At Cowboy Cowgirl Sportfishing, we’re not just another charter company—we’re a family-run operation with roots going back three generations in Key West. From deep sea to inshore, our fleet of top-rated boats and experienced captains have earned us a reputation as one of the best Key West fishing charters.
We specialize in:
Offshore deep sea fishing for pelagics like mahi, sailfish, and tuna
Reef & wreck fishing for snapper, grouper, and amberjack
Inshore and backcountry fishing with light tackle
Unique combo trips: sandbar & fishing or snorkeling & fishing
Shark fishing charters (private or shared)
Trips typically begin between 7:00 and 8:00 AM. Our crew welcomes you aboard, gives a quick safety rundown, and ensures you’re fully geared up. Rods, reels, bait, and even your license—it’s all included.
Depending on your trip type, your captain will head offshore into the deep blue or stay close to the reef or mangroves. Expect incredible views and maybe even dolphins or sea turtles on the ride out.
Whether you’re targeting marlin in deep waters or snapper over the reef, we tailor each trip to the conditions and your goals. First-timer? We’ve got you. Seasoned angler? Let’s chase the big ones.
Spring/Summer: Mahi, blackfin tuna, tarpon, yellowtail snapper
Fall/Winter: Sailfish, grouper, king mackerel
Year-Round: Sharks, jacks, snapper, amberjack
Every trip is different, and your captain will plan based on tides, moon phase, and what’s biting.
We offer a range of boats from center consoles to air-conditioned sportfishing yachts. Whether you’re looking for a private deep sea fishing experience or an affordable shared fishing charter, we have a boat that fits your budget and group size.
Shared/Split/Group Trips (Starting at $200)
Light Tackle Charters (2 Boats to Choose from)
Private Charters (6 Boats to Choose from)
Key West Shark Hunters (Shark Trips)
Why We’re the Top Choice for All Types of Anglers
Whether you’re a solo traveler, a family with kids, or a group of friends on vacation, we offer a professional, safe, and unforgettable experience. We’re consistently rated as one of the best fishing charters in Key West—and once you fish with us, you’ll see why.
Fishing license
Rods, reels, and bait
Experienced captain and mate
Ice and cooler
Catch cleaning and filleting
Optional photo ops at the dock
Sunscreen (reef-safe is best)
Polarized sunglasses
Snacks and drinks
Towel if snorkeling
Camera or GoPro
Cash tip for crew (15–20% appreciated)
Whether you want to chase offshore giants or enjoy a relaxing reef trip, we’ll help you find the right option.
📲 Call or text: 305-304-2946
💬 Live chat on the site (talk real time to owners)
🔗Book Your Trip Now
Before your trip, check out BiteBackBrand for premium charter-tested shirts and gear. Under “Local Legends,” visit Cowboy Cowgirl Sportfishing and stock up like the pros.