Cowboy Cowgirl Sportfishing
    Deep sea fishing rods ready for action on a Key West charter boat
    Cowboy Cowgirl Sportfishing Key West FL

    Deep Sea Fishing Key West

    Experience true deep sea fishing in Key West aboard classic sportfishing boats targeting mahi, tuna, sailfish, marlin, and other big game species in the Florida Keys.

    60+ Years Experience
    USCG Licensed Captains
    All Equipment Included
    Free Parking for All Guests!

    Since 1965

    Three generations of local captains

    USCG Equipped

    All required safety equipment

    6 Offshore Boats

    Fleet for any group size

    Two Marinas

    1801 N. Roosevelt & 5950 Peninsular

    Trip Options & Pricing

    Our deep sea fishing charters range from 4 to 12 hours, with pricing based on trip length and boat selection. Private charters start at $850 for a half-day trip on our 36' Hatteras Cowboy — our best value option for families and small groups. For a complete overview of our fleet and trip styles, browse all of our Key West sportfishing charters.

    Prefer not to book the whole boat? Our shared fishing charters start at $200 per person for a 4-hour trip. You'll fish alongside other anglers on a scheduled departure — same great fishing, lower cost.

    All charters include rods, reels, tackle, bait, fishing licenses, ice, and fish cleaning. Just bring sunscreen, snacks, and a sense of adventure. Book online or call/text us at (305) 304-2946 to check availability.

    What's Included

    Fishing Gear & Equipment

    • Quality rods, reels, and tackle
    • Fresh bait and live bait when conditions warrant
    • All fishing licenses and permits

    Onboard Amenities

    • Ice and coolers for your catch and drinks
    • Fish cleaning and bagging after the trip
    • USCG-licensed captain and mate

    What to Bring

    • Sunscreen (reef-safe preferred)
    • Polarized sunglasses
    • Hat for sun protection
    • Comfortable, non-marking shoes
    • Snacks and drinks (no glass containers)
    • Camera or phone for photos
    • Motion sickness medication if needed
    • Cash or card for crew gratuity (15-20% customary)

    What You Can Catch

    The deep waters off Key West hold some of the most sought-after gamefish in the Atlantic. Mahi-mahi (also called dolphin) are the most popular catch — fast, acrobatic fighters that put on a spectacular show and taste incredible on the grill. Peak season runs March through June, but we catch them year-round.

    Wahoo are prized for their blistering runs — often hitting 60+ mph on the initial strike. Fall and winter bring the best wahoo fishing. Blackfin tuna are powerful fighters that show up strongest in January and February, making excellent sashimi and steaks.

    Sailfish are the acrobats of the deep sea — known for spectacular jumps and bill-walking across the surface. November through March is prime sailfish season. And for the ultimate trophy, blue marlin patrol these waters from May through September. Marlin are catch-and-release, but there's nothing like seeing a big blue light up behind the baits.

    Key West Deep Sea Species by Season

    Mahi-Mahi

    Peak: March-June

    Fast, acrobatic, and delicious - the most popular deep sea catch

    Wahoo

    Peak: October-February

    Lightning-fast runs and excellent table fare

    Blackfin Tuna

    Peak: January-February

    Powerful fighters and great eating

    Sailfish

    Peak: November-March

    Spectacular jumps and bill-walking action

    Blue Marlin

    Peak: May-September

    The ultimate deep sea trophy - catch and release

    Snapper & Grouper

    Year-round

    Reef fish classics - excellent table fare from our local wrecks and reefs

    Where We Depart

    Our deep sea fishing fleet departs from two Key West marina locations, both with free parking for charter guests:

    1801 N. Roosevelt Blvd

    Key West, FL 33040

    Easy access from US-1, near the commercial district. Free parking lot adjacent to the dock.

    5950 Peninsular Ave

    Stock Island, FL 33040

    Located on Stock Island, just minutes from Key West. Free parking available on-site.

    Your captain will confirm the exact meeting location when you book. Both marinas put us within 30-60 minutes of prime deep sea fishing grounds.

    What Is Deep Sea Fishing in Key West?

    Deep sea fishing in Key West means heading offshore — typically 5 to 30 miles from shore — into the deep blue waters of the Atlantic Ocean and the Gulf of Mexico. Unlike reef fishing or inshore trips that stay in shallower water, deep sea charters target open-ocean gamefish that live in depths of 100 to 1,000 feet or more. The Gulf Stream current runs just a few miles south of Key West, carrying warm water, baitfish, and big predators close to the island. That proximity is what makes Key West one of the best deep sea fishing destinations in the country.

    On a deep sea fishing trip, your captain trolls artificial lures and fresh bait behind the boat at varying speeds and depths to attract pelagic species — fish that roam the open water rather than holding near structure. When a fish strikes, the rod loads up and the reel screams. The mate hands you the rod, coaches you through the fight, and nets or gaffs the fish when it comes boatside. Some fights last two minutes; others last forty. That range of action is what draws people back to deep sea fishing in Key West year after year.

    What to Expect on a Deep Sea Fishing Trip

    Your Key West deep sea fishing trip starts at the dock, where your captain and mate greet your group, load the gear, and walk through a quick safety orientation. Within minutes you are heading out of the harbor and into open water. The ride to the fishing grounds takes anywhere from 20 minutes to over an hour depending on where the fish are biting and which trip length you booked.

    Once on station, the mate deploys a trolling spread — typically four to six lines fanning out behind the boat at different distances and depths. Each line runs a different lure or bait to cover the water column and appeal to different species. You sit back, watch the rods, and wait for the strike. When it happens, you will know — the reel sings, the rod tip plunges, and the crew springs into action to get you hooked up and fighting.

    Between trolling passes, the captain may stop over a wreck or reef ledge to drop baits for bottom species like snapper and grouper. This change of pace keeps the action steady and adds variety to your cooler. At the end of the trip, the crew cleans and bags your catch at the dock so you can take fresh fillets to dinner that evening. Several Key West restaurants offer hook-and-cook service — hand them your fish and they prepare it however you like.

    Why Deep Sea Fishing Is One of the Best Things to Do in Key West

    Key West sits at the end of the Florida Keys, surrounded by deep water on three sides. The Gulf Stream passes closer to Key West than almost any other point in the continental United States, pushing warm, nutrient-rich water within easy reach of even a half-day charter. That geography means you spend less time running and more time fishing compared to deep sea trips from Miami, Fort Lauderdale, or other Florida ports.

    The variety of fish available on a single trip sets Key West apart. In one morning you might catch mahi-mahi on the troll, drop down for yellowtail snapper on a wreck, and hook a wahoo on the ride home. Few places in the world offer that kind of diversity within a few miles of the dock. Add warm weather year-round, calm seas most days, and professional captains who have fished these waters for decades, and you have one of the best deep sea fishing experiences available anywhere.

    Beyond the fishing itself, a deep sea charter gets you away from the crowds and onto the open ocean. You see dolphins riding the bow wake, sea turtles surfacing alongside the boat, and frigate birds circling overhead to mark feeding fish. It is a full day on the water that combines sport, scenery, and a cooler full of fresh fish to take home.

    Who Deep Sea Fishing Is Perfect For

    Deep sea fishing in Key West works for just about everyone. Families with kids book half-day trips and spend the morning reeling in mahi-mahi and snapper with help from the mate. Couples looking for something more exciting than a sunset cruise book a four-hour charter and come back with fish stories and fillets. Groups of friends split a full-day trip and turn it into the highlight of their vacation.

    First-time anglers are our specialty. Our crews have introduced thousands of beginners to deep sea fishing over the past 60 years, and they know how to make the experience approachable and fun. You do not need to know how to tie a knot, rig a bait, or operate a reel — the mate handles the technical work and puts the rod in your hands when the fish is on. All you need to do is hold on and reel.

    Experienced anglers appreciate the quality of our tackle, the local knowledge of our captains, and the range of species available on any given day. Whether you want to troll for pelagic gamefish, bottom-fish on deep structure, or target a specific species like sailfish or wahoo, our captains build a game plan around your goals.

    Best Time of Year for Deep Sea Fishing in Key West

    Key West produces fish twelve months a year, but each season brings different targets and conditions. Spring — March through June — is peak mahi-mahi season. Schools of dolphinfish migrate through the Gulf Stream, feeding on flying fish and sargassum weed lines. This is when our crews see the highest catch rates and the most consistent action for anglers of all skill levels.

    Summer extends the mahi bite and adds blue marlin, blackfin tuna, and amberjack to the mix. Water temperatures rise into the 80s, baitfish pile up along weed lines and current edges, and the offshore grounds light up. Full-day trips during summer months regularly produce double-digit fish counts across multiple species.

    Fall brings wahoo season. These narrow, torpedo-shaped fish hit trolled lures at speeds over 60 miles per hour and produce some of the most exciting strikes in deep sea fishing. Kingfish also show up in strong numbers through October and November, adding steady action on the troll. Winter shifts the focus to sailfish and blackfin tuna. The cooler water temperatures push sailfish through the Florida Straits, and January and February are the best months to target them. Bottom fishing on the reef stays productive year-round, making even the slower offshore months a solid choice for a Key West deep sea fishing trip.

    Choose Your Boat

    All deep sea fishing trips are private charters aboard our offshore fleet. Each boat offers the same great fishing experience with different amenities and price points.

    Learn more about offshore fishing in Key West → · Looking for shared/split charters? →

    Cowboy – 36' Hatteras

    Cowboy – 36' Hatteras

    36 feet Hatteras Sportfisher

    From $850

    Irish Cowboy – 40' Luhrs

    Irish Cowboy – 40' Luhrs

    40 feet Luhrs Sportfisher

    From $950

    Cowgirl – 45' Hatteras

    Cowgirl – 45' Hatteras

    45 feet Hatteras Sportfisher

    From $1,050

    Sanctuary – 47' Hatteras

    Sanctuary – 47' Hatteras

    47 feet Hatteras Sportfisher

    From $1,150

    Knotty Cowgirl – 37' Contender

    Knotty Cowgirl – 37' Contender

    37 feet Contender Center Console

    From $1,000

    Blue Cowboy – 34' Contender

    Blue Cowboy – 34' Contender

    34 feet Contender Center Console

    From $1,100

    Swipe to see more boats →

    Wreck Fishing in Key West — Grouper, Amberjack & Snapper

    Key West sits on top of one of the densest collections of artificial reefs and historic wrecks in Florida. Our deep sea charters regularly anchor over the Vandenberg, Joe's Tug, the Cayman Salvager, and dozens of unnamed wrecks in 90 to 200 feet of water. Wreck fishing is heavy-tackle, hand-to-hand combat — black grouper, gag grouper, amberjack, mutton snapper, and African pompano hold tight to the structure and pull hard for the rocks.

    We use live bait and butterfly jigs depending on the bite. It's a favorite stop on full-day trips and a popular add-on between offshore trolling passes. Prefer calmer, shallower water? Try our Key West reef fishing charters — or go all-in on bluewater with our offshore trolling trips.

    Deep Sea Fishing FAQs

    Ready to Book Your Deep Sea Adventure?

    All deep sea fishing trips depart aboard our offshore charter fleet. View available boats and book your trip today.

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