From Shirley Heights to St. Kitts: Rum Punches, Railways & Ridiculous Laughter

So, six had become four.
Our floating circus had downsized — but fear not, darling, the fun most certainly hadn’t.

It was a Sunday in Antigua, and we’d heard whispers (more like enthusiastic shouts, actually) about a place called Shirley Heights Lookout. A restored military lookout and gun battery turned legendary sunset party spot. Rumour had it, the Sunday evenings there were the stuff of Caribbean legend. So, naturally, we had to investigate.

.

We took a taxi up the winding hill, and before we’d even made it inside the main area, the views hit us — the kind that make you involuntarily say “Oh, stop it!” at the horizon. The first thing you see? A bar offering two-for-one rum punches. Well, when the universe gives you a sign that clear, you obey.

.

Inside, the party was already in full swing. The band? Electric. The crowd? Glorious chaos. The smell of barbecued heaven drifting through the air? Irresistible. As luck would have it, Kelley and Jamie were still on the island, so they joined us for the Shirley Heights shenanigans — and what an evening it was. The dancing, the laughter, the absolute refusal to take anything seriously… I’ll let the photos tell the rest, but let’s just say my hair was doing the salsa long before I was.

.

The next morning? Let’s call it a “slow start.” Two of us were still ever so slightly… rum-punched. But the sea waits for no hangover, so off we went — sailing from Antigua to St. Kitts under a perfect Caribbean breeze. The kind sailors dream about: calm seas, steady wind, and just enough salt spray to make you feel heroic. Eight hours later, anchor down, and time for the boys (Ian and Erik from Moose) to check us into St. Kitts.

.

Meanwhile, I organised a day tour — because, of course, I can’t resist a plan. By sunset, the crew were wing-foiling, the wine was open, and we were laughing ourselves silly about the night before.

---

Exploring St. Kitts: Trains, Rum & a Bit of Chaos (Naturally)

The next day, we went full tourist mode — starting with the St. Kitts Scenic Railway, one of the most beautiful train rides in the world. Built back in 1912 to haul sugarcane across the island, it’s now an absolute gem of a journey — complete with sweeping ocean views, rolling green hills, and, bizarrely enough, alcoholic slushies at 10 a.m.

.

Yes, you read that right. Slushies. With rum. Before breakfast. And somehow, it was absolutely perfect. We chugged along, passing the old sugar mill chimneys and learning how St. Kitts’ history of sugar farming shaped the island. The views were breathtaking, and the commentary was as sweet as the rum.

.

After two hours of sightseeing bliss, our taxi driver whisked us off for lunch at a local spot, you know it’s good when locals are queueing for takeaway. The food was divine, the laughter infectious, and our bellies very, very happy.

Next stop? A local rum distillery, because clearly we hadn’t tried enough rum this week. (Purely for research purposes, of course.) Then it was off to the beach for sundowners, salty swims, and yet another round of “let’s order one more just because.”

We ended up at a lively little beach bar, where Caroline somehow ended up behind the counter mixing drinks while the waiter had his dinner. Honestly, the woman could charm her way into Buckingham Palace with that smile. Afterward, we strolled down the beach to a seaside restaurant for dinner under the stars.

.

The night finished with a dinghy race back to the boat — pitch black, no torches, just laughter echoing across the water. I’d love to say we arrived gracefully… but let’s be real.

---

Goodbyes & New Horizons

The next morning, we sipped our coffee and tea as the sun rose over St. Kitts — that soft, pink Caribbean light that makes everything feel cinematic. We waved goodbye to the Moose crew, who’d been absolute legends, and hoisted anchor once again.

.

Next stop: St. Martin, the final chapter before Kelly and Colin’s journey back to the UK.

Another sunrise, another sail, another story waiting just beyond the horizon.

---

---

Disclosure/disclaimer: Hey there!  Links on here contain affiliates. When you buy through one of our links, we will receive a small commission. (Every little bit helps) This is at no cost to you. So thank you for supporting us and our odyssey