A legacy shaped by seven flags and generations of family stewardship, the Buccaneer dates back to 1653 and features a historic sugar mill from 1733 on St. Croix. Founded as an inn in 1947 by the Armstrong family, it is the Caribbean’s longest-running family-owned resort, offering 131 rooms blending colonial charm with modern amenities across 340 acres.
St. Croix, known to its earliest inhabitants as “Ay Ay”, has long been a place shaped by culture, trade, and the rhythms of the Caribbean Sea. Over time, seven nations laid claim to the island, giving rise to its name as the “Island Under Seven Flags,” beginning with Spain following its sighting by Christopher Columbus in 1493.
One of the earliest chapters of The Buccaneer estate dates to 1653, when a small plantation house was built on the hillside during the era of the Knights of Malta, marking the beginning of a story that would continue for centuries.
In 1733, St. Croix entered its Danish period under the Danish West India and Guinea Company. During this time, the original Great House and sugar mill were established – forming the architectural and cultural foundation of The Buccaneer.
Nearly two centuries later, in 1917, the United States purchased St. Croix and the U.S. Virgin Islands from Denmark for $25 million in gold, ushering in a new era.
Just five years later, in 1922, the Heyliger family sold a historic seaside estate and working ranch to Douglas Armstrong. Together with his wife, Rachel Armstrong, they restored the ruins of the Danish Great House and, in 1947, opened an intimate 11-room inn, the first hotel in St. Croix built and operated by an island family, laying the foundation for what would become The Buccaneer Resort.
Rachel Armstrong guided the property with vision and grace until her son, Robert Armstrong, assumed leadership in the late 1950s. Under his stewardship, the resort expanded to include the second floor of the main hotel, 62 beachfront rooms, an 18-hole golf course, and an eight-court tennis facility – transforming The Buccaneer into a full-scale Caribbean resort while preserving its character and sense of place.
Alongside Robert, his wife Patricia Armstrong brought her own distinctive influence to the resort, founding its first boutiques. Known for her effortless style and personal approach, she became a beloved presence among guests and the local community, helping each find just the right piece with warmth and confidence.
In 1994, the third generation of the Armstrong family, Elizabeth Armstrong, became General Manager, guiding the resort through thoughtful enhancements including the Beach House, Beauregard’s restaurant, and expanded suites above the Grotto Pool.
Today, the fourth generation, Charlotte Halk Armstrong, continues this legacy, curating the Mermaid and Lobby boutiques and carrying forward her grandmother Patricia’s eye for style and personal touch.
Guests continue to enjoy the gracious, family-owned atmosphere that defines The Buccaneer, often meeting Elizabeth and Charlotte, when she is home from university, at the weekly Sugar Mill Cocktail Party, a longstanding tradition set against the backdrop of the estate’s historic ruins.
What truly defines The Buccaneer, however, is its people. Many members of the team have been part of the resort for decades, welcoming returning guests not as visitors, but as part of an extended family. It is this continuity – this sense of the Caribbean as it once was – that sets The Buccaneer apart and brings guests back year after year.
For those who wish to explore the island’s rich past more deeply, guests are invited to join Elizabeth on her weekly History and Nature Tour, an experience that brings the stories of St. Croix to life through the landscape itself.
As The Buccaneer approaches its 80th anniversary in 2027, this enduring connection between place, people, and history remains its greatest hallmark.
We look forward to sharing our heritage, culture and friendliness with you on beautiful, sunny, St. Croix!
“Fighting Ships” mural by the famous artist Stanley Stubenberg, showcased in The Buccaneer’s Lounge. Learn about Studenberg
