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People Thought We Were "Too Old' to Sail the World. We Did It Anyway.

But we did it anyway

A large sailboat on the water with hills in the background

Courtesy Ronna Benjamin

Ronna Benjamin is currently finding adventure in the western Caribbean (Colombia, Panama, San Blas, St Andres, Bay Islands, Belize) with her husband on their Hylas ’49 sailboat.

If we had told our three adult children we were traveling to Papua New Guinea for bird-watching, or that we were making a pilgrimage to India to hone our yoga practice, they would have thought we had lost our minds.

But they were not surprised when we told them we were selling our family home and all our possessions, and moving onto our 49-foot sailboat to explore the world. They simply wondered what had taken us so long.

The decisions we make about how we will spend our time when we finish (or take a break from) working do not come from nowhere; they are influenced by our passions, which are no secret to our friends and family.

In the early 1990s, my husband, Mike, and I chartered a sailboat in the Caribbean with our best friends. One evening at a local beach bar, we met an older couple who lived on their sailboat. They were lean and muscled, brown and wrinkled. She had long gray hair, and explained that she dried her own fish, made her own yogurt, and stitched up her husband’s skin when he cut himself. I looked over at my best friend. We both had fashionably cut and colored hair, perfect manicures and fresh new clothes.   

“That’s me in 20 years,” I whispered to her, and we both had a good laugh. But I knew it was true. My husband’s dream since he was a boy was to move onto a boat and sail away. After 30 years of sailing together, it became my dream, too.

In 2012, after decades of chartering boats all over the world, we bought Exodus, a 49-foot, bluewater Hylas. It was ready to cross oceans, but we were not. On land, we had plenty to deal with. It wasn’t just the children. I buried my mother and father, and was diagnosed with breast cancer. I had a mastectomy, chemo, radiation and reconstructive surgery. 

Selling and giving away our possessions was an incredible feeling of freedom. The sea was calling us, and we were answering.

By 2016, I was feeling great. Our kids were completely “off the payroll,” and the dog was long since dead. Mike’s mother, our one remaining parent, was in good health at 83. We had found our sweet spot.

We decided it was now or never. Just days after Mike’s 60th birthday, we sold our house of 30 years. Selling and giving away our possessions was an incredible feeling of freedom. The sea was calling us, and we were answering.

We moved aboard Exodus, casting off from our mooring in Padanaram, Mass. We headed south, down the East River in Manhattan, around the Statue of Liberty and into the Chesapeake, to Hampton, Va. There, we met up with the Salty Dawgs, a group of sailors who make a yearly ocean crossing from Virginia to Antigua. 

We did our first ocean crossing, with two in crew, in early November. I was a nervous wreck about the 1,200-mile trip and 11 days at sea, and our passage was not easy. The freezer, filled with food for the passage, died on the third day.

Our autopilot worked sporadically, requiring us to steer mostly by hand. Our rudder broke in a squall, so the men were forced to take one-hour shifts at the emergency tiller to complete the last 100 miles. There were plenty of times I thought this life was simply too hard, too scary, too frustrating. More than once, we discussed giving up and going home. 

But while docked in English Harbor, Antigua, fixing our rudder, we had an attitude adjustment. Mike was in the engine room, and when he heard Prince Charles was touring the marina, he popped up on deck in his sweaty T-shirt. Prince Charles, wearing a three-piece suit (he doesn’t sweat), made his way over to Exodus, and had a long chat with Mike about our voyage. We realized that despite hardships and frustration, this was going to be a life of adventure.

We embraced the cruising life — the warm, gin-clear waters; the dolphins, turtles and reef fish. We embraced the iguanas, the sloths and the monkeys. We embraced new cultures, months of no rain and oppressive heat, and “Caribbean time.” We embraced 34-knot trade winds off our stern, and flying fish landing on Exodus at night. We embraced countless sunsets and rainbows. Against all odds, I even learned to embrace moonless night passages, on watch by myself in the inky darkness. We embraced constantly monitoring and maintaining the engine, water, electrical, sanitation, rigging, HVAC, bottom growth, refrigeration, and the never-ending battle to fight the constant corroding effects of salt water and UV rays.

Most importantly, we embraced a sailing community that looks after each other like no other. We embraced new friends from all over the world. We help each other fix engines, rigging, and computer and electrical problems. We provide tools and spare parts. And we provide each other with emotional support. We sing, laugh and drink. Boy, do we drink.

We are now well into the second leg of our journey. We have joined a group of 40 sailboats (the OCC Suzie Too Rally) heading into new and unchartered (at least for us) lands: the coast of Colombia, the San Blas Islands, Panama, the islands off of Honduras and Nicaragua, and Belize. We will make our way to Mexico, and then head back to the United States, where we will spend the summer seeing family and friends.

Most of our friends from home thought we were a little nuts when we set out on this adventure: There were so many reasons not to do this, so many obstacles; we were too old; it wasn’t the right time (but when is?). I think now they are proud of us — and a little jealous — for following our dream. I hope that we have inspired others to follow theirs.

We don’t know how long this journey will last, or even where we will go next. We know life will sometimes be difficult and exceedingly frustrating. We know there will be stretches of boredom interrupted with moments of terror. We also know there will be celebrations with friends, more beautiful sunsets, and plenty of adventure. We could not be happier that we took this leap of faith.

Ronna Benjamin is a former real estate lawyer turned writer, and a partner in and regular contributor to She has no idea how long her adventure will last or where she will explore next.