THE VOYAGE SOUTH:  A SAILOR'S TRIAL BY WIND, STEEL AND MEMORY

Written by Jeff Roth, SV Calypso

A Promise Carried Forward

I never expected my retirement to look like this—at the helm of a 45‑foot catamaran named Calypso, chasing the horizon toward Antigua.  Years ago, my late wife Minnie and I dreamed of this kind of freedom: blue water, empty sky, and the slow rhythm of a long ocean passage.  But life had other plans.  Ovarian cancer took her in 2019, and the dream went quiet for a time.

Several years later, it returned—unexpectedly—through Shannon.

Shannon: The Mate, the Heart, the Quiet Strength

Shannon is six months older than I am, beautiful in that steady, grounded way earned by living fully.  A retired radiology technologist, a former military brat who grew up all over the world, she spent many years in Minnesota and never lost her love of open spaces.

She was athletic from the start—swimming, diving, softball, gymnastics, ballet—and as a teenager she bought her first little sailboat with babysitting money.  She loves dogs, horses, the outdoors, and, lucky for me, keeping me happy.  She has three grown children and one elderly mother still living.  On Calypso, she is usually my first mate, but for this passage we hired a co‑captain, Bernie.  Shannon fully managed the galley, prepared the boat for sea, and backed us up on watches.  None of us would have eaten half as well without her.

The Crew Comes Together

Bernie, our co‑captain, is a retired electrical engineer who once worked on fighter jets.  Later he became a business professor.  His wife died of breast cancer a year ago, and the grief still lived close to the surface.  A swimmer and a sharp technical mind, he was immensely capable - though sometimes an absent‑minded professor type.  We had some friction over weather and our departure timing, but his commitment never wavered.  He was determined to help us finish this voyage.

Jeremy was the third member of our watch‑standing trio: soft‑spoken, perceptive, and deeply thoughtful.  He wasn’t Bahamian, but we met in the Bahamas years earlier, where he once saved our dog Lylah after she went overboard.  When things became stressful, Jeremy grew even quieter—not out of fear, but focus.  He noticed what others missed.  He solved problems before they grew.  Though he later admitted he had been terrified at moments - his knees literally shaking - he never let fear show.  He stood every watch with quiet bravery.  Shannon and I plan to attend his wedding next year.

The Rotation

The three of us - Bernie, Jeremy, and I - rotated watches: four hours at night, three during the day.  It was a rhythm that demanded trust, humility, and teamwork.  And, thankfully, we worked well together.

Departure from Hampton

Shannon was worried about the weather before we left Hampton.  A cold front was approaching fast.  Bernie had been pressing to depart earlier - some boats did - and they ended up hitting the same heavy weather we later met.  We took the middle ground, leaving November 4th.

The Gulf Stream was kind to us—calm, organized, deceptively gentle.  But beyond it, the Atlantic turned hostile.

The Atlantic Turns Hostile

For days the wind built and the seas grew.  Walking became difficult; leaving the berth required planning.  Ceiling panels that had never so much as rattled fell from their mountings.  Everyone except Shannon grew queasy.

We double‑reefed the main and jib and kept pushing southeast.  At one point I saw us hit 18 knots surfing a wave - too fast for comfort, but the right direction for survival.

Then the wave hit.

A Breaking Sea and a Shattered Window

A breaking crest slammed into our starboard forward portlight with a sound like a gunshot.  The acrylic shattered inward.  Water poured into the owner’s head.  The shower sump pump roared to life.

At the very same moment, something shorted in our 230‑volt system.  Smoke drifted from behind the breaker panel.  

We had one priority: keep the starboard side out of the waves.  I gybed to put the seas on our port quarter.  The loads were massive.  Our boom brake - installed at the recommendation of an experienced rigger - was supposed to soften accidental gybes.  Instead, it failed catastrophically.  The force of two heavy gybes ripped the brake from the boom and severely compromised the spar.

I didn’t realize it was broken at first.

Night Watches in Wild Seas

Shortly after, I relieved Bernie from his watch and stood my 1 a.m. to 5 a.m. shift.  We were being pushed too far north, but there was nothing to do but ride it out.

When Jeremy came on deck, he immediately spotted the problem: the boom was cracked more than 60% through.  A squall had shifted the wind and forced a minor gybe - just enough for the weakened boom to give way.

We lowered the mainsail in the largest wave I have ever climbed under power.  Jeremy later admitted his knees had been shaking uncontrollably.  Mine probably were too.

The Decision to Divert

With the boom broken and a window shattered, Bermuda was the closest lifeline.  Even turning the boat into the wind to drop sail had been harrowing; offshore repairs were impossible.  We stabilized the boom with wood braces, halyards, and an act of shared willpower.  Gorilla tape sealed the broken portlight.  The seas eventually eased.  We motored toward Bermuda.

Repairing Calypso in Bermuda

We arrived on November 9th.  A new boom would cost $27,000 and take a month.  No spare could be found.  Welders were hesitant—until one finally agreed.

T.S. Simpon’s yard med‑moored us in a chaotic ballet of lines, hands, and shouted instructions.  Their electrician traced our electrical short to a washer‑dryer junction box that had taken on seawater when the window blew.  We sourced sheet plastic to replace the window and sealed everything with silicone.  The welders spent Veterans Day week plating, reinforcing, and bringing the boom back to life.  Mass Steel helped us reinstall it.  By Thursday the 14th, we were anchored, the mainsail bent back on, and Calypso was ready.  We left that evening—exhausted but restored.

The Final Days to Antigua

The second half of the passage felt merciful by comparison: some motoring, some good sailing, big following seas but nothing like the earlier gale.  We fished - mahi and bigeye tuna - and Shannon kept us fed with the love and precision only she brings.  Lylah, our little mascot, kept morale up.

In Falmouth Harbour, Antigua, we shared Thanksgiving dinner with forty other Salty Dawgs.  We were bruised, tired, proud, and deeply grateful.

A Promise Kept

This voyage was more than a crossing.  It was an inheritance - a continuation of a dream that began with Minnie, carried forward with Shannon, and made real by the courage of everyone aboard.  Now, after thousands of miles, broken gear, sleepless nights, and moments of fear and wonder, we are finally here - ready to explore the Caribbean for years to come.

Calypso brought us home.