Cruise the waters of Key West aboard the Blind Squirrel, a custom 63-foot yacht offering private fishing charters from half a day up to three days. Reel in your next big catch and enjoy onboard comforts in this unforgettable Florida adventure.
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Difficulty
moderate
Duration
4 hours to 3 days
Fitness Level
Moderate fitness recommended for handling fishing gear and moving safely on the boat deck.
Wildlife
History
Key West has a rich maritime heritage as a historic fishing and shipping hub, influencing the local culture and cuisine.
Conservation
Efforts are underway in Key West to protect coral reefs and marine habitats, promoting sustainable fishing practices within charter operations.
Key West Florida Fishing
Cruise the waters of Key West aboard the Blind Squirrel, a custom 63-foot yacht offering private fishing charters from half a day up to three days. Reel in your next big catch and enjoy onboard comforts in this unforgettable Florida adventure.
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.
Fleet Size
5 Trip Options
Range of boats for every trip
Max Capacity
Up to 41 people
Large group and private options
Charter Range
25–65 miles offshore
Gulf and offshore fishing grounds
Trip Lengths
2 hours to 3 days
Sunsets to multi-day charters
Select a Windy Day, Blind Squirrel, Compass Rose, or Shrimp Boat trip — book the right boat for the right adventure.
Bring Sun Protection
Key West sun can be intense, so pack sunscreen, sunglasses, and a hat to stay safe during your fishing trip.
Stay Hydrated
Drinking plenty of water is vital as you'll be exposed to sun and sea breeze for hours aboard the yacht.
Wear Non-Slip Shoes
The yacht deck can get wet and slippery; sturdy, non-slip footwear will ensure your safety while moving around.
Bring a Camera
Capture your catches and stunning Key West seascapes, especially during sunrise or golden hour light.
Polarized Sunglasses
Reduces glare off the water to help spot fish and protect your eyes.
summer
Lightweight Long-Sleeve Shirt
Protects your skin from the sun while keeping you cool on deck.
summer
Light Rain Jacket
Useful for sudden showers during hurricane season or afternoon rain.
fall
Non-Slip Boat Shoes
Provides secure footing on wet and slippery deck surfaces.