High-performance boats and group-friendly yachts operating from Key West, Florida for fishing, sunset cruises, and multi-day charters.
Choose from private sportfishing boats, a custom yacht, shrimp-boat adventures, and sunset cruises.
fishing · Key West
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Range of boats for every trip
Large group and private options
Gulf and offshore fishing grounds
Sunsets to multi-day charters
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Key West Florida Fishing listing.
Key West Florida Fishing offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Select a Windy Day, Blind Squirrel, Compass Rose, or Shrimp Boat trip — book the right boat for the right adventure.
boat-charters · Key West
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.
water-activities · Key West
Join a Gulf Shrimp Boat Charter in Key West for an action-packed fishing experience amid spectacular feeding frenzies and vibrant marine life. Perfect for anglers of all levels, this trip offers a window into the region’s rich fishing heritage.
water-activities · Key West
Experience a memorable sunset aboard the Blind Squirrel Sunset Cruise in Key West, where stunning views and marine wildlife come together for a perfect evening. Discover why this charter is a top choice for groups seeking relaxation and adventure on the water.
fishing · Key West
Join Compass Rose in Key West for an unforgettable fishing trip in the Gulf of Mexico. Perfect for beginners and seasoned anglers alike, discover the rich marine life and pristine waters that make this area a top fishing destination.
water-activities · Key West
Experience the thrill of fishing aboard the Compass Rose in Key West. With expert guides and stunning sunset views, this trip offers both adventure and relaxation in a premier marine setting.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.