Nine Days Until the Azores and Already Feral

We leave Bermuda and begin our Atlantic crossing to the Azores aboard our trawler with our dog Gypsy. Ocean life quickly descends from romantic sailing fantasy into stained clothes, fake grass potty struggles, Bermudan fashion obsessions, and a slow transformation into maritime goblins.

Nine Days Until the Azores and Already Feral
Dramatic limestone. Angle Beach, Bermuda May 16, 202

I am sitting in the trawler pilot house while around me my husband and dog snooze the afternoon away .Its a full nautical snore-fest. The ocean is calm, with the occasional swell gently rocking the boat in a way that feels soothing and not nauseating. I once again thank the universe for bequeathing me, a London born land lubber, with a seemingly iron-clad stomach… so far anyway.

We left Bermuda yesterday and 150 miles ago. Only another 1,643 miles to go. We loved Bermuda. In fact, I accidentally began what can only be described as a Bermudan-themed collection. “Did you collect photographs of the extraordinary birds?” I imagine cultured readers asking. “Or perhaps sketches of the dramatic limestone formations?” No, dear reader. You know I am far too shallow for that: I became unhealthily obsessed with the dress style of the Bermudan businessman. Specifically a certain type of deeply confident Bermudan gentleman who strolls around Hamilton wearing snug pastel shorts, knee-high socks, brogues, and a blazer with the energy of a man who has never once doubted himself in his entire life. There are apparently bonus points if the colors resemble Easter eggs or the primary colors of the British flag. There seems to be no age limit either; I saw young hip Asian types, old-man-of-the-sea sorts, Dad-bod types and everything in between.

Who wore it better? These were the salty sea dog types.They clearly lost some bonus points for the generous length of their shorts, and the lack of pastel, but the sync stepping in brogues is a winner. Royal Bermuda Yacht Club, Hamilton, Bermuda May 15, 2026


The truly fascinating thing is that they all look magnificent. Not ridiculous. Not funny. Unashamedly magnificent. Like retired MI6 agents who now spend their days discussing yacht insurance and rum. (We learned that billions flow through Bermuda for “re-insurance,” which is apparently insurance for insurers and, rather alarmingly, becomes especially lucrative when disasters happen.) There are actual stores in Bermuda with names like The English Sports Shop, founded in 1806 with its own crest, devoted entirely to this aesthetic. I briefly attempted to persuade Captain Silver Fox to purchase a pair of these hot fashion tickets for the modest sum of $150, but thankfully he declined. Probably for the best since I have not seen the man change clothes since departure. At this point I believe his T-shirt may actually be achieving structural integration with his body. An authentic, and cheaper, sporting look.

An aspirational life size photo at a store front in Hamilton Bermuda, where this look can be yours for about $1,000. But if you’re an insurer to the insurers this is apparently peanuts.
Despite the frustrating chair obstruction, this one is a fave in my collection - as Mr Tommy Bahama Tourist looks on clearly in awe at the local Bermudan dandy’s brazen bare knees and precocious pastel accents. Hamilton, Bermuda May 18, 2026

We are on day one of the longest boat passage I have ever been on. Crossing the Atlantic — from Bermuda to the Azores — on our own boat. It sounds wonderfully romantic to say that, doesn’t it? Like something involving matching nautical sailing outfits, stunning sunsets, and standing wistfully at the bow holding a spyglass and a rum cocktail. So far, however, my experience of ocean crossing has involved more trying to remember whether I have brushed my teeth today or when I last showered. Clothing changes are no longer an essential daily commitment, and Captain Silver Fox is dead against drinking any alcohol whilst under way (there may be a mutiny brewing on that one at some point). Admittedly the sunsets are spot on.

It is true the sunsets are breathtaking. Taken just now, somewhere in the Atlantic, May 21, 2026

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There is something deeply strange about being at sea for days. Time begins to unravel almost immediately. Breakfast appears to happen every eleven minutes. I’m drinking coffee in the evening and decaf tea at noon. I’m day napping for hours and then up all night like a retired Ibiza DJ. This is not out of choice; we are a crew of two, and someone always has to be on watch (the dog sensibly refuses to participate in this madness) and so we have to take shifts. Tiny decisions become major events. “Is it too early to open up the good biscuits yet?” suddenly carries the emotional weight of a hostage negotiation.

Even the news now feels bizarrely detached from reality. Reading headlines from land is a bit like watching a David Attenborough documentary. You observe from a safe distance strange creatures living in an entirely different habitat, worrying about traffic and politics, whether a billionare’s data center is going to ruin their town and whether the barista remembered to make their latte with oat milk - while you yourself are floating through the middle of the Atlantic with the sole purpose of trying to convince a dog to pee on fake grass attached to the bow of a moving house.

Earlier today Ken casually mentioned that we might arrive in the Azores on Saturday. I was thrilled. Saturday sounded perfectly manageable. A jaunt even. Then I discovered he meant next Saturday. Not in two days. In nine. NINE. Nine days is such an absurd amount of time to be away from land that my brain simply refuses to process it. And oddly, that is also what feels wonderful about it. Out here there are no errands to run (I just stare at dirt and then look away — how dirty can dirt really get?). No Amazon packages arriving (we still have a new camera and digital binoculars stranded in St Thomas. No more attempting online purchases for me). Nobody asking whether you have “just a quick minute.” The Atlantic has very firmly informed us that we do not. And a schedule completely determined by the sun and the ocean. Ok, that bit sounded quite romantic.

Of course, we are not exactly floating hermits. To observe life as we knew it we have Starlink onboard, feeding us information all day long, one expensive gigabyte at a time, plus a backup mini Starlink just in case the primary internet for our floating split-level fails. I genuinely cannot comprehend what it must have been like crossing oceans with no communication whatsoever. By now either me or Ken would almost certainly have been formally banished to the dinghy like a drunk MAGA uncle at Thanksgiving.

Meanwhile, outside, the Atlantic stretches endlessly in every direction looking smug and ancient, and somewhat like a giant organism, like it has watched generations of optimistic sailors leave harbor full of dreams and coordinated nautical outfits only to descend into damp goblinhood by day three. It looks calm and tranquil right now, but we are fully aware the Atlantic can decide to spice things up a bit whenever it gets bored. We are at its mercy. No wonder sailors prayed to Neptune. See why I‘m hanging on to my stash of wine?

As for Gypsy, we have attempted a bold new strategy for this crossing. We moved her potty patch to the bow where it is quieter and more pleasant than the back deck. We are hoping the improved ambiance will encourage her cooperation. Perhaps she simply objected to offering her “gifts“ so close to the engine room. Maybe she requires an ocean view and a calming spa atmosphere. So far, after twenty hours at sea, she remains emotionally committed to the principle of holding it forever. I have expensive Bermudan pumpkin and organic duck dog food laced with mineral oil at hand.

As we now know, there is something deeply strange about being at sea.

Apparently this position is desirable for napping. Gypsy The Sea Dog. The North Atlantic Ocean, May 21, 2026

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