5.0(10 Reviews)Key West Private Fishing Charters
5.0(10 reviews)
Private Trip
Offshore Fishing
Top RatedMost Reviewed
Private fishing charters accommodate up to 6 guests comfortablyTarget species include Mahi, Wahoo, Tuna, Sailfish, and MarlinFlexible trip durations from 4 to 12 hours available
When you're looking for serious fishing action in the waters around Key West, Cowboy Cowgirl Sportfishing Charters delivers exactly what you came for. Captain Mark and his crew know these waters like the back of their hand, and they've got the track record to prove it. Whether you're planning a quick half-day trip or want to go all-out with a 12-hour marathon, they'll put you on fish. These aren't your typical tourist boats – this is real fishing with captains who live and breathe it every single day.
Your day starts early if you're serious about catching fish. The crew meets you at the dock with everything rigged and ready to go – no wasted time, no amateur hour. You'll head out on a boat that's built for fishing, not sightseeing, with professional-grade tackle and electronics that actually work when you need them most. The captains run a tight ship but keep things relaxed enough that everyone can enjoy themselves, whether you're bringing the kids or it's your first time holding a rod. They'll adjust the trip based on what's biting and where the action is hottest that day. Some days that means trolling the nearshore reefs, other days you're running 20 miles offshore chasing blue water and pelagics. The beauty of a private charter is flexibility – if the mahi are thick in one spot, you stay there until arms get tired from reeling.
These guys run a proper spread when they're trolling – usually four to six lines out with a mix of ballyhoo, lures, and teasers that trigger aggressive strikes from pelagic species. They know exactly how to rig baits so they swim naturally, and they're constantly adjusting speed and direction based on water temperature, current breaks, and what the fish finder is showing. When you're targeting mahi, they'll work the weed lines and floating debris where these fish love to hang out. For billfish like sailfish and marlin, it's all about finding the right water color and temperature breaks where baitfish concentrate. The captains watch their electronics religiously and aren't afraid to make long runs to find productive water. When something hits, they coach you through the fight without taking over – you do the work, but they make sure you don't lose the fish due to rookie mistakes.
"Captain Mark of Cowboy Cowgirl Charters is the best in the business! His knowledge of the local waters and commitment to customer satisfaction are unmatched. Whether you're a seasoned angler or a beginner, Mark ensures a successful and enjoyable trip. Highly recommended!" - Cassie
"These guys are so good at what they do!! We did not go fishing - we went CATCHING!! I can't say enough about Captain Pel & 1st Mate John giving us the best experience and showing us all the fishing techniques!!! From departure to return, these guys have it down to an art and know where the fish are!! I can't recommend them enough. If we come back, we know who we are calling!! Thanks Pel & John for the BEST fishing trip and sending us back to TX with a freezer full of fish!! True fishing masters!" - Kelsey
"Captian Chris and mate Will knew right where to go. They were dialed in to the fish and very knowledgeable about the waters. They put us on fish early and often on our 6hr charter. We caught so many mahi we told them to start throwing them back because we already had enough to eat. Will kept the baits fresh and worked the entire trip making sure the gear was ready for the big one. Which Capt. Chris found us in the last hour of the trip, a beautiful Key West sailfish! I would recommend this charter to anyone and will book again next time we are down." - John
Atlantic Sailfish are the crown jewel of Key West fishing, and when one crashes your spread, you'll understand why billfish get anglers so fired up. These fish average 6-8 feet long and put on an aerial show that'll have everyone on the boat grabbing cameras. Peak season runs from December through April when they migrate through in big numbers, following massive baitfish schools. Sailfish are notorious for their lightning-fast initial run and multiple jumps – they'll strip line off your reel faster than you think possible. The captains know exactly where to find them along temperature breaks and current edges, particularly around the reef line in 80-200 feet of water.
Mahi Mahi are pure fun on light tackle and absolutely gorgeous fish that fight like bulldogs. Also called dolphinfish or dorado, these guys love floating structure and weed lines where they ambush smaller baitfish. They're most active during warmer months from May through October, though you can find them year-round in South Florida waters. Mahi typically range from 5-25 pounds, with occasional bulls pushing 40-50 pounds that'll test your drag system. What makes them special is their willingness to bite and their habit of traveling in schools – once you find one, there are usually more nearby. Plus, they're fantastic eating fish that make the cooler trip home worthwhile.
Greater Amberjack are the muscle cars of the reef – powerful, aggressive, and absolutely relentless when hooked. These fish live around structure like wrecks and reef ledges, typically in 60-150 feet of water. AJs can grow massive, with fish over 50 pounds common in Key West waters. They bite year-round but are most active during cooler months when they're not spawning. What separates amberjack from other species is their incredible pulling power – they use their broad shoulders and deep body to generate tremendous force. The captains target them with live baits around known structures, and once hooked, these fish will test both your tackle and your back muscles.
Cast off aboard our beautifully restored 40-foot Luhrs sportfisher with Captain Mark for your Key West deep-sea adventure. This 2005 vessel got a complete makeover in 2018 and comes loaded with everything serious anglers need - fish finder to locate the action, GPS navigation, VHF radio, and a spacious flybridge for spotting fish. Whether you're targeting King Mackerel and Mahi nearshore or heading offshore for Wahoo, Blackfin Tuna, Sailfish, and Marlin, this boat handles it all. The air-conditioned cabin keeps you cool between bites, while the onboard toilet, bed, and icebox for your catch and refreshments make longer trips comfortable. From half-day runs to extended full-day charters, we'll customize your fishing experience. Want to tangle with Tarpon or chase Sharks? Just ask - Captain Mark knows these waters and where the fish are biting. Six anglers max means plenty of room to work the rods without bumping elbows.
Istiophorus AlbicansThese fish are absolute speed demons and put on quite a show when hooked. Sailfish average around 7 feet and 50 pounds, with that signature sail-like dorsal fin they flash when hunting or fighting. We find them in 30-65 feet of water, often hunting baitfish near the surface. Winter months are prime time here in Key West - the cooler water brings them in closer to shore. What makes them special is their acrobatic fight - they'll jump, dive, and change colors from blue to black right before your eyes. The key to landing one is patience - when they take the bait, let them run first before setting the hook. They'll try to shake it off immediately, so keep steady pressure but don't rush the fight.
Seriola dumeriliAmberjacks are the bulldozers of the reef - powerful, stubborn fish that'll test your tackle and your arms. These bruisers average 20-40 pounds but can push much bigger, with that distinctive amber stripe running down their blue-gray sides. You'll find them around wrecks, reefs, and structure in 60-200 feet of water, where they patrol like underwater bouncers. They bite best during cooler months when they're more active, though we catch them year-round. What makes them a favorite is their raw power - once hooked, they'll head straight back to the bottom and make you work for every inch. They're also excellent table fare when prepared right. My advice: use heavy tackle and don't give them any slack, or they'll wrap you around the nearest piece of structure faster than you can blink.
Coryphaena HippurusMahi are hands-down one of the most beautiful fish you'll catch, with their golden sides and electric blue-green backs that light up like a rainbow when they're brought to the boat. They typically run 15-30 pounds and love hanging around floating debris, weed lines, and current breaks in open water. We target them year-round here, but spring through fall gives you the best action when they're feeding actively. What guests love most is their aggressive strike and the fact that they're fantastic eating - firm, white meat with a mild flavor that's hard to beat. Plus, where you find one mahi, you often find more. Pro tip: when you hook one, keep it in the water near the boat while you get more lines out - the school will usually stick around trying to help their buddy.
Lutjanus AnalisMutton snapper are one of the most sought-after fish on the reef, and for good reason - they're excellent fighters and even better eating. These pinkish snappers with blue streaks around their eyes typically run 5-15 pounds, though we occasionally see them pushing 20-plus. They hang around coral reefs, wrecks, and sandy areas adjacent to structure in 30-100 feet of water. Spring and summer months are prime time when they're spawning and more aggressive. What guests love is their strong, determined fight and the sweet, flaky meat that's perfect for the dinner table. They're also smart fish that require finesse - use the freshest bait you can get and light weights. The key is letting your bait drift naturally in the current; they'll reject anything that looks suspicious.
Kajikia AlbidaWhite marlin are the ultimate offshore prize - elegant billfish that can reach up to 9 feet and 180 pounds, though most run smaller. These apex predators cruise the deep blue water beyond the continental shelf, hunting flying fish and squid in the top of the water column. Best fishing happens during warmer months when they're most active and feeding near the surface. What sets them apart is their spectacular aerial display when hooked - they'll jump, dive, and put on a show you'll never forget. They're also one of the smartest fish out there, so presentations need to be perfect. The trick with white marlin is watching the spread, not just the baits - they'll often come up behind the lures to investigate before striking. When they do hit, don't set the hook immediately; let them eat the bait first.
5.0 out of 5.0Captain Mark of Cowboy Cowgirl Charters is the best in the business! His knowledge of the local waters and commitment to customer ...
\Thank you for the fantastic review! Captain Mark truly is one of the best, and his knowle...
Captain Mark and Cowboy Cowgirl Charters are top-notch! Mark's expertise and friendly demeanor made for a memorable day on the wat...
hank you for the great review! Captain Mark and the crew always go the extra mile to make ...
These guys are so good at what they do!! We did not go fishing - we went CATCHING!! I can’t say enough about Captain Pel & 1st Mat...
Outstanding experience, Capt. Cole and Sean know their fishing. There were four of us, left on time and put us on fish quickly. Ve...
Captian Chris and mate Will knew right where to go. They were dialed in to the fish and very knowledgeable about the waters. They ...
An absolutely fantastic fishing experience with Cowboy Cowgirl Charters and Captain Mark Baumgarten! From the moment we stepped on...
Highly recommend Cowboy Cowgirl Charters with Captain Mark at the helm! Mark's passion for fishing is contagious, and his skill in...
What an incredible day of fishing with Cowboy Cowgirl Charters and Captain Mark! Mark's expertise and professionalism made for a s...
Captain Mark and Cowboy Cowgirl Charters provided us with an amazing fishing experience! Mark's dedication to finding fish and ens...
Highly recommend Cowboy Cowgirl Charters with Captain Mark Baumgarten! Mark's knowledge of the area and his commitment to customer...
Captain Mark of Cowboy Cowgirl Charters is simply outstanding! His passion for fishing and his expertise in navigating the waters ...
An amazing fishing adventure with Cowboy Cowgirl Charters and Captain Mark! Mark's professionalism and knowledge of the local wate...
Captain Mark and Cowboy Cowgirl Charters provided us with an incredible day of fishing! Mark's enthusiasm and expertise made for a...
Key West, FL