Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.8/5
Based on 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY worth booking?
Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY is a 4-hour experience in Key West, United States, from $850 per person. It scores 51 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.8/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 51 / 100
- Rating
- 4.8/5 (6)
- Duration
- 4 hours
- From
- $850 per person
Experience an Unforgettable Fishing Adventure in Key West! Join us for an exhilarating private deep-sea fishing adventure on the vibrant waters of Key West. Led by a skilled and experienced captain, our charters cater t
What you get
About this experience
Experience an Unforgettable Fishing Adventure in Key West! Join us for an exhilarating private deep-sea fishing adventure on the vibrant waters of Key West. Led by a skilled and experienced captain, our charters cater to both seasoned anglers and first-timers, ensuring an unforgettable experience. Reel in magnificent mahi, wahoo, sailfish, and more. Our knowledgeable crew will guide you to prime fishing spots, employing techniques like trolling, reef, or wreck fishing and many more to maximize your chances of landing a trophy catch. Choose from flexible charter options: 1/2-day, 3/4-day, full-day, or extended 10-12 hour trips tailored to your preferences. Our 36-foot Hatteras "Cowboy" offers comfort and safety with clean facilities, restrooms, , a flybridge, and state-of-the-art equipment. Book now and discover why our private charters are the ultimate choice for a thrilling day on the water in Key West.
What's included
Included
- Fishing Permits
- Bait
- Use of All Tackle
Not included
- Foods and Beverages
- Gratuity for Crew
- Fuel Surcharge due at the boat ($150)
What you'll see and do
Offshore Fishing in Key West (Private Charter): • You will enjoy a private deep sea fishing charter in the waters of Key West. • We will board a well-equipped sportfishing vessel and venture out to prime fishing spots guided by experienced Captain and crew. • You will have the opportunity to reel in a variety of fish species, including mahi, king mackerel, sailfish, and more, while taking in stunning views of the ocean. Note: The duration of the charter will be 4 Hrs.
240 minutes here · Admission included
Where it starts and ends
Meeting point
Key West
Free Parking behind the boat. Look at the signs behind each boat.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Free Parking behind the boat. Look at the signs behind each boat.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Cowboy Cowgirl Sportfishing Charters
Know before you go
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Not recommended for travelers with spinal injuries
- Suitable for all physical fitness levels
Photos
What travelers are saying
Outty’s summary of the themes that recur across 5 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Value for money
1 mentionTravelers feel they got more than they paid for.
Food and drink
1 mentionThe tastings and food stops are a highlight for most reviewers.
Small groups
1 mentionThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
5 verified traveler reviews for Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY. Ratings and reviews provided by Viator and Tripadvisor.
Our captain (Sam) and mate (Jess) were the best - hard working on the water. We did catch two Mahi and 3 barracuda - di
Our captain (Sam) and mate (Jess) were the best - hard working on the water. We did catch two Mahi and 3 barracuda - dinner and a show. Highly recommend
Response from the operator: Thank you for the great review! We’re thrilled to hear that Captain Sam and Mate Jess provided a hard-working and enjoyable Key West fishing experience. Catching two Mahi and three barracuda made for an unforgettable trip. We look forward to welcoming you back for more amazing fishing adventures with Cowboy Cowgirl Charters!
via Tripadvisor
Awesome Trip
Arrived at 6:30 for 7:00 am departure and Capt. AJ and Shaun were ready roll. The day we went the wind was non existent which was beautiful for riding out on water but made fishing a bit of a challenge. We booked an 8 hr trip but the Capt. asked of we could stay a little longer because we were fishing hard and he wanted us to have a good trip, which we did….ended up with a pretty good catch of Mahi, but had to run approximately 30 miles out. I will say Capt. AJ and Shaun are absolutely awesome folks. They were very helpful and educational as well as both having great personalities and a joy to be around. Personally I would highly recommend them and if at all possible do the 8 hr trip.
Response from the operator: Thank you for sharing your experience with Captain AJ and Shaun on your recent trip! We're glad to hear that despite the calm winds making fishing a challenge, you had a successful outing with a good catch of Mahi. It's wonderful to know that Captain AJ and Shaun went above and beyond to extend your trip to ensure a rewarding day. Their dedication to providing a helpful, educational, and enjoyable experience really stands out, and we appreciate your high recommendation. We look forward to welcoming you back for another great day on the water with Cowboy Cowgirl Sportfishing in Key West!"
via Tripadvisor
The thrill of the catch!
It was an amazing day at sea! Captain Chris was very attentive to everyone on board. The fish were not biting as much as we hoped on the day we went out but Chris & Will made it the best experience they possibly could. We caught some Bonita and very large Amberjack. The thrill of the catch was worth it! Highly recommend!!
Response from the operator: Thank you for sharing your experience with Captain AJ and Shaun on your recent trip! We're glad to hear that despite the calm winds making fishing a challenge, you had a successful outing with a good catch of Mahi. It's wonderful to know that Captain AJ and Shaun went above and beyond to extend your trip to ensure a rewarding day. Their dedication to providing a helpful, educational, and enjoyable experience really stands out, and we appreciate your high recommendation. We look forward to welcoming you back for another great day on the water with Cowboy Cowgirl Sportfishing in Key West!
via Tripadvisor
A real fisherman's charter, not a tourist boat.
We have chartered with Cowboy about 5 or 6 times over the last 15 years. More often than not Mark "The Shark" the owner skippered for us but not always. In every case though, the charter was a true fisherman's charter. By that I mean they worked hard and skillfully to put us on fish and help us refine our fishing technique. If you just want a shiny new boat to go for a ride on, then Cowboy may not be your favourite. We just had a 3/4 day trip with them again on May 15th, 2024. Mark and John the mate worked hard and employed experience, local knowledge and networking with other boat captains to find and catch fish. Our final score on this trip was 4 Bonito, 1 Barracuda, 3 Mahi and 1 Wahoo. If you want a hard-working, skilled and experienced crew to fish with, they have always been a good charter for us.
Response from the operator: Thank you so much for your continued loyalty and for choosing Cowboy Cowgirl Sportfishing for your fishing adventures over the last 15 years! It's always a pleasure to have seasoned anglers like you aboard. We're thrilled to hear that Mark 'The Shark' and John provided another true fisherman's charter experience on your recent 3/4 day trip, utilizing their skills, local knowledge, and connections to ensure a productive day. Your catch of Bonito, Barracuda, Mahi, and Wahoo sounds fantastic, and we're glad we could deliver. We appreciate your recognition of our crew's hard work and expertise, and we look forward to many more successful fishing trips with you in the future!"
via Tripadvisor
Three great private charters!
I booked three trips for clients. Capt AJ and mate Cole (two trips) and Capt Nels and mate Justin (one trip) were excellent. They made my guests feel welcome and at ease. They interacted with my guests in a positive and professional manner. Each of my guests had significant and quality time on the rods. They helped create great memories. While it was a primarily a fishing trip for my guests, it was still a business outing for me and the team made me look great. Many thanks to Michelle for coordinating lunches and additional beverages.
Response from the operator: Thanks for booking your trips with us and for sharing your experience! We're delighted to hear that Captains AJ, Nels, and mates Cole and Justin made your guests feel welcome and managed to ensure everyone had a quality experience. It's great that the trips were not only enjoyable but also professionally beneficial for you. At Cowboy Cowgirl Sportfishing Charters, we aim to make every aspect of our charters smooth and accommodating for our guests. We look forward to hosting you and your clients again!
via Tripadvisor
Good to know
- Duration
- 4 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 2
- Verdict
- Worth a Look
Why this scores 51
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Key West.
How much does Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY cost?
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Prices start at $850 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Key West usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY take?
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Plan for about 4 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Key West is not rushed.
Is Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY worth it?
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It holds an Outty Ranking of 51 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.8/5 across 6 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Key West, and how flexible the cancellation terms are.
Can I cancel or reschedule Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 4-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Key West can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Key West and add a light layer if any part of the 4-hour experience runs outdoors or after sunset.
Where does Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Key West within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Key West?
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Key West is a boat town. The only living coral barrier reef in the continental US sits seven miles offshore, and reef trips, sunset catamarans and backcountry kayak runs are the core bookings, alongside Hemingway house and Duval history walks. Our ranking weighs boat capacity and reef site rotation, which separates the good operators from the party cruises. On Outty we rank every Key West experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Shark and Wildlife Viewing Adventure in Key West, Southernmost Food & Cultural Walking Tour by Key West Food Tours, Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Key West?
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December to April, dry season and calm reef water. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Key West?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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