Stuck in the Middle

Sometimes we find ourselves stuck in the middle — between two opinions, two extremes, or two possible paths forward. Most of us have been there. And sometimes those situations overlap in ways we don't immediately recognize.

For me, Dominica represents what it means to be stuck in the middle.

Five years ago, I couldn't have picked Dominica out on a map. I knew it was somewhere in the Caribbean — and that was about it.

Sailing north, REIMAGINED stopped in the northern part of the island for over a week. Some of that was intentional exploration. Some of it was weather. And by the end, some of it was simply because it felt good to be there.

The sail in was… confused. Squalls rolled through, the wind swung wildly, and the sea state made no sense at all. We went from 25 knots of wind and 11 knots of boat speed to barely 3 knots of breeze — and no speed at all. Two-meter seas came from every direction: south, north, nowhere in particular. It was messy. Swinging between two extremes.  

But then you approach Dominica.

It feels like the helicopter scene from Jurassic Park. Mountains rise straight out of the sea. Dense, emerald rainforest replaces the usual southern port city most islands greet you with. Waves crash against the Scotts Head (the southern point), and there's nothing manicured or softened about the first impression—just raw, green mass.

Geographically, Dominica sits between two fully French islands — Martinique to the south and Guadeloupe to the north. And when I say French, I mean France: customs, grocery stores, infrastructure, systems. Dominica is literally and physically stuck in the middle.

Dominica gained independence from the UK in 1978 and is part of the Commonwealth. But unlike other independent islands I've visited, you wouldn't know it from the infrastructure or the rhythm of development.

It has an international airport — but not really.

Tourism infrastructure — but only just.

Growing relationships with China — maybe, but tentatively.

A collaboration with the country of Morocco to build an epic hotel that sits decaying, 95% built but not completed.

Everything feels… undecided.... in the middle

Should it lean into global partners or protect its independence?

Should it develop tourism or preserve what makes it wild?

Should it make its epicness accessible — or leave it earned?

Dominica feels like an island paused between choices.

And yet — that's exactly what makes it compelling.

Coming from places that are highly developed and carefully curated — Sugar Beach being a perfect example — Dominica offers something increasingly rare. A friendliness that feels unpolished. A sense of exploration that isn't packaged. A wildness that hasn't been "optimized".

If you truly want to get off the grid — not in theory, but in practice — and you're trying to figure out where that still exists, I'd point you to Dominica.

Stuck in the middle, maybe.

But not lost.

And a reminder that being in the middle is sometimes a good thing.