Ten Voyages and Counting

My Introduction to Windjamming

In 1984, my girlfriend, Debbie, and I felt the need for an adventurous vacation. There were no resources like the internet, so we visited a travel agency where we were shown a few cruise ship options, none of which appealed to me, as they seemed so big and cold. I asked if there were any smaller options. As the agent flipped through a file drawer full of thick brochures of other “foo foo ships,” the image on the cover of a thin pamphlet caught my eye; it was a majestic three-masted “pirate ship.” The agent said that she didn’t know much about it. Neither did we, but I knew it was the one we had to try. From books and movies, I’d long been fascinated by tall ships, but never imagined that sailing on one was an actual possibility. We chose the smallest ship and booked our first of many Windjammers with very little idea of what to expect.

We packed two army duffle bags, flew to St. Thomas, then boarded a puddle-jumper to Tortola. After a high-speed, nail-biting, winding half-hour drive to the port, we approached the beautiful S/V Flying Cloud and could barely contain our excitement, but a crew member informed us that it was too early to board. After he tossed our bags aboard, we explored the quaint town and stopped into the Road Town Pub to kick off the trip with a couple of rum shots. At that time, Pusser’s was a 400 square foot shack with four chairs and one table.

When we finally boarded, we knew that we had made the right decision - the warm deck, the handcrafted woodworking, the soaring masts, and the genuinely welcoming crew and officers. Before long, we were asked to grab a halyard and assist in hoisting the sails, accompanied by a surprisingly moving rendition of “Amazing Grace” from the deck’s speakers. It still gets me every time.

Each day, we set sail and anchored off a different small island, where we enjoyed amazing beaches and snorkeling. The rest of the time was spent sharing a variety of activities with the crew and fellow passengers: fun games, local entertainment brought aboard, delicious meals, afternoon “swizzle time,” and evening music and dancing.

Our cabin was quite small, had a unique odor, and a head in which you could shower, brush your teeth, and take care of business all at the same time and without getting off the commode. There was no menu; you ate what was prepared. There was no hot water other than what was heated in the pipes by the sun, and no fresh water due to a local drought, so we had to buy our own ashore for drinking. In other words, everything was perfect, and we were hooked!

The following year, we cruised on the Polynesia out of St. Maarten and the year after that, Deb and I married, and we honeymooned aboard the Fantome out of Nassau. In 1988, after deciding to try to expand the family, we splurged and booked two weeks on the Mandalay out of Grenada, knowing that, if successful, we’d be grounded several years. Nine months later, our first child was born. Over the next four decades, we introduced dozens of friends and family to these unique and exciting vacations, including our daughter and son as soon as they were old enough. We’ve explored lush islands that large ships cannot visit, hiked to waterfalls, swam inside a shipwreck 80 feet down, and had close calls with volcanoes and a dismasting, but those are stories for another time.

Sadly, we lost Debbie to cancer in 2014. A year later, I treated the kids and their significant others to two weeks on the Mandalay in her honor. Since then, I met and married Katia and took her on the Mandalay in 2019, but she was showing signs of neglect – the ship, that is, not Katia. The six of us cannot wait for the chance to board the new incarnation of the Mandalay in the near future.

Voyage Years: 1984, 1985, 1986, 1995, 2000, 2002, 2005, 2007, 2015, 2019

Been carrying a Windjammer memory all these years? We’d love to hear it. Share yourTales from the Deck story here →