Cocktails & Dreams - Crewed Catamaran Charter

Captain Jason

With over three decades of maritime experience and a deep passion for the sea, Captain Jason brings a steady hand, a warm personality, and a guest-focused mindset to every charter. Originally from Hanover County, Virginia, Jason’s love for the water began in the Chesapeake Bay and Outer Banks, fishing with his family as a teen. That connection only grew stronger during his service in the U.S. Navy, where he served as assistant to the navigator aboard the USS Dwight D. Eisenhower.

Jason’s diverse professional journey - ranging from Navy navigation to seafood entrepreneurship and a successful real estate career - has given him a unique edge when it comes to leadership, hospitality, and problem-solving. But it was his deep-seated dream of becoming a full-time captain that led him to the Virgin Islands, where he now delivers unforgettable experiences on the water.

Since making the career switch, Jason has logged thousands of nautical miles across the USVI, BVI, Bahamas, and Florida Keys as captain aboard luxury catamarans such as numerous Bali 5.4´s and Lagoon 56´s. Whether navigating customs, leading snorkel excursions, maintaining complex onboard systems, or helping serve dinner, Jason is a true team player who prioritizes guest safety, comfort, and enjoyment at every turn.

Holding a USCG 100GT Master’s License with sailing endorsement, STCW, ENG1, and CPR certification, Jason also brings strong mechanical and technical knowledge to every vessel he commands. He’s equally comfortable at the helm, on the swim platform helping guests into snorkel gear, or setting the tone for a relaxed and fun onboard atmosphere.

Above all, Jason’s goal is to make each guest feel at home on the water, creating space for lifelong memories and a deep appreciation for the islands he now calls home.


Chef Kylie

Meet Kylie, your vibrant Chef and First Mate from Johannesburg, South Africa. With a background in Fine Arts from the University of Cape Town, Kylie’s journey to the yachting world began with what was meant to be a short detour - a “gap year” working in video production for a leading cruise line. But that year evolved into a global adventure, taking her to over 70 countries and igniting a lifelong passion for hospitality, travel, and the culinary arts.

Along the way, Kylie discovered that her true joy lies in creating meaningful connections with people and sharing experiences through food. Inspired by her diverse travels and fueled by a deep appreciation for the ocean, she transitioned into the marine industry, finding the perfect canvas for her creativity aboard luxury yachts.

Kylie’s cooking is a celebration of global flavors and healthy, wholesome ingredients. Her dishes are simple yet bold, often infused with exotic twists drawn from her journeys around the world. Whether you’re craving a nourishing post-dive bowl or a beautifully plated multi-course dinner, Kylie crafts every meal with heart, imagination, and an artist’s eye.

Outside the galley, she’s a certified yoga instructor, scuba diver, avid fisherwoman, and film enthusiast - always bringing warmth and energy to every aspect of the charter experience.

With Kylie on board, every voyage becomes a blend of unforgettable flavors, soulful experiences, and the magic of life at sea.