Tailwalker Charters at Hawks Cay Resort offers the premier Florida Keys offshore fishing experience with direct access to some of the richest fishing grounds in the world. Within minutes of stepping aboard our top-notch vessel, you will be fishing clear blue waters of the Atlantic Ocean for trophy game fish, hard-fighting bottom dwellers, and delectable table fare species.

Whether you’re vacationing in the Florida Keys with your family and just want to venture out for a fun day at sea, or you're on a non-stop fishing adventure with your friends and seek constant rod-bending action, our locally-respected captain and crew will go out of their way to ensure you catch fish and have a great time while doing so. From anchoring up on the beautiful reefs for Snapper/Grouper and many other species (great for kids and family fun), bouncing out to the offshore wrecks in hopes of big jacks, muttons, and other fish for a tough fight, to targeting Sailfish, Mahi, Tuna, and Swordfish offshore the TAILWALKER is ready and eager to guide you on a trip of a lifetime.

Give us a call today and book your Florida Keys fishing experience of a lifetime!

The TAILWALKER is tournament ready when it comes to sail fishing, equipped with top of the line rods, reels, and tackle this crew is seasoned and efficient. from kite fishing to sight fishing our captain and crew are readily available to share their tricks and tips aboard this fine sportfishing vessel. Come catch your trophy on one of the most premier sail fishing boats the Florida keys has to offer.

Tailwalker Charters at Hawks Cay Resort offers full-day swordfishing excursions. Come test your luck with one of the most sought-after trophy fish in south Florida. These swordfish can grow upwards of 500+ lbs. and are an incredible creature from the depths of the ocean residing in 1500-1900ft of water. The Tailwalker is equip with the best of the best when it comes to rods and reels for a battle that could take hours.

Captain Brandon Simmons of Tailwalker Charters is participating in the Billfish Foundations Tag and Release program.

The Tailwalker is an air-conditioned 44’ Custom Sunny Briggs that is fast, smooth, comfortable and built to fish. The Tailwalker is fully rigged with top-of-the-line Simrad electronics and Shimano tackle and comes equipped with a 35-foot tuna tower, large baitwells, and the expertise of Managing Capt. Brandon Simmons. It also has all the tools onboard for a memorable day of catching trophy fish in the Florida Keys.

     Charters cancelled within 72 hours of the scheduled departure time will be charged full charter price. Cancellations are to be made only with Tailwalker Sportfishing at (321)-750-7369. Weather cancellations are made by the captain only and are not charged a cancellation fee. Deposits will be returned if cancelled outside the 72 hour window or upon cancellation of captain.