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.

Offshore fishing in Key West means running beyond the reef line into deep, open water—typically 100 to 1,000+ feet. The Gulf Stream runs close to shore here, sometimes just 10 miles out, bringing warm blue water and the pelagic species that follow it.

Most offshore trips range from 4 to 12 hours depending on your target species and how far offshore conditions require. Half-day trips (4-5 hours) are ideal for families and first-time anglers. Full-day trips (8-12 hours) let us run further offshore to target tuna, wahoo, and marlin in the deep blue water.

No experience is necessary. Our captains have decades of experience with anglers of all skill levels—from kids catching their first fish to seasoned tournament fishermen. We handle the boat, the tackle, and the technique. You focus on the fight.

Key West's offshore waters hold some of the most sought-after gamefish in the world. Mahi-mahi (also called dolphin) are the most popular catch—fast, acrobatic, and delicious on the grill. Peak season runs March through June, but we catch them 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.

Key West and the Lower Florida Keys sit at the southern tip of the continental United States, where the Atlantic Ocean meets the Gulf of Mexico. This unique geography creates world-class offshore fishing opportunities you won't find anywhere else.

The Gulf Stream—that warm, fast-moving current that carries baitfish and predators—runs closer to shore here than almost anywhere on the East Coast. Some days we're fishing blue water just 10 miles from the dock. The Lower Keys also offer protected reef systems, deep wrecks, and open ocean all within reach of a single charter.

Our fleet departs from Key West's two most convenient marinas: 1801 N Roosevelt Blvd for every boat except the Sanctuary, which departs from 5950 Peninsular Ave on Stock Island. Both offer free parking for charter guests. From either location, we can reach prime offshore fishing grounds in under an hour—maximizing your time on the water.

See what's biting month by month on our Key West fishing calendar →

Offshore fishing in Key West takes you past the reef line and into open ocean where the bottom drops from 60 feet to over 1,000 feet within a few miles. This is blue water fishing — targeting fast, powerful pelagic species that migrate through the Gulf Stream and the Florida Straits. The water changes color from turquoise to cobalt as the depth increases, and the fish change with it. Out here you are pursuing predators built for speed and endurance: mahi-mahi, wahoo, blackfin tuna, sailfish, and blue marlin.

Key West's position at the southern tip of the Florida Keys gives offshore anglers a geographic advantage that few other ports can match. The Gulf Stream — a river of warm, fast-moving water that carries baitfish northward along the Atlantic coast — passes within 10 to 15 miles of the island on most days. That means your captain can reach prime blue water in under an hour, even on a half-day trip. Compare that to ports like Miami or Fort Lauderdale, where the run to productive offshore grounds can eat up a significant portion of your charter time.

Reef fishing, wreck fishing, and inshore trips all produce excellent catches in Key West — but offshore fishing operates on a different scale. Reef charters anchor over structure in 30 to 80 feet of water and target bottom species like snapper and grouper using cut bait and chum. Inshore trips work the flats, mangroves, and channels for tarpon, permit, and bonefish using light tackle and sight-casting techniques.

Offshore fishing is about covering water. Your captain trolls at cruising speed across miles of open ocean, dragging a spread of lures and baits at precise depths to intercept fish that are constantly moving. The strikes are explosive — a wahoo hits at 60 miles per hour, a sailfish lights up in neon blue before crashing the bait, and a marlin can strip 300 yards of line in seconds. The gear is heavier, the fights are longer, and the fish are bigger. A typical mahi-mahi weighs 10 to 30 pounds; a blue marlin can exceed 500.

The tactical approach also differs. Offshore captains read water temperature breaks, current edges, color changes, and bird activity to locate concentrations of baitfish — and the predators feeding on them. A good captain does not just drive to a GPS waypoint and drop anchor. He hunts, adjusting course based on what the ocean is telling him in real time. That instinct is something our captains have developed over decades of daily trips in these waters.

Three factors make Key West one of the premier offshore fishing destinations in the Western Hemisphere: proximity to the Gulf Stream, species diversity, and year-round fishability. The warm current that drives the Atlantic's pelagic food chain passes closer to Key West than to any other major fishing port on the U.S. mainland. That short run means more fishing time per charter dollar and access to species that other ports only see during narrow seasonal windows.

Species diversity is the second advantage. On a single offshore trip from Key West, you can troll for mahi-mahi, drop on a deep wreck for amberjack, jig for blackfin tuna over a temperature break, and hook a sailfish on the ride home. Few destinations anywhere offer that range of action in one outing. The Florida Straits act as a migration highway, funneling gamefish between the Gulf of Mexico and the Atlantic — and Key West sits right at the bottleneck.

Finally, Key West fishes well twelve months a year. Winter brings sailfish and blackfin tuna. Spring delivers the mahi-mahi migration. Summer produces marlin, tuna, and wahoo. Fall offers trophy wahoo and kingfish. There is no off-season — just a rotating cast of target species that keeps every month productive. Our captains adjust their tactics and target species with the seasons, and they have been doing it since 1965.

Offshore fishing charters in Key West attract a wide range of anglers, but they hold special appeal for those who want to test themselves against powerful, open-ocean gamefish. If you have fished freshwater lakes, inshore flats, or party boats and want to step up to something bigger, an offshore charter is the natural next move. The fish are faster, the fights are harder, and the stakes feel higher when you are standing on the back of a sportfishing boat with a bent rod and 200 yards of line disappearing into blue water.

Groups of friends and corporate outings consistently book full-day offshore trips because the shared experience of landing big fish creates the kind of memories that last. Bachelor parties, bachelorette parties, milestone birthdays, and annual fishing trips make up a significant portion of our bookings. A 43-foot sportfisher with a crew of two, a fighting chair, and a cooler full of drinks is a hard combination to beat for a day out.

Serious anglers who travel specifically to fish also choose Key West offshore charters for the shot at species they cannot catch at home — sailfish, blue marlin, and wahoo are not available in most U.S. waters, but they are regular catches here. Our captains work with experienced anglers to build a game plan around specific targets, using the right tackle, techniques, and locations to maximize your chances at the fish you came for.

Trips run 4 to 12 hours, and pricing follows trip length and boat. Private charters start at $850 for a half day aboard our 36' Hatteras Cowboy — the best value for families and small groups. Six-hour trips buy enough time to mix trolling with a stop on the wrecks, and full days open up the Gulf Stream and the humps.

Not looking to book an entire boat? Our shared fishing charters start at $200 per person for a 4-hour scheduled departure — the same water, the same crews, a lower price. A full cost breakdown lives in our guide to Key West fishing charter prices.

Every trip includes rods, reels, tackle, bait, licenses, ice, and fish cleaning. Fuel surcharges may apply on longer runs, and 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.