For 10 hours, Jack O’Rourke of Buffalo, Wyoming, had fought through 40-foot swells. He had sailed out on a new 45-foot sailboat from Puget Sound to San Francisco Bay and was busy the entire trip.
Every shift in the sea demanded his full attention, sail adjustments and precise helm control. The goal was to take the swells at an angle, climbing each crest without stalling and descending without burying the bow.
Nothing in his youth had prepared him for a life at sea.
O’Rourke had grown up camping in the Cloud Peak Wilderness area. His dad was a forest ranger, and the family of five lived on the edge of the forest in Buffalo, Wyoming. The closest he had gotten to being on the open water was a canoe trip in Minnesota.
“I didn't do any boating at all,” O’Rourke said. “We did a lot of fly fishing in the mountain lakes. My brother and I would backpack into the Bighorn Mountains. That was our backyard.”
With his brother, Jim, he would just walk out their back door and be gone for days, enjoying Wyoming’s nature. It was only after getting an engineering degree that Jack ended up getting a job on the coast and fell in love with the ocean.
“It seems so incongruous,” O’Rourke said. “People ask how a boy from Wyoming ended up in the Virgin Islands.”
He said that it was the water that attracted him.
Discovering A Sailor’s Life
Fresh out of college, O'Rourke worked on a test site in the Marshall Islands where they launched missiles. In his spare time, he learned to sail and enjoyed the time on the water.
His next job was at McDonnell Douglas in California. However, after six years, he realized he didn't want to be an engineer all his life. It seemed only logical to start a sailboat dealership in San Francisco Bay.
For nine years, he struggled to make a living while living and breathing sailboats in Northern California.
“It was really just a business on a lark,” O’Rourke said. “I was 28 and just fell into it.”
It was a tough business and not viable since the profit margins were so low. He worked seven days a week and loved what he was doing, even though he was not making any money.
“A lot of people get into it for the fun of it,” he said. “And they go broke.”
The Thrill Of The Sail
Since he was living on the ocean, he was able to start racing. Despite the low paycheck and long days, O’Rourke found himself developing a passion for sailing and improving his skills. He even equipped his fleet of inventory boats to be to competitors on the bay.
O’Rourke believes his engineering background is what attracted him to sailing in the first place. He loved fine tuning his skills and thought it was fun to find the most efficient way to sail.
“There's a lot to it,” he said. “Trimming sails and tactics. I didn't get too enamored with it, though, until I got into the business and then started dabbling with racing.”
O’Rourke was hooked and enjoyed how busy sailing kept him. He would take visitors out on the water and allow them to steer, sharing his love of the sport. He was also able to join day sails and enjoyed pitting himself against professional competitors.
Jack and Mary O’Rourke sailing together on one of their many charters in the Virgin Islands and after more than 50 years of marriage, living for three years while working in the south pacific as an Engineer, one charter in the South Pacific and nine years in the yacht business in San Francisco Bay. (Courtesy Jack O'Rourke) 
Jack O’Rourke is preparing to raise the mainsail on a 43-foot sailing yacht. (Courtesy Jack O'Rourke) 
Living for a week on a sailboat in the Virgin Islands. (Courtesy Jack O'Rourke) 
Jack and Mary O'Rourke having dinner ashore at the Bitter End Yacht Club in Virgin Gorda in the BVI. The large resort was destroyed in 2017 by Hurricane Irma. (Courtesy Jack O'Rourke) 
Sailing with friends in the Virgin Islands. (Courtesy Jack O'Rourke) 
Rail down in a stiff breeze in the Virgin Islands. (Courtesy Jack O'Rourke) 
Jack O'Rourke and a longtime friend who bought a big boat from me when Jack was in the sailboat business in San Francisco Bay, sailing a nice new dual-steering 43 ft Beneteau Yacht. (Courtesy Jack O'Rourke) 
Jack O'Rourke standing looking for an obscure channel marker on the way to Anegada, a remote low lying British Virgin Island (BVI), not visible when departing the North Sound of Virgin Gorda, and initially off limits to inexperienced Charters due to navigation issues and a shallow channel. (Courtesy Jack O'Rourke) 
Bareboat chartering for a week in the Virgin Islands. (Courtesy Jack O'Rourke)
Sailing Into Love With The Virgin Islands
When he finally gave up his sailboat business and moved to North Carolina with his wife, neither of them were willing to completely give up on their love of the ocean.
“My fix was to go down to the Virgin Islands and charter a boat with either another couple or our two boys,” he said. “We had seven just perfect one-week vacations down there sailing around.”
They would sail from anchorage to anchorage each day. During the week on the ocean, they would settle into a routine of getting up in the morning, eating, and then raise the sails so they could sail into in the next harbor and drop an anchor. They would then either go ashore and eat in the restaurant or cook on the boat.
“One of the nice things about the Virgin Islands is there's a lot of good anchorages where you can get out of the weather and have fairly comfortable anchorages,” O’Rourke said. “It's real easy navigation, and it's really protected water.”
After experiencing the brutal weather on the east and west coasts of America, O’Rourke found the sailing easy and relaxing.
He said that being in the islands is all about being on the water. Visitors are either boating, fishing or enjoying the sun and the sand on what he said are some of the nicest beaches in the world.
The Villa
In recent years, O’Rourke has exchanged his time in a sailboat for an ocean front villa.
On one of their sailing trips to the Virgin Islands, he was fortunate enough to discover land for sale on St. Johns which, until then, was virtually unheard of.
Lawrence Rockefeller had bought about two thirds of the island and donated it to the national park except for one peninsula called Lapointe. The heirs decided to split the peninsula up and sell the lots. O’Rourke was the first one to take advantage of the opportunity and begin building his dream home on Ditleff Point.
After growing up in the wide-open spaces of Wyoming, O’Rourke values his space and made sure that he would have that on the island.
“I bought land on both sides of me,” he said. “We'll have the privacy forever.”
O'Rourke designed his house and was very involved in the building. It took two years to complete and is one of the highest ranked rated houses on Saint John. He now spends two months a year at the house, enjoying the ocean views and beach. The rest of the time, it is rented out so others can enjoy the island life.
No Blizzards, Hurricanes Instead
O’Rourke said that the warm weather year-round is one of his personal favorite things about being on the Virgin Islands. The temperatures usually stay in the 1980s so air conditioning is rarely needed and heaters are unheard of.
“It doesn't get as hot as Wyoming,” he said. “We also don't have to worry about freezing pipes. It's really a year-round destination. Of course, Wyoming can be year-round as well if you're into the snow.”
Yet, there is one danger on the islands that is not faced in Wyoming. Hurricanes.
In 2017, Irma and Maria hit St. John hard. The house built by the engineer withstood the 200-mile gusts but much of the islands were devastated. The hurricanes were just 11 days apart and blew the airport away.
“It was a real mess,” O’Rourke said. “But because of the way our house was built and I had the big diesel engine, we had an oasis with refrigeration and water.”
O’Rourke was still stateside when he got a call from Kenny Chesney. The country star was living on the island and wanted to use the home as his headquarters.
“I ended up just donating the house to the Kenny Chesney Foundation,” O’Rourke said. “They had raised millions for the island and needed a place to store all the supplies.”
With hurricanes continuing to be a threat in the area, O'Rourke said that they are still taking steps to protect the home against future hurricanes. There is always something to do as he battles different elements than what he encountered in his years growing up in Wyoming.
“It is a brutal environment in the Virgin Islands because the hurricanes and earthquakes,” he said. “The salt air is just brutal, and termites get into everything. You have to really keep an eye on stuff.”
As O’Rourke makes his plans for his vacation this year, he will be returning to his home state. He has always wanted to go flyfishing in the Wind River Canyon in Thermopolis. He just booked his stay and is ready to get on the water.
Jackie Dorothy can be reached at jackie@cowboystatedaily.com.
