St Maarten Sailing Adventures: Thrilling Simpson Bay Bridge Crossings and Plane Spotting.

Darlings, gather round with your rum punch (or tea, if you’re feeling particularly civilised), because our St Maarten sailing escapade was equal parts magical and mildly terrifying, like auditioning for a dragon-riding role but with actual currents and a very narrow gap instead of CGI.

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We set sail for St Maarten (or St. Martin, depending on which side of the island you’re fancying), and oh, what a lovely sail it was. Smooth seas, steady winds, the kind that make you feel like the queen of the Caribbean. We dropped anchor around 2 pm in Simpson Bay, tendered ashore, and dashed straight to check-in before the offices decided to call it a day. Procrastination? Not on our watch.

The next morning, we had a date with destiny: the infamous Simpson Bay bridge opening at 11:00. Up came the anchor, into line we slotted, hearts pounding like I’d just been told to improv a speech in front of a live audience. The current was cheeky, the gap ridiculously narrow, nerve-wracking? Absolutely. Fun? Ridiculously so. We made it through without incident (or dramatic capsizing), giggling like schoolkids the whole way. There’s something gloriously absurd about squeezing your floating home between concrete walls while cars honk impatiently on the bridge above. Caribbean cruising at its finest.

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Once inside the Sint Maarten lagoon that magical divide between the French and Dutch sides—we motored gently to our booked marina slip. Secured the boat, ticked off the marina check-in list like responsible adults, and then the four of us (Ian, me (Dee) and our dear friends Kelley and Colin) hopped a bus to the legendary Maho Beach for some prime plane spotting St Maarten action.

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Picture this: lounging on the sand, cocktails in hand, late lunch devoured, while massive jets roar overhead so close you could high-five the pilots. The sheer thrill of it! Planes landing practically over our heads, the whoosh of engines, the sand kicking up, pure adrenaline. We spent hours there, laughing, pointing, and generally behaving like excited tourists (which, let’s be honest, we were). Absolute bucket-list joy.

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Back on the boat, we spruced up for our last dinner with Kelley and Colin at Roxxy Beach restaurant (tragically closed now, but forever legendary in our hearts). Great food, greater company, and the kind of evening that makes you grateful for every nautical mile shared.

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Bright and early the next day, we waved a teary goodbye as Kelley and Colin headed to the airport. I perched on the bow with a cup of tea and waited for them to fly over and then there it was their plane soaring right over the marina. Bye-bye, darlings. Sniff. Waving like a scene from a rom-com,

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With the island waking up, we zipped to an outboard shop for our pesky engine woes. The lads there? Absolute heroes. Diagnosed it in seconds (“Easy fix, love”), handed us a few spare parts, gave crystal-clear instructions, and boom less than 30 minutes later, our outboard purred like new. Sailing gods smiled upon us.

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Our friends from Infinity rolled in for watermaker repairs, so naturally we celebrated with food and drinks. Because what’s St Maarten without good mates and great grub?

We crossed the St Martin bridge again the next day this time far less white knuckled, far more “haha, we’ve got this.” Confidence is a wonderful thing.

We’d planned just a quick stop in St Maarten to drop off friends before pushing to the BVI, but the weather had other ideas. So we stayed nearly a week, bliss! Sleeping in, deep-cleaning the boat, restocking the fridge and cupboards, and just chilling. Caribbean downtime? Don’t mind if I do.

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Our departure was set for March 16th Ian’s birthday so the night before, he requested McDonald’s for his special dinner. Yes, darlings, McDonald’s exists in the Caribbean. The catch? Only the drive-thru was open. So I, heroic Dee, marched through said drive-thru on foot, ordered like a boss, paid at the window, and carried the bags back to the dinghy where Ian waited. Birthday king in his element. We laughed until we cried.

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The next day: naps galore to prep for our overnight sail. And joy of joys our Infinity pals decided to join us (on their boat, naturally) for the passage to the BVI. Sailing in convoy with the famous “king and queen of cows” from the Isle of Wight? May the odds be ever in our favour.

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BVI, here we come. Bring on the next chapter of this wild, wonderful Caribbean cruising odyssey.

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What about you, loves? Ever braved the Simpson Bay bridge? Survived Maho Beach plane spotting without losing your hat? Or walked through a drive-thru for birthday nuggets? Spill in the comments, I’m dying to hear your tales!

(And if you’re plotting your own St Maarten sailing adventure, drop me a note. I’ve got tips, laughs, and probably a spare rum punch recipe or two.) 💙⛵✈️

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