Key West Offshore & Deep Sea Fishing Charters

When you book with Cowboy Cowgirl SportFishing Charters, you're fishing with Key West's most experienced charter operation. Three generations of our family have guided anglers in these waters since 1965, running one of the most established sportfishing charter operations in the Lower Keys.

Our captains have years of experience fishing these waters. Every morning, they get together at the dock to discuss conditions, water temperatures, and where the fish are biting. They share intel and throw fishing plans to each other - working together so every boat has the best shot at putting you on fish.

Every vessel in our fleet carries all required USCG safety equipment and is fully equipped for offshore adventures. We maintain tournament-level tackle, fresh bait, and everything needed for blue water fishing. We operate from two convenient locations - 1801 N Roosevelt Blvd for most of the fleet and 5950 Peninsular Ave on Stock Island for the Sanctuary - both with free parking for all guests.

We don't cut corners. Our crews arrive early to prep the boat and tackle. Your trip starts the moment you step aboard, not 30 minutes into your charter. That's the difference experience makes. For details on what different trips cost, see our guide to Key West fishing charter prices. Still deciding between booking solo or chartering the whole boat? Our breakdown of shared vs private fishing charters can help.

Species vary with season and conditions. Mahi-mahi (also called dolphin) are fast, acrobatic, and popular table fare. Peak season runs March through June, although mahi can show up year-round.

Wahoo are prized for their lightning-fast runs and excellent table fare. October through February is prime wahoo season. Blackfin tuna are powerful fighters that show up strongest in winter, while sailfish put on spectacular aerial displays from November through March.

Blue marlin—the ultimate offshore trophy—patrol our waters from May through September. These are catch-and-release only, but there's nothing like seeing a big blue light up behind the baits. We also target reef species like snapper and grouper on mixed offshore trips.

Offshore trips work for first-time anglers, families, experienced anglers, and groups who want a private day on the water. The crew handles the tackle and coaches guests who want help, while experienced anglers can discuss their goals with the captain before departure.

Families often choose a shorter option, while groups planning a longer day may value a boat with an air-conditioned cabin and restroom. Bachelor parties, bachelorette parties, and other groups can compare the six boats below by size, layout, and comfort.

No experience level or trip length guarantees a species. Tell the captain about your group and goals so the day's plan can account for weather, sea conditions, seasonal patterns, and what has been active.

Trips run 4 to 12 hours, and pricing follows trip length and boat. Private charters start at $850 for 4 hours aboard our 36-foot Hatteras Cowboy. More time gives the captain greater flexibility, but it does not promise a particular fishing ground, technique, or catch.

Not looking to book an entire boat? Our shared fishing trips cost $200 per person for 4 hours, $250 for 6 hours, or $300 for 8 hours. They require at least four guests to depart. A full cost breakdown is available in our guide to Key West fishing charter prices.

Every trip includes rods, reels, tackle, bait, licenses, ice, and fish cleaning. Listed charter prices exclude applicable fuel surcharge and crew gratuity; food and drinks are not included. Text or call (305) 304-2946 with your dates and group size and we will send back boat options and availability.

What separates a real sportfishing charter from a boat ride with a few rods in the holders is preparation. Our cockpits are rigged with Shimano Tiagras and Talicas, custom Calcutta and Crowder rods, fresh fluorocarbon leader on every trip, ballyhoo rigged that morning, and a livewell of pilchards or threadfins when the bait is around.

The techniques change with the target. We slow-troll live baits off kites for sailfish through the winter fronts, pull high-speed planer spreads for wahoo, chunk and jig the humps for blackfin tuna, work weed lines and frigate birds for mahi, and drop live bait or butterfly jigs on structure when the bite goes deep. Crews set up for stand-up fights or fighting-chair battles depending on the fish, and they clear lines and reset the spread while you stay on the rod.

That playbook came out of sixty years of logbooks. Captain Ralph "Cowboy" Baumgarten started running charters here in 1965 with a compass, a wristwatch, and the color of the water. When one of our captains tells you the mahi push closer after a south wind, or that kingfish stack on a particular wreck the week of the November full moon, that is inherited knowledge — not a guess off a forum. Meet the people running the boats on our crew page.

Key West sits on one of the densest collections of artificial reefs and historic wrecks in Florida. On longer trips we regularly anchor over the Vandenberg, Joe's Tug, the Cayman Salvager, and dozens of unmarked wrecks in 90 to 200 feet of water. This is heavy-tackle, hand-to-hand work — black and gag grouper, amberjack, mutton snapper, and African pompano hold tight to the structure and pull straight for the rocks. New to blue-water trips? Read what to expect on a deep sea fishing charter before you book.

Wreck stops are a favorite on full-day charters and a productive break between trolling passes, especially when the blue water is slow. Prefer shallower, calmer conditions? Our Key West reef fishing charters stay inside the reef line, and our tuna fishing charters focus on the humps and color changes offshore.