New video - Private Island, Public Beach… and our Rock Star Guest

A private island, a forbidden tree line, and a dog who keeps introducing us to famous people. Guana Island delivers perfect sand, strict rules—and a very unexpected guest list.

New video - Private Island, Public Beach… and our Rock Star Guest
White Bay, Guana Island. Nothing but smug sand, a better shade of sun and discretely placed “private island” signs. January 31, 2026

Ah, Guana Island-an island, in an already posh corner of the world, that gently reminds you paradise comes with rules. With multiple discrete PRIVATE ISLAND. NO TRESPASSING signs dotted along the beach it is clear that the owners will allow you to enjoy the beach… but do not cross the vegetation line or else. And yet—we love it.

After what has become an unscientific but extremely committed study of roughly 100 beaches (margin of error: rum), this one still wins. There is nothing here but beach. No sun loungers staging a coup. No vendors selling coconuts or ”authentic” shark necklaces. No jet skis auditioning for “Fast & Furious: Necker Island Drift”. Just uninterrupted, slightly smug sand.

The opposite esthetic to Guana: Cane Garden Bay on Tortola. I am sure that underneath all of those empty plastic chairs, there is a good beach wishing to come out to play. Gypsy enjoyed finding the odd discarded chicken bone and “authentic” shark tooth.

Which probably explains the understated clientele. Including, as it turns out, Billy Squier and his lovely wife Nicole.

We didn’t meet them because of our dazzling charm or Ken’s thrilling lectures on marine engine parts. We met them because of Gypsy. She’s essentially running a global meet-and-greet for people missing their own dogs. You can spot them a mile off-approaching with purpose, smiling warmly… at her. We’re just the slightly irritating admin team on the end of the leash.

Gypsy, she hooks people in with those soul searching eyes and closes the deal with unlimited kisses and drewl.

One thing led to another, and suddenly we were inviting a rock legend onto the boat like this is a thing that happens now. (Younger me would have had a caliption, but age does in fact bring some advantages.)

The video is below-chock a block with a perfect beach, doggy dinghy drama, dinner with a rock star and Ken making light of a sewing chore - further evidence that our life has taken a sharp and slightly baffling turn.

While you’re there, hit YouTube’s subscribe button: We’re planning to start YouTube Live sessions as we edge toward our Atlantic crossing - scheduled to start on May 7th - so you can join the adventure virtually, which feels like the safer option for everyone involved.

Enjoy…

Crew Members: scroll below the video for where we are now and what questionable decisions are coming next.

What’s next?

You may recall our recent “light brush with reality” (read: I briefly considered retiring as a sea creature and booking a spa week on land). Since then, Ken and I had polite discussions about my learning style and his teaching style and after some deep thought (on his part) we came up with a plan that works well for both of us: He will now teach to my learning style.

Join the Crew

Like following two semi-capable adults who sold everything and sailed into the unknown? Become a crew member and get new episodes, stories and questionable decisions not for public consumption delivered straight to your inbox.

It also turns out—per my entirely unqualified (but equally mental) sister—that I come with a starter pack of ADHD, RSD, and PDA. Me and boating have more in common than I thought; we are both challenging, often tempestuous and acronym-heavy. So now I have medical reasons why I am someone who struggles to focus, hates being told what to do, and doesn’t love criticism… Ken is such a lucky man to have such a challenging student to teach ocean safety to. That said—we’re making progress.

We’ve practiced man-overboard drills (no actual men harmed), during which I learned that pointing at nothing in the ocean is apparently serious business and not something to snigger at. I’ve suited up in my PFD (Personal Flotation Device), leapt in, and briefly transformed into a distressed jellyfish while locating various emergency attachments—whistle, beacon, tube—like a nautical escape room. Fortunately my former life as a busy real estate broker often had me driving, while negotiating a deal on the phone, and also putting make up on….so I aced this grabbing at things while under duress test.

Does this make my head look small? Be honest. Me testing out my PFD. Peter Island, BVI April 21, 2026

I’ve also successfully helmed the boat onto three mooring buoys. THREE. This means I drive, Ken hooks, and I experience deeply unattractive levels of smugness as I boss him around. All of these drills are building actual confidence. That-and the fact it costs about $50,000 to have someone else take the boat over the Atlantic-means I’m now feeling both capable and financially virtuous.

Next stop: Crown Bay Marina in St. Thomas on May 1. We’ll provision, collect approximately one thousand packages kindly received by our saintly friends Gene and Mary, and attempt to rehabilitate boat carpets which are on the verge of producing their own life forms - only they can’t do night watches - so they need to go. The only useless creature on the boat will be the dog.

Then we head to Bermuda—five days, five nights, no land, and no beach for Gypsy. Just a square of astroturf and what will become the Crapper Crucible….the Toilet Tribunal……the Great Potty Reckoning. This will of course all be reported on in great detail for you dear reader, and in our YouTube Livecasts.

But first—one last hurrah in the BVI: Necker Island. Yes, that Necker. Tomorrow, we finally get to go past the vegetation line on another billionaire’s island.

I will report back… assuming we ever leave.

Join the Crew

Like following two semi-capable adults who sold everything and sailed into the unknown? Become a crew member and get new episodes, stories and questionable decisions delivered straight to your inbox.