Salty Bowline Charter Co. started in Islamorada in 2025 with a simple idea: a day on the water should feel like an adventure, not just another fishing trip. Whether you're a seasoned angler, a first-time fisherman or just want to cruise the islands and catch a sunset, there's a trip built for you.
Captain Trentin Leary runs the Caymas, Captain Dalton Kirby the Contender, and Captain Robyn Leary the eco tours and sandbar trips. Owner Nick Apro handles the planning, so the captains can focus on the fishing. Every trip leaves from Safe Harbor Angler House in Islamorada.
Lead captain · The Caymas
Born into a family of fishermen, Captain Trentin Leary has spent his life fishing inshore and offshore. He runs the Caymas 281HB, with action-packed trips for every skill level.
He isn't just here to put you on fish. Whether it's teaching your kids to reel in their first catch or making sure everyone goes home with a story to tell, he goes out of his way to make it a day you'll remember.
Captain · The Contender
Captain Dalton Kirby runs the Contender, our restored 2022 Contender 25 Bay. He grew up fishing lakes and streams for bass and trout in Pennsylvania and West Virginia, and saltwater trips on family vacations turned it into a career.
At Coastal Carolina University he went to work in the charter business: three years as a first mate out of Murrells Inlet, then a season running trips as a licensed captain near Myrtle Beach. He fished alongside Captain Trentin for several months before taking the Contender, and this is his fifth season in the charter business. Whether you're an experienced angler or brand new to fishing, he'll make it a productive day you'll want to come back for.
Captain · Eco tours and sandbars
Captain Robyn Leary runs the eco tours and sandbar trips. She's spent years on the water in the Florida Keys, piloting everything from center consoles to 60-foot catamarans, and she knows these waters inside and out.
She's here to show you the Keys beyond the fishing. Whether she's taking you to a hidden sandbar or pointing out the wildlife in the mangroves, she makes every trip relaxed and easy to enjoy.
