Captain Alan
Alan’s love for the water began early, during family sailing vacations on Cape Cod and Lake Huron’s North Channel—home to some of the finest freshwater sailing in the world. Those formative experiences sparked a lifelong connection to the sea and set the course for the life he now leads.

Before trading city life for island time, Alan spent over 20 years in Canada’s hospitality scene in Ottawa, mastering his craft in top restaurants and nightlife venues. From busboy to bartender, restaurant manager to nightclub owner in Ottawa’s vibrant Market district, he developed a deep understanding of exceptional service, attention to detail, and the art of a perfectly crafted cocktail—skills that now elevate every moment onboard.

Now in his 20th season chartering in the Virgin Islands, Alan brings a wealth of experience as both an owner-operator and private charter captain. With years of sailing these waters, he is known for his calm, confident presence and his unwavering commitment to guest comfort and safety. His intimate knowledge of the BVI allows him to effortlessly curate days filled with hidden anchorages, turquoise bays, and just the right amount of adventure.

As a certified Dive Instructor, Alan offers Discover Scuba Diving (DSD) experience as well as full scuba instruction for those ready to go deeper. He leads all in-water activities—from guided dives and snorkeling to water sports and sea scooter exploration.

Randeen – Chef / Mate
Originally from the Canadian prairies—where winter is more of a lifestyle than a season—Randeen made the inspired decision to swap snow boots for sandy toes and sunshine. Leaving behind a successful corporate career, she followed her passion for hospitality, food, and adventure to the Caribbean.

With a background in corporate event planning and customer service, Randeen brings a refined sense of organization, creativity, and attentiveness to every charter. She has a natural talent for anticipating guests’ needs and creating an experience that feels both effortless and thoughtfully curated.

In the galley, Randeen blends creativity with Caribbean flair, crafting fresh, vibrant dishes using local ingredients and global inspiration. Her menus are as flexible as they are flavorful, with a keen ability to cater to dietary preferences while still delivering beautifully presented, satisfying cuisine.

A natural social host with a quick wit and easy charm, she effortlessly sets the tone onboard—whether it’s a relaxed afternoon, sunset cocktails, or a lively evening under the stars. She leads everything from scenic island hikes and hidden beach escapes to expertly curated beach bar outings and lighthearted game nights, always with a touch of style and a sense of humor that keeps guests smiling.

Alan Roberts

Captain /Chef / Dive Master

Canadian

Languages: English

Ritz

Admiral

Alan

Dive Master