Our Story
Ryan and Madison’s journey began in the summer of 2011, working on the iconic Crab Island ice cream boats as wide-eyed high school freshmen. Madison’s dad owned the boats, and back then, Crab Island was a quaint, tight-knit community of locals with just a handful of vendors. Among them were Erick with his inflatable slide, Robby selling boiled peanuts, and Jimmy’s Ice Cream boats—simple but unforgettable staples of the Crab Island experience.
Over the years, Crab Island has transformed from a laid-back local hangout to a bustling, festival-like destination. Today, it’s a vibrant playground on the water with everything you could imagine: floating BBQ joints, fruit boats, general stores, and even floating burger shops. It’s become a must-visit hotspot for bachelorette parties, families, and adventurers alike, offering breathtaking scenery, dolphin sightings, social energy, and endless opportunities for fun. Whether you’re paddleboarding, snorkeling, or simply soaking in the sun, Crab Island truly has something for everyone.
For Ryan and Madison, Crab Island was more than a summer job—it was the place where their love story began. The couple spent their high school and college years navigating dinghies together, laughing, selling ice cream, and creating lifelong memories. The vendors felt like a second family, and Ryan and Madison loved being part of a community that brought so much joy to visitors year after year.
Madison’s connection to the water only deepened as the years went by. At 19, she decided to earn her Captain’s license, not entirely sure what she would do with it but confident it would play a role in her future. Her plans initially pointed toward the Air Force—she had been in ROTC throughout college at FSU—but after graduating, her entrepreneurial spirit took over. With encouragement from Ryan, Madison made a bold decision: she would start her own boat charter company.
In 2019, Crab Island Adventures LLC was born. At the time, only two private captained charter companies operated in the area. Madison saw a unique opportunity to bring a fresh, woman-owned perspective to the industry and set out to share her love for Crab Island with as many people as possible.
After searching for the perfect boat, Ryan and Madison found their Tritoon in Gulf Shores, Alabama, and prepared to launch their new venture. But just as they were getting started, COVID-19 brought the world to a halt. With beaches closed, insurance companies shuttered, and plans on pause, Madison used the downtime to hone her boating skills, document the area’s beauty, and connect with local businesses to spread the word. When Florida reopened in May 2020, Crab Island Adventures took off like a rocket. Madison ran nearly 200 cruises that first season, working long days to meet the growing demand.
By the end of that whirlwind first year, Madison and Ryan knew they had built something special. They brought on additional captains to keep up with bookings, and eventually tied the knot—officially becoming partners in both life and business. (They even exited their wedding throwing out ice cream on the Ice Cream Boats!)
Over the years, they’ve expanded their operations, helped other local charters get started, and embraced new ventures, always staying true to their love for Crab Island and the community they’ve built around it.
In 2024, Ryan and Madison welcomed their first mate, Hudson, into the crew. As their family grows, so does their passion for sharing this slice of paradise with others. For them, Crab Island isn’t just a destination—it’s where it all began. Together, they’re lighting the way for new adventures, one unforgettable cruise at a time.