MEET YOUR CREW:
CAPTAINS:
Bruce Whitehead (Dec, Jan - April, May - Aug, Sept)
Pieter Van Steenis (Oct, Nov - Feb, March - June, July)
CHEFS:
Cassie Peppin (Dec, Jan - April,May - Aug, Sept)
Ashley Cook (Oct, Nov - Feb, March - June,July)
STEWARDESS: Angelina Ready (Full time)
FIRST MATE/SCUBA INSTRUCTOR: Caydon Harris (Full Time)
Captain Bruce:
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 such as 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 winter seasons in the Bahamas and 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.
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Captain Pieter:
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 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.
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Chef Cassie:
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.
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Chef Ashley:
Born and raised in Louisiana, Ashley grew up on soul food and southern hospitality. With her grandparents being travel agents, she started traveling at a young age, which sparked her interest in other cultures and cuisines. After graduating University with a Bachelor of Science, Ashley became an au pair on the coast of Italy where she was introduced to the Yachting Industry. Over the past 9 years, she has been a chef on charters and deliveries in various places such as Croatia, Greece, Montenegro, Italy, French Polynesia and the Virgin Islands.Her love of travel has brought her to 60 countries, including England where she received her Culinary Certification from the Ashburton Chefs Academy, as well as attended The Galley Gang yacht chef workshops.
Chef Ashley is also passionate about health and nutrition. She is a certified health coach and is currently studying to become a personal trainer and nutrition coach, so her dishes are guaranteed to be full of color and fresh ingredients.
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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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First Mate: Caydon Harris
Born in Plettenberg Bay, Caydon grew up surrounded by the ocean, developing a natural love for adventure and life on the water. His passion led him to sailing in Cape Town before completing his diver training in Tofo, Mozambique, where he discovered a deeper connection with the underwater world.
Now a qualified Scuba Instructor and experienced captain, Caydon combines his sailing and diving experience to create memorable experiences both above and below the water. Confident on deck and underwater, he enjoys everything from yacht operations and watersports to leading dives and snorkeling adventures.
Friendly, energetic, and always ready for the next adventure, Caydon’s goal is simple: to help guests make the most of their time onboard and leave with memories that last long after the yacht disappears over the horizon.
