Basil said, “You can’t have an acre, but how would you like the whole place”?
Richard Hokin on the offer his parents couldn’t refuse.
It is relatively recent history that, when Columbus sailed past this dense array of islands in 1493 without ever setting foot ashore, he named the archipelago in honor of St. Ursula and her 11,000 virgin martyrs, and Virgin Gorda for her resemblance to a voluptuous reclining woman. Drake’s connection is more intimate because, in 1595, on the voyage that cost him his life, he and Sir John Hawkins assembled a fleet in North Sound for their failed assault on the Spanish in San Juan.
Nearly 400 years later, Drake’s attractive, protected and breezy anchorage in North Sound’s northeast corner became the destination of choice for yachtsmen, charter skippers and adventure sailors. One of those skippers, Basil Symonette, acquired the adjacent shoreline and hillside property at John O’Point in the 1960s and built the Bitter End Yacht Club — consisting of a small jetty, a few moorings, five rustic hillside guest cottages and a seaside pub, which remains the core of today’s Clubhouse.
Following our family’s 1964 exploratory visit, we established a beachhead in the Virgin Islands centered on Alianora, a 72’ North Sea sailing trawler, rigged for tradewind cruising, and Reef Sampler, a downeast-style lobster boat equipped for sport fishing and diving (and destined to become the flagship of Bitter End’s utility fleet). Naturally, there were many visits to the North Sound anchorage during Bitter End’s early years, so my parents, Myron and Bernice, got to know Basil well.
By 1970, we were convinced that North Sound was the epicenter of all our passions — sailing, fishing, diving, beachcombing, exploration and simply being surrounded by magnificent nature. My mom was intrigued by the idea of having a shoreside cottage at John O’Point, so one evening at cocktails she asked Basil if he would sell or lease them an acre. He responded that he needed to think about it and would have an answer the next time they visited Bitter End. When they returned a few weeks later, his answer was, “I thought it over and you can’t have an acre, but you can have the whole place!”
When the transaction closed in 1973, we set about making Bitter End into a family retreat with just enough commercial activity to convince ourselves it wasn’t pure folly. Soon, however, we discovered that Bitter End was riding the wave of a new yachting experience called bareboat chartering — a phenomenon that would bring the magic of North Sound to many more adventuresome visitors. Once we realized that, our mission became sharing with like-minded adventurers from around the world the magic, character and passion of our family retreat. As a family, to this day, we remain committed and passionate stewards of the Bitter End experience and, most especially, the exquisite stage Mother Nature has built for it.
Soon, word spread. Bitter End became a beacon for kindred spirits: sailors, divers, wind surfers, conservationists, and explorers. Charter crews dropped anchor. Regattas plotted. Sea-loving families returned season after season. Guests came and went, but the essence of the place remained unchanged. By the 1980s and 90s, Bitter End had evolved organically into one of the most iconic watersports destinations in the Caribbean. The harbor served as a proving ground for athletes and a playground for beginners. Locals mingled with global travelers and professional sailors. Bitter End’s warm welcoming culture and spirit of adventure was cemented worldwide.
The legacy that has grown and evolved organically over fifty years was forever changed on September 6, 2017, when Irma, the most powerful hurricane to strike the eastern Caribbean, passed directly over Bitter End. While our buildings, some of which dated back to the 1960s, were leveled, we are forever grateful that the Bitter End crew made it safely through the storm. Through this all, the strength and commitment of our community – the heart and soul of Bitter End – has grown stronger than ever.
While we knew that Bitter End the place was iconic, we learned firsthand that no storm of any category could extinguish our spirit, and that our need to stay connected as we rebuild the property felt more important than ever. A big part of remaining connected for us is our commitment to supporting our community through philanthropic outreach. As a result, we launched The Bitter End Foundation, a 501(c)(3) aimed at supporting the continued success, unique needs, and wellbeing of seaside communities by providing in-kind, financial, and educational support, protecting sea life, undersea and surrounding habitats, and encouraging conservation efforts. To date, we have raised over $1,000,000 and given away $900,000.
Then came September of 2017, when Hurricane Irma swept through North Sound, the most powerful hurricane to ever hit the Eastern Caribbean. Lauren and I reached Puerto Rico two days later aboard a relief plane, communications with Bitter End having gone silent as the storm raged. For twenty-six hours we knew nothing of the colleagues who had sheltered there, until word came that they were safe — a blessing amid the uncertainty. What awaited us was sobering: a shattered shoreline and, more troubling still, a community confronting a humanitarian crisis of no water, power, fuel or reliable shelter. Yet almost immediately, an armada of friends — from Puerto Rico and beyond — rallied with boats, supplies and unflagging resolve, reminding us that Bitter End has always been sustained as much by people as by place.
In the years that followed, rebuilding became less about replacing what was lost and more about reaffirming who we are. We returned to first principles — honoring the geography, respecting the trade winds and letting the shoreline lead. What stands today is not a replica, but an evolution: stronger docks, thoughtfully reimagined cottages and a renewed commitment to stewardship. Through 2026 and beyond, as new generations make landfall at John O’Point, we remain mindful that Bitter End has never been defined by its structures alone, but by the enduring privilege of caring for this remarkable corner of North Sound and sharing it with kindred spirits drawn to its timeless call.
-Richard Hokin
