Captain: Robert Jennings

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 Bright’s life has always been shaped by the sea, adventure, and a profound love for creating unforgettable experiences. Raised on boating adventures in Mauritius and part of her high school sailing team in Southern Maryland, Lelani also joined the Sea Scouts before launching into a journey that would span continents, cuisines, and cultures. She is a seasoned world traveler, having explored over 19 countries—and counting!

After beginning her studies in broadcast journalism at American University in Washington, D.C., Lelani pivoted toward her true calling in hospitality, transferring to the University of South Florida, where she rowed third seat on the USF crew team in Sarasota. It was here that she stepped into the culinary world professionally, working as a sous chef in the university’s student mess hall and at the Embassy Suites hotel on the Tampa campus.

Her passion for island life led her to the Caribbean, where she cooked for weddings and events in Saint Croix through Island Weddings and completed her first culinary and assistant management internship at the iconic Scrub Island Resort in the British Virgin Islands. Along the way, she sailed charters across Washington D.C., the Bahamas, Key West, Puerto Rico, the U.S. Virgin Islands, and the British Virgin Islands, enriching her global palette with spices and traditions from the world’s waters.

Chef Lelani’s approach to cuisine is soulful, dynamic, and deeply intentional. Blending the vibrant flavors of Hawai‘i, the Caribbean, and her Afrikaans heritage—rooted in the Dutch East India spice trade—her dishes invite guests to transcend the ordinary. Every meal from her galley is a dance of anthropology, spirituality, artistry and the sounds of Bach wafting over her special homemade pasta dishes!

When not crafting unforgettable menus, Lelani is an offshore fishing angler and first mate, a kids’ tennis coach, and a lifelong student. She is currently studying Film and Media Documentaries at Full Sail University, an institution known for its Emmy and Grammy Award-winning alumni. Her passions include acting and modeling, reading, farming, sustainability, off-grid building, free diving, spear fishing, surfing, yoga, ribbon dancing, crafting haku-leis, writing poetry, developing her company Beautiful Life LLC, and authoring a children’s book series. She is also a Reiki practitioner, intuitive guide, and devoted companion to her spirited 4.6 lb chihuahua, Kealoha Mokuʻula.

Chef Lelani lives her life—and runs her galley—with a singular philosophy:
“My love letter to the sea is being in service to others’ heart chakra openings while onboard. A vacation is a mere lens into transmuting the mundane into pure magic and manifestation. Through food, we embark together on a journey of flavor, connection, and celebration of life’s most meaningful moments.”