The Oldest Family-Owned Hotel in the Caribbean Has 3 Beaches, an Oceanfront Golf Course, and an Authentic Island Experience 

Just before sunset, the old stone walls of the sugar mill catch the last light, and the sound arrives first. Steel pan, bright and rhythmic, carries across the lawn. Then the Moko Jumbies appear, rising high above the crowd on stilts, their costumes catching the breeze as they pass between tables and the bar. You hear laughter, glasses clinking, the low hum of conversation that turns into applause as the dancers sweep through.

This is where you understand St. Croix.

Not through a brochure or a map, but through a moment like this, on a special Caribbean island like this, with rum in your hand and music that feels tied to the ground beneath you. The gathering happens every week at The Buccaneer, and it draws both guests and locals, a quiet convergence that says more about the island than any guide ever could.

The hotel has been here for generations. The island has been here far longer. And right now, in this light, they meet.

The Caribbean’s Oldest Family-Owned Hotel

The Buccaneer isn’t new. That’s what makes it so special.

Opened in 1947 and still run by the same family, it carries a continuity that’s rare in the region, now celebrating its 80th year. You feel it in the way the property is laid out, in the familiarity of returning guests, in the way staff greet people by name and remember how they take their coffee.

The buildings stretch across a long sweep of land above the sea, with rooms and suites facing out toward Christiansted Harbor and the open Caribbean beyond. Many have private terraces or balconies, with views that change throughout the day, from the early light over the water to the deeper blues that settle in by late afternoon.

Inside, the rooms lean classic Caribbean: tile floors, wood furniture, soft tones that keep the focus on what’s outside. Some accommodations are closer to the beach, others higher up the hillside, giving you a different vantage point depending on where you land.

You don’t come here for novelty. You come for consistency, for a place that knows what it is and doesn’t try to be anything else.

Three Beaches, Each With Its Own Feel

What sets The Buccaneer apart immediately is access. Three distinct beaches, each with its own character, all within the same property.

Mermaid Beach is the most active. This is where you’ll find the beach bar, water sports, and a steady flow of guests settling into lounge chairs with a drink in hand. The sand is white, the water clear, and the energy stays easy but present throughout the day.

A short walk brings you to Grotto Beach, smaller and quieter, edged by rock formations that break the waves just enough to create calm pockets of water. It’s the kind of place you end up lingering longer than you planned, especially in the late afternoon when the light softens.

Then there’s Whistle Beach, the most removed of the three. Reaching it takes a bit more effort, and that’s exactly why it feels different. Fewer people, more open space, and long stretches where it’s just you, the sound of the water, and the steady wind coming off the sea.

Three beaches, three ways to spend the day, without ever leaving the property.

The Beachside Pool With A Straight Line To The Horizon

Just above Mermaid Beach, the resort’s main beachside pool runs parallel to the shoreline, its edge lining up cleanly with the sea beyond.

From the water, your eye goes straight across the surface to the Caribbean, with palm trees framing the view and low hills in the distance. Lounge chairs sit just behind the pool deck, a few steps from the sand, so you can go from swim to sea without changing your pace.

An Oceanfront Golf Course That Stays Close To The Water

Golf here isn’t an afterthought. The Buccaneer’s 18-hole course runs along the coastline, with several holes playing directly against the sea. You see it immediately on the front nine, where fairways open up to wide views of the water and the trade winds come into play.

The course has been here for decades, originally designed in the mid-20th century, and it still holds that classic Caribbean layout: rolling terrain, natural contours, and holes that reward precision over power.

There’s a rhythm to playing here. Early morning rounds with cooler air, the sound of waves carrying across the course, and a pace that feels unhurried. You’re not racing to finish. You’re out there to take your time.

Even if you don’t play, the presence of the course shapes the property. It opens the landscape, creates long sightlines, and gives the hotel a sense of space that’s hard to replicate.

Dining That Stays Rooted In The Island

Food at The Buccaneer stays close to the island.

At The Terrace, breakfast comes with views over the water, with a spread that leans into fresh fruit, local flavors, and dishes that don’t overcomplicate what’s already good. It’s where the day begins, with coffee, sea air, and a steady pace that sets the tone.

Dinner shifts to The Mermaid Restaurant, right by the beach. Here, you’re eating with the sound of the water just steps away. The menu brings together Caribbean staples and broader influences, with seafood at the center: fresh catch, grilled preparations, sauces that complement rather than overwhelm.

There’s also the beach bar, where lunch turns into afternoon drinks without much transition. This is where you order something cold, sit back, and let the hours pass without watching the clock.

And then there’s the weekly gathering at the sugar mill, where food, music, and culture come together in a way that feels specific to this place.

A Property That Moves At Its Own Pace

Time works differently here.

You notice it in small ways. The way mornings stretch out a little longer. The way afternoons settle into the beach without urgency. The way evenings build slowly, from dinner to drinks to music.

The Buccaneer doesn’t push you into a schedule. It gives you options and lets you find your own rhythm. You can stay active—tennis, golf, water sports—or you can do very little at all.

That balance is part of what keeps people coming back. It’s a place where you can shape the experience around what you need, without feeling like you’re missing something if you choose to slow down.

St. Croix: The Caribbean’s Under-The-Radar Standout

Step beyond the hotel, and you start to understand why St Croix has such a cool, unique vibe.

This is an island that hasn’t leaned into heavy development in the same way as other islands. You won’t find large clusters of high-rise resorts. What you will find is depth: history, culture, and a food and drink scene that’s been building quietly and steadily.

Christiansted, just minutes from The Buccaneer, centers around a waterfront with historic Danish architecture, pastel buildings, and a harbor that stays active throughout the day. Walk the boardwalk, stop into shops, and then find your way to one of the restaurants lining the water.

Frederiksted, on the west end, brings a different pace. Wider streets, a long pier that draws divers and snorkelers, and sunsets that turn the entire sky into a spectrum of color.

The island carries layers of history, from colonial structures to plantation ruins, all set against a landscape that feels open and largely unchanged.

A Food Scene That Keeps Getting Better

What sets St. Croix apart right now is its food.

Restaurants across the island are doing work that feels both grounded and creative. You’ll find classic Caribbean dishes done well—fresh fish, stews, rice and beans—but also menus that bring in broader influences without losing that connection to place.

In Christiansted, spots like Savant serve refined Caribbean cuisine in a historic courtyard, while Too Chez Restaurant & Bar offers a more contemporary approach with a strong cocktail program.

Beachside, you’ll find places where the focus is simpler: grilled fish, cold beer, and a table right by the water.

There’s a consistency to it. The food feels intentional, the ingredients fresh, and the experience tied closely to the island itself.

Cocktails, Rum, And A Strong Sense Of Place

Drinks on St. Croix carry their own identity.

Rum plays a central role, as you’d expect, but it’s how it’s used that stands out. Bartenders across the island are building cocktails that highlight local flavors—tamarind, passion fruit, citrus—without overcomplicating the final result.

You can spend an afternoon at a beach bar with a simple rum punch, or sit down in a more refined setting and work through a menu that treats cocktails with the same attention as the food.

There’s also a growing interest in craft and detail, with bars focusing on balance, presentation, and the overall experience.

It all feels connected. The drinks, the food, the music—they come from the same place.

Beaches Beyond The Resort

While The Buccaneer offers three strong options, the rest of the island adds even more.

Cane Bay on the north shore brings clear water and a strong snorkeling scene, with coral reefs just offshore. It’s a favorite for both locals and visitors, with a few beach bars and restaurants nearby that keep things relaxed.

Sandy Point, when open, stretches wide and quiet, with long runs of white sand and very few people. It’s part of a national wildlife refuge, and the sense of openness is immediate.

Then there are smaller, less marked spots—places you find by driving, turning down a road, and seeing where it leads.

That’s part of St. Croix’s appeal. You’re not confined to one experience. You can explore, find your own places, and come back to the hotel with something new each day.

Culture That Shows Up In The Details

St. Croix carries its culture in visible ways.

Music is present, from live bands to steel pan to the sound systems that appear during local gatherings. Art shows up in galleries and on walls, in small studios and larger exhibitions.

Festivals, food events, and community gatherings happen throughout the year, each one adding another layer to the island’s identity.

At The Buccaneer, that connection comes through in moments like the sugar mill gathering, where the hotel opens its space to something broader than just its own guests.

You’re not separate from the island here. You’re part of it, even if just for a short time.

Why The Buccaneer Still Stands Out

In a region filled with new developments and constant change, The Buccaneer holds its position through consistency.

It offers three beaches that give you options without requiring travel. It has a golf course that connects directly to the coastline. It provides dining that reflects the island without overreaching. And it sits just close enough to Christiansted to make exploring easy.

Most of all, it carries a sense of continuity. The same family, the same property, the same approach, refined over decades rather than reinvented every few years.

You feel that when you arrive. You feel it when you leave.

Where It All Comes Together

Back at the sugar mill, the light fades, and the music continues.

The Moko Jumbies make another pass, rising above the crowd, their silhouettes cutting across the last of the sunset. The steel pan carries on, steady and bright. Conversations pick up, drinks are refreshed, and the night settles in.

This is the point where everything connects.

The hotel, the island, the people, the history, the present moment.

You could stay here the entire time and leave satisfied. You could spend your days exploring St. Croix and come back each night with something new.

Either way, you’re in the right place.

Getting There

You fly into Henry E. Rohlsen Airport on St. Croix, with nonstop service from cities including Miami, Fort Lauderdale, Charlotte, and Atlanta, along with connections through San Juan.

From the airport, it’s about a 25-minute drive across the island to The Buccaneer, with routes that pass through open stretches of countryside before reaching the hills above Christiansted. Rental cars are easy to arrange at the airport (we like the very well-run Centerline), and taxis are readily available for direct transfers.

Prices at The Buccaneer

I found rates at The Buccaneer for $407 right now in the resort’s Great House with an ocean view on Google Hotels.

For a deluxe ocean view, the rate goes to about $455 per night, and for a deluxe oceanfront room between the Grotto Beach and Mermaid Beach, you’re looking at $558 per night. 

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