The destination was the verdant Caribbean island nation of Dominica, in the Lesser Antilles chain, sandwiched between the French isles of Guadeloupe and Martinique. The goal was to partake in the fun, music, food and camaraderie of the second-annual PAYS Dominica Yachting Festival, a weeklong celebration to benefit the Portsmouth Association for Yacht Security.
My ignorance regarding this entire venture was twofold: I’d never been to Dominica, and I had no clue what PAYS was all about. However, when my old mate Hank Schmitt invited me to come along for the festivities aboard his sweet Swan 48, Avocation, I reckoned there was nothing to lose.
What transpired was one of the best weeks of my sailing life.
But first, we had to get there.
It was almost precisely 170 nautical miles, more or less due south, from our departure point on St. Maarten’s Simpson Bay to Dominica. We were closehauled in the easterly trades for our entire one-tack overnight voyage, and it was a bumpy ride. But there were some definite highlights. Off St. Barts, we caught a glimpse of the impressive fleet of superyachts competing in the annual St. Barts Bucket regatta. At sunrise, we enjoyed a respite from the relentless easterlies, sluicing down the lee of Guadeloupe. The last 17 miles of open water were sporty, but exactly 26 hours after hoisting sail, we picked up a mooring in Prince Rupert’s Bay fronting the volcanic black-sand beach and the funky coastal town of Portsmouth on Dominica’s northwest coastline.
After catching a ride ashore on one of the PAYS water taxis, I had the first of many surprises. One of the locals caught a glimpse of our skipper, a dude I’ve known for decades—but never by this handle.
“Look!” he called to his pals. “It’s Daddy Hank!”
Who’s Your Daddy?
There are several good reasons that Hank Schmitt is a rather beloved father figure along the waterfront of Dominica. After decades of roaming the oceans under sail—and through his related business, Offshore Passage Opportunities, the networking service that has helped countless sailors realize their own voyaging dreams—Schmitt is continuing to pay it forward with PAYS.
The tale of how a native New Yorker from Long Island Sound became a favored patron to a faraway Caribbean island is, well, a winding one indeed.
The sailing bug bit Schmitt early, at the tender age of 7, when he started racing dinghies in junior programs at various yacht clubs on his home waters. During high school, he matriculated to Rhode Island’s Portsmouth Abbey, and starred on the sailing team while working summers at a boatyard back home and sailing his dad’s Cal 2-30. After graduation in 1977, with a one-way ticket to Florida, he finagled his way aboard a Morgan One Tonner to race in the prestigious Southern Ocean Racing Conference, the major big-boat yacht-racing series of the time.
At 19, in Houston, he hopped aboard his first offshore oil rig; that began a seven-year odyssey that took him from the United States to Europe to Africa, and included his first transatlantic voyage, from Boston to Italy on a 400-foot drill ship at 8 knots. Thus, a pattern of movement was established. The equal attractions were new adventures and blue water. And it turned out, he was just getting going.
Back home in Huntington, New York, after the oil business cratered, he launched his own rigging and dive business, spent a few harrowing winters fishing commercially out of Montauk, and started doing yacht deliveries. Lots of them. Hundreds of thousands of miles. After one, in 1987, he landed a repossessed Tayana 37 that he renamed Hunk-a-Schmitt and lived aboard for 13 years. In 1992, he sailed it in Jimmy Cornell’s America 500 rally commemorating the 500th anniversary of Columbus’ famous voyage, visiting 25 ports in 10 months with a pair of solo Atlantic crossings.
That led to, among other things, founding Offshore Passage Opportunities and the annual North America Rally to the Caribbean, during which he eventually ran a fleet of Swans back and forth from their charter bases in Rhode Island and St. Maarten each year (and earned some extra dough selling crew berths to fledgling voyagers). His own Swan, the 48-foot Avocation, always led the parade.
That annual Caribbean pilgrimage is what first drew Schmitt to Dominica. For years, after arriving in the islands, he’d do a standard circuit of charters for members of Offshore Passage Opportunities: the St. Maarten Heineken Regatta, a swing through the British Virgin Islands, Antigua Sailing Week. When the BVI portion started to get old, a fellow skipper offered a fresh suggestion: Check out Dominica.
During that first visit, around 2012, Schmitt met a boat boy named Albert, who was operating a dilapidated skiff. He tapped some members of Offshore Passage Opportunities for a contribution for the materials to build Albert a new boat. The next time he visited (with some cache with the PAYS locals after helping out Albert), he realized that the few moorings he’d seen off Portsmouth were missing. The Offshore Passage Opportunities crew stepped up again, eventually raising more than $20,000 for several dozen new moorings.
That led to the first organized PAYS fundraisers, originally called Yachtie Appreciation Weeks (the second one, in 2015, drew more than 100 boats). They helped to fund a seaside PAYS pavilion and adjacent docks. The pandemic stopped the momentum, though Schmitt continued to raise and send money to help several Dominican families, and somewhere in there landed a nickname. Once normalcy returned, so did the weeklong celebration, rebranded as the Yachting Festival, with barbecues, tours, beach parties and more.
For me, arriving for the 2024 PAYS party aboard Avocation, something was clear right from the outset. It’s pretty great showing up in Dominica in the company of Daddy Hank.
Embracing “Nature’s Island”
It’s hard to say what was the best part of the festival because it was all pretty damn festive. But we’ll start with the people, especially Team Avocation: Daddy, of course; his longtime Long Island mates, Alex Hummel and Dave Evans (the latter sailed down aboard skipper Peter Bourke’s Class 40, Imagine, a nifty yacht that added much to my own personal experience); and Offshore Passage Opportunities member Don Geier, a Kansas man who, in retrospect, probably had no idea (like me) of what he was getting himself into. And then there was the PAYS posse, with ringleader Eddison Laville playing a prominent role, and a cast of characters as colorful as their own monikers: Cobra, Chronic, Blackie, Boy-Boy, Kenny G and so many more.
A few more things stand out, especially the dazzling beauty of this rich, fertile island. Dominica has been called the Caribbean’s “nature island,” and with good reason. With its steep peaks, dense rainforest, rushing waterfalls, and abundant flora and fauna, it is jaw-droppingly gorgeous.
It’s become known for eco-tourism, also with good reason. Those aforementioned black-sand beaches (which, to my eye, are nothing less than sensational) luckily deterred the arrival of Club Med-style resorts that afflict many a Caribbean island. The overall vibe remains inviting, laid-back and unspoiled. (That said, there’s plenty of new development underway, including major roads and a big international airport. My advice? Go. Now.)
Perhaps the best, easiest, most inclusive way to experience this island is also the simplest: Take a hike. As Avocation was a bit crowded, Alex and I decamped to shoreside quarters at the Mango Garden Cottages, which are run by Eddison’s Swiss wife, Sylvia, who invited us on “a morning stroll.” With a spirited quartet of happy pooches, we ascended an uphill trail past wandering goats and terrace gardens of cabbage and bananas to the Diablo Canyon, an arresting destination near a pretty spot called Sulphur Springs (its cool water was a lovely place to dip weary toes). A couple of hours later, Alex and I were drenched in sweat, while Sylvia and the dogs appeared fresh as daisies. Much too late, Alex made an astute observation: “It’s probably not a great idea to go on a steep hike with a Swiss woman.” Thanks, Captain Obvious.
That turned out to be just a warm-up for the next day’s trek. Dominica is circled by a 14-stage, 115-mile long-distance hiking route called the Waitukubuli National Trail. Sylvia dropped off Alex, Dave and me at the trailhead to Stage 13, the Penville section, listed on the map as a “moderate” hike of 8 kilometers, or about 5 miles. All I can say is, I’m glad we didn’t tackle a “difficult” route. It was a true wilderness trail with crazy vegetation, incredible cliffside ocean views, and plenty of sharp switchbacks—on one of which I was almost knocked into oblivion on a narrow path by a burro going up while I was headed down. By the end, some five hours and a rainstorm later, we were all toast—but also beginning to understand Dominica in elemental terms.
The next excursion, thankfully, was back to sea level and decidedly more mellow: a float up the Indian River with Albert, a fine guide, on the oars. The “indians” for which it was named were the indigenous island Carib people, before the colonists from Spain, France and Great Britain showed up, with predictably horrible results. Dominica boasts some 365 rivers, Albert told us as we slipped beneath a dense canopy of foliage and past century-old trees, their roots deep and tangled. Along the way, he pointed out the nests of termites and hummingbirds. Coconut crabs skittered along the shoreline. What’s left of the original Carib clans now live in villages to the north, but this was a serene place. Their spirit was still there.
We didn’t get a true sense of how vast and diverse Dominica was, however, until we piled into a van for an overland tour with another knowledgeable local named Kenneth Gussie. (He spelled it out in my notebook and said, “Don’t call me Kenny G,” though unfortunately for him, everybody does.) By any name, Kenneth was a passionate, knowledgeable ambassador for his homeland, which he called “the island of dreams. What are you looking for? Rivers and mountains? Caribbean culture? Fresh organic food? Eco-tourism? Where you can just be yourself without worries, and have great times?
“I’m going to make Dominica smile,” he continued. “That’s what I’m going to do.” He was as good as his word. It actually took us two days to take it all in, and that we did.
Kenneth spoke of the place’s rich history, the different and lasting influences of all those earlier European colonizers (Columbus, on his second voyage, gave Dominica its name: Latin for Sunday, the day he sailed past), and its tumultuous break for independence from Great Britain in 1979. Kenneth also had fond comments about the recent influx of Chinese people to the island: “Very good friends. They teach us farming techniques, fishing techniques.” He also waxed poetically on the perfection of curried goat.
We drove from the top of the island to the bottom, all 29 miles. We took in the national parks, including the one called Morne Diablotins, home to Dominica’s highest peak (4,747 feet). We had a look at the banana plantations, the fishing harbors and the botanical gardens in Roseau, the country’s busy capital. We stopped at the Indian reserve and picked up some crafts and souvenirs. We swam in the Titou Gorge and paid a visit to the Trafalgar Falls, where Hank and I scrambled up the boulders and had a refreshing soak in the cool, rocky pools. Everything was amazing. Thank you, Mr. Gussie; you did a wonderful job. All smiles.
Last, there was the one activity that put me firmly back in my more natural element: racing sailboats. The midweek Race to Mero was as casual as could be, and meant to showcase the new set of PAYS moorings installed off the beachfront of Mero Beach. There was no start or finish line; you could motor for five minutes at the outset; and the whole idea was just to go sailing and have fun, which I’m always up for.
That’s precisely what transpired on board Peter Bourke’s Imagine, aboard which he’d invited me to sail as a doublehanded entry. Bourke had originally planned to do the Global Solo Challenge singlehanded round-the-world race aboard the boat, but an untimely bout with COVID-19 sidelined those plans. Now he was cruising the islands. His well-prepared 40-footer was a joy to sail, and even with fitful breeze, we managed to make 8 knots at one point and had a fine time slipping down Dominica’s coastline in the company of another half-dozen racers. And Mero Beach was a sweet spot to pick up that mooring.
In a related aside, it must be noted: Cannabis is legal for the residents of “nature island.” If you (like me) happen to enjoy an occasional puff, the beach party on Mero, with a crazy street parade in the middle of it, is a good place to be. My new island brothers were more than happy to share.
Peter and I had another cool sail back to Prince Rupert’s Bay. I might’ve still been high, because at the very end of it, by virtue of the fact that we were the only boat to complete both light-air legs entirely under sail, Imagine was declared the winner. At the awards ceremony that evening, Peter even got a trophy. More smiles.
With that, my work on Dominica was complete.
Heading North
Our festival experience had commenced with an overnight sail from St. Maarten, and as all good things must come to an end, it concluded with one too. Alex and I enjoyed a delicious lunch of coconut-curry conch and backed down a couple of blazing shots of cinnamon rum at our new favorite beach bar. We all bid the PAYS posse thanks and adieu, and we were off.
It was an absolutely fantastic sail. The breeze had freed a bit on the way back to St. Maarten, which meant more of a reach than the upwind thrash we’d experienced on the trip down. It seemed fitting. After a week on Dominica, our souls were a bit freer as well.
I deliberately crashed until midnight, with the plan to stay up for the rest of the evening because I love catching dawn at sea. It proved to be a smart call; I also saw the rise of a brilliant moon. Best of all, as I came on deck, there in our wake was the Southern Cross. I hadn’t expected to see it this far north.
In that moment, it was hard to tell which was tugging more on my heartstrings: that beautiful southern sky, or wishing that I was still on that unforgettable volcanic rock called Dominica, afloat on the sea beneath it.
It PAYS to Sail to Dominica
The third annual PAYS Dominica Yachting Festival, with a weeklong program of tours, beach parties and casual sailboat racing, is scheduled to take place March 22-30. For more information, visit paysdominica.com. § While Hank Schmitt is scaling back on his own voyaging, his Offshore Passage Opportunities networking service is still connecting sailors and skippers for mutual oceanic adventures. Learn more at sailopo.com.
Herb McCormick is a CW editor-at-large.
