Originally from New England, Cayleigh never expected to build a career on the water. After relocating to the Caribbean, she quickly found her place in the maritime industry, learning to sail aboard a custom-built trimaran where she worked as a deckhand and snorkel guide. What began as an adventure evolved into a lifelong passion and profession.

In 2019, Cayleigh earned her USCG 50-Ton Master’s License and has since operated and managed both sailing and power vessels throughout the Caribbean. Her experience includes serving as skipper on crewed charter yachts, coordinating vessel maintenance and operations, supporting private owners, and helping guests and clients experience the cruising lifestyle firsthand.

This real-world experience gives Cayleigh a practical perspective that extends far beyond the sales process. Having spent years working aboard vessels throughout the Caribbean, she understands the realities of yacht operations, cruising logistics, maintenance planning, charter programs, and life on the water.

Based in St. Croix, Cayleigh is focused on growing Catamaran Gurus’ presence throughout the U.S. Virgin Islands while showcasing the unique boating lifestyle that makes the region so appealing. From local cruising opportunities to island living and yacht ownership, she helps clients understand not only which boat is right for them, but also how that boat fits into the lifestyle they envision.