The Legendary St. John Bar That Proves the Best Caribbean Restaurants Don’t Try Too Hard

St. John’s Delightfully Scruffy Side

Most visitors to St John, U.S. Virgin Islands spend their time on the Cruz Bay side of the island. That’s where the ferry arrives from St. Thomas, where the shops cluster, and where the beach bars line up within easy walking distance of the dock. But if you ask longtime visitors where the island’s most beloved bar lives, they’ll point you across the mountains to Skinny Legs St John in Coral Bay.

Getting there requires a scenic 25-minute drive over Centerline Road, which climbs through lush hills before dropping down toward the island’s quieter eastern harbor. Sailboats rock at anchor. Fishing skiffs bob along the docks. The occasional yacht looks like it wandered in from Monaco and decided to stay awhile.

Coral Bay feels different from the moment you arrive—less polished, more bohemian, and a little proudly weird. Artists live here. Sailors anchor here. Locals who came for a vacation and never left tend to settle here. And for more than three decades, 

Skinny Legs has been the unofficial hang spot for all of them.

A Bar With History

Skinny Legs dates back to May 1991, when best friends Doug “Dougie” Sica of New Jersey and Maurice “Moe” Chabuz of Massachusetts decided Coral Bay needed a proper neighborhood bar. At the time, Coral Bay was even quieter than it is today. Only a scattering of homes dotted the hillsides and a small cluster of sailboats rested in the harbor.

Dougie and Moe had spent the 1980s tending bar together at the well-known Back Yard Bar in Cruz Bay, where they perfected two essential island skills: pouring drinks and making people feel welcome. Armed mostly with bartending experience, a talent for conversation, and a vision for a laid-back gathering spot, the pair took over a small bar previously known as Red Beard’s. They renamed it Skinny Legs—a tongue-in-cheek nod to their famously lanky frames.

More than three decades later, the name stuck. So did the bar.

What hasn’t changed is the spirit.

The place still feels like it grew organically. License plates, stickers, and nautical relics cover nearly every surface. Ceiling fans spin lazily overhead while reggae or classic rock drifts through the air. Tables spill out onto a shaded patio where chickens occasionally wander past like they’re part of the staff. N

Just good food, good drinks, and a great vibe.

Nobody here is trying to impress you. They’re just trying to feed you a really good burger and make sure your drink stays cold.

Not Your Typical Island Tourist Trap

There are plenty of restaurants in the Caribbean that feel engineered specifically for cruise passengers. Skinny Legs is not one of them.

Yes, visitors come here—many after hearing about the place from friends or travel writers—but it still belongs primarily to the people who live on the island. Prices are refreshingly reasonable by Caribbean standards. The staff is friendly without being performative. And nobody is trying to upsell you a souvenir margarita glass.

The restaurant closes during hurricane season each year, which tells you everything you need to know about its priorities. When the weather turns rough, the island rests. Skinny Legs simply waits for the next season to begin again.

The Wild Beauty of St. John’s East End

One of the reasons Skinny Legs feels so special is its location. St. John is unique among Caribbean islands because nearly two-thirds of it is protected as Virgin Islands National Park. That means no mega-resorts dominating the coastline and no sprawling cruise infrastructure. The eastern side of the island, near Coral Bay, feels particularly untouched.

Nearby adventures include:

  • snorkeling at Salt Pond Bay
  • hiking the Ram Head Trail for one of the best panoramic views in the Caribbean
  • exploring quiet beaches like Haulover Bay and Hansen Bay

After a day of salt water, sun, and hiking, Skinny Legs becomes the natural landing spot for a cold drink and a plate of something satisfying. It’s the island’s version of a living room.

Travelers often talk about “hidden gems,” but the truth is that once a place becomes famous enough to be called a hidden gem, it usually isn’t hidden anymore. Skinny Legs somehow dodges that fate. Maybe it’s because Coral Bay sits just far enough from the ferry docks to discourage casual visitors. Maybe it’s because the place refuses to evolve into something trendier. Or maybe it’s simply because the Caribbean still has room for establishments that exist primarily to serve their communities rather than chase Instagram fame. Whatever the reason, Skinny Legs remains exactly what travelers hope to find when they visit St. John: a little rough around the edges but full of personality.

Resources and Travel Planning

If you’re planning a visit to Coral Bay and Skinny Legs, these resources can help:

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