Stuart Sailing Charters began as a dream realized by Captain Paul (Popeye) and his wife, Judy, whose love for sailing and dedication to sharing the joys of the water laid a strong foundation for this cherished business. Together, they built a legacy of exceptional sailing adventures aboard the beautiful 40-foot catamaran, Sailfish.

For the last 3 years I have been honored to continue their vision as the owner of Stuart Sailing Charters. My journey here began as the business manager, first mate, and hostess, where I worked alongside Captain Paul to create memorable experiences for our guests. Now, I bring my own passion for sailing and commitment to providing the same exceptional service that our customers have come to love.

The Sailfish remains a spacious, stable, and comfortable vessel, perfect for sailors of all experience levels. Whether you’re a seasoned mariner or stepping onto a boat for the first time, Stuart Sailing Charters offers something for everyone—relaxation, adventure, and an unforgettable connection to the water.

While Captain Paul and Judy have passed the helm to me, their legacy is ever-present. They remain dear friends and an integral part of our story, occasionally joining us on the water. Their love for sailing and belief in sharing that joy continues to inspire everything we do.

I invite you to join me and discover why sailing has captivated us all. Let’s make new memories together on the beautiful waters of South Florida.

Call or text today to learn more or book your private cruise: (561) 801-0080.

Erinn Hennessy, Owner, Stuart Sailing Charters