Christmas at Sea in the Caribbean-Drones, Family and Island Life

A funny, honest take on Christmas at sea in the Caribbean-drones, family, private islands, and learning to feel at home while unanchored.

Christmas at Sea in the Caribbean-Drones, Family and Island Life
Moonfleet's Christmas Crew, Great Harbor, JVD, British Virgin Islands. December 21, 2025

I cannot believe I managed to get the above shot. I love modern technology, but I’m fairly certain it does not love me back.

The above photo was taken 2 days ago in Great Harbor, Jost Van Dyke, and required the kind of coordination usually reserved for difficult equestrian real estate negotiations (if you know horse people I know you are nodding your head in sympathy). First, I had to wrestle the crew (including the dog) into some vaguely festive attire. Then I had to wait for the gusts to die down, consult my rune stones, whisper an incantation to the sea gods, launch the drone, and finally hide the console behind my back so I didn't look like a weird middle-aged gamer who’s wandered into the wrong matrix.

We achieved exactly one usable shot before it all disintegrated...including our smiles. At which point Ken had to lunge and grab the drone mid-descent before it committed suicide by Caribbean.
Ken: 1. Drone: 0. What would I do without this man?…

We’ve had our Daughter, Elsa on board for just over a week now. Her near-constant yawning has eased, and she has even referred to the boat as “home,” which feels like a small but meaningful victory. She arrived bearing a travel-weary English Christmas pudding and some battered Christmas crackers, so we’ll have a few jolly Holiday relics from the Mother Country. It’s wonderful to have at least one family member with us for Christmas—even if it’s hard to feel festive when you’re turning a deep shade of crispy bacon (you will not find this color in the Dulux paint catalogue) and standing on sand instead of snow (and yes, I know, nobody feels sorry for us).

One of our new top 5 beaches in the world. White Bay, Guana Island, British Virgin Islands, December 23, 2025

The last few days were spent off Guana Island, BVIs which is absurdly idyllic. It’s privately owned, has a boutique hotel where rooms run about $1,200 per night per person, and is apparently popular with celebrities and billionaires who are too cheap—or too lazy—to buy their own island. We stuck to the beach, which is legally open to the public up to the vegetation line. We scanned that vegetation thoroughly with discreet marine binoculars, and our "bird dog" hoping to spot someone famous. Anyone. But alas, not even a lesser injected Kardashian was seen.

It was nice to spend a few days in relative peace and tranquility after the JVD Soggy Dollar bar crowd. (Thanks for the drinks Heidi and William!) Now we’re chugging toward Virgin Gorda (apparently named by Christopher Columbus because he thought it looked like a fat virgin - it has to be said he had been at sea a long time) and Bitter End Yacht Club, where we’ll be forced to do things like shower and wear clothes, preferably with a symbol of wealth on it…like an exclusive golf club or a tiny whale….in an attempt to appear less boatferal, less "gorda" and re-enter civilization without alarming anyone.

There has been no Amazon to smooth the path of Christmas shopping—no shops at all, really—except for the hippie at the Soggy Dollar on Jost Van Dyke selling crochet bikinis, a baby goat and magic mushrooms. I considered all options with solmen dedication, but eventually decided the crocheted bikini would not be enough to tame Ken's chest hair, and Elsa can't keep goats in her student digs - so instead this year we’re giving each other experiences. Granted, our entire life is currently one long experience, but to make it feel festive and little more deranged I’ve booked a wing-foiling lesson for three (one participant, two hecklers), followed by scuba. That Christmas pudding doesn’t stand a chance.

And finally—thank you. Truly. To everyone who has waded this far through the journey and this post. Over the last almost two months of traveling, I’ve realized how much remote connection matters to me—how much it makes me feel part of a community, even when I’m floating somewhere between islands with questionable Wi-Fi. So thank you for being part of our worldo. It means more than I can probably explain without getting sentimental and blaming the magic mushrooms that I maybe did buy after all - only me and Santa know the truth.


Ok Cap’n Silver Fox chiming in. First off, Merry Christmas and/or Happy Holidays to all our family and friends. We miss you and thank you also for following along. I’m writing this sitting on Moonfleet’s bow having had a chance to really relax while in a secure slip at the Bitter End Yact Club Marina in East Virgin Gorda. I truly love being at anchor off some seclude island beach but it isn’t until we tie up on a secure dock that feel a modicum of relief from the ceaseless stress and responsibility of being the Captain of a boat at sea. Even at the dock it’s still there but I don’t have to worry about dragging anchor, or breaking a mooring line or is the dingy secure or why is there a funny noise awaking me at 0335 (that was a huge yacht weighing anchor near us last night). Generally while at anchor I wake up at least twice a night for a quick security check. I cannot help it, just about everything I love is on this boat. So here we are, several cocktails in and relaxing in a secure environment (almost) for the next several days, including Christmas. We’ve come a long way since November 1st when we cast off from the Sailfish marina in West Palm Beach and it’s been such a rewarding journey, but here we are settled in and enjoying some shore time as we prepare to celebrate Christmas in the Caribbean.

Beach Bar, BEYC Virgin Gorda

The world seems crazy when I look too closely , but when I open my view and see the bigger picture, especially where we are, it’s just one big beautiful miracle.

Scrub Island Resort
M/Y NAHLIN , 300ft steam powered ship owned by Sir James Dyson
Still Married! 🤣

We wish you all a Merry Christmas and Happy New Year !

Ken and Kirsten