Calypso Cowboy Charters Fishing, Tours Adventures Prices

Relax and enjoy a private half-day sandbar tour in the Florida Keys with a local captain who knows the area well. Choose a 5- or 6-hour private boat trip perfect for families, couples, and small groups looking to unwind on the water. Visit shallow sandbars ideal for swimming, wading, and soaking in the Florida Keys scenery at a comfortable pace. Departing from Big Pine Key, this personalized sandbar tour offers flexible timing, plenty of space, and a laid-back atmosphere tailored to your group’s preferences, making it a great option for sightseeing, social time, and coastal relaxation.

Join Capt. Paul for a private half-day mackerel fishing trip in the Florida Keys, perfect for families, beginners, and experienced anglers. Choose a 5- or 6-hour inshore adventure targeting king and Spanish mackerel, with all rods, reels, bait, and tackle provided. Fishing licenses are included, so you can focus on learning techniques and catching fish. Departing from Big Pine Key, trips take place aboard a 26’ Twin Vee center console with plenty of space and a smooth ride. Each private charter is tailored to your group’s pace, ensuring an enjoyable, educational, and memorable fishing experience.

Enjoy a private half-day grouper fishing trip in the Florida Keys with Capt. Paul, perfect for families, beginners, and experienced anglers. Choose a 5- or 6-hour inshore fishing adventure targeting gag grouper, with all rods, reels, bait, and tackle provided. Fishing licenses are included, so guests can focus on catching fish and learning techniques. Trips depart from Big Pine Key aboard a comfortable 26’ Twin Vee center console, offering plenty of space and a smooth ride. Each private charter is tailored to your group’s pace, ensuring a fun, educational, and memorable fishing experience.

Experience a private half-day sea trout fishing trip in the Florida Keys with Capt. Paul, ideal for beginners, families, and experienced anglers. Choose a 5- or 6-hour inshore fishing adventure targeting sea trout, with all rods, reels, bait, and tackle provided. Fishing licenses are included, so you can focus on learning techniques and catching fish. Departing from Big Pine Key, trips take place aboard a comfortable 26’ Twin Vee center console with ample space and a smooth ride. Each private charter is customized to your group’s pace, ensuring an educational, fun, and memorable fishing experience.

Target red snapper on a private half-day fishing trip in the Florida Keys with an experienced local captain. Choose a 5- or 6-hour inshore snapper fishing charter designed for beginners, families, and seasoned anglers. All rods, reels, bait, and tackle are provided, and fishing licenses are included. You’ll fish aboard a comfortable 26’ Twin Vee center console with plenty of room for your group. Departing from Big Pine Key, this private snapper fishing trip focuses on hands-on guidance, relaxed pacing, and a customized approach to help your group enjoy a productive and enjoyable day on the water.

Explore the natural beauty of the Florida Keys on a private half-day eco tour led by an experienced local captain. Choose a 5- or 6-hour wildlife-focused boat tour designed for families, couples, and small groups. Cruise calm backcountry waters, mangroves, and shallow flats while learning about the Keys’ unique ecosystem and local wildlife. This relaxed nature tour offers flexible pacing, comfortable seating, and a personalized experience tailored to your group’s interests. Departing from Big Pine Key, each private tour provides a peaceful way to enjoy sightseeing, wildlife viewing, and quality time on the water with a knowledgeable guide.

Enjoy a private half-day guided fishing trip in the Florida Keys with an experienced local captain. Choose a 5- or 6-hour inshore fishing charter designed for families, beginners, and seasoned anglers alike. Trips target popular species such as gag grouper, red snapper, sea trout, and Spanish mackerel. All rods, reels, bait, and gear are provided, and fishing licenses are included. You’ll fish aboard a 26’ Twin Vee center console with plenty of space and a smooth ride. Departing from Big Pine Key, this private charter focuses on hands-on instruction, relaxed pacing, and a customized experience tailored to your group’s goals.