Pirates Cove Watersports
(305) 453-9881
103800 OVERSEAS HIGHWAY
KEY LARGO, FL
Meet the Crew
Who We Are
Caiti
Lead Boat Captain
Caiti is our lead boat captain from St. Charles, Missouri, with a background in anthropology and a passion for exploration. Originally interested in marine archaeology, she quickly realized life in a lab wasn’t for her and found her place out on the water instead. Since joining the boating world, she’s fallen in love with the freedom, adventure, and endless horizon that comes with life at sea. Whether she’s running trips offshore or sharing stories with guests, Caiti brings energy, curiosity, and a genuine love for the ocean to every day on the water.
Favorite site: Molasses Reef, Carysfort Reef, Key Largo Dry Rocks
Favorite creature: Porcupine pufferfish
Brad
Captain
Brad is a retired rugby coach, scuba instructor, lifelong learner, and firm believer that every great day on the water should end with a cold beer. With his outgoing personality, quick wit, and endless supply of stories, Brad has a knack for turning every charter into an experience guests won't soon forget. He loves sharing knowledge, learning something new, and making sure everyone on board is having a good time. Whether he's pointing out wildlife, answering questions, or keeping the group laughing, Brad's goal is simple: make every trip fun, memorable, and just a little more entertaining than expected.
Kenny
Maintenance Captain
Kenny is a Florida Keys native and the guy who keeps everything at Pirates Cove running smoothly. A lifelong waterman and talented mechanic, he can usually tell what’s wrong with a motor just by listening to it. Known for his hard work, quick fixes, and willingness to help anyone at any time, Kenny is the kind of person who’d give you the shirt off his back without a second thought. When he’s not keeping boats running, you can usually find him fishing, out on the water, or making sure everyone around him is taken care of.
Joe
Scuba Instructor | Captain | Mate
Joe is a PADI Master Instructor, SDI/TDI Instructor, and US Coast Guard 100 Ton Captain originally from Oklahoma. With years of experience both above and below the surface, he’s known for his calm leadership, extensive dive knowledge, and ability to make every trip safe, smooth, and enjoyable. Whether he’s teaching new divers or running offshore charters, Joe brings professionalism, experience, and a great sense of humor to every adventure.
Gabrielle
Scuba Instructor | Captain | Mate
Gabrielle is a dive instructor and captain with a background in marine science and coral conservation. Originally from Portland, Oregon, she earned her degree in biochemistry before heading to the Florida Keys to intern with the Coral Restoration Foundation. Known for her calm demeanor and patience underwater, she loves helping new divers build confidence and feel comfortable in the ocean. When she’s not underwater, she's most likely on an adventure or trying to catch a lizard.
Favorite site: Molasses Reef and USS Spiegel Grove
Favorite creature: Sharks and trunkfish
Bobby
Eco and Sunset Captain
Bobby is our personality hire and one of our Eco and Sunset Tour captains, known for his outgoing personality, quick wit, and ability to make every trip memorable. With a sharp eye for wildlife and extensive knowledge of the local waterways, he enjoys helping guests discover the natural beauty of the area while sharing stories and insights along the way. Whether you're spotting dolphins, birds, and other wildlife or simply taking in a beautiful sunset, Bobby's enthusiasm and sense of humor ensure there's never a dull moment on board. No matter what the day brings, guests can count on leaving with a smile and a great experience.
Favorite creature: Sea turtle
CJ
Beach Boy
CJ is originally from Jamaica and brings a laid-back, welcoming energy to the Beach Hut team. As a watersports guide, he enjoys sharing the beauty of the local ecosystem with guests and helping them create unforgettable experiences on the water. His favorite part of the job is leading tours through the winding mangrove trails, where he gets to combine adventure with his knowledge of the area's unique environment. When he's not guiding tours, CJ is always happy to share fun facts about local wildlife and marine habitats. His favorite animal is the orca, and his calm, friendly nature makes him a favorite among both guests and coworkers alike.
Favorite creature: Orca
Wayne
Retail & Guest Services
Wayne is a Florida native with a lifelong connection to the water. After years working in both the dive industry and construction, he now brings his experience, local knowledge, and laid-back personality to the retail center. Known for his friendly attitude and good stories, Wayne is always happy to help guests find the right gear, share local recommendations, or talk diving with anyone who stops by.
Favorite dive site: Bay Islands, Honduras
Favorite creature: Sea Turtle
Savanna
Retail & Guest Services
Savanna is a Florida Keys local with a passion for the ocean, marine life, and helping visitors make the most of their time in the Keys. When she's not at work, she can often be found snorkeling, exploring local reefs, spending time with her dog Zeus, or working toward her college goals in marine science. She enjoys meeting new people and loves sharing her favorite places, activities, and hidden gems throughout the Keys, helping guests experience the area like a local.
Favorite creature: Shark (hammerhead)
