Experience private fishing aboard the Windy Day in Key West, Florida. This 42-foot Carbon and Kevlar boat offers stability and comfort for up to six anglers seeking an unforgettable deep-sea adventure.
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Difficulty
moderate
Duration
4–6 hours
Fitness Level
Suitable for most fitness levels; requires ability to stand for long periods and basic balance on a moving boat.
Wildlife
History
Key West has a rich maritime history as an important fishing and shipping hub since the 19th century.
Conservation
The region actively promotes sustainable fishing practices to protect fragile reef ecosystems and marine life.
Key West Florida Fishing
Experience private fishing aboard the Windy Day in Key West, Florida. This 42-foot Carbon and Kevlar boat offers stability and comfort for up to six anglers seeking an unforgettable deep-sea 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 Reef-Safe Sunscreen
Protect your skin and the delicate marine life by choosing sunscreen that is free of harmful chemicals.
Stay Hydrated
Long hours on the boat in the Florida sun can dehydrate you quickly; bring plenty of water.
Wear Non-Slip Footwear
Boat decks can be slippery, so sturdy, non-slip shoes will keep you safe while fishing.
Pack a Light Jacket
Ocean breezes can make mornings and evenings chilly, so a light jacket is recommended.
Polarized Sunglasses
Reduce glare from the water surface to improve visibility and protect your eyes.
summer
Lightweight Fishing Gloves
Protect your hands while handling fishing lines and equipment.
Wide-Brim Hat
Provides shade and extra protection from the strong Florida sun.
summer
Reusable Water Bottle
Keep hydrated throughout your adventure on the water.