Captain David Elenbaum
Captain David is a lifelong boating enthusiast whose passion for the water began during childhood summers on Lake St. Clair in Michigan. He earned his first boating license at just 14 and has spent more than 30 years building broad, hands-on experience across a wide range of vessels and waterways.

His background includes offshore fishing in the Florida Keys, captaining classic houseboats on Lake Hartwell in South Carolina, and operating a seasonal 33-foot tri-toon charter business with his wife, Heather. David has also personally restored and maintained several boats, handling everything from electrical systems and engine repairs to interior renovations. That mechanical experience has earned him a reputation for calm, practical problem-solving at sea.

Together, David and Heather have sailed extensively throughout the U.S. and British Virgin Islands and as far south as Grenada, welcoming guests aboard for relaxed and adventurous cruising experiences.

With additional experience in restaurant management and food service, David combines professionalism with genuine warmth. He enjoys guiding guests to beautiful anchorages, sharing stories over sunset cocktails, and creating safe, memorable days on the water. For him, captaining is the fulfillment of a lifelong dream.

Chef Heather Elenbaum
Chef Heather brings boundless energy, warmth, and an easy ability to make guests feel immediately welcome. With a magnetic personality and a natural gift for connecting with people, she creates an atmosphere onboard that feels relaxed, personal, and full of fun.

Having moved frequently during childhood, Heather learned early how meaningful strong connections and lasting relationships can be. That instinct has carried through a successful professional background spanning sales roles in content management, advertising, real estate, and mortgages, where she consistently ranked among the top performers.

A natural entertainer, Heather loves creating memorable moments through food, drinks, music, and shared laughter. Whether she is preparing a tropical cocktail, setting the mood for dinner, or simply making someone’s day brighter, she brings infectious positivity to every interaction.

Her approach to hospitality is rooted in genuine care, thoughtful details, and helping guests feel seen, celebrated, and right at home. For Heather, life is best enjoyed with good company, great conversation, and a healthy dose of fun.

3rd Mate Stella
Stella is a 10-year-old tri-color Springer Spaniel with a heart as big as the ocean. Affectionate, gentle, and famously well behaved, she is a seasoned sailor and a much-loved member of the crew.

Her favorite activities include lounging in the coziest spots onboard, greeting guests with a wagging tail, keeping watch over the horizon, and fitting in plenty of naps between duties. Clipped for comfort and minimal shedding, Stella blends easily into the rhythm of life at sea.

Whether offering quiet companionship or politely requesting belly rubs, Stella has a natural way of making guests feel at home. Dog lovers and newcomers alike quickly discover that a little four-legged company adds an extra layer of warmth to the charter experience.

Fair winds, salty paws, and warm snuggles await.