Sailing Antigua – Rum Punches, Rainstorms & a Leaky Surprise

After the drama of Montserrat, we set our sails for Antigua, that jewel of the Caribbean sailing world. And would you believe it, for the first time ever we actually beat Mooze (our sailing pals) thanks to a cheeky little wind angle. Not just by a few boat lengths, darling — we were a whole two hours ahead. Victory tastes sweet, especially at seven knots.

We dropped anchor in Jolly Harbour, which is just as delightful as its name suggests. Ian hopped off with Rik from Mooze to do the dreaded check-in dance, while the rest of us got straight to the important business: rum punch and exploring Jolly Beach. Two nights of this and we’d already had too many cocktails, too many plates of local delicacies, and far too much fun pretending we were on holiday instead of, you know, actually living on a boat.

Wing Foiling Like Schoolboys

While anchored in Jolly Harbour, Ian and Rik decided to take a full-day wing foiling lesson. Off they went, like two adventurers on a quest. Caroline and I, much wiser, settled into a beach café for a civilized coffee-and-lunch date.

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When the boys returned, they were grinning ear to ear, buzzing like schoolboys who’d just conquered the playground. Within 24 hours, both had bought themselves shiny new foils. Honestly, I’ve seen toddlers with less determination in a toy shop.

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A Rainy Surprise in Antigua

We waved goodbye to Mooze (again… it’s becoming a running theme), and tucked ourselves into a snug anchorage on Antigua’s west coast to hide from incoming strong winds and rain. Later that evening, our friends from OV surprised us by dropping anchor nearby — clearly, great minds think alike. Naturally, this meant sundowners on the beach, where they also introduced us to new friends from Honutime. Another round of friendships forged over beer this time around. The sailing community never fails to deliver.

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Then came the chaos: at 2 a.m., the wind spun 180 degrees, dragging both us and OV across the anchorage. Picture it — boats far too close, gusts howling, pitch-black skies. Not exactly the Caribbean dream. We took turns on anchor watch until daylight, then tried to reset the anchor. Cue torrential rain. Not a gentle drizzle, no — this was biblical. Try anchoring when you can’t even see your own hands in front of your face. It took three sweaty attempts before we finally set the hook properly.

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And just when I thought we’d earned a break, I noticed water dripping inside the boat. Never a good sign. Turns out the flybridge hardtop hadn’t been sealed properly when installed, so the rain had gleefully poured its way through screw holes and into our saloon. We spent two days living inside what felt like a construction site, drying everything out and sealing leaks.

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Antigua Sailing & Marina Life

Luckily, Antigua doesn’t stay gloomy for long. Once everything was patched and dry, our friends from Infinity popped over for coffee, and we had front-row seats to Antigua Sailing Week action right from the deck. There’s something magical about watching world-class racers skim by while you sip your morning brew.

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Finally, with our boat dry and spirits restored, we slid back into Jolly Harbour Marina to meet friends flying in for a visit. Because if there’s one constant in sailing life, it’s this: as soon as one adventure ends, the next one is already knocking.

A Little Icelandic Surprise

We’d just tied up in Jolly Harbour Marina when I (Dee) went off to do the check-in paperwork. Sitting there, waiting in line, I kept staring at something on the shelf, thinking, no… it can’t be. And then — lightbulb moment! It was an Icelandic book. In Antigua. I mean, really? There aren’t many Icelandic sailors bobbing around the Caribbean, so stumbling across that was an absolute treat — and made me laugh out loud in the customs office.

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Then the rest of the day was spent scrubbing the boat, catching up on laundry, and tidying everything in preparation for Jamey and Kelley’s arrival the next day. Nothing like a bit of elbow grease (and fresh sheets) before welcoming guests aboard in paradise.

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