CAPTAIN BRUCE (Dec, Jan – April, May – Aug, Sept)
Matthew “Bruce” Whitehead has over 15 years in the maritime industry and a lifetime of experience in, on, and around the water. Growing up in Florida, he spent his youth racing high-performance sailboats, teaching and coaching sailing, and went on to campaign for the 2016 Olympics in the Sport of Sailing. Bruce then competed on several professional circuits, including the World Match Race Tour, the Red Bull Youth America’s Cup, and the Extreme Sailing Series.
Since a serious injury in 2018, Bruce shifted his focus from sailboat racing to working as a Yacht Captain. For the past 8 years, he has captained charter and delivery yachts in various destinations in the Mediterranean, Caribbean, South Pacific, and Indian Oceans. Bruce has spent many winters in the Bahamas and the British Virgin Islands and loves the sailing, diving, and lifestyle of the islands.
In his free time, Bruce enjoys traveling, hiking, and spending time with family and friends.
CAPTAIN PIETER (Oct, Nov – Feb, March – June, July)
Originally from the Netherlands, Pieter began his professional journey with Tesla during its pioneering years before making the conscious decision to turn his lifelong passion into his profession: sailing. Since then, he has built extensive experience across some of the world’s most diverse and demanding waters, including the North Sea, Mediterranean, Caribbean, and the Bahamas.
Holding a Yachtmaster Ocean certification and working as an ASA Instructor, Pieter combines strong technical expertise with a calm, confident leadership style. He has sailed extensively throughout the Caribbean and knows its islands, anchorages, and conditions intimately.
Pieter brings an energetic and adventurous spirit to life on board. When he’s not navigating, you’ll likely find him kitesurfing, wakeboarding, e-foiling or wing foiling, or exploring the underwater world through snorkeling. He also enjoys quieter moments with a good sudoku or a (relaxed) board game, as well as taking in nature—especially the rich marine life the Caribbean has to offer.
Known for his positive attitude and team-oriented mindset, Pieter loves working with a great crew to deliver exceptional charter experiences. His goal is simple: to create a safe, relaxed, and unforgettable time on the water for every guest.
1ST MATE JAMES
Hailing from the UK, James Webb is an experienced and highly skilled diving professional with over a decade in the industry. As a PADI Master Scuba Diver Trainer and SSI Advanced Open Water Instructor, he has built a reputation for excellence through both teaching and real-world expedition work. His career has taken him across the globe—from managing dive shops in Thailand to working directly with great white sharks in the waters of Mexico—giving him a depth of experience that few can match.
Over the past five years, James has expanded his expertise into the maritime world, working aboard luxury charter vessels and diving liveaboards. Complementing this hands-on experience, he holds a Yachtmaster Offshore certification, underscoring his capability and leadership at sea.
Driven by a passion for adventure and the outdoors, James spends his free time kite surfing, running, reading, and exploring new corners of the world
CHEF CASSIE (Dec, Jan – April,May – Aug, Sept)
Chef Cassie is a versatile and globally experienced Yacht Chef with a strong background in both sailing and motor yacht charters. Having served as Sole Chef aboard multiple Bali 5.4 catamarans and an 86ft motor yacht in the Caribbean, she specializes in full-board charters for up to 8–12 guests, delivering refined, globally inspired menus tailored to each guest’s preferences.
Trained at the Institute of Culinary Education in New York, with advanced pastry studies from the Culinary Institute of America and Escoffier School of Culinary Arts, Cassie blends classical technique with creativity and presentation. Her diverse culinary style spans Mediterranean, Asian, Latin American, and modern coastal cuisine, complemented by strong provisioning, budgeting, and charter-hosting expertise.
With additional experience in event management, floral design, and yacht hostess duties, Cassie brings a natural flair for tablescapes, guest experience, and seamless service. Energetic, adaptable, and passionate about life on the water, she combines culinary excellence with warmth and professionalism to elevate every charter she joins.
STEWARDESS ANGELINA
Angelina grew up in New York before moving to Florida to attend the University of Tampa. She spent a total of seven years in the Sunshine State, during which time she prioritized traveling as much as possible, backpacking around Europe, and cultivating a global perspective and a love for adventure.
Her career in hospitality began at age 14, and through years of serving and bartending, she developed a genuine passion for entertaining. As a natural people person, she thrives in fast-paced environments and takes great pride in providing a high level of service and connection with guests.
In 2019, a sailing yacht charter with friends sparked her transition into the maritime industry. This passion led her to Australia, where she completed her Yachtmaster Offshore Sailing license while simultaneously working as a chef to broaden her professional capabilities on the water.
More recently, she has expanded her expertise below the surface by pursuing a diving career and earning her PADI Advanced Open Water certification. Currently serving as a stewardess, Angelina combines her extensive service background with her technical maritime training to ensure an exceptional experience for everyone on board.
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Region: Caribbean
