Key West Fishing Charters: Sportfishing, Sunset Cruises & Specialty Charters
High-performance boats and group-friendly yachts operating from Key West, Florida for fishing, sunset cruises, and multi-day charters.
Featured Charters & Trips
Choose from private sportfishing boats, a custom yacht, shrimp-boat adventures, and sunset cruises.
About Key West Florida Fishing
Key West Florida Fishing operates out of Key West, Florida, offering a range of private and group charters tailored to anglers and casual cruisers alike. The company fields a fleet that includes the Windy Day, a 42-foot Carbon and Kevlar sportfishing boat accommodating up to six anglers; the Blind Squirrel, a 63-foot custom yacht available for half- to three-day charters and outfitted with a full galley; and the Compass Rose, a 39-foot Model 37 designed for a smooth, dry ride for up to six passengers.
Additional offerings include a Gulf Shrimp Boat Charter that ventures 25 to 65 miles offshore for feeding-frenzy fishing and fly-fishing opportunities, and the Blind Squirrel Sunset Cruise, a two-hour charter accommodating up to 41 passengers for group outings and celebrations. Trips emphasize comfort, stability, and the opportunity to catch edible fish, with options to arrange replica mounts of prized catches. Guides focus on delivering a memorable day on the water by matching boat choice and trip length to guest goals—whether targeting sportfish offshore or enjoying a relaxed sunset cruise.
All descriptions reflect the fleet, capacities, and trip formats provided by Key West Florida Fishing. Prospective guests can choose from short sunset cruises, half-day and multi-day charters, and specialty excursions like shrimp boat adventures. Safety protocols and local regulations are followed on every charter trip. Booking details vary.
Reserve a Key West Charter Today
Select a Windy Day, Blind Squirrel, Compass Rose, or Shrimp Boat trip — book the right boat for the right adventure.