Calypso Cowboy Charters offers private boat charters in the Florida Keys designed for anglers, families, and groups looking for a personalized day on the water. Operated by a Florida native Captain Paul with over 14 years of professional guiding experience and 25 years of service in the U.S. Coast Guard, this charter blends local knowledge, safety, and a hands-on approach that welcomes both beginners and experienced guests.

Trips depart from Big Pine Key and explore the clear, shallow waters of the Florida Keys, targeting popular local species such as snapper, grouper, trout, and mackerel. Fishing trips are structured as private 5-hour charters and include rods, reels, bait, and gear. Captain Paul is known for his patient teaching style and enjoys helping adults and kids learn techniques, understand local conditions, and gain confidence on the water.

In addition to fishing, Calypso Cowboy Charters offers private sandbar tours. Sandbar trips are perfect for families, couples, and small groups who want to relax, swim, and enjoy the Keys’ shallow flats and surrounding nature!

All trips are run aboard a spacious 26’ Twin Vee center console powered by twin 150 Suzuki engines. The boat offers a smooth, stable ride with plenty of room to move, a trolling motor for shallow water access, and onboard radio for safety. While the vessel can accommodate up to eight passengers, private trips are limited to smaller groups for comfort and quality.

Calypso Cowboy Charters runs year-round, making it easy to plan a Florida Keys fishing charter, or sandbar day any time of year. Whether you’re booking a family-friendly fishing charter, or a private sandbar day, every trip is customized to your group’s goals, pace, and experience level.