Rachael Pereira

The Islands · June 15, 2026

The Calypso Boats of St. Thomas

By Rachael Pereira

Before there were runways in Las Vegas or boardrooms on NASDAQ, there was Red Hook — the working end of St. Thomas, where the ferries load for St. John and the water is the exact impossible blue the postcards promise and never quite deliver.

The vintage Calypso Boats 'Explore Me' power boat rental brochure, St. Thomas
The rental card we handed out at the docks: Explore me. Get adventurous.

That is where Calypso Boats, Inc. kept its harbour — American Yacht Harbour, Red Hook, St. Thomas, U.S. Virgin Islands 00802 — with a rental desk out at Compass Point and a franchise up at the Ramada Yacht Haven. The logo was hot pink with a little sun sitting on top of it, and the tagline was the kind of thing you only earn honestly: a boating tradition in the Caribbean for over fifty years.

The pirogue, refined

Down island, everyone knows the pirogue. It is the fisherman's boat, shaped by hand out of wood long before anyone thought to sell it, and it has carried the Caribbean's living for generations. Calypso's boats grew from that same lineage — the same silhouette the fishermen trusted — modified, hull by hull, for performance and for the comfort of a family who wanted to spend a lazy, warm day out on the sea rather than haul a net across it.

By the early nineties the yard was turning out four boats a month: 22- to 27-foot center consoles, Mercury outboards on the transom, each one rigged with a VHF radio, a bimini for the sun, an ice chest, a stereo, a fish finder, and every piece of Coast Guard safety gear it was supposed to have. We built the dock boxes too, made the dinghies, and took on a sizeable repair contract with one of the big cruise lines. My husband Paul ran it as president; the family ran it the way island businesses are always run — everyone, all at once, all the time.

$150 and a full tank

The rental pitch was gloriously simple. Imagine an island far away from the rest of the world; lush green hills, magnificent blue water, powder-white beaches — in a word, paradise. One hundred and fifty dollars a day, fuel included. Present the card at Compass Point. Go fishing, go diving, or go nowhere in particular, which was always my favorite itinerary.

The feud in the mailbag

No good island story is complete without a rivalry, and ours played out — where else — in the letters pages of Caribbean Boating. A gentleman in Florida took public exception to who, exactly, deserved credit for the design of a small Caribbean powerboat, and Paul answered him in the "C.B. Mailbag" with the particular relish of a man who has both the paperwork and the last word. The exchange ran for issues. At one point Paul, in what he described as recognition of the other man's confusion, announced he had named a boat in his honor: Silly Old Man.

A 1991 Caribbean Boating 'C.B. Mailbag' clipping about Calypso Boats of St. Thomas
Caribbean Boating, 1991 — the great Calypso Boats correspondence, in full.

I keep the clipping and the little pink brochure together, because between them they hold something the résumés never do: the sound of a working dock at Red Hook, the smell of two-stroke and salt, and the certainty — earned one hull at a time — that beauty and hard work have always been the same tide.

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