Couples like Clare and I are a rare and fortuitous breed. We are white and from wealthy English-speaking countries. We have no debt, children, or careers. We both come from healthy and supportive families. And now we own a sailboat that is in the Caribbean!  That’s right folks, Champagne has finally departed the North Atlantic waters of the Bahamas and plunged straight through the heart of the Windward passage—a notorious piece of water that separates the island of Hispaniola from Cuba that lives up to its namesake. Steady 25-knot winds with gusts into the thirties keep us barreling down the 5-7 meter waves. At one point SeaJay remarks, “I think I should be scared, but this is just too much fun”…hence why I married the girl.

By the second afternoon of the 230-mile journey we receive our first glimpse of Haiti through the fuzz of a reluctant haze, but there is no mistaking the dramatic outline of a boisterous coastal mountain range flanking the seashore. From out of the haze a tiny white spec draws across the horizon, at first appearing like some overgrown swan plying the water with equally oversized webbed feet. But no, such is a local handmade sailboat, with a crew of two, riding the breeze to some deepwater fishing ground. We are more than 20-miles offshore, in thousands of meters of water, and yet one such boat is beyond us. Our gaze follows the small vessel to where a massive cargo ship emerges from the haze and passes between us before plowing out of view, leaving us to grapple with such glaring disparity. Here these tiny wooden boats, with masts not much taller than a basketball hoop and propelled by quilt-work sails (or oars if the wind dies), venture without a single light, radio, or piece of electrical wire into the deep blue in search of livelihood all the while dodging the giants of modern transportation using the same water to pursue their own livelihood.

As we draw closer to the shoreline, not only do these sailboats become more prolific, but their ranks are joined by an array of human-powered craft…mostly tippy dugout canoes. Many a crew member flip their hands towards the sky in a “What’s Up” or “What Do You Need” gesture. Some hold up fresh catch offering to sell and others shake empty plastic fuel jugs hoping for a top-up. We toss a can of food to one nearby canoe but miss by an arm length…not sure why I thought canned goods would float, but for the record, they do not.

All of these sea-goers have ventured from one of any number of small villages that line the coast and can now be plainly viewed through binoculars, nothing more than a series of piecemeal huts mostly with thatched roofs. Undoubtedly all of these have only just recently been reconstructed since the wrath of Matthew, the latest hurricane to have past directly over these shorelines. Villagers can be seen strolling along the beach, wringing out laundry, securing their vessels, or tending to cook-fires and all of this is backdropped by the dramatic folds and cleaves of tropically forested mountains which tower thousands of feet overhead and form a rich canopy of swirling clouds. The sight is breathtaking. Clare and I can do little else but stand on deck, wave to passing boats, and attempt to take it all in.

Fifty miles remain to the island of Ile A Vache, our intended destination, and so we spend another night traveling across the seas, but this one mostly under motor as the wind completely abates. By the next day we are rounding up into the Bahia de les Cayes and at the final turn are approached by a small dugout canoe. Two smiling boys are digging their oars and rapidly closing on our position. We will come to know these (and many other) boat-boys well enough during our brief visit, all of which are eager to hustle-up some scratch from visiting yachts, and considering the dearth of income-earning prospects, you can’t blame them one bit. At any rate, these boys are so eager to offer their services that they attempt to grab hold of our boat while we are still motoring along at 4-knots. They give a valiant effort and we try to slow down in time but alas the canoe capsizes and they go swimming in the water. We turn back around to help overturn and empty their canoe and instead just end up tying it off our stern and taking them aboard as crew. Mark, the bold one, is glad to take the helm and pilot us into the tight anchorage while we pick up another canoe and even more boys en route.

By the time the anchor is down we must have a half-dozen boats tied-on and as many or more scrappy black teenagers galloping all over deck, which certainly makes storing the sails and launching the dinghy a breeze. Clare produces cups of water and a small spread that we all enjoy while cracking jokes in broken english and passing around various nautical apparatuses of interest. They are eager to absorb all they can and some already know how to use devices—like winches—with proficiency. More boats come and go, always offering their services, but also mindful of the fact that we have only just arrived and need to get our bearings. The shadows are now long and the sun low, so we make plans to see everyone at this evening’s Valentine’s Day party—“Jus on da beech o-ya dar Cap-tan,” Sinclair motions to the nearby shore—and send the lot on their way. We have arrived in Haiti.

It appears as if the lofty ideals boldly posted on cheesy high-school posters actually can manifest—Follow Your Dreams; Never Give Up; Be Whatever You Want To Be; Keep Your Focus—or at least they can for the privileged few such as us. Exploring exotic foreign countries by means of my very own sailboat! Such a longstanding dream always seemed utterly preposterous and fanciful, and yet here I find myself doing just that and sharing it with such a puzzle-fitted partner. Maybe I should start playing the lotto.

Here’s to finding your own fortune.