Ohana 59

CAPTAIN BRIAN

Born and raised in Connecticut, Brian developed a deep love for the ocean at an early age, spending his childhood sailing on Long Island Sound and enjoying summer vacations in Rhode Island. His passion for sailing runs in the family—his grandfather was one of the original crew members to establish a friendly racing circuit on Long Island Sound.

While studying at the University of Rhode Island, Brian joined the sailing club, which fueled his confidence to explore the waters of New England. Over the years, he owned and operated several sailing vessels along the East Coast. Eventually, he decided to trade harsh winters and frozen dock lines for the warm breezes of the Caribbean. Driven by passion, Brian sold everything he owned to purchase a catamaran and set sail in the islands.

After years of exploration, Brian found his true home in the Virgin Islands, where he now shares his love of sailing and adventure with guests. When not on the water, Brian embraces his adventurous spirit through backcountry and helicopter skiing in the Rocky Mountains—a rare retreat from his life at sea.

Today, Brian calls the Virgin Islands his home, ready to guide guests through its stunning beaches, vibrant marine life, and unforgettable sailing experiences.

CHEF JESSI

Born and raised in Johannesburg, South Africa, Jessi’s love for the ocean began early, despite living far from it. Her family spent holidays in Knysna, a scenic coastal town perfect for watersports like sailing, waterskiing, wakeboarding, and fishing. By a young age, Jessi had already mastered driving boats and earned her PADI Junior Open Water certification at just 12 years old, dreaming of one day becoming a Dive Instructor and exploring the world.

In 2005, Jessi’s family relocated to Cape Town, South Africa, where she put her scuba diving dreams on pause to follow her passion for design. She earned a BA in Creative Brand Communication and Marketing, building a successful career as a Graphic Designer and Social Media Manager. However, the ocean’s call was too strong to ignore.

In 2015, Jessi became a certified Dive Instructor and moved to the Seychelles, where she was introduced to the yachting industry. Since then, she has worked aboard various superyachts, motor yachts, and sailing vessels, taking on multiple roles, including Deckhand, Dive Instructor, Stewardess, and Chef. This breadth of experience has given her invaluable insights into every aspect of yacht life.

Cooking has always been one of Jessi’s great passions. Wherever her travels take her, she seeks out local cooking classes to immerse herself in the flavors and techniques of different cuisines. Her mission is to create fresh, flavorful dishes that elevate her guests’ dining experience, often describing her meals as “paradise on a plate.”

Jessi is dedicated to providing a professional yet relaxed and friendly atmosphere for her guests. Her meticulous attention to detail and commitment to excellence ensure every dish is not only delicious but also a memorable part of the onboard experience.