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
Jennifer M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Amazing!

VERIFIED   3/4 Day Trip on January 2, 2025
Captain Jimmy and Mate Bonnie listened to what we were looking for and worked really hard to achieve it. We caught two sailfish...
Jennifer M. recommends Hooked Up Charters
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Patricia P.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Outstanding Job!!!

VERIFIED   3/4 Day Trip on August 23, 2024
Jimmy and his hand help, Bonnie, absolutely amazing helper Truly will be going back and definitely will only book with Hooked...
Patricia P. 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   Half Day Trip on July 11, 2025
Rachelle P. recommends Hooked Up Charters
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Thomas L.
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 April 2, 2025
Thomas L. recommends Hooked Up Charters
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JB H.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

We will be back for another trip

VERIFIED   Half Day Trip on February 2, 2025
Amazing trip, had a great time. Jimmy and Bonnie are amazing and make the experience even better. Thanks for a great day on...
JB H. recommends Hooked Up Charters
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