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About Us

Owner's Bio


Owning a catamaran and charter business has long been a dream for this family. Jay is a wooden boat builder by trade and has built several 50’ wooden catamarans- some are in the islands, including Adventurer, Allura, & Katarina.

Currently, he is General Manager and Master Distiller at a distillery in Charleston, SC. Kimberly is a registered nurse. Together they have 5 children ages 10-20 years old. They are passionate about being on the water, traveling, and trying to live an authentic life. They enjoy dreaming about their 8-year plan when all their children fly the nest, and they can move to the islands.

In October of 2017, Irma and Maria hit the islands hard. One of Jay’s old-time boatbuilding buddies has lived on St. John for years and runs a successful sailing cat there. Before and after the hurricanes, the Jay was in contact with him. The Virgin Islands were devastated by the storms, so Jay offered to help and was on the first plane inbound to St. John with supplies.

He spent a week there and helped pull the boat on the hill to be repaired. That trip alone reignited his drive and determination to get back to the islands despite working full time and raising a family. The camaraderie, community, and hard, rugged life by the sea is who he is. He has saltwater running through his veins.

In June 2018, Jay and Kimberly found out that Island Flyer was for sale. They contacted the owners, and after many twists and turns, hurricanes watches, tropical storms, and even a government shut down, they purchased the boat and business on February 8, 2019!!

They are overwhelmed with gratitude for all those that helped them get to where they are today. They would not have purchased this business without knowing Capt. Hillary would be on board. She is the face of the company, and they are so grateful for how she cares for Island Flyer and who she is as a person. Her character and integrity inspire all who know her. #dreamteam

In 2021 they welcomed a new team member- Madolyn! She is exceptional at taking care of the guests by answering all of their questions and booking their trip. Her joy and spunk is evident each time she is on the phone with a customer. She aims to please and will stop at nothing making sure you have a good time on Island Flyer. 

They all look forward to many years enjoying Island Flyer with friends, family, and loyal customers. Come visit soon!

Captain's Bio


Hillary grew up in Richmond, Virginia. After graduating from college, she travelled through South Africa, South Asia and Southeast Asia. While working as a dive master on an island off the coast of Thailand, her passion for small island countries and their development was born.

After leaving Thailand, Hillary lived in Europe before returning to the U. S. to attend graduate school at the Monterey Institute of International Studies. In 2002, Hillary received a Master’s of International Environmental Policy with a concentration in small island developing countries.

When Hillary moved to the U.S. Virgin Islands, she worked on environmental issues affecting the islands. Her interest in (fascination with) the marine environment led to her work on boats where she shares her knowledge of the marine environment with others.

Hillary holds a 50T Captain’s license. After more than fifteen years as captain and crew, the yachting industry is Hillary’s career. When she is not out on Island Flyer, she enjoys travel, spending time with her many pets and working with rescue animals.

Captain Hillary looks forward to welcoming you on board Island Flyer.

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Admin's Bio


Madolyn, first and foremost, is a wife and mother. She and her husband Keith have been married since 1989 and have three extraordinary grown children. In addition, she is an avid traveler and lover of all things Caribbean. Her passion is making memories and sharing new adventures with her family and friends. Madolyn has had an extensive and very successful career in Commercial Real Estate in Atlanta, only a short drive from where she grew up in Stone Mountain, GA.

Madolyn is a wanderlust and has been fortunate enough to have traveled all over the world. Her travels have taken her all over Europe, North & South America, and of course, the stunning Caribbean Islands. Experiencing new cultures, foods and seeing incredible places is what makes her such a travel enthusiast. However, her most favorite place in the world is the beautiful Caribbean. She is most at home on and in the water!

Madolyn is a natural-born people person and has never met a stranger. Her energy, love for life, and adventure, coupled with her attention to detail, will ensure your experience with Island Flyer is excellent from the first point of contact until the moment you step off the boat. She is excited about this new chapter in her life and looks forward to helping you book your next great adventure on Island Flyer.

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