Key West Fishing Charter Fleet
Explore the Cowboy Cowgirl Sportfishing fleet of offshore and light tackle fishing boats operating daily in Key West, Florida. With multiple vessels to choose from, we offer options for private charters, shared fishing trips, shark fishing, and family-friendly adventures.
Shared Charters
Join other anglers for an affordable deep sea fishing experience
Shared Charter
Join Other Anglers
The most affordable way to fish Key West. Join up to 6 anglers for deep sea fishing at a per-person rate. Perfect for solo travelers, couples, or small groups.
Sportfishing Boats
Classic offshore sportfishers for deep sea adventures
Cowboy
36' Hatteras Sportfisher
Our most affordable private charter. A proven fish-catcher with decades of successful trips, perfect for families looking for quality deep sea fishing.
Irish Cowboy
40' Luhrs Sportfisher
The perfect balance of performance and comfort. Known for her smooth ride even in choppy conditions with cold A/C cabin.
Cowgirl
45' Hatteras Sportfisher
A classic sportfisher meticulously maintained for serious offshore fishing. Cold A/C, sky lounge, and plenty of deck space.
Sanctuary
47' Hatteras Sportfisher
Our flagship vessel. Luxury meets performance with tournament-winning crew and the capability to chase the biggest game fish.
Light Tackle Boats
Center consoles for inshore, reef fishing, and Marquesas Keys adventures
Knotty Cowgirl
37' Contender Center Console
A unique vessel combining exhilarating fishing with sandbar relaxation. Catch fish in the morning, then anchor up at a pristine sandbar.
Blue Cowboy
34' Contender Center Console
Excels at light tackle fishing and exploring the pristine Marquesas Keys. Versatile for both inshore and offshore adventures. Learn more about the Marquesas in our destination guide.
Explore the Marquesas Keys
Discover Key West's most untouched fishing destination. The Marquesas Keys are a pristine natural atoll 30 miles west of Key West — uninhabited, undeveloped, and teeming with marine life. Our Blue Cowboy is the perfect vessel to explore this hidden paradise.
Read the Marquesas Keys GuideNot Sure Which Boat is Right for You?
Give us a call and our team will help match you with the perfect vessel for your group size, budget, and fishing goals.