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A Good Expectation: Antigua to St. Bart’s In An Old Smuggling Sloop

By Wendy Heisler

So there we are: a rogue crew of 7, bobbing in a lazy circle not far from Antigua. Just us and an engine-less wooden Carriacou Sloop called Good Expectation, which we had previously believed was called Great Expectations. We had been floating in approximately the same position for 24 hours. The wind? Taking a vacation somewhere else. The sea? Glass. Our morale? AMAZING – because we were about to crack frosty beers on a sunny day.

Let’s rewind. It’s Thursday morning in Antigua and the Picton Castle crew are doing their Picton Castle thing. Tidy up, hoist the small boats, prepare the ship for departure. Just as I had finished flexing my bulging ladypirate muscles while single-handedly hauling the rescue boat into position (ok, I admit that another 20 people may have been involved), Mate Mike summoned me to the bridge. If you aren’t aware, trainees such as myself are normally not to set foot on **~~The Bridge~~**, which is a lookout spot exclusively reserved for Captain and the Mates. Naturally, I concluded that I must be in trouble.

6 of us stood wide-eyed as Mate Mike presented a scenario to us: our mission was to deliver a Carriacou Sloop to St. Barth, with a stop-over in Anguilla; the sail would take about 2 days. Were we interested in joining as crew? Um…. how about YESYESYES.

We immediately gathered provisions and necessary cargo. Food for several days, propane, water, dishes, passports. A change of clothes, camera, notepad. Also beer and ice (very important). 45 minutes later we were stepping on board our new (temporary) home. The captain took us aside and told us that this would be very different than Picton Castle; we were going from a big steel ship with all sorts of gear to a small wooden sloop with no engine.

Soon we were out on the open water, waving buh-bye to our Picton crewmates, celebrating the adventure ahead of us. There was Mate Mike, the brains behind the operation and all-around sailing guru. Paula and Katelinn; Picton pro crew, back-up brains and bada** ladies. Davey and Fred; bros, brawn and skill. Me: slightly nerdy, very clumsy trainee with 2 months sailing experience. And bonus crew member Ollie, the bonvivant who would be documenting our expedition. Smells like a sitcom?

We’re screaming along at a terrifying 2 knots, smiling like fools. We’re free, baby! This is living! This is the stuff dreams are made of! And then… nothing. The wind takes an extended coffee break and leaves us staring at Montserrat, an active volcano, several miles off our port quarter. Antigua looms behind us and a tiny island called Radonda peeks from the horizon dead ahead. The calm does not faze us – we jump in the water and open chilled beverages, then eat dinner while watching one of the most spectacular sunsets I’ve seen with these virgin eyes. Katelinn pulls out her violin and we sit in a content post-supper haze, and life seems perfect.

Oh, wait. Speaking of Katelinn, let’s focus for a moment on this lady’s genius. With Paula’s assistance, she rescued a propane tank SANS REGULATOR into something workable using only chopsticks, duct tape, a latex glove and small empty tube of sunscreen. People of earth, because of these modern day MacGyvers’ brains and persistence, we were able to eat hot food on Good Expectation. Praise Neptune, hallelujah.

I’ll spare you from the hourly logging of our 2 day bobbing session, but let it be known that we floated on glass for practically 48 hours. Antigua jeered, Montserrat blew its smoke with Parisian arrogance and Radonda remained as a mere chocolate chip on the horizon. Ollie stood at the bow, all 7 feet of him, and called out, “heeeere puffy wuffy!” Fred and Paula dove underneath the hull to remove a seaweed beard that had grown in the harbour. We took naps to avoid blistered lips (and also because we could). We took down the mainsail and put up the awning. We jumped in the water for multiple swim calls (Paula avec coffee). We rationed Heinekens so that a) they wouldn’t disappear in one foul swoop and b) they would be much more exciting to drink as a reward for our patience. We weren’t going anywhere, but we were relaxed and we were happy.

Then… DAY THREE. MAGIC. The wind found us overnight and by jove, we were moving! Sayonara, Antigua! See ya never, Montserrat!** Davey was prepping the fishing lines and he asked me what the catch of the day should be? We agreed that mahi mahi would be best. No lie – the guy hadn’t even finished tying the lines when he called, “FISH ON??” Somehow – whether it was brute strength or sheer determination – the boys hauled a massive mahi up on deck, which proceeded to flop violently and desperately… straight into our cockpit. Mate Mike tackled it like a rodeo ninja and … well, I’ll spare you the details, but 5 minutes later he and Davey were fileting a 40ish pound mahi mahi.

Oh, sweet bliss. Soon I was scarfing down the best galdang fish I’ve probably ever eaten – Mike fried it up with some oil, salt and pepper – and by day’s end, the 7 of us ate pretty much the entire thing (please, hold your applause). Other things that were awesome: we were speeding by St. Kitt’s & Nevis; a whale surfaced to say hello; we had decided to go directly to St. Barth aaaand once again our evening concluded with a violin serenade. Ladies and gents, this was a perfect day.

The next morning we sailed triumphantly into Gustavia Harbour, St. Barth. I imagined that the giant Beyonce yachts gazed at our charming dreamboat of a sloop with yearning in their eyes, for we had successfully spent three days experiencing a real ol’ fashioned sailing adventure. Our vessel was small but sturdy, we caught our own food, we slept under the stars on deck (or in a pile below), we used paper charts (gasp!), we had no engine and were therefore at the whim of the elements. It was epic.

After sailing gracefully to the dock (again, no engine required thankyouverymuch), we spent the next 5 days bumming around St. Barth before Picton Castle arrived. Some of us had no wallet, some of us had no shoes (aka: me), but all of us had an unforgettable time. Of course, that’s another story…

**This is actually a lie. On our passage from St. Barth to Carriacou I woke up early one morning to see Montserrat glowing behind us. I shook my fist, lovingly.

Fred at the helm of Good Expectation
Good Expectation in the calm Caribbean Sea
Major cleanup aboard Good Expectation while stern-to at St Barts
Mike cooks supper on the Good Expectation
Sunrise on board the Good Expectation

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