Captain
Jimmy Bailey

Member since June 2017 Key West, United States
Background
Captain Jimmy Bailey is a native Floridian, who grew up in Key West. Jimmy started fishing the local waters at a very young age. He has now been fishing for over four decades, and his passion never stops growing. Captain Jimmy is often found guiding his friends and clients through the productive waters in and around Key West. If you are looking for a professional and reliable captain you could trust, Jimmy is your best choice!

Hey, I'm Captain Jimmy Bailey

Key West, United States
Background
Captain Jimmy Bailey is a native Floridian, who grew up in Key West. Jimmy started fishing the local waters at a very young age. He has now been fishing for over four decades, and his passion never stops growing. Captain Jimmy is often found guiding his friends and clients through the productive waters in and around Key West. If you are looking for a professional and reliable captain you could trust, Jimmy is your best choice!
Anglers Choice
257
Reviews
1
Fishing Reports

My Charter Listing

Hooked Up Charters

Excellent
4.8 / 5
(257 reviews)
Angler's choice
Key West
 7 bookings in the past week.
 Instant Confirmation
Trips from US $1,000

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 257 reviews
See details
Boat
Excellent
4.8 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (232)
Great family trip
Captain Jimmy and First Mate Bea were awesome. Great experience. \ud83d\udc4d
Captain Jimmy and First Mate Bea were awesome. Great experience. \ud83d\udc4d
+229
Angler rating
227
14
5
5
1
Anglers claimed
Good experience
94%
Friendly captain
98%
Recommend this charter
93%
Appropriate for children
90%
Satisfied with the boat
98%
Caught fish
88%
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Featured  
Showing:
5 of 257 reviews
Chris E.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Jimmy

VERIFIED   3/4 Day Trip on October 11, 2025
Chris E. recommends Hooked Up Charters
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Miken S.
Excellent
4.7 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Very good
4.0 / 5
Overall

Hooked up

VERIFIED   3/4 Day Trip on April 11, 2025
Was a fun trip, captain jimmy and first mate are great people and know what they are doing, we had an enjoyable time on the...
Miken S. recommends Hooked Up Charters
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Miken S. recommends Hooked Up Charters
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James M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great!!

VERIFIED   3/4 Day Trip on April 7, 2025
Fishing trip was great. Caught lots of fish and had a great time. The crew really knows how to catch some fish!
James M. recommends Hooked Up Charters
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James M. recommends Hooked Up Charters
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John J. N.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Good day fishing

VERIFIED   3/4 Day Trip on May 22, 2025
Captain Jimmy and first mate Bonnie were awesome. Had an enjoyable day! Caught a lot of of fish
John J. N. recommends Hooked Up Charters
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John J. N. recommends Hooked Up Charters
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Chris D.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great friendly crew that knows where to find the fish

VERIFIED   Full Day Trip on May 2, 2025
Jimmy and Bonnie were fantastic. We caught over 20 fish, where ever we went, other boats showed up.
Chris D. recommends Hooked Up Charters
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Chris D. recommends Hooked Up Charters
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