By Captain John Borden
This past Thanksgiving (2025) during our post-turkey discussion at the dinner table, I found myself particularly agitated with my wife and offspring while recounting this years’ annual November Virgin Islands charter yacht inspections. The contention began when my 93 year old mother innocently
asked what my contribution was to booking these charter yachts. I started to mention clients who were also friends when my wife and senior broker informed me that those didn’t count being her friends too. Her comment gave me pause. As slight as it was, it was pause enough for the two chicks to take part in hen pecking yours truly even more veraciously than they had the holiday bird. I wasn’t even fractionally as amused as they were.
It can sometimes be a curse as well as a blessing being married to someone much smarter than you. In the mid-eighties during my first season sailing the Virgin Islands as a modest bareboat Captain, my college sweetheart had already worked her way up the ladder as an accomplished Addy award winning television writer/producer for a large ABC affiliate broadcasting across three states. I’m still a little surprised that when I proposed she agreed to give it all up for a life of relative poverty at sea. Before we were to exchange rings I felt it necessary to procure a vessel in which we could sail off into the Caribbean sunset, all be it with total strangers boarding each week. At first I was mostly attracted to old classic wooden sailing yachts, landing me in the office of John Alden at The Bahia Mar Marina in Ft Lauderdale. I am forever indebted to him for the wisdom he imparted, even though I chose to only take half of it to heart. Probably from a lifetime of toil keeping his family yachts in pristine fashion, he advised finding a more maintenance free plastic boat. Secondly, he advised possibly captaining someone else’s private vessel. I had the distinct impression that he didn’t really consider charter yachts very profitable, but more a rich persons toy write off. He added, a skilled hired Captain is treated with more admiration by the owners than that given to their own children. While I stubbornly wanted our own boat, I had also started looking at more modern and roomy French, Frers fiberglass designs. I eventually settled on Aquarius. With two double cabins aft, a large cockpit, and a shallow draft wedge keel inspired by Australia II; she was fast, practical and spacious, the perfect four passenger charter sailing yacht.
This brings me to my very first Virgin Islands Charter Yacht show some forty years ago, which begged the question mom so aptly put, “What would be my contribution to booking the charters?” The answer for me was simple, marry the love of my life and make her my first and only mate to cherish always! I may have followed Alden’s second suggestion if not for Carole. We wanted to build something together that was ours, something that would afford a life and freedom we had to this point only dreamt of. We both knew the importance of making an impression on the charter brokers. Thankfully we did, becoming one of the most booked yachts in the most popular cruising ground in the world. We were affordably priced, attracting couples who were only strangers for as long as it took to help stow their bags. Many of these charter guests remain friends to this day.
The vessels at Yacht Haven, St.Thomas and Nanny Cay, Tortola this year were very different from those in the eighties. Carole and I, mostly Carole, have done our part to help grow the charter yacht industry to what it is today, not only in the Virgin Islands but also Worldwide. It wasn’t long before the Aquarius first mate began to turn heads, becoming secretary of the Caribbean Yacht Brokers Association (CYBA), and continuing to not only book guests on modestly priced charters but also aboard large mega yachts. One such client, on a three hundred fifty foot yacht in the Med., even added a private tour of the Roman Colosseum & private audience with the Pope. There weren’t any yachts quite so grandiose based in the Virgin Islands this year although I was more than impressed by the size, accommodations, and water sports toys aboard the newer power catamarans. While I will always be a sailor at heart, tacking back and forth into the wind along the south shore of St. Thomas, or up the Sir Francis Drake Passage can be far less comfortable and more time consuming than aboard a larger, faster and more stable power cat that can simply point and go. I don’t believe however that power cats will ever completely take over as long as there are Trade Winds and the joy and exhilaration that harnessing them brings.
Sailing yachts were well represented at the Virgin Islands Charter Yacht Show in St Thomas, USVI. Our son Jack joined us to inspect sailing and motor vessels gathered at Yacht Haven Marina. He has become even more aquatinted with the show than I have been in recent years. At his last inspection he took a day off for exploring to share a hidden gem that I was totally unaware of even after all my years cruising the VI. Jack was eager to show me an unspoiled bay located on the north west side of St Thomas named Santa Maria, after another explorer’s sailing vessel who discovered the cove at the turn of the sixteenth century. A small Danish ruin left from the Zufriedenheit rum plantation is the only reminder of western civilization as the bay remains as it always was, even before Columbus first arrived. The coconut palms which line the beach are broken only by a fresh water stream which winds down from the rain forest and kisses the salty Caribbean Sea. Jack was so proud to lead me down the tiny path from the main road to what was a highlight of our visit, and a gift from son to father that we will both always treasure.
A much larger display of charter yachts were gathered in Nanny Cay, Tortola by the Charter Yacht Society of the British Virgin Islands (CYS). The three of us landed on Tortola before the opening of the show and were able to do some more exploring. Whether arriving by yacht or jeep, Smugglers Cove has always been a special destination for our family. Tortola as a whole and all of the British Virgin Islands island are drenched in pirate lore dating back to the golden age of Buccaneers. During this period around the turn of the eighteenth century Tortola and the BVI served as a Pirate Mecca for the likes of William Kidd, wealthy privateer turned pirate during the 9 years war, followed by Edward Teach, aka Blackbeard, who was relentless in his plundering during Queen Anne’s war. Armed with cannons to the teeth, his prize vessel, Queen Anne’s Revenge was known to utilize Tortola’s Sopers Hole for careening at the island’s west end while the beach around the point was perfect for smuggling. Smugglers Cove today has a gorgeous white beach and is a wonderful spot to spend the day sunning, snorkeling and enjoying a barbecue of local chicken, which we found of the free range variety wandering around oblivious to their fate!
At his pinnacle, Blackbeard amassed an impressive fleet of commandeered naval, merchant and slave ships sailing between New York and the Caribbean. He was known to frequent the Carolina coast and even held the entire port of Charleston hostage during his reign of terror. I probably know way more than most about Charleston pirate history, largely due to my long time mate, historian and friend Russell Robinson. In the summer, when Alexandria & Jack were youngsters, Russell (their school history teacher) and I would bring other young passengers along with parents and grandparents aboard our US Coast Guard Certified sailing yacht Serena for a two hour Pirate Sailing Adventure! During this same period of time, Carole and I brought the kids with us to Tortola where we rendezvoused with my fellow pirate and college friend Eric Zilling, his wife Holly and son Justin. Justin, like Jack, was the perfect age to play pirate for a day. We plotted to take a page from Treasure Island before boating over to snorkel the caves on Norman Island, as mentioned in the first Virgin Islands Captain John’s log, the very Island which inspired the novel. Bringing with us a handful of fake gold doubloons, we snorkeled ahead of the boys into the cave to plant the legendary “Beardo’s Treasure”. It took a little longer for them to discover it than we anticipated, however their reaction was well worth the wait! No doubt another memorable treasure but this time from father to son.
Alexandria and Jack both sailed into adulthood as indentured servants aboard our Charleston charter vessels so they have more of an appreciation for the VI yachts and crews than most young brokers in our industry. Jack was a hundred ton USCG Licensed Captain by age eighteen and not long after college,
purchased his first charter sailing yacht while working in New York. Eventually we sailed her south to join Serena. In August of 2018 Jazz, Jack’s deep keeled Sparkman and Stephens design, made an unplanned maintenance stop in Beaufort, North Carolina only to find we had landed in the front row of the town’s annual pirate festival, that year celebrating the 300th anniversary of Blackbeard’s demise. Edward Teach used the narrow inlets along “The Grave Yard of the Atlantic” to his advantage and eventually built a home in Beaufort, NC which I visited while we were there.
He would have been far better off staying south with the other pirates of the Caribbean. My own ancestors also found advantage in this port town migrating south from Newport, RI in the eighteenth century as well. Their treasure as sail makers was the cotton growing in abundance across the eastern part of the Carolinas. We are direct descendants of these Bordens, including my afore mentioned cousin Dick, who resided in Beaufort for years. Yet again, Jack and I got to play pirate joining in with the thousands of costumed re-enactors and revelers, this time for a whole weekend before heading home (a serendipitous treasure for both of us).
The 2025 Tortola show accommodated both a record number of Charter Brokers and Charter Yachts. So many yachts in fact they spilled over onto Virgin Gorda, east of Tortola. This is a testament to the Virgin Islands popularity as a must see cruising ground for “AquaSafarians” arriving from all corners of the globe.
It was Virgin Gorda where I first set foot on the British Virgin Islands at the wide eyed age of seventeen. My father Jack was well aware of his four chicks becoming more free range, and decided to take us on an epic family vacation to be remembered and cherished. What he showed us, and me in particular, helped chart the course of our future. That first visit to the “Fat Virgin” if nothing else helped soften my hard rock musical taste after slipping out of the resort and finding my way to a back street outside Spanish Town, drawn by the irresistible sound of live Reggae music. To this day I have rarely missed the opportunity to hear the greats live: Bob Marley (on his final tour), his son Ziggy, Bunny Whaler, Lucky Dube, Gregory Isaac, Steal Pulse and of course Jimmy Cliff who produced my favorite album “The Harder They Come, The Harder They Fall”. The track “Many Rivers to Cross” was actually playing on my Walkman as a student crossing the English Channel and seeing the White Cliffs of Dover for the first time. That initial visit to the British Virgin Islands for me was a treasure given from father to son. Jimmy Cliff’s music was a treasure given by him to the entire world.
I could go on and on about the Virgin Islands which continue to play an important part in my life. If you read Part Two of my original entry you already know about our family ties to this tropical paradise. The house my father and brother William were partners in is still home to my brother much of the time, and the last time I talked to my father just before he died was in this house.
I am extremely thankful to still have my mom who has played an enormous roll in shaping the lives of my children. Anyone who knows Dot Borden is in awe of her and the love she has shared during her amazing journey.
The most successful Pirate to sail the Caribbean Sea was Bartholomew Roberts, other wise known as Black Bart. He seized more vessels and took on more treasure than all the other pirates combined. A surprising teetotaler, his pirate law was in many ways more of a capitalistic democracy than our government today. Bart was elected as Captain by a melting pot of crew who he generously shared with, while never having to wear a suit! Not entirely unlike Bart’s crew, my parents raised me and my sibs with an understanding of uncompromising fairness, equality, and inclusion. All that I contribute in my own life, professional and otherwise, is largely in tribute to them. That being said, I am painfully aware that there is still an infinite amount of room for growth regarding both me, and the world in which we all endeavor to reside. There is no future without working together, and “I can see clearly now” that there are indeed still “many rivers to cross.”
Rest assured and in peace, Jimmy Cliff.