen face. I mentioned I was scheduled for the midnight turn at the helm, which wasn’t happening. He smiled and asked, “How would you like to take us out?”

Would I ever! I thought this maneuver might be too complicated for a passenger, but he reassured me I could handle it. I leapt to take my place beside him, grasping the spoked wooden wheel, and, like Thurber’s Walter Mitty, morphed into a sailor of old.

We slipped away from the dock and motored out of the harbor when the magic began – it was time to set the sails. The Polynesia was a 248-foot schooner fitted with four massive wooden masts. She carried gaff-rigged sails, an unusually heavy arrangement requiring a team of six hauling on each line to raise them. To the piping of “Amazing Grace,” passengers and crew heaved on the thick ropes as the sails soared skyward, transforming us from a mere motor vessel to a true sailing ship.

There’s a reason a ship is called a she. As the wind swelled the sails, you could sense her coming to life. While the deck planks creaked and the big masts bowed, the canvas ruffled and popped like giant lungs inhaling the warm trade winds. 

I spun the wheel to the right, settling us on a northwest course for the pinnacle-shaped island of Saba. The sea spray whispered as the sails fluttered. The winking stars above were silent.

“Steady as she goes,” said the captain.

“Aye aye, sir,” I replied, feeling at peace to be contentedly moving forward.

EDITED Sunrise rainbow over Saba Sept 22 1994

Nearly three decades have passed. I’m now approaching 60. Recently, I saw an article about the sad demise of the Windjammer Company and breakup of its fleet. Like that evening in St. Kitts before taking the helm, I could waste time and energy pining away about the fate of the once-proud Polynesia. I’ve changed though.


Instead of feeling bitter, I will be grateful for one magical night, when I turned 30 and took my place at the helm of a graceful tall ship.


Do you have any memories of the Windjammer fleet or something similar? Please share your comments and like this article if you enjoyed it.

passport stamp to St Maarten

5 thoughts on “Taking the Helm of a Tall Ship: One Magical Night

  1. I visited St. Kitts in 1983, during a Windjammer cruise on the Polynesia. We left from St. Maarten and also went to Saba and St. Barts (twice). So much fun! I wish I could do it again. Headed for St. Kitts again in a few weeks, this time on a big cruise ship. It won’t be the same, but I’m still looking forward to it.

    Liked by 1 person

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