Two Legends In The Caribbean: The Grenadines

I still remember my first sail in the Grenadines 16 years ago. Rollicking winds lifted the 45-foot sailboat we'd chartered, and heeled us over as soon as we popped out of the protection of Grenada to face open water. We sailed right over an active underwater volcano named Kick-'em-Jenny, heading for Carriacou. In the pitching cockpit, I recall reading aloud about that volcano from the cruising guide, promising it wouldn't be a bother, as my all-woman crew held on, double-checking my expression for signs of concern. I really wasn't worried. It was a beautiful day with blue skies and puffy tradewind clouds. We didn't see any unusual bubbling, but knowing a volcano is boiling beneath your keel is disconcerting. Or, exciting! The women sailing with me seemed to straddle the two emotions, while I kept pointing out what a heck of a gorgeous sail we were having and how much they were going to like the Grenadines.

This had been my old stomping ground. When I was 17, at the beginning of my sailing life, my father left me to take care of his 40-foot sailboat in Antigua for a couple of months. Now, as a mother of two boys long past the 17-year mark, I wonder what on earth he was thinking. No way I would've given my offspring the chance to have as much fun as I did. It was 1984, a blast. All my new friends who'd worked as crew on the fancy yachts by day, and partied at night, had spoken of the Grenadines with longing, describing it as a bucolic tropical ideal. Years after the party ended, I never forgot that the Grenadines were loved by people I liked.

Flash Forward

So there I was on my first charter, lots of sailing miles later, finally exploring the Grenadines for myself with a group from the women's sailing school I co-owned — in my job leading overseas charters with seamanship lessons thrown in. Though I'd already dropped anchor in many other fantasy islands around the world, that week in the Grenadines was my first solo charter without my business partner Jill London skippering a second boat. The day before, five women from around the U.S., and spanning multiple decades in age, had come aboard in one of the craggy jungle bays of Grenada, full of excitement for a great week. It's a pretty self-selecting bunch of people who'll sign up for a sail in a relatively small space with strangers. But it works out well, with new friendships forged quickly and many intense new memories created. These trips are so much fun that for a while there, when my kids were young and he was my favorite author, Jill and I used a Dr. Seuss quote as a logo: "It's fun to have fun, you just have to know how."

So my plan to sail from one beautiful anchorage to another unfolded. From Carriacou, we sailed up to Union Island, then across a narrow channel to Palm. It was on the way to Palm that one of the women told a story that made a profound impression. In 1946, she said, after World War II ended, a young soldier named John Caldwell was stranded in Panama after trying unsuccessfully, for way too long on ships that kept getting recommissioned, to return to his new wife in Australia. Without any prior sailing experience, he was frustrated enough to buy a derelict 29-foot sailboat to carry him back Down Under. In 1949, the classic he wrote about that harrowing journey, Desperate Voyage, became an international bestseller. He and his wife Mary had two children, and continued sailing, eventually arriving in the Caribbean. In 1965, they bought a 99-year lease to the 135-acre Palm Island, with a vision of turning it into a beautiful resort and home.

Turns out, John Caldwell and I both had experienced unlikely solo sailing adventures in our younger lives, and so once my charterboat arrived at Palm that day, he and I were brought together and chatted about everything from solo sailing at a young age to home-building adventures. Even in that, he and I had much in common. We sat in his heady restaurant of tropical blooms and shady palms, signed copies of our books for one another, and too soon, just before the evening dancing began, he went off to bed. It was hard to imagine that this place had once been a swamp, that one intrepid couple had transformed it into a tropical ideal.

Johnny Coconut

Everyone called him Johnny Coconut because when he and Mary arrived in the Caribbean, they were dismayed by the lack of coconut palms, which were ubiquitous in the South Pacific. John knew that these fast-growing trees quickly made themselves indispensable as food, drink, fuel, and building material, and decided to introduce them to Palm Island. So, while building his paradise, Johnny sailed up and down the island, planting coconuts everywhere he went.

By the time we visited the island, the trees were towering and plentiful, and the resort was a picture-book version of what one imagines when dreaming of a tropical paradise. I soaked up this character of legend, wondering how a person could accomplish as much as he had by 80.

Finally, we pulled ourselves away from Palm and sailed on, up to the Tobago Keys, a cluster of islets surrounding an enormous and exquisite turquoise lagoon. Around the white sandy islets of this tableau swayed Johnny's palm legacy, which I would have taken for granted as being what one expects of a place like this if we hadn't just met the man who planted the trees. It's impossible to imagine that these universal symbols of island life didn't exist here before John.

We also sailed to Canouan, the laid-back island; Bequia, the island of eclectic whaling culture turned artsy; and Mustique, playground getaway for the rich and famous except for the charterboat guests who flock ashore with paparazzo aspirations.

Since that first charter, when I met John Caldwell, I've been back to the Grenadines several times over the years — with guests and with my family — but never again to Palm Island. A year after my first visit, John died, his oasis was sold to a resort company, and I haven't wanted to see how his legacy has been packaged. These days, with new groups of guests, I've discovered other nooks of these extraordinary islands, places that were loved by people I liked, such as the extraordinary Johnny Coconut.