Experience the best fishing charters in Key West with Cowboy Cowgirl Sportfishing. Our family-owned fleet has been taking guests offshore, reef, and shark fishing since 1965. Whether you’re after a private adventure or an affordable shared trip, our captains know where the fish are biting. Explore our boats and trip options below to start planning your Key West fishing adventure today.
For nearly 60 years, Cowboy Cowgirl Sportfishing has been the trusted name for fishing in Key West. Our family-owned fleet offers something for everyone — from private deep-sea and reef trips to shared and shark fishing charters. Each boat has a local captain who knows these waters well. This ensures every trip is safe, comfortable, and full of fun. You can have a luxury trip, a budget-friendly adventure, or a fun family day on the water. Our team is here to help you make great memories.
Every vessel in our fleet is equipped for serious fishing and real comfort. The larger boats have comfortable features. They include the Cowgirl, Irish Cowboy, and Sanctuary. These boats have air-conditioned cabins, restrooms, and shaded decks. These features are great for longer trips or families with different ages. The Blue Cowboy, Cowboy, and Knotty Cowgirl are great light-tackle boats. They are perfect for inshore fishing, reef trips, and sandbar combos.
The Blue Cowboy offers a special fishing tour to the Marquesas Keys. This adventure combines light tackle fishing with stories and sights from one of Key West’s most interesting island chains.
No matter which you choose, you’ll enjoy professional gear, clean boats, and a crew that treats every charter like family.
Thinking about which trip or boat fits you best? Look at the options above. Visit our blog for local fishing tips. You can also call us to plan a great day on the water.
Our boats depart daily from Historic Charter Boat Row in Key West — just minutes from downtown, the cruise docks, and major hotels. You’ll be fishing blue water within minutes, with the reef, wrecks, and Gulf Stream right at our doorstep. Guests love how fast we get to the action and how effortless the day feels from start to finish.
Depending on the season, our guests catch mahi-mahi, tuna, sailfish, wahoo, grouper, snapper, and more. They also enjoy the excitement of shark fishing for bull, lemon, and hammerhead sharks. Our captains adjust each trip to target what’s biting best, giving you the best shot at trophy catches and great eating fish. No two days are ever the same, and that’s what keeps anglers coming back year after year.
Which boat is best for families or beginners?
Our larger boats, like the Cowgirl and Sanctuary, are great for families. They have spacious layouts, shade, and air conditioning. The crews are experienced with kids and first-timers, ensuring everyone has fun and catches fish.
Do you offer both private and shared fishing charters?
Yes, we offer both. Private charters are reserved just for your group. Shared charters combine small groups for a more affordable trip. You still get great quality with shared charters.
Can we go shark fishing on any boat?
Absolutely! But mostly, the Cowboy is for shorter inshore and reef trips. Shark fishing trips are very popular. Our captains can arrange these trips on different boats. This depends on the group size and conditions.
Do the boats have restrooms or air conditioning?
Some of our boats, like the Cowgirl, Irish Cowboy, and Sanctuary, have A/C and restrooms for extra comfort.
What kinds of fish can we expect to catch?
You might catch mahi-mahi, wahoo, tuna, grouper, sailfish, snapper, or even a strong shark. This depends on the season and type of trip. Our captains will recommend the best option for what’s biting when you visit.
Where do your trips depart from?
Most of our charters leave from Historic Charter Boat Row. It is at 1801 N Roosevelt Blvd in Key West. This location is close to downtown and popular hotels.
No matter which boat you pick, you will get the same professionalism and local knowledge. You will enjoy the warm hospitality of Cowboy Cowgirl Sportfishing. This company has been a trusted name in Key West since 1965. Find out more about each boat above. You can also check our blog for insider stories, fishing reports, and seasonal tips. These will help you plan your perfect adventure in the Florida Keys.