You’ll swim ashore at White Bay for Painkillers at Soggy Dollar Bar, meet local legends like Foxy and Pizza Dave in Great Harbor, hike or relax at Diamond Cay’s Bubbly Pool, then leap off the Willy T pirate ship—all with customs handled by your crew. Expect laughter, sun-warmed skin, and stories you’ll remember every time you smell coconut rum.
I didn’t expect to be worrying about my passport while standing barefoot in the sand, but that’s how our day trip to Jost Van Dyke started—me digging through my bag as our captain, Mike, grinned and told us not to stress. He took care of all the customs stuff (I still don’t really get how it works), so we got to wander Great Harbor instead. There’s this lazy energy there—someone strumming a guitar outside Foxy’s, salty breeze mixing with barbecue smoke. Foxy himself was holding court at the bar, telling stories I only half-caught over the laughter. Vinney poured me something called a VooDoo Punch that tasted like summer and slight regret. Pizza Dave actually handed me a slice straight from the oven—burned my tongue a little but worth it.
After that, we bounced over to White Bay for the Soggy Dollar Bar. You can’t actually walk up—you have to swim in from the boat, which is hilarious if you’re carrying anything (my towel was soaked). The Painkiller here isn’t just a drink; it’s kind of a rite of passage. Coconut cream and nutmeg hit first, then rum warmth sneaks up after you’ve already started laughing with strangers about your soggy dollars. The sand is almost blindingly white. I found myself just staring at the color of the water for way too long—there’s nothing like it back home.
Diamond Cay was next—a quick hike if you want (I did, though I nearly turned back halfway because my flip-flop broke). The Bubbly Pool is wild when the waves are right; seawater rushes in and fizzes around your ankles like nature’s jacuzzi. Some folks just stayed at Foxy’s Taboo with cold drinks and watched us slip around on the rocks. Passing Sandy Spit was more of a “hold up your phone for two seconds” moment than an actual stop, but honestly it looked exactly like those Corona commercials—tiny island, one tree, nothing else.
The last bit was Norman Island and the Willy T pirate ship bar. It’s loud, messy fun—music blasting, people daring each other to jump off the top deck (I did it once; heart pounding all the way down). Mike kept an eye on everyone but still let us feel like we were getting away with something. Heading back across open water with salt drying on my skin and that slightly dizzy feeling from sun and rum—I still think about that view behind us as dusk started creeping in.
Yes—a valid passport is required for this international excursion into the British Virgin Islands.
No hotel pickup is mentioned; you’ll meet at the departure point.
The boat has an open bar with alcoholic beverages and bottled water included.
Yes—you’ll stop at both Soggy Dollar Bar in White Bay and The Willy T pirate ship bar on Norman Island.
You must enter the water from the boat and swim to shore—it’s part of the fun!
No formal lunch is included but you can buy food from local spots like Pizza Dave or Foxy’s Taboo.
This trip isn’t recommended for pregnant travelers or those with spinal or cardiovascular issues.
The exact timing varies by group mood but you’ll have time to explore each main spot before moving on.
Your day includes all customs paperwork handled by your crew so you can relax from start to finish. Enjoy an open bar onboard with bottled water and alcoholic drinks as you travel between stops like Great Harbor (with Foxy’s), White Bay (Soggy Dollar Bar), Diamond Cay (Bubbly Pool), Sandy Spit photo op, and Norman Island’s Willy T pirate ship—all led by your captain plus fuel covered too.
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