Cowboy & Cowgirl Sportfishing runs the widest menu of any deep sea operation in Key West, a family fleet that has fished the island since 1965 across three generations. Cowboy & Cowgirl Sportfishing fields six boats, from a 36 foot Hatteras to a 47 foot sportfisher and two fast center consoles, and it is one of the few here to sell a shared seat alongside the private charters. That range is its real strength. It lands in the middle of the port because the rotating roster swings from very good to flat, and because the mount upsell and the front office draw recurring complaints.
The verdict and where it ranks
At 6.9 Cowboy & Cowgirl is a mixed pick and the fifth ranked boat in Key West: book it with caveats, depending on the trip. The case for it is choice. The shared seat at $200 is the cheapest way onto a private style boat here, and the night snapper, shark, and Marquesas trips give the fleet a reach no single boat in the port matches. The case against it is consistency. With six boats and a rotating roster, the captain and mate you draw vary, the reviews swing with them, and a recurring strand reports a push to buy a taxidermy mount and slow front office communication. Book it for the shared seat or a specialty night or shark trip, go in ready to decline the upsell, and weigh it against the steadier boats on the Key West ranking.
The boats
The fleet is six boats, which is the draw and the variable. The Cowgirl is a 45 foot Hatteras and the Sanctuary a 47 foot Hatteras, the larger, more comfortable hulls for a full day offshore; the Cowboy is a 36 foot Hatteras and the Irish Cowboy a 40 foot Luhrs; and the Knotty Cowgirl and Blue Cowboy are 37 and 34 foot Contender center consoles for faster, lighter trips. Each is licensed for up to 6 anglers. The spread means you can match a boat to the trip, but it also means the boat and the crew you get depend on the day and the booking, so confirm which boat you are on when you reserve.
The fishing and what you target
Cowboy & Cowgirl fishes the full Key West spread: mahi mahi from spring into fall, blackfin tuna and king mackerel through the year, wahoo in the cooler months, and sailfish in winter offshore, with snapper, grouper, and amberjack on the reef and wrecks. The night snapper trip targets the reef after dark, the shark trip runs nearshore, and the Marquesas trip reaches the western grounds. The crews fish the season rather than a fixed menu, and on the better days the reviews credit them with real local knowledge and a box of fish.
Trips and prices
This is the most flexible pricing in the port. A shared seat starts at $200 per person for a 4 hour trip, the cheapest private style option here. A private 4 hour charter runs by the boat, from $850 on the Cowboy to $1,150 on the Sanctuary, and the night snapper, shark, and Marquesas trips are priced separately, the night snapper around $1,050 for the boat. Bait, tackle, and the fishing license are included; gratuity is extra, and a taxidermy mount, if you choose one, is a separate cost worth pinning down in advance. Our cost guide sets the shared seat against the whole boat, and the party boat versus private charter guide helps you choose between a shared seat here and a walk on at the head boat.
The crew
The crews run on a rotating roster across the six boats, and that is where the score turns. At their best, reviewers name captains and mates, Brett, Mark, and their mates among them, as polite, hard working, knowledgeable, and patient with first timers. The weaker reviews are not rare: a slow, fishless trip handled without much grace, and the recurring report of pressure to buy a mount of the catch that a few reviewers call a scam. The fishing reputation is solid; the service around it is the inconsistent part, which is why this sits below the owner run boats above it in the port.
Booking and what to know
Book by phone or through the operator’s site, or on FishingBooker. The boats leave from Garrison Bight Marina on North Roosevelt Boulevard, the main Key West charter row. Reviewers note the front office can be slow to respond, so call to confirm your boat, captain, and trip details rather than relying on email. Bring your own food and drinks and a soft cooler for your fillets. No license is needed, and the crew cleans your catch at the dock.
How we scored it
Cowboy & Cowgirl scores 6.9: the widest trips and access in Key West and a capable fleet, marked down on value and transparency, track record, and service for the recurring mount upsell, the slow front office, and a rotating roster that makes the experience uneven. Trips and fishing access is its strongest factor; service and the consistency of the record are where it slips. See how we scored this boat, and compare it against the rest of the Key West fleet.