In 1983 Connie Oak was living and working for a large insurance company in Toronto, Canada. She had been divorced for a couple years, and life was moving slowly. Connie lived in a dumpy rental house with her sister Carol and brother-in-law Bob. Even with a swimming pool liner on the roof, when it rained, water dripped from the ceiling would fill a five-gallon pail.
But Carol and Bob didn’t care, they were putting all their money into their plans for the future. Bob and Carol had bought a steel hulled sailboat and were finishing off the inside. For two years, they worked on the boat in the backyard, outfitting it with bunks, building cupboards and installing the woodwork and a bathroom. The two were planning on leaving everything behind in Canada and sailing around the Atlantic for some months.
In 1985, they finally launched the boat in Lake Ontario, and traveled down the Hudson river to the Atlantic ocean. In September, Connie received a letter from Carol and Bob from Europe inviting her to come travel with them. With nothing much holding her back, Connie gave notice at work, packed some of her stuff and put the rest in storage. By December, she had left the cold world of Canada for the warm waters of the Canary Islands.
Connie first met Will Flynt in the harbor of Arrecife. Will was sailing around the islands with his brother and father. They had commissioned their sailboat to be built in London – it was cheaper at the time – and were now sailing it back to their home in Maine.
When traveling by boat, a very tight community forms. At the docks, people from all over the world come together to eat, drink, socialize and be merry. Each boat has a flag to represent the home country of its owners. So seeing the Canadian flag on Connie’s boat, Will’s father Bill invited the three Canadians over to his boat for cocktails.
At this first meeting, Will’s dark hair was out of control. His bushy beard covered his whole face and neck and his hair ran wild down to his wool-shirt covered shoulders. Connie had a fleeting feeling that this was the kind of guy that appealed to her. Your basic man’s man.
The two families had a lot in common, which surprised Connie. The night was spent laughing and drinking rum.
The next day Connie, Carol and Bob sailed over night 100 miles to Gran Canaria. Connie wasn’t expecting to ever see Will again. But lo and behold, there in the harbor were the Flynts. Bill saw the Canadian’s boat and invited them over for dinner. Connie learned that Will had a wife back in the states. With this and the uncertainty of ever seeing him again, Connie thought of Will as only a friend.
For the next week the two families began to make preparations for crossing the Atlantic and sailing into the Caribbean, which meant being at sea for three weeks without seeing land. They would take buses into town and do their daily shopping at the local markets, stopping at the wine store to taste test the wine from enormous wooden barrels and buy bottles for 75 cents.
As is common in island hopping, people tend to encounter the same boats and people at each harbor. But being new to sailing, Connie didn’t know this. Connie and Will would run into each other at each harbor in the Canary Islands. In Tenerife the two families rented a car together and explored the depths of the island.
On Christmas eve, Bill, Will and John came over for chicken curry dinner. The Oaks wrapped the mast in green sail cloth and red ribbons and stuck pine cones on it for a Christmas tree and made a Christmas card for the Flynt family. That night, Will’s brother John announced that Will was in the process of getting divorced. Connie’s first thought was, “that doesn’t mean they won’t get back together again.” And she didn‘t even consider that it could mean that she and Will would have a relationship.
One Christmas day, the families played trivial pursuit and wiffle ball before enjoying Christmas dinner together.
On December 31st the Oaks departed for Barbados in the Caribbean. Connie sailed off with the information that the Flynt’s were planning to hit land in Antigua and wasn‘t planning on ever seeing Will again. Sailing north through the islands of the Caribbean Connie again ran into the Flynts in Martinique. Bill had gone home because he had business back in Maine. On Martinique Connie spent time alone with the brothers, while Carol and Bob sent time alone. One day Connie and the Flynt brothers rented a car traveled inland up river to some water falls where they had drinks and dinner. Other days they would take day sails around the reefs and go snorkeling.
After leaving Martinique in early February of 1986, the Canadians and Americans met again in Guadaloupe. Around this time Bob seemed unhappy and decided that three was a crowd. Connie decided it was time to leave and began preparing to go home. She needed to leave Carol and Bob but wasn’t ready to go home because she had no idea what to do with the rest of her life. So Connie asked Will and John if she could sail with them for two weeks until Bob was scheduled to return to the boat.
They went to the Grenadines and spent time snorkeling, fishing and hanging out exploring islands. Two weeks later, Connie and Will found out that, while in Maine, Bill had become sick and couldn’t return.
So Connie stayed on, and they sailed to Antigua for race week, when all the boat manufacturers sponsor races and the breweries sponsor parties. During the course of these parties, Connie and Will hooked up and the relationship began to develop. When they went ashore, Connie cut Will’s hair and he shaved. She could finally see his face, and she was pleased to discover he was pretty cute under all that hair. She was hooked.
Leaving the Grenadines they sailed across the Bahamas to Florida, and then continued along the intercoastal waterway up the east coast to Maine.
They spent the next several months on the boat snorkeling, fishing, exploring and celebrating. They lived bare footed and wore ratty t-shirts. Because of the tight quarters, the two got to know each other intimately and rapidly during their care-free time together on the boat.
After docking the boat for good in Maine the two decided they wanted to stay together. They have been married for 21 years.