5 Caribbean Beach Bars Worth Sailing to This Summer — And What to Wear When You Arrive
Sip, Savor & Sail in the Caribbean this Summer
This season, trade traffic for tradewinds and set your compass toward warm Caribbean waters. From Anguilla to St. Lucia, a string of iconic beach bars beckons — where the cocktails are cold, the vibes are easy, and the only dress code is something breezy, breathable, and made for sea spray.
Whether you're barefoot on the sand or just dropped anchor off a secluded cay, here’s our handpicked list of the best beach bars to hit by boat — where yachtwear feels like the uniform of the island.
Chat ‘N’ Chill – Stocking Island, Bahamas
No frills. No rush. No shoes, probably. A short water taxi from George Town, this spot is legendary for its conch salad and salt-air simplicity. The charm isn’t curated — it’s natural: wild stingrays glide through shallows, kids build sandcastles, and boaters sip ice-cold Kalik under the shade of sea grape trees.
🧭 What to wear: SPF tee, sunhat, and something you don’t mind getting wet — you’ll want to wade in.
Sandbar & Sandy Island – Anguilla
This two-stop combo is for the barefoot sophisticate. Sandbar in Sandy Ground surprises with its refined wine list (yes, even a chilled albariño) and small plates like kung pao cauliflower and lobster salad. Then hop a short ride to Sandy Island — a literal sandbar — for grilled mahi, live tunes, and a chilled glass of Domaine Ott rosé with your feet in the sand.
🧭 What to wear: Lightweight linen and slip-ons that come off easily — both islands demand toes in the sand.
Shipwreck Beach Bar – South Friar’s Bay, St. Kitts
This open-air thatch-roofed bar faces the Caribbean side, tucked in golden sand and palm fronds. It's a local favorite for fresh fish tacos and their Green Flash cocktail — a neon blend of coconut rum, pineapple, and blue curaçao. Watch out for the local vervet monkeys — they like to people-watch too.
🧭 What to wear: Something casual and quick-dry. Monkeys don’t care, but you might get caught in a splash.
The Soggy Dollar – Jost Van Dyke, BVI
You’ll need to swim to shore here — it’s part of the fun. Known as the birthplace of the Painkiller (dark rum, pineapple, orange juice, coconut cream), this laid-back legend oozes charm. Sun-soaked sailors stash damp dollar bills and spend hours in hammocks without a care. A classic.
🧭 What to wear: Swimwear, boat shoes you can slip off fast, and sunglasses with a strap (trust us).
Sunset Bar & Grill – Maho Beach, St. Martin
Here, planes roar overhead so close you can feel the jet wash. You’re sipping cocktails with sand between your toes and jumbo jets overhead — and somehow, it all works. It’s chaotic, surreal, and oddly satisfying. A Caribbean rite of passage.
🧭 What to wear: Something secure, especially if you’re planning a selfie under a 747.
Bar-hopping, yacht-style
These aren’t just bars. They’re markers of memory — places where you laugh too loud, get your salt fix, and toast the view you’ll never forget. Each one blends casual elegance with Caribbean authenticity — and they all pair beautifully with fresh yachtwear.
Packing tip: Don’t forget your linen button-down, a rashguard for post-lunch snorkeling, and polarized sunnies. The only thing you won’t need? Shoes.