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
254
Reviews
1
Fishing Reports
Verified

My Charter Listing

Hooked Up Charters

Federally permitted
Excellent
4.8 / 5
(254 reviews)
Angler's choice
Key West
 Last booking: 4 hours ago
 Instant Confirmation
Trips from US $1,000

Customer reviews

Rating summary
Excellent
4.8 / 5
out of 5 stars from 254 reviews
See details
Boat
Excellent
4.8 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (231)
Captain Jimmy and First Mate Bea were awesome. Great experience. \ud83d\udc4d
Captain Jimmy and First Mate Bea were awesome. Great experience. \ud83d\udc4d
Captain Jimmy and First Mate Bea were awesome. Great experience. \ud83d\udc4d
+228
Angler rating
224
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%
Sort by:
Featured  
Showing:
5 of 254 reviews
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
Mark review as helpful
You found this review helpful
Angel B. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
Read more
Greg M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Captain Jimmy and First Mate Bea were awesome. Great experience. ๐Ÿ‘

VERIFIED   Full Day Trip on December 6, 2025
Greg M. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
Greg M. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
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
Mark review as helpful
You found this review helpful
Chris E. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
Brian O.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Jimmy

VERIFIED   Full Day Trip on August 16, 2025
Brian O. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
Brian O. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
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   3/4 Day Trip on August 3, 2025
Jonathon S. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
Jonathon S. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
  • Settings