Florida Keys Fishing Charters

Private, family-friendly charters targeting snapper, grouper, trout, and mackerel in the Keys.

Rated #1 by Customers

Calypso Cowboy Charters Available Trips

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Half Day Sandbar Tour in Florida Keys

Starting at undefined500.00

5-hour or 6-hour Sandbar Tour with Captain Paul

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Half Day Guided Mackerel Fishing Trip in Florida Keys

Starting at undefined700.00

5-hour or 6-hour Fishing Adventure with Captain Paul

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Half Day Grouper Fishing Trip in Florida Keys

Starting at undefined700.00

5-hour or 6-hour Guided Fishing Adventure with Capt. Paul

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Half Day Trout Fishing Trip in Florida Keys

Starting at undefined700.00

5-hour or 6-hour Guided Fishing Experience with Capt. Paul

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Half Day Snapper Fishing Trip in Florida Keys

Starting at undefined700.00

5-hour or 6-hour Guided Snapper Fishing Experience with Capt. Paul

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Half Day Eco Tour in Florida Keys

Starting at undefined500.00

5-hour or 6-hour Nature Tour with Captain Paul

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Half Day Guided Fishing Trip in Florida Keys

Starting at undefined700.00

5-hour or 6-hour Guided Fishing Experience with Captain Paul

Big Pine Key, FL, United States Fishing with Calypso Cowboy Charters

Florida Keys private boat charters – book your adventure today!

Meet the Captain

Captain Paul Peter

Big Pine Key, FL, United States Fishing, Tours Adventures

Experience the best family-friendly fishing trips in the Florida Keys with Calypso Cowboy Charters. Captain Paul Peter brings over 13 years of guiding experience and a lifetime of local knowledge to every outing. Target popular species like snapper, grouper, sea trout, and mackerel while enjoying hands-on instruction, a smooth ride on a 26’ Twin Vee center console, and a trip tailored to your family’s pace. Perfect for beginners and seasoned anglers alike, these private charters combine fun, learning, and unforgettable memories. Book your trip today and discover the ultimate Florida Keys fishing adventure!

Calypso Cowboy Charters Fishing Photos

Big Pine Key, FL, United States Catches & Fish Photos

Big Pine Key, FL, United States Fishing Near Me

JOIN ME OUT ON THE WATER

Prices range from $500 - $800

Fishing, Tours Adventures Locations on Big Pine Key, FL, United States

Florida Keys fishing charters offer some of the best inshore and backcountry fishing experiences in the region. Target species like snapper, grouper, sea trout, and mackerel thrive in the area’s crystal-clear waters, making the Keys a top destination for anglers of all skill levels. Explore Florida Keys fishing hotspots, from mangrove-lined flats to shallow reef edges, where the action is always exciting. With local knowledge and years of guiding experience, Capt. Paul Peter ensures you’re fishing in the best spots for each species, providing hands-on instruction and a memorable adventure. Whether you’re after your first catch or a trophy fish, the Florida Keys offers some of the best species fishing in the state.