Budget-Friendly
Shared & Split Fishing Charter
starting at$200
Per Person (4-Hour Trip)
Join other anglers on a 4-, 6-, or 8-hour trip for up to six guests. Shared trips need at least four guests to depart.
4-8 Hours
Up to 6 People
Cowboy Cowgirl SportFishing Charters · Family Owned Since 1965
Key West Fishing ChartersSince 1965
Choose a private charter for your group or join a shared fishing trip. Our Key West fleet offers offshore and deep-sea fishing, reef, shark, and light-tackle trips, with help choosing the right boat and trip length.
Maximum 6 guests per boat
Private Fishing ChartersFrom $850 per boatCompare boats, trip lengths and pricesApplicable fuel surcharge and gratuity are extra.Shared Fishing TripsFrom $200 per personScheduled 4-, 6- or 8-hour tripsApplicable fuel surcharge and gratuity are extra.
4.8 on Google(1,000+ reviews)
4.7 on Tripadvisor(448 reviews)- Three Generations
- Local Captains
- All Skill Levels
Recent Catches
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Free Parking for All Guests!
Our Fleet
Best Fishing Charters in Key West
Scroll through our six-boat fleet and find your trip.
Best Value
Cowboy – 36' Hatteras
starting at$850
4-Hour Charter, up to 6 people
Our lowest-priced private boat offers offshore and shark fishing trips for groups of up to six.
4-12 Hours
Up to 6 People
Private Offshore
Irish Cowboy – 40' Luhrs
starting at$950
4-Hour Charter, up to 6 people
Fish offshore aboard a 40′ sportfisher with an air-conditioned cabin and two fighting chairs.
4-12 Hours
Up to 6 People
Flagship Vessel
Cowgirl – 45' Hatteras
starting at$1,050
4-Hour Charter, up to 6 people
A spacious offshore sportfisher with air conditioning and a fighting chair for groups of up to six.
4-12 Hours
Up to 6 People
Best Offshore
Sanctuary – 47' Hatteras
starting at$1,150
4-Hour Charter, up to 6 people
Our largest sportfisher offers air-conditioned space for longer offshore trips. It departs from Stock Island.
4-12 Hours
Up to 6 People
Light Tackle Comfort
Knotty Cowgirl – 37' Contender
starting at$1,000
4-Hour Charter, up to 6 people
An open-deck center console for hands-on light tackle fishing or a fishing-and-sandbar trip, with a cabin and restroom.
4-12 Hours
Up to 6 People
Marquesas Explorer
Blue Cowboy – 34' Contender
starting at$1,100
4-Hour Charter, up to 6 people
A center console for light tackle and reef fishing, with longer trips that can explore the Marquesas when conditions allow.
4-12 Hours
Up to 6 People
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Specialty Trips
Unique Fishing Experiences
Looking for something different? Try our shark fishing, night snapper, or historical Marquesas adventures.
Most Popular
Key West Shark Fishing
starting at$600
3-Hour Inshore Trip, up to 6 people
Test your strength with the ultimate thrill — Key West shark fishing charters. Go head-to-head with bull sharks, hammerheads, and blacktips. Trusted local experts since 1965.
3-6 Hours
Up to 6 People
Seasonal: May - August
Night Snapper Fishing
starting at$1,050
4-Hour Charter, up to 6 people
Night snapper fishing done right — grouper and good times every night. Beat the heat, skip the crowds, and hook serious fish when the sun goes down.
4-12 Hours
Up to 6 People
Signature Experience
Marquesas Keys Adventure
starting at$1,100
Half Day Charter, up to 6 people
Explore the remote Marquesas Keys — a pristine natural atoll 30 miles west of Key West. Light tackle fishing meets remote exploration aboard the premium 34' Blue Cowboy.
4-12 Hours
Up to 6 People
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Start Here
Choose Your Key West Fishing Trip
Start with a trip type, then visit its full page for boats, options, and booking details.
Private Fishing
Starting at $850 per boat
Compare our boats, trip lengths, and private charter prices.
View Trips
Shared Fishing
Starting at $200 per person
Book individual spots; shared trips require a four-guest minimum to depart.
View Trips
Offshore & Deep Sea
Explore our offshore trips, boats, trip lengths, and fishing options.
View Trips
Shark Fishing
Starting at $600 per trip
Compare private inshore, reef, and offshore shark charters.
View TripsLight Tackle & Specialty
See light tackle boats and specialty fishing experiences.
View TripsNot sure which trip is right for you? Call or text us at (305) 304-2946 and we'll help match your group with the right boat and trip.
Listed charter price excludes applicable fuel surcharge and crew gratuity.
Our Story
Fishing Key West Since 1965
Three Generations. One Family. These Waters Are Home.
Cowboy Cowgirl SportFishing Charters began in Key West in 1965 and has grown into a three-generation family fishing operation. What started with founder Hans Baumgarten and the original Cowboy continues today with the Baumgarten family taking anglers onto the same Key West waters they have fished for decades.
Our captains are U.S. Coast Guard licensed locals, and our fleet gives us the right boat for families, first-timers, and serious anglers alike.
Since 1965Three GenerationsLocal CaptainsMultiple BoatsAll Skill Levels
Read Our StoryWhat's Included on Every Charter
Up to 6 guests per boat. Beginners welcome — the crew handles the rest.
Fishing Gear
Bait & Tackle
Fishing License
Ice & Cooler
Fish Cleaning for Legal Fish Kept
Professional Crew
Listed charter price excludes applicable fuel surcharge and crew gratuity.
Great for
FamiliesBeginnersExperienced AnglersCouplesSmall Groups
Bringing kids? Start with a family-friendly fishing charter.
Fishing Key West Year-Round
Key West offers fishing opportunities throughout the year, with different species and techniques changing by season.
