Summer/Winter Operating Area: U.S. Virgin Islands, British Virgin Islands
Dock Holiday is a sleek and stylish 54.0 ft catamaran designed for unforgettable escapes. With 4 spacious queen cabins—each featuring a private en-suite head,—she comfortably hosts up to 8 guests, offering a boutique floating retreat with room to unwind.
A professional 2-person crew ensures every detail is taken care of, from personalized service and tailored experiences, to crafting you delicious gourmet meals. Whether you’re lounging on deck, sailing turquoise seas, or dining under the stars, Dock Holiday brings the perfect mix of adventure and indulgence to your charter.
Born in South Africa and raised in Louisiana, Captain Jason Mackay has always been drawn to the water and the sense of freedom it brings. With an adventurous spirit and a deep respect for nature, Jason has built a life around exploration, community and the sea. From spearfishing along the coasts of Mexico to navigating the crystal waters of the Caribbean, Jason’s journey has been defined by his passion for the ocean and the connections it inspires. Over the years, he has hosted more than 65 charters and welcomed over 600 guests aboard, earning a reputation for his calm leadership, professionalism and genuine care for those in his charge. Now entering his fourth season in the Virgin Islands, Jason takes the helm of Dock Holiday as her captain – bringing together his love for the sea, his hands-on experience and his dedication to creating unforgettable adventures under sail. Whether charting a course through hidden coves or sharing stories at anchor, Jason ensures every guest experiences the magic of life on the water.
Captain Jason hails from Columbia, Maryland, where his love for sports and the outdoors began. He earned a degree in Criminal Justice and Criminology from the University of Maryland before relocating to the Virgin Islands in 2009, a place he has proudly called home for over 15 years.
Jason’s professional journey began in the hospitality industry, including fine dining, where he gained extensive experience hosting elegant, high-end events that prioritized exceptional guest experiences. Following the devastation of Hurricanes Irma and Maria in 2017, Jason shifted his career focus to the sea, discovering his true passion for life on the water.
Since then, he has spent the majority of his time captaining day charters from the Ritz-Carlton and Westin resorts, serving guests exploring the stunning waters around St. Thomas and St. John.
When he’s not on the water, Captain Jason enjoys snowboarding, golfing, and exploring new travel destinations. His dedication to providing unforgettable experiences and his enthusiasm for adventure make him a valued leader and host on every voyage.
