Offshore Fishing: Key West's Top Adventure

Embark on a thrilling 4-hour deep-sea fishing adventure in Key West. Target Mahi-Mahi, Tuna, and more with expert guidance. Book now!

Duration: 8 hours
Cancellation: 24 hours
Highlights
  • Cowboy Cowgirl SportFishing Charters - Offshore Fishing in Key West (Shared Charter – Max 6 Guests)
    Embark on an 8-hour shared deep-sea fishing excursion in the waters of Key West, ideal for anglers of all levels or small groups eager for offshore excitement.
    Step aboard a fully-equipped sportfishing vessel and journey to top fishing locations…
What's Included
  • Fishing Permits
  • Bait
  • Use of All Tackle
What's Not Included
  • Fuel Surcharge ($50) Due at Boat
  • Foods and Beverages
  • Gratuity for Crew
Additional Information

Experience the Excitement of Offshore Fishing in Key West
Join a 4-hour shared deep-sea fishing adventure on a premium 6-passenger sportfishing boat (maximum of 6 per boat)! This trip is ideal for solo anglers or small groups eager to catch some of the most thrilling offshore species in the waters near Key West.
What to Expect
Target Species: Depending…

Location
Cowboy Cowgirl SportFishing Charters
North Roosevelt Boulevard
Free Parking behind the boat. Look at the signs behind each boat. You will get a text message after dinner the night before with clear instructions for you trip in the morning.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(12 Ratings)
5 stars
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U4989rvjeffk
Feb 20, 2026
No Experience, No Problem - I don’t really have experience deep sea fishing and was a little nervous about that. Caleb was right there at every minute making sure my lack of experience was zero problem. SUPER fun day on the water. Looking forward to eating the supper we caught. Captain Hans inspires confidence, was never the least bit worried even when seas got choppy. Highly recommend.
Review provided by Tripadvisor
L9665abryanc
Feb 20, 2026
Best damn fishing trip - My buddies booked a group fishing tour for my bachelor party. Caleb and Hans were beyond incredible, and easily hands down the best fishermen I’ve seen. They taught us tricks and tips along the way, as we were extremely busy reeling all the fish they found. Thank you!!!
Review provided by Tripadvisor
E7839eajulianc
Feb 20, 2026
Caught a wahoo! - Shout out to Caleb and Captain Hans, who were relentless in helping us find fish. We even caught a once in a lifetime wahoo - you can’t beat that!
Review provided by Tripadvisor
Jonathanrn8565tn
Jan 8, 2026
Elite Crew, Epic Catches, Unforgettable Day on the Water - Hans and Caleb with Cowboy ⭐️ Cowgirl Key West Charters absolutely knocked it out of the park for us. Hans knew exactly where to take us, Caleb had everything perfectly rigged, and before we knew it we were into nonstop action—sport fishing at its finest. We landed King Mackerel, Barracudas, Sailfish, and even a massive Grouper (which we unfortunately had to release due to season—but still an incredible experience). From start to finish, this team was professional, knowledgeable, and top-tier in every way. If you’re honestly looking for the best sport fishing experience in the Keys, look no further. We’ve been visiting the Keys for years and have done plenty of deep-sea fishing, but these guys take it to a whole different level. We’ll absolutely be booking with them every year moving forward. 🛥️ ⭐️⭐️⭐️⭐️⭐️
Review provided by Tripadvisor
Kevinbj1848og
Dec 5, 2025
Best split charter we have ever been on. First time with this charter company but you can bet it won't be our last - Our boat landed two Wahoo, three Mahi Mahi, one Tuna and a Bonita (which we saved for bait but didn't use). We got enough fish for six to eat two or three good sized meals. GREAT TRIP!
Review provided by Tripadvisor
R3199rlclairea
Nov 28, 2025
Hope to come again! - The best time! My daughter and I had a once in a lifetime experience! The captain and crew were so helpful and knowledgeable!
Review provided by Tripadvisor
340alyxb
Nov 20, 2025
We caught a fish! - We caught a sailfish! Yes, part luck… but more because our captains (Nell and Sam) knew what they were doing. We also caught enough food for the whole vacation.
Review provided by Tripadvisor
Bernardcm7944gp
Oct 27, 2025
I will be back in the spring. - I will go fishing with Capitan AJ and first mate Eric any day feeling confident that I will bring some fish home. Eric moved with a speed of light, hooking one fish after another. Capitan AJ is an expert in finding fish and a well of knowledge. The 40ft "Cowgirl" boat can easily handle 4-5 ft waves and it is very comfortable. The 8hr trip allows enough time to go off shore and get full experience without rushing. I love the shared charter so you can meet some new fantastic people and share your experience. Thank you Michelle for arranging the trip, it was awesome.
Review provided by Tripadvisor
Wittekindl
Oct 23, 2025
Fantastic crew, amazing day, lots of fish. - Amazing fishing day with a fantastic crew. Everyone was highly skilled and worked together seamlessly. The first mate, Eric, must have some octopus blood - his hands seemed to be everywhere at once, managing rods, reels, and bait while calmly guiding a group of strangers through the chaos of the catch. The captain navigated the vessel effortlessly, setting a relaxed and enjoyable tone for the entire trip. It was the highlight of my time in Key West and truly one of the best days of the vacation. We caught plenty of fish, and I can fully recommend this trip.
Review provided by Tripadvisor
Dream768247
Jul 1, 2025
Fish in the cooler!! - Great day with an awesome crew, very knowledgeable and courteous. The captain called first thing in the morning and according to his experience and know how recommended we switch boats for a more comfortable and enjoyable experience. If not for Chris's advice the start to the day would've been exactly as he predicted with high wind and rough seas, which was opposite of what the weather was supposed to be according to the weather man, trust the fisherman's intuition! We caught Mahi pretty much all day despite the odds and what the chatter was on the radio, Chris was relentlessly. Would definitely book again when i visit!
Review provided by Tripadvisor
From $300
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).