Your Captain
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Paul Peter
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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 with over 13 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- or 6-hour charters and include rods, reels, bait, and gear. Captain Mike 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 and nature eco tours. Sandbar trips are perfect for families, couples, and small groups who want to relax, swim, and enjoy the Keys’ shallow flats. Eco and nature tours focus on the unique backcountry, mangroves, and wildlife that make this region special, providing a calm and educational experience suitable for all ages.
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, private boat tour, or eco experience any time of year. Whether you’re booking a family-friendly fishing charter, a private sandbar tour, or a guided nature cruise, every trip is customized to your group’s goals, pace, and experience level.
What's Included
Your Guide has some important details about your trip with them.
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When you book your fishing trip, you will need to first put down a deposit to hold the reservation.
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What's Included
Your Guide has some important details about your trip with them.
Show More
When you book your fishing trip, you will need to first put down a deposit to hold the reservation.
Show More
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.
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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.
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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.
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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.
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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.
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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.
Pick Your Date
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.
Pick Your Date
26' Twin Vee Center Console
Boat Type:
Boat Guest Capacity:
8
Boat Length:
26 ft
Manufacturer Name:
Twin Vee
Model Year:
2006
Engine Manufacturer Name:
Suzuki
# of Engines:
2
Horsepower Per Engine:
150
Maximum Cruising Speed:
32
Features: Trolling Motor VHF Radio
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This 26’ Twin Vee center console delivers a smooth, stable ride powered by twin 150HP Suzuki engines. Built for versatility and comfort, it features a wireless trolling motor and VHF radio, making it well-suited for fishing trips, sandbar outings, and eco tours throughout the Florida Keys.
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26' Twin Vee Center Console
Boat Type:
Boat Guest Capacity:
8
Boat Length:
26 ft
Vehicle Details