Crew Profiles:
Captain Robert Jennings
Captain Robert, affectionately known as "Captain Rob," has been sailing the Caribbean for over 30 years—most of that time spent exploring and mastering the waters of the British Virgin Islands. Born and raised in Cape Town, South Africa, his connection to the ocean began early through sailing, surfing, and lifesaving. That passion eventually led him to the Caribbean, where his family opened a sailing school in the BVI in the early 1990s.

A seasoned sailor and natural teacher, Captain Rob has spent many years instructing students and sharing his deep knowledge of seamanship with those eager to learn. But his talents extend well beyond the helm. He is also a skilled chef and accomplished artist, often found painting live at scenic locations throughout the islands, capturing the vibrant spirit and beauty of the BVI on various mediums.

Whether he’s guiding guests through a perfect day under sail, preparing a delicious meal, or creating art inspired by the sea, Captain Rob brings creativity, experience, and a calm, steady presence to every adventure.




Chef Lelani Bright
Chef Lelani is your culinary visionary aboard your dream sailing adventure through the Caribbean seas. Originally from South Africa, she now calls the Hawaiian island of Maui home—where the spirit of aloha perfectly complements her love of nature, culture, and cuisine. A proud Afrikaans Boer, Lelani is always happy to share the story behind her heritage with curious guests.

Educated in South Africa’s capital, Lelani has since traveled the world, immersing herself in rich cultures and learning a wide variety of global culinary techniques. Her cooking is a celebration of her journeys—bold, flavorful, and inspired by the diverse people and places she’s encountered along the way.

Lelani’s energy is as dynamic as her dishes. When she’s not creating unforgettable meals at sea, you’ll find her surfing, sailing, playing tennis and basketball, paddleboarding, snowboarding, spearfishing, and free-diving. A true creative at heart, she also writes poetry, practices Hula, crafts Haku leis, dances with ribbons, gardens, reads voraciously, and explores the world of herbology and innovative cooking methods—all often in the company of her spirited 4.5 lb Chihuahua.

Now based in the Virgin Islands, Lelani brings her passion and culinary artistry to term charters, creating bespoke, flavorful experiences for every guest. Whether she’s plating a beautifully balanced meal or sharing stories of her global adventures, Chef Lelani brings warmth, curiosity, and an unmistakable passion for life to every charter.