The Caribbean Beach Hotels with Seriously Good Bars
- GirlWellTravelled
- Jul 27
- 4 min read
Updated: Jul 28
A good hot coffee is a great start to any morning. Something fruity fresh with an alcoholic kick and icy cold, a nice finish to the day.
But on holiday, there isn't anything that says the day shouldn't start as it is meant to finish. When the bartender has sized you up and created you a drink that's just you. That tickles and tingles with all your emotions and senses, you have it to start the day too.
Because, while sometimes we travel for the history, the culture, a little adventure. Other times, it is the sand between our toes, swaying palm trees while something delicious clinks in our glass that makes a holiday so much better.
The Caribbean does this very well. Barefoot beach shacks pouring the island’s best rum punches to stylish boltholes serving cocktails you’ll try (and fail) to recreate at home. I’ve rounded up the best Caribbean beach hotels with bars worth flying for.
Gyp Sea Hotel & Villas — St Barths
Boho Bliss with a Side of Rum
At Gyp Sea (one of the coolest hotels to stay in the Caribbean, things are as easy-going as the island breeze. The beach club spills straight onto the sand, the music hums along just loud enough and the bartenders shake cocktails like they’ve been doing it since birth.
Their Coco Bar is the star—stacked high with rare bottles and secret recipes you’ll swear taste better by the sea (of course). One sip of their house spiced rum with fresh coconut and you’ll be disappointed you didn’t book longer.
Bar Highlight: Your cocktails served in coconuts
Cocktail to Try: Gyp Sea Punch—light, fruity, with just enough kick to make the sunset look even more beautiful.
The Lone Star — Barbados
Beachfront Cool and Cocktails on Tap
A place you can imagine in black-and-white photos: movie stars, linen table cloth and the gentle clatter of ice in tall glasses. Lone Star is relaxed but never dull. The terrace restaurant and bar sit right at the water’s edge, making it dangerously easy to lose track of time between rum sours and grilled catch of the day.
Bar Highlight: Sea-view terrace with old-school charm and a drinks list that refuses to take itself seriously.
Cocktail to Try: Lone Star Rum Sour. That's the local Mount Gay Eclipse with lime and sugar syrup, as it should be.
Jakes Hotel — Treasure Beach, Jamaica
Colourful, Quirky and So Very Cool
Jakes isn’t like the others. It’s bright, a little wild around the edges and entirely irresistible. The bar here is pure island life: driftwood furniture, reggae in the ear and cocktails tasting like sunshine poured over ice.
Locals, they drift in and out. Artists, they gather at dusk. Two drinks, maybe three, four and you're dancing barefoot on the sand without a care in the world.
No problems activating holiday mode here.
Bar Highlight: Dougie’s Bar—legendary for its charm, local following and no-fuss cocktails.
Cocktail to Try: Dougie’s Rum Punch... It's famous for good reason.
Eden Rock — St Barths
Chic Sips Above the Sea
You might arrive for the views, but you’ll stay for the drinks. The Rémy Bar, perched above the bay, serves cocktails with a French twist and all the sparkle to match the glamorous crowd.
Drinks here are always a celebration, even if you’re only toasting the fact that it’s Tuesday.
Bar Highlight: The Rémy Bar... very stylish with a list of cocktails that lean French Riviera via the Caribbean.
Cocktail to Try: The Saint-Barth Royale. That's champagne, rum and tropical fruit. Ahaa!
Zemi Beach House — Anguilla
Rum, Sunsets and Stories to Tell
Rum afficionado's come gather at Shoal Bay. As postcard-worthy as beaches in Anguilla come. Zemi Beach makes sure you've got the drinks on tap to accompany the view. The Rhum Room here stocks one of the island’s best rum collections—each pour comes with a story and the staff are more than happy to share them.
After a day in the sun, there’s nowhere better to settle in with a cocktail, absolutely nothing in the diary and good conversations.
Bar Highlight: The Rhum Room—seriously good rums
Cocktail to Try: Not a cocktail but their Pirates of the Caribbean rum tasting discovery
Le Barthelemy Hotel & Spa — St Barths
Island Sophistication, One Glass at a Time
Sea breezes, easy listening music and cocktails thoughtfully made. The vibe is relaxed, playful, with bartenders who remember your name (and your drink) by the second day.
Le Turquoise Pool Bar practically demands you linger well into sunset.
But it’s not just about that one bar. From six pm onwards find yourself in the Seven Stars Bar, a little universe of its own. Inspired by the stars and too, Spanish flair. An immersive space where cocktails are paired with poems to capture spirit. Think zodiac‑themed creations served in very bespoke glasses, perched on personalised leather coasters. Where the tables are works of art, plates are from an exclusive Juan Miró collection and the menu itself is a handcrafted astrology wheel. Live music drifts through every evening, making it impossible not to stay for “just one more.”
Bar Highlight: Le Turquoise Pool Bar for beachfront sips; Seven Stars Bar for celestial cocktails and a touch of artistry.
Cocktail to Try: The Barthelemy Breeze—fresh mint, tropical fruit and a generous splash of aged rum.
This Round is on Me...
The Caribbean isn’t just about palm trees and turquoise waters. It’s about slowing down, tuning in and raising a glass to the art of doing very little. And doing it very well.
Next time you’re dreaming of your escape, don’t just think about the beach. Think about the bar. Think about the first sip of something cold, the clink of glasses, the cheers and the laughter that goes up with it.
And then book the ticket.
If you enjoyed this feature, you may also like The Coolest Boutique Hotels in the Caribbean
Or click here to contact me to book.
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