When a fishing operation has been running since 1965, they're doing something right. Cowboy Cowgirl SportFishing Charters is a family-owned Key West institution now in its third generation under Captain Mark Baumgarten. With a tournament-tested fleet of six boats and over 60 years of local knowledge, they've built a reputation for putting anglers on fish while keeping trips affordable and beginner-friendly.
What caught my attention isn't just the longevity—it's the volume of positive feedback across platforms. With 273+ reviews averaging 4.6 stars across TripAdvisor, Yelp, and other platforms, customers consistently praise the crew's knowledge, patience with first-timers, and ability to deliver successful fishing days.
The Fleet: Six Boats for Every Budget and Style
The fleet diversity here is impressive. Whether you're a solo angler looking to save money on a shared charter or a family wanting a private boat with air conditioning, they've got options:
The Hatteras Sportfishing Yachts:
- •Cowboy (36' Hatteras) - The original tournament-tested vessel
- •Cowgirl (45' Hatteras) - Handles larger groups, cold AC for those brutal Key West summer days
- •Sanctuary (47' Hatteras) - The flagship for serious offshore runs
- •Irish Cowboy (40' Luhrs) - Air-conditioned cabin, dual fighting chairs, flybridge, and bathroom. Customers specifically mention this boat for comfort.
The Center Console Speed Boats:
- •Blue Cowboy (34' Contender) - Fast runs to the bite
- •Knotty Cowgirl (37' Contender) - Speed fishing when the mahi are running
If you're fishing Key West in July, that air conditioning isn't luxury—it's survival. Multiple reviewers on TripAdvisor specifically praised the Irish Cowboy's climate-controlled cabin as a game-changer for family trips.
What to Expect on the Water
Cowboy Cowgirl runs both shared and private charters, which is actually smart for customers. Shared charters start at $200 per person—that's accessible for folks who want to experience deep sea fishing without dropping $800-1200 on a private boat. You're fishing with strangers, but you're also saving money while still getting the same crew expertise.
Private charters range from 4-hour reef trips to 12-hour offshore marathons. They target the full spectrum of Key West species: mahi-mahi, tuna, wahoo, sailfish, marlin, grouper, snapper, king mackerel, tarpon, and sharks. The shark fishing here is catch-and-release, which I appreciate—they're running these trips for the experience, not killing apex predators for dock photos.
Trip options include:
- •Deep sea offshore fishing
- •Reef fishing for grouper and snapper
- •Night snapper trips (productive in summer)
- •Light tackle backcountry fishing
- •Marquesas Keys expeditions (serious anglers only)
- •Catch-and-release shark adventures
Everything's included: all equipment, bait and tackle, fishing licenses, and free marina parking at 1801 N. Roosevelt Blvd. They'll also clean your keeper fish—a nice touch that saves you the hassle of finding a fish cleaning station after a long day.
The Captain Mark Baumgarten Difference
Captain Mark Baumgarten owns the operation and frequently runs trips himself. Born and raised in Key West, he's got the local knowledge that matters when conditions change. One TripAdvisor reviewer noted, "Mark's skill in locating fish is impressive," while another wrote, "Captain Mark and his crew were knowledgable, patient and entertaining, caught plenty of fish."
The fleet also includes Captains Bobby, James, Nels, and "Sharky Mark," along with mates like Cole, Chase, Larry, Jesse, Dalton, and Niles. What stands out in the reviews is how many captains and mates get mentioned by name—that suggests consistent quality across the crew, not just one good captain carrying the operation.
A Yelp reviewer fishing with Captain Bobby said, "Bobby and Jesse were such a wonderful crew, Jesse worked his butt off to make sure the 6 of us all caught fish." Another on TripAdvisor wrote about Captain Bobby: "His mate Larry was awesome, and he was constantly doing any and everything to help us catch fish."
What Customers Are Saying
With 89 Yelp reviews and hundreds more across TripAdvisor and Google, the feedback is overwhelmingly positive. Here's what actual customers report:
The Good (and it's mostly good):
One customer wrote on TripAdvisor: "Caught plenty of fish, kept what was in season and Mark cleaned them for us." Another reported going shark fishing and catching and releasing six sharks—exactly what you want from a shark trip.
For beginners, the crew gets consistent praise. One first-time angler wrote, "Captain Mark, the owner of the fleet, was insightful and Cole was patient showing the hubs some new knots." Another said about the Irish Cowboy: "A great way for her to start her fishing experience she fell in love with fishing."
The catch reports are solid. One group landed 17 keepers, with the reviewer noting, "They were both very knowledgeable and knew exactly where to take us to fill that cooler full of fish." Another reported catching "yellowtail snapper, mackerel and mutton snapper" on a successful reef trip.
Several customers book repeat trips. One family "went fishing on the Cowgirl with Captain Mark for the second time in the past year," and another "came back for a second day of fishing." That's a good sign—people who've fished with them before choose to come back.
The Negative (transparency matters):
Here's the thing—with 273+ reviews, you're going to have some unhappy customers. One reviewer on Yelp had a notably bad experience, claiming the captain and mate Darrel "were very rude to all passengers on board" and that the captain said they wouldn't catch anything before even leaving the channel. The same customer reported the captain backed the boat over their line when they hooked a big fish, causing it to snap. They titled their review "rip off" and claimed the owner wouldn't return calls.
I'm including this because transparency builds trust. However, this appears to be an isolated incident—I couldn't find other reviews mentioning similar professionalism issues or customer service problems. With hundreds of positive reviews praising the crew's patience, knowledge, and professionalism, this seems to be the exception rather than the rule.
It's worth noting that even great operations can have off days or personality conflicts. What matters is the pattern, and the pattern here is overwhelmingly positive across multiple platforms over many years.
Practical Information
Pricing:
- •Shared charters: From $200 per person
- •Private charters: Pricing varies by boat and duration (contact for quotes)
- •All fishing licenses included
What's Included:
- •All fishing equipment, bait, and tackle
- •Florida fishing licenses for all anglers
- •Free marina parking
- •Fish cleaning for keeper fish
Location & Hours:
- •1801 N. Roosevelt Blvd, Key West, FL 33040
- •Hours: 6 AM – 11 PM daily
- •Phone: (305) 304-2946
- •Website: cowboycowgirlsportfishing.com
Booking Platforms:
Available through their website, FishingBooker, and Guidesly. They're also active on Instagram at @cowboycowgirlsportfishing if you want to see recent catch photos.
Who This Charter Is Best For
Perfect for:
- •First-time anglers - The crew gets consistent praise for patience and instruction
- •Families with kids - Air-conditioned boats with bathrooms make it comfortable for everyone
- •Budget-conscious anglers - Shared charters at $200/person are accessible
- •Shark fishing enthusiasts - They run dedicated catch-and-release shark trips
- •Anyone fishing Key West - With 60+ years of local knowledge, they know these waters
Maybe not ideal for:
- •Anglers who want guaranteed solitude (shared charters put you with other groups)
- •Those who need guaranteed pricing up front (private charter rates require contact)
The Bottom Line
Sixty years in business isn't an accident. Cowboy Cowgirl SportFishing Charters has earned their reputation through three generations of putting customers on fish while keeping trips accessible and comfortable. The fleet diversity means they can accommodate solo anglers, families, and serious offshore crews. The crew's local knowledge shows in the catch reports, and the beginner-friendly approach means you don't need to be an expert to have a successful day.
Are they perfect? No operation is—that isolated negative review shows even long-standing charters can have off days. But with hundreds of customers praising the crew's professionalism, knowledge, and ability to deliver successful trips, the odds are heavily in your favor.
If you're fishing Key West and want a crew that's been doing this since 1965, Cowboy Cowgirl is worth calling.
Tight lines!
Sources:
- •Cowboy Cowgirl SportFishing Charters website: cowboycowgirlsportfishing.com
- •TripAdvisor Reviews: TripAdvisor Listing
- •Yelp Reviews: Yelp Listing
- •FishingBooker: FishingBooker Profile
- •Guidesly: Guidesly Profile
Last updated: January 22, 2026
