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!
244
Reviews
1
Fishing Reports
Verified

My Charter Listing

Hooked Up Charters

Federally permitted
Excellent
4.8 / 5
(244 reviews)
Key West
 6 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 244 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
214
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
87%
Sort by:
Featured  
Showing:
5 of 244 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
Mark review as helpful
You found this review helpful
Marshall B. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
Read more
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
Kathy P.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Wonderful day of fishing!

VERIFIED   Half Day Trip on November 30, 2024
Captain Jimmy was very knowledgable; he created a perfect morning of fishing for our family.ย  Deckhand Bonnie made sure we...
Kathy P. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
Kathy P. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
Read more
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
Mark review as helpful
You found this review helpful
John J. N. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
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
Mark review as helpful
You found this review helpful
Chris D. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful
  • Settings