Budget-Friendly
Shared & Split Fishing Charter
starting at$200
Per Person (4-Hour Trip)
Join other anglers on a 4-, 6-, or 8-hour fishing trip for up to six guests. Shared trips need at least four booked 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.
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)- Since 1965
- Three Generations
- Local Captains
- All Skill Levels
- Up to 6 Guests
Free Parking for All Guests!
Start Here
How Do You Want to Fish Key West?
Pick the kind of trip that fits your group. We'll help you match it to the right boat afterward.
Shared Fishing
Starting at $200 per person
For solo anglers, couples and small groups who want an affordable day of fishing without booking a whole boat.
See Trips
Private Fishing
Starting at $850 per boat
Reserve the entire boat for your group. Pick your trip length and fish the way you want to fish.
See Trips
Shark Fishing
Starting at $600 per trip
Inshore, reef and deepwater shark trips. Heavy tackle, big fish, catch and release.
See Trips
Light Tackle & Adventures
Light tackle fishing, Marquesas Keys runs, snorkel-and-fish combos and other specialty trips.
See 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.
What We Offer
Key West Fishing Experiences
Pick the experience that fits your group. Each page covers seasons, target species, and pricing in detail.
Reef & Wreck Fishing
Steady action in calmer water over reefs and historic wrecks.
Shark Fishing Adventures
Heavy tackle, big predators, and ethical catch-and-release.
Our Fleet
Best Fishing Charters in Key West
Private, shared, and shark fishing trips since 1965. Choose from our tournament-tested fleet of sportfishing vessels.
Six Tournament-Ready Vessels • Expert Local Captains • All Skill Levels Welcome
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
Swipe to see more
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
- Most Popular
- Top Rated
- Catch & Release
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
- Sunset Departure
- Cool Night Fishing
- 45' Hatteras Cowgirl
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
- Remote Atoll
- Historical Tour
- Premium Light Tackle
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.
