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!
241
Reviews
1
Fishing Reports
Verified

My Charter Listing

Hooked Up Charters

Federally permitted
Excellent
4.8 / 5
(241 reviews)
Key West
 Instant Confirmation
Trips from US $1,000

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 241 reviews
See details
Boat
Excellent
4.8 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (225)
Fishing with Jimmy
Fishing with Jimmy
Non-stop action
+222
Angler rating
212
13
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
87%
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Featured  
Showing:
5 of 241 reviews
Marshall B.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Seaweed trouble

VERIFIED   3/4 Day Trip on July 8, 2025
We had a great day of fishing. Bonnie was amazing all day on the deck. She fought the seaweed all day and never gave up hope....
Marshall B. recommends Hooked Up Charters
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Angel B.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Hooked Up

VERIFIED   Full Day Trip on May 17, 2025
Capt Jimmy got us hooked up with lots of Mahi! Bonnie did a great job keeping are rods in the water with fresh bait. We were...
Angel B. recommends Hooked Up Charters
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Jonathon S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Jimmy

VERIFIED   NEW  3/4 Day Trip on August 3, 2025
Jonathon S. recommends Hooked Up Charters
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Rachelle P.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Jimmy

VERIFIED   NEW  Half Day Trip on July 11, 2025
Rachelle P. recommends Hooked Up Charters
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Rachelle P. 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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