The Mediterranean season is done. You have crossed the Atlantic (hopefully without too many seasickness tablets), and now you have landed in the Caribbean, the season of barefoot vibes, steel drums, and, of course, cocktails.
But the Caribbean is not just about guests sipping rum punch on deck. For crew, it is also about those rare nights off where you finally get to swap your whites for flip-flops and explore the islands yourself. From legendary bars to signature drinks, here is your ultimate Caribbean bar hopping and cocktails guide, yacht crew edition.
1. Soggy Dollar Bar – Jost Van Dyke, British Virgin Islands
The soundtrack at the Soggy Dollar Bar is laughter, splashes, and the clink of Painkillers being mixed. Sand under your feet, salt on your skin, and half the crew swimming ashore to pay with damp cash.
Signature: Painkiller (dark rum, pineapple juice, orange juice, cream of coconut, nutmeg)
Image source: Kegworks
2. Sunset Bar & Grill – St Maarten
Engines roar overhead as jumbo jets skim the beach, sending hats flying while margaritas flow at Sunset Bar & Grill. It is chaotic, noisy, and unforgettable, the only bar where the main act is aviation.
Signature: Frozen Margarita (tequila, triple sec, lime juice, ice)
Image source: Sunset Bar's Instagram
3. Le Ti St Barths – St Barths (Saint-Barthélemy)
Enter Le Ti St Barths where sequins, feather boas, and waiters in costume. One minute you are sipping an espresso martini, the next you are dancing on the table with billionaires who forgot their age.
Signature: Espresso Martini (vodka, coffee liqueur, espresso, sugar syrup)
Image source: Canva
4. Shirley Heights Lookout – Antigua
Shirley Heights Lookout provides an “on-top-of-the-world experience” in their own, well-deserved words. Steel drums carry on the breeze as the sun sinks over English Harbour. Smoke from the BBQ mingles with rum punch in hand, and for a moment, everyone, locals, yachties, and tourists, feels like family.
Signature: Classic Rum Punch (rum, lime juice, grenadine or sugar syrup, orange juice, pineapple juice, bitters, nutmeg)
Image source: Canva
5. Basil’s Bar – Mustique, Grenadines
Basil’s Bar is low-lit, salty, and casual, but with an undercurrent of glamour. One night you are watching live calypso, the next you are bumping into a Rolling Stone at the bar.
Signature: Basil’s Mojito (white rum, lime juice, sugar, mint, soda water)
Image source: Canva
6. Nikki Beach – St Barths (Saint-Barthélemy)
At Nikki Beach, you’ll enjoy white loungers, champagne buckets, and DJs spinning barefoot by the sand. It is the French Riviera transplanted into the Caribbean, polished but still kissed by sea spray.
Signature: Champagne Mojito
Image source: Caroline's Cooking
7. Foxy’s – Jost Van Dyke, British Virgin Islands
Foxy’s has been serving food and strong rum drinks to sailors and visitors since 1968. Anticipate strings of lights, live music, and a mischievous host who might break into song mid-order. By midnight, the entire harbour feels like one big family reunion with a lot more rum.
Signature: Foxy’s Firewater Rum (rum, lime juice, mint, sugar syrup, Champagne)
Image source: Foxy's Instagram
8. Catherine’s Café – Pigeon Point Beach, Antigua
At Catherine’s Café you can sink into a beanbag under the trees, sip a Caribbean spritz or chilled rosé, and watch yacht tenders pull up along the shoreline. The vibe is barefoot French-Caribbean chic, and long lunches here often stretch into sunset.
Signature: Cucumber Refresher (gin, cucumber, lime, mint, soda)
Image source: Catherine's Cafes Instagram
Crew Favourite Cocktail: The BBC
It is not what you think. The BBC is Bailey’s, Banana, and Coconut, usually blended with piña colada mix. Creamy, boozy, and dangerously easy to drink, it is the cocktail yacht crew love to order when they want something sweet. You will find it at plenty of island bars, especially in the BVIs and Bahamas.
Image source: Gluten Free Easily
Crew Tips Hidden in the Rum
From Painkillers in the BVIs to rum punch in Antigua, Caribbean bar hopping is part of the rhythm of the season. You enjoy the good times even more when the rest of your season is under control.
Know the seasons: Med runs April to October, Caribbean November to April. Time your job search around these peaks.
Recruitment spikes: Yachts hire crew just before the season starts. October to December in the Caribbean is prime time.
Paperwork matters: Visas like C1/D or B1/B2 are often needed. Do not assume Schengen covers you.
Be pre-checked: Captains want crew who are verified, safe, and ready to go. Having your CrewPass profile complete means fewer awkward questions and more last-minute job offers.
Keep your flip-flops handy, your paperwork in order, and your CrewPass profile verified. That way, when the work is handled, you can sip the rum and savour the view, guilt free.
