Taylor Grieger and Stephen O’Shea faced pirates, navigated the 
Furious Fifties and came to blows during a life-changing voyage from Florida around Cape Horn

Taylor Grieger and Stephen O’Shea share with YM’s deputy editor Katy Stickland the highs and lows of their sometimes tumultuous voyage to Cape Horn.

‘We were in Roatán, Honduras heading back to Ole Lady when a comment from Taylor about my mishandling of 
a line resulted in us punching each other in the face.

‘He knocked me onto my back, and I knocked Taylor off the dinghy. He didn’t stop, though. He got me in a chokehold from the water, pulling me down from below.

‘We both thought the trip was over then, that we were going to pack it in and return home. However, we came back together 
in the cockpit that same night. We cried a little, laughed a lot, drank even more whiskey, and finally, made a pact to not punch each other in the face again, no matter how drunk or angry we got.’

Solace in a sailing mission to Cape Horn

Sometimes voyages can test any close friendship 
but add post-traumatic stress disorder (PTSD) 
into the mix and it is easy to see why emotions sometimes ran high for Taylor Grieger, the skipper 
of the leaking 1983 Watkins 36CC, Ole Lady, and 
his crew Stephen O’Shea, 29.

The pair spent 15 months sailing the 36ft sloop rigged yacht from Pensacola, Florida, through the Panama Canal and down the South American coast 
to Cape Horn.

For Grieger, a 28-year-old retired US Navy rescue swimmer living with PTSD, the voyage was not only a personal odyssey to face his demons but to raise awareness of the difficulties veterans face moving from the military to civilian life; a battle many of them lose including four of Grieger’s friends.

‘When I got out of the military I was just this angry, mean and confused person who had ruined every relationship I had ever had and had come too close 
to taking my own life. The last thing I had to hold on to was this sailing trip: sailing and this old boat with too many holes were the only things I had,’ explained Grieger, who had always harboured dreams of sailing around the world.

A skipper helming a Watkins 36CC on the ocean

Ole Lady made it across the Gulf of Mexico to Puerto Juarez just before Hurricane Nate passed off the Mexican coast. Credit: Taylor Grieger & Stephen O’Shea

He said sailing to Cape Horn seemed to be the 
‘biggest, baddest thing in this world’ that he could 
do to highlight the ‘epidemic’ of veteran suicides, 
and to prove to himself and others that you can ‘conquer something that many people believe is unconquerable’.

The result is the documentary film, Hell or High Seas, which follows the voyage of Ole Lady and Grieger’s mistakes and struggles to shift from the pace of military to civilian life.

O’Shea, a writer and high school friend, came onboard with the project early, having reconnected with Grieger while writing a collection of short stories based upon interviews with American soldiers who had fought in Iraq and Afghanistan.

Whilst studying for his creative writing doctorate at Glasgow’s University of Strathclyde in Scotland, O’Shea acted as a sounding board for Grieger during the six months it took them to find the ideal boat.

Repairs on a budget

The ‘used and abused’ Ole Lady was discovered in a boatyard in Tampa, Florida.

‘There were cracks in 
the deck, she had old sails and a rusty engine, but 
she had a super heavy keel, a protected cockpit [and doghouse] which was high off the water, and she was really beamy, which meant she took broadside waves like a champ,’ recalled Grieger.

Having paid the $20,000 (£16,302) asking price, he plotted a rhumb line straight across the Gulf of Mexico to Pensacola and sailed straight into a forecast 30 knots to test the boat’s Cape Horn credentials.

‘It was one of the stupidest decisions I’ve ever made. I broke absolutely everything on the boat, when the first squall line hit,’ he said.

A Watkins 36CC crossing the equator

Ole Lady is a Watkins 36CC. Her protective doghouse was invaluable while sailing in the rougher seas off Chile. Credit: Taylor Grieger & Stephen O’Shea

Having limped into Pensacola, Grieger began refurbishing the yacht and ended up spending a further $50,000 (£40,756) on parts.

He had saved for the voyage while stationed out in Guam, fishing the Marianas Trench on his days off for mahi-mahi and yellow-fin tuna and selling the fish to local restaurants.

With these funds now depleting fast, Grieger learned how to make repairs via YouTube videos.

He worked on the boat at night for the next six months, having spent the day sailing charter 
boats to keep himself financially afloat.

Grieger admitted his naivety and lack of experience meant he spent more money than necessary on the ‘best’ parts.

‘What I didn’t know was, sailing in heavy weather, it was all going to break anyway. There is no amount of preparation that will make your boat bulletproof; the only thing that keeps you alive is your sail configuration and patience in those storms. The moral of the story is to make sure the boat’s sturdy and set sail with spares; don’t waste time and money on the best gear, top-of-the line rigging and lines because it doesn’t matter what you have – the sea will break it eventually,’ he said.

Taylor Grieger checks the sails on his Watkins 36CC, Ole Lady in the south Pacific

Taylor, who learnt to sail while in the US Navy, refurbished much of Ole Lady himself, learning via You Tube videos. Credit: Taylor Grieger & Stephen O’Shea

By this time O’Shea had joined him and together they continued the restoration before finally setting sail from Pensacola on 25 September 2017; Grieger still coming to terms 
with civilian life and O’Shea grappling with the unfamiliar, having only sailed twice, both times off the coast of Scotland.

Dwindling funds and the fear of never leaving 
were their justifications for setting sail in the 
middle of hurricane season.

Unsurprisingly it was a steep learning curve, with many incidents testing their seamanship and their courage.

When Ole Lady’s engine seized while rounding the border between Honduras and Nicaragua in the middle of a tropical storm, the pair decided to sail for Panama: a decision that resulted 
in them sailing straight into the Doldrums.

‘We barely moved for an entire week,’ recalled O’Shea.

They began rationing food and water and prayed for ‘a whisper of wind’ to carry them across the Caribbean Sea to Panama.

Eventually a series of squalls came to their rescue and they made it to Colón, with only a few litres of drinking water left onboard.

Pirates and high seas

As is almost always the case when cruising, weather shaped the narrative of the pair’s adventure.

Ole Lady had been ‘stalked’ off the Colombian coast in the day by suspicious looking boats, mainly fishing skiffs ‘with no trace of fishing gear onboard’.

Grieger and O’Shea used to regularly go below deck to change clothes and hats in order to convince the suspected pirates that there were more than two men onboard.

But a nighttime boarding was the biggest concern.

Off Buenaventura this almost became a reality when the yacht was actively pursued, even though the 
crew used precautions such as no lights on deck and no engine.

Despite tacking several times they were unable to outrun the boat and its powerful outboard.

An evening squall allowed them to escape the ‘pirates’, providing them with enough cover to 
hide and avoid detection.

A large wave while cruising in the Roaring Forties

The Roaring Forties experience strong, often gale-force, winds throughout the year. Credit: Taylor Grieger & Stephen O’Shea

By the time Grieger and O’Shea reached Ecuador they realised a third crew member was needed.

Ole Lady wasn’t fitted with self-steering, and constantly helming while sailing into headwinds and the Humboldt Current was taking its toll on the pair.

At all costs they wanted to avoid Peru.

Now broke, they were unable to afford the $2,500 fees to clear into the country so it was necessary to sail direct from Salinas in Ecuador to Valparaíso, Chile.

Continues below…

It was at this point that another veteran, John Rose, joined them.

Like Grieger, Rose was a former US Navy rescue swimmer who was also living with depression and struggling to find his place on Civvy Street.

Their passage to Chile was to test all of them.

It took 3,700 miles, most of it without an engine 
after their transmission broke off Isla de la Planta 
in Ecuador, although they were still able to charge 
the batteries.

A yacht anchored in Patagonia

It is best to sail and anchor in daylight while cruising Patagonia due to unreliable charting and narrow channels. Credit: Taylor Grieger & Stephen O’Shea

‘A lot of those days, after we got far enough south, were windy, choppy and we were fighting headwinds the entire time. Our boat took a beating. We took a beating,’ recalled O’Shea.

With little money to provision properly in Ecuador, rationing was introduced early on.

By this time, Ole Lady’s hull had cracked, so the bilges needed pumping every four hours.

Ironically, this saved the yacht when an engine fire broke out, 600 miles offshore.

A snapped furling line was the last of the breakages before Ole Lady arrived in Valparaíso.

The inevitable repairs followed and the crew pushed on to Valdivia, where Ole Lady overwintered at Club de Yates before the final push to Cape Horn.

Cape of hope

They spent December 2018 navigating the coastline 
of Chile and Patagonia before entering the Strait 
of Magellan, the natural channel which separates South America from Tierra Del Fuego.

Initially, they planned to sail to the Beagle Channel via the open ocean, but 53-knot winds and several knockdowns in 72ft (22m) waves, which shattered the yacht’s rolling furler on the forestay, meant they had to abandon the route and instead sail south through the channels of the Strait of Magellen.

Once in Puerto Williams, it was just a four-day 
sail to round Cape Horn.

Passing the oceanic equivalent of Everest for climbers left Grieger 
crying ‘like a baby’.

Two sailors inside the shelter of the cockpit of a Watkins 36CC

The Strait of Magellan provided a sheltered route to the Beagle Channel after storms prevented an open ocean approach. Credit: Taylor Grieger & Stephen O’Shea

‘It was a pretty big day for all of us and represented the coming together of a lot of years and low moments. I don’t think I’ll ever be able to put that feeling into words,’ he said.

For O’Shea seeing Cape Horn was an ‘almost mystical experience. It was real, it was within reach, and it was menacing,’ he recalled.

With Cape Horn conquered, does Grieger wish he had done anything differently?

‘Other than saving more cash, having an aluminum boat and more experience working on boats in the beginning, I can’t say I’d do much differently. There were a lot of things I messed up and learned the hard way; all of those experiences I cherish now. I know exactly what a boat can take, what you truly need 
and what you don’t need, and how to sail in big seas and stay alive.’

Grieger is now working towards offering sailing expeditions to others living with PTSD, believing that ‘maybe sailing can save their lives as well’.

Their first voyage is planned soon.

About the crew

Taylor Grieger & Stephen O'Shea

Credit: Taylor Grieger & Stephen O’Shea

Taylor Grieger, 28 (left), and Stephen O’Shea, 29, met while on the swim team at A&M Consolidated High School in College Station, Texas.

After graduating the pair went in very different directions and lost touch for six years.

Taylor joined the US Navy as a rescue swimmer. 
He learnt to sail in 2011-12 while stationed in San Diego.

Stephen (www.stephenjoshea.com) went into academia, completing a PhD in Creative Writing from the University of Strathclyde in Glasgow.

They reconnected in Guam, where Taylor had been stationed. Stephen had also just finished From the Land of Genesis, a collection of short stories based on interviews with American soldiers who had fought in Iraq and Afghanistan, which was published in October 2020.

Taylor currently works with Sailing Angels, a non-profit charitable organisation which offers sailing trips for veterans.

He also runs Cape Horn Tequila to raise funds for the American Odysseus Sailing Foundation, which provides sailing expeditions for veterans and first responders living with PTSD (www.amodsailing.org)

The first draft of their documentary about their Cape Horn voyage, Hell or High Seas (www.hellorhighseas.com) has now been finished and a distributor is being sought.

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