Retirees of the Caribbean

Bert and Dorothy Dorrestyn have been cruising in their sailboat Island Girl since the morning after Bert retired. What was supposed to be a one and a half-year “test” trip became an ongoing quest for freedom.

Story by Rebecca L. Bennett, Photo courtesy of Bert Dorrestyn.

This story first appeared in the Summer 2018 issue of Connections.

“At first, we were scared to death,” says 71-year-old Bert Dorrestyn, who retired in December 2012 from Bexar Appraisal District with more than 12 years of service. “We were sailing off the coast of the Dominican Republic. It was one of those lazy afternoons and we were both dozing off. Suddenly there was an explosion of water and a humongous whale came out of the water and landed flat next to us.”

“He jumped like that five different times and then started slapping his flukes in the water,” Bert continues. An hour later, Bert and his wife Dorothy met another boat who had received the same performance. “It was so clear he did it to amaze us.”

Bert and Dorothy have been cruising South America and the Caribbean in their Bluewater sailboat Island Girl since the morning after Bert retired. To date, they have visited 38 different countries on their sailing excursions and their plans of leaving the lifestyle keep getting pushed back.

What was supposed to be a one and a half-year “test” trip became an ongoing quest for freedom and connection with South American culture and other “cruisers” — or, travelers who use their sailboats to move between ports to explore on land among locals.

“It’s a very different lifestyle,” Dorothy says. She goes on to describe what it’s like to shop for vegetables, fruit, meat and other supplies, ride in colectivos, or taxi vans, along treacherous mountain roads, and receive genuine hospitality and kindness from strangers. “There is so much acceptance. We get to see a lot of beautiful things and meet so many different people. It really enriches your world view.

From mates to shipmates 

In January 1978, Bert and Dorothy met and fell in love in Suriname while Bert was employed by KLM Royal Dutch Airlines and Dorothy was with the Dutch Foreign Service. As Dorothy puts it, they have “always been close to each other”.

However, the challenges of co-piloting a vessel and constantly being in each other’s presence has refined and strengthened their marriage even further. “You cannot say, ‘I need my space today, so I’m going to step off,’” says Dorothy.

In the past, the couple wore head­sets to talk to each other while work­ing in different areas of the boat — usually with Dorothy at the helm steering and Bert on deck raising or lowering the sails or anchor. Their communication skills and trust have improved so much that they only need hand gestures now.

“She always follows me for one reason or another,” Bert says, giving Dorothy a sly look. “She didn’t like the idea of sailing so much in the beginning.”

“No I did not,” she laughs.

Socializing with sailors 

Socializing with fellow cruisers at ports provides strong motivation for Bert and Dorothy to continue sailing. Connected through Facebook, blogs, WhatsApp and an organic daily radio net, members of the cruising community forge strong bonds quickly while they are briefly in port at the start of sailing season in October and November, and in April and June — which is the beginning of hurricane season.

“Hopefully next year, or somewhere along the way, you meet each other again, but you usually never meet again,” explains Bert.

The Dorrestyns maintain their own sailing blog to document their journeys, provide travel advice, and keep their family and other cruisers updated along the way. They also frequently contribute to TripAdvisor, seeking to guide fellow vagabonds to great adventures.

Smooth sailing in retirement 

TCDRS’ automatic electronic benefit payments have given the Dorrestyns retirement confidence and dependably fueled their cruising adventures. “Most of the time, we have no phone or internet connec­tion,” Bert explains. “Imagine sitting somewhere in your sailboat or on a remote island like Guna Yala and thinking, ‘Oh my gosh, I hope that [payment] comes through.’”

“For me, it is very important that I have the feeling that everything is taken care of, and the only way you can do that is by having a retirement fund you can trust,” he continues. “With TCDRS, I know that whatever happens — hurricane or no hurricane, snow or rain — the money will be there in my account.”

Bert and Dorothy have also set themselves up for financial success by eliminating debt, reducing the amount of bills they’re responsible for, and automating all of their financial processes, such as bill payments and retirement income.

They also maintain a strong sup­port network of family members and friends back in San Antonio, whom they can depend on if trouble does arise.

“I tell people all the time, ‘This is the best part of my life,’” Bert says. “I enjoyed my work. I did my work until the last day with all the pleasure in my life, but now I never have to think about it anymore.”

“With sailing, you go where you want to go,” he continues. “You’re liv­ing completely by weather and your own desire. It’s absolute freedom.”

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