Heads & Tails Fishing Charters
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Welcome aboard Heads or Tails, our 26-foot World Cat 246—the perfect platform for exploring the waters of Key West. This stable, comfortable catamaran accommodates up to six guests and is powered by twin 150 HP Suzuki outboards, delivering a smooth, reliable ride whether you're fishing the backcountry, chasing reef species, or cruising to a secluded sandbar after the rods are put away.
The boat is fully equipped for a productive and enjoyable day on the water, featuring GPS, fish finder, a trolling motor with Spot-Lock for precise positioning, and plenty of rod holders. You'll also find an easy-to-use Armstrong boarding ladder, a spacious cooler stocked with ice and bottled water, and a private portable marine toilet inside the console. For guests on a combo trip who want to cool off after fishing, we also carry a 10-foot floating water hammock that's perfect for relaxing at a sandbar.
Your captain holds a USCG 100-Ton Master's License and has spent a lifetime boating and fishing the Florida Keys. With extensive local knowledge of the backcountry, nearshore waters, and hidden spots around Key West, every trip is tailored to your group's goals. Whether you want to target local species, introduce the family to fishing, or combine a few hours of fishing with sightseeing and a sandbar stop, your captain will customize the experience to make the most of your time on the water.
Whether you're looking for a fun day of light tackle fishing, a family-friendly adventure, or a combination fishing and sandbar charter, Heads or Tails offers a relaxed, personalized experience showcasing the very best of Key West.
Welcome aboard Heads or Tails, our 26-foot World Cat 246—the perfect platform for exploring the waters of Key West. This stable, comfortable catamaran accommodates up to six guests and is powered by twin 150 HP Suzuki outboards, delivering a smooth, reliable ride whether you're fishing the backcountry, chasing reef species, or cruising to a secluded sandbar after the rods are put away.
The boat is fully equipped for a productive and enjoyable day on the water, featuring GPS, fish finder, a trolling motor with Spot-Lock for precise positioning, and plenty of rod holders. You'll also find an easy-to-use Armstrong boarding ladder, a spacious cooler stocked with ice and bottled water, and a private portable marine toilet inside the console. For guests on a combo trip who want to cool off after fishing, we also carry a 10-foot floating water hammock that's perfect for relaxing at a sandbar.
Your captain holds a USCG 100-Ton Master's License and has spent a lifetime boating and fishing the Florida Keys. With extensive local knowledge of the backcountry, nearshore waters, and hidden spots around Key West, every trip is tailored to your group's goals. Whether you want to target local species, introduce the family to fishing, or combine a few hours of fishing with sightseeing and a sandbar stop, your captain will customize the experience to make the most of your time on the water.
Whether you're looking for a fun day of light tackle fishing, a family-friendly adventure, or a combination fishing and sandbar charter, Heads or Tails offers a relaxed, personalized experience showcasing the very best of Key West.

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Capt. Zachary runs trips out of Key West aboard 26' Worldcat Center console. The crew has you covered if you wish to try bottom fishing, spinning, trolling, or other techniques. The only way to learn is to join them on the water.
Capt. Zachary runs trips out of Key West aboard 26' Worldcat Center console. The crew has you covered if you wish to try bottom fishing, spinning, trolling, or other techniques. The only way to learn is to join them on the water.
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