Pirates of the …. Caribbean?
British Virgin Islands // Travel Logs v.004
January 1st, 2023 // 2:00am
“Everyone in the dinghy” … I faintly hear from Captain Steve declare at around 2:00 am. “Back in the dinghy..?”, I silently wonder. Confused. Intrigued though. We’ve just arrived back after a night of guzzling beers dancing barefoot like fools at the Caribbean’s most famous New Years Eve party (If you’re in the know, then you know where I’m talking about). I’m not entirely sold on getting back in the dinghy but I don’t ever question Steve. He’s one of the few people in this world that I would follow blindly. And not just for his adventurous charm, I trust him to never steer me astray and, more then likely, a good time follows. So back in the dinghy we get! All seven of us, shoeless, inebriated fools. What mischief are we up to now? I have a hunch. I’ve heard these fables of what Steve calls a “Cat Dive” … but have yet to live one myself… Until now.
A Cat Dive is the ultimate yachters mischief. What we consider modern day piracy because unfortunately, looting and sinking ships is no longer practiced. At least we still have the rum I guess.. Anywho.. Cat Divin’ is the ultimate harbor prank. And in a world where most people who “yacht” in the Caribbean for New Years are… posh, uppity and snobby to say the least, this bit of mischief is just the humbling that they need. The mission is simple: Gather all of your rowdiest friends in a dinghy, quietly dispatch from your vessel and sneak around the harbor looking for a target — the richer looking yacht the better. Once that target is agreed upon, you have your driver steer you underneath and in between the catamarans two hulls. Quiet so that you don’t blow your cover. Finally, once underneath the hull… you let it rip. Banging, shouting, hooting and hollering and pretty much anything else you can think of to disrupt their peaceful sleep. A Cat Dive is all in good humor and a majority of victims laugh it off and applaud our stealth. However, some of the snobbier targets take to anger and ridicule. Threatening to call the harbor police as if we aren’t about to cat dive them too HA. Call me petty but, this reaction makes it even more entertaining for us delinquents — gotcha.
That’s how we spent the first waking hours of our new year. We hit roughly 75% of the yachts in the harbor that night, some giving us funnier reactions than others. We evaded the harbor police by impersonating a water taxi — I still don’t know how that worked — and we laughed until it was physically too painful to continue. I fell asleep, drunk, underneath the stars.
I don’t often like to visit a place more than once. And I try to schedule my years so that I don’t. Maybe my theory isn’t for everyone, but I think the world is just too damn big to continue going to the same destination year after year. This place is different though. This trip is different. The British Virgin Islands are an extraordinary chain of islands in the Caribbean blessed with natural wonder both above and below sea level. The land is scattered with rolling green hills, lush palms and white sand beaches. Home to some of the worlds most famous beach bars and… inventor of the Painkiller — A rum cocktail that, if you haven’t tried it you have only lived half a life. While the underside is host to flourishing reefs, colorful marine wildlife and water so warm and perfect that you can, and should, bathe in it.
Every year a group of 8-10 of us spend our New Year holiday sailing these islands. There’s been a core group of mainstays each year with newcomers that tag along to complete our crew. For myself, after a full year of adventure, filming and creating, this is the trip that I get to fully relax. No camera (for the most part), no agenda or expectations. Just simple freedom to breath in the years successes and failures and dream about the one ahead. I pay for a cabin with a bed but I usually end up sleeping in the cockpit or on the deck beneath the stars. Waking up to percolated coffee and that morning ocean bath I was talking about. There’s never a “too early” for beer or rum and we typically crack the first one at breakfast. Which is deliciously whipped up by whoever’s hospitality gene is itching that morning. The itinerary is quite fluid and we tend to go wherever we feel like going. The only requisition is having a kick ass time and being in the water or on the beach. The thing I love about this crew is our uninhibited imagination for fun. We’re by no means the only group that sail these waters every year but I am convinced we have the most fun. And the most stories. For instance, we love to spend New Years Eve day at the Soggy Dollar on Jost Van Dyke. It’s where the party is and we love it. Rum is flowing, sun is shining and people are dancin’, laughin, swimming and partyin’. And whilst joining in on the festivities, we get creative. With a childlike giddiness, we rig the dinghy for some epic dinghy launches or some paddle board wake surfing — I admit the wake is nonexistent on a single 10hp dinghy engine but that’s not the point.
A dinghy launch is a degenerate sport that does indeed have serious implications should you either rig it wrong or mistime your let go. We take the halyard (sailing rope - I don’t know, I’m still learning) and attach one end to the dinghy and the other up and around the mast creating a lever system. Real basic Huckleberry shit. And one at a time we launch ourselves second level deck, let the dinghy pull us out into the open ocean and let go. About 25 feet above the water, free fallin’ our best trick into the sea. While nailing the perfect backflip will indeed land you applause and a great conversation starter to those who watched, getting it wrong will hand you a black eye and a rattling headache — also a great conversation starter. You really can’t go wrong. My friend Josh (I call him Moose) took several of these beatings and earned himself the honors of being the most durable man in the Caribbean. An honor I one day hope to earn.
As far as pirates go, Steve, who I previously mentioned, is as close as they come. Him and his brothers, Sam and Jonny, organize this trip every year and when I grow up (I’m 26…) I hope to be like him. He’s spent years traveling the world, riding motorcycles and sleeping in hammocks on unfamiliar beaches. A proficient sailor and even better rum drinker, he sets the tone for these trips. No bullshit, no drama, just a kick ass time
This trip revives my soul. Reignites my spirit for adventure and refreshes the inner child inside of me. We have our fair share of mischief, modern day piracy and — for the sake of preserving an exhilarating yet confidential story — enemies made in those waters. All good pirates do, right? But we also have a damn wholesome time as well. Every evening we eat family dinner while watching the sunset from our boat, telling stories of the day, laughing, drinking and smoking. Dancing like fools and getting high under the stars. Strangers leave as friends who go on to adventure new places together and stories are lived that will forever be cherished. I like to think of ourselves as the exception to the masses of wealthy leisure sailors who share these islands with us. We’re a far cry from the prim and proper yachting snobs. The same ones who get the angriest at our cat dives. No no no. We do it different. Better in my opinion. And I eagerly await the my next dinghy launch, cat dive and 7am painkiller.
Cheers,
Blake
