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.

    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.

    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 →

    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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