OHANA 59

Brian Velesbir

Captain

Born and raised in Connecticut, Captain Brian grew up sailing the waters of Long Island Sound, where his grandfather helped pioneer one of the region’s original friendly racing circuits. That early exposure to life under sail sparked a lifelong love for the ocean. While studying at the University of Rhode Island, Brian joined the sailing club, quickly earning a reputation for chasing wind and adventure far beyond the classroom. His sailing exploits expanded across New England, eventually leading him to own and operate several vessels up and down the East Coast.

But frozen dock lines and icy winters couldn’t compete with turquoise waters and steady trade winds. So — in true sailor fashion — Brian sold everything, bought a catamaran, and set sail for the Caribbean. Years later, he’s found his home in the Virgin Islands, where the landscapes are lush, the anchorages are stunning, and the sailing is as good as it gets.

When not at the helm, Brian is known to swap the sea for snow, sneaking off for backcountry and helicopter skiing missions in the Rocky Mountains. But for now, he’s happily anchored at sea level, ready to share his love of island life, marine wildlife, and off-the-beaten-path adventures with his guests.

Jessi Shipley

Chef/First Mate

Jessi was born and raised in Johannesburg, South African, despite the distance, Jessi has always loved the ocean! Her family spent most holidays in Knysna, a picturesque coastal town, perfect for sailing, waterskiing, wakeboarding, and fishing, Jessi learned how to drive boats at a very young age, and she received her PADI Junior Open Water certification at the age of 12, dreaming of one day becoming a Dive Instructor and travelling around the world.

In 2005, Jessi and her family relocated to Cape Town, South Africa and put the Scuba Diving dreams on hold to pursue another passion - Design. Jessi earned a BA in Creative Brand communication and Marketing, but despite building a successful career as a Graphic Designer and Social Media Manager in Cape Town, the ocean was calling.

In 2015, Jessi became a Dive Instructor and relocated to the Seychelles where she was introduced to the Yachting Industry. Since then, Jessi has worked on various size Superyachts, moto ryachts and sailing vessels, taking on multiple roles, as a Deckhand, Dive Instructor, Stewardess, and Chef, gaining invaluable experience in every department.

Jessi’s passion for cooking has always been a significant part of her life, while travelling she eagerly participates in cooking classes to taste the local cuisine and learn new cooking techniques. She is always looking for ways to elevate her guest’s culinary experience onboard, while making sure to prepare fresh and flavorful dishes, often saying “it’s paradise on a plate”

Jessi is deeply committed to providing a professional level of service in a relaxed and friendly atmosphere. Jessi’s dedication to excellence ensures that every dish not only satisfies but also delights her guests..