Hooked Up Charters invites you to explore the fishing opportunities in Key West, Florida. Enjoy your trip with a native guide and come back with an ice chest full of memories!

Step aboard the “Hooked Up Too,” a 34’ Hatteras offshore sportfishing boat. It was originally built in 1968 and was fully up hauled in 2017. Its twin 350 HP Cummins engines will power you to the hottest fishing grounds in the area, and the latest professional accessories and navigational electronics will save you time while searching for fish.

The boat can comfortably take up to 6 anglers, who will make good use of the flybridge and the fighting chair. Plus, there is a toilet on board – a much-needed thing when spending your day on the water.

From bottom fishing for King Mackerel, Snapper, and Grouper to offshore trips for Sailfish, Tuna, Wahoo, and Mahi-Mahi, you can do it all. Captain Jimmy will put you on the fish and will teach you a technique or two. Fish with a local and see the difference!

Just as you depart from the Historic Charter Boat Row, you will soon find your hooks baited and your rods bending. All the necessary equipment is included in the charters’ rates, such as rods, reels, tackle, lures, and bait. You will also be provided with a license and fish cleaning and filleting at the end of your adventure. Just bring something to eat and drink, and show up!

Book a trip with Hooked Up Charters and have a Floridian fishing adventure you won’t forget!



Select date to see available trips and rates:

  • Private trip
    Full Day Trip
    In demand! Last booked: 3 days ago
    Low rate deposit non-refundable
    8 Hour Trip, starts at 7:30 AM
    $1,100
    Full day trips are ideal during the hot summer months. Check the morning and the afternoon bite, spend your day farther out from the shore, target Mahi Mahi, Tuna, Marlin, and many more!
  • Private trip
    3/4 Day Trip
    In demand! Last booked: 5 days ago
    Low rate deposit non-refundable
    6 Hour Trip, starts at 7:30 AM
    $900
    This trip is great for anglers of all skill levels and expertise. You will be fishing for a variety of species depending on your personal preferences, such as Snapper, Mahi Mahi, Grouper, Kingfish, and who knows what else?
  • Private trip
    Half Day Trip
    In demand! Last booked: 5 days ago
    Low rate deposit non-refundable
    4 Hour Trip, starts at 7:30 AM
    $750
    These trips are ideal for winter months. The weather might be a bit colder, but the fishing is definitely hot! Check the morning bite and go after Yellowtail Snapper, Mutton Snapper, Mangrove Snapper, Grouper, King Mackerel, and many more.
There are 21 people looking at this charter.

About the Captain

Jimmy Bailey
Key West, Florida, United States
Angler's Choice
ID & License verified
30 Customer Reviews
Response time 1 hour
Member since June 2017
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!

About this listing

Targeted Species

Dolphin (Mahi Mahi) Dolphin (Mahi Mahi)
Grouper (Black) Grouper (Black)
Grouper (Red) Grouper (Red)
Marlin (Blue) Marlin (Blue)

Marlin (White) Marlin (White)
Sailfish Sailfish
Snapper (Mangrove) Snapper (Mangrove)
Snapper (Mutton) Snapper (Mutton)

Snapper (Yellowtail) Snapper (Yellowtail)
Tuna (Blackfin) Tuna (Blackfin)
Wahoo Wahoo

Boat Specs

Hatterras (Offshore sport fishing) originally built in 1968, and restored in 2017. Powered by 2 350HP Cummins engines, with a maximum cruising speed of 21 knots.

Length
36 ft
Capacity
6 persons

Types of Fishing

Inshore Fishing
Nearshore Fishing
Offshore Fishing
Reef Fishing
Wreck Fishing
Backcountry Fishing

Fishing Techniques

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning
Deep Sea Fishing

Amenities

Toilet
Fighting Chair
GPS
Fishfinder
Flybridge
Live Bait Well
Outriggers
Ice Box
Toilet
Fighting Chair
GPS
Fishfinder
Flybridge
Live Bait Well

Trip Includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
First Mate
Fishing License

Cancellation Policy

Deposit non-refundable

If it is unsafe to travel, you may still cancel free of charge or change the date(s) of your booking.

Listing Policies

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
You Keep Catch
Catch and Release Allowed

Payment

Book with 20% deposit
When the captain confirms your trip, FishingBooker charges your credit card a 20% deposit to guarantee your reservation.
Pay remaining balance to captain
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express

Key West Fishing Calendar

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Customer Reviews

Rating Summary
Photos & videos by reviewers (26)
4.90
Excellent Excellent Excellent Excellent Excellent
out of 5 stars from 30 reviews
Boat
Excellent Excellent Excellent Excellent Excellent
Crew
Excellent Excellent Excellent Excellent Excellent
Experience
Excellent Excellent Excellent Excellent Excellent
May fishing trip
May fishing trip
May fishing trip
+23
Angler Rating
26
4
0
0
0
Anglers Claimed
Good experience
100%
Friendly captain
100%
Recommend this charter
100%
Appropriate for children
81%
Satisfied with the boat
100%
Catch intended fish
85%
Sort By:
Featured  
Showing:
5 of 30 reviews
Kimberly G.
Aliso Viejo, California
Excellent Excellent Excellent Excellent Excellent  5.00
Experience:
Excellent Excellent Excellent Excellent Excellent Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

Incredible crew—Amazing Day!

VERIFIED   NEW  Full Day Trip on May 11, 2021
I chose Captain Jimmy based on reviews of this site. They were spot on. Captain Jimmy was great and his boat was immaculate....
Kimberly G. recommends Hooked Up Charters
Mark as helpful
1 person finds this review helpful
You and 1 other person found this helpful
  Jimmy Bailey Captain replied

Kirk C.
Forks, WA
Excellent Excellent Excellent Excellent Excellent  5.00
Experience:
Excellent Excellent Excellent Excellent Excellent Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

3/4 day

VERIFIED   3/4 Day Trip on April 3, 2021
Water was rough and colored but captain Jimmy put us on fish.  Got a bunch of mutton snapper, a big yellow tail snapper, mackerel,...
Kirk C. recommends Hooked Up Charters
Mark as helpful
1 person finds this review helpful
You and 1 other person found this helpful
Kirk C. recommends Hooked Up Charters
Mark as helpful
1 person finds this review helpful
You and 1 other person found this helpful

James M.
Winston, GA
Excellent Excellent Excellent Excellent Excellent  4.67
Experience:
Very Good Very Good Very Good Very Good Very Good Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

3/4 Day trip with Jimmy on Hooked Up

VERIFIED   NEW  3/4 Day Trip on April 27, 2021
It was a great day on the water. The fish weren’t biting but Jimmy did his best to put us on fish. Bonnie had her work cut...
James M. recommends Hooked Up Charters
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James M. recommends Hooked Up Charters
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Ken M. M.
Fayetteville, NY
Excellent Excellent Excellent Excellent Excellent  5.00
Experience:
Excellent Excellent Excellent Excellent Excellent Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

6 hr trip

VERIFIED   3/4 Day Trip on March 16, 2021
Had amazing day with captain Jimmy… ! he put us on fish!! Wahoo and Mahi Mahi to the boat… just missed a sail… First...
Ken M. M. recommends Hooked Up Charters
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Ken M. M. recommends Hooked Up Charters
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Paul B.
Romeo, MI
Excellent Excellent Excellent Excellent Excellent  5.00
Experience:
Excellent Excellent Excellent Excellent Excellent Boat
Excellent Excellent Excellent Excellent Excellent Crew
Excellent Excellent Excellent Excellent Excellent Overall

Full day trip...amazing family experience

VERIFIED   Full Day Trip on April 1, 2021
I took my wife, my 10 year old, my 8 year old and my 4 year old out for a full day. It was a amazing time. The captain and...
Paul B. recommends Hooked Up Charters
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Paul B. recommends Hooked Up Charters
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FAQs about Hooked Up Charters

Hooked Up Charters offers the following trips to customers:
  • $750 per group - Half Day Trip (4 hours)
  • $900 per group - 3/4 Day Trip (6 hours)
  • $1,100 per group - Full Day Trip (8 hours)

When you book a trip with Hooked Up Charters, you can expect the following amenities onboard:
  • Toilet
  • Fighting Chair
  • GPS
  • Fishfinder
  • Flybridge
  • Live Bait Well
  • Outriggers
  • Ice Box

Trips booked with Hooked Up Charters include:
  • Rods, reels & tackle
  • Live Bait
  • Lures
  • Catch cleaning & filleting
  • First Mate
  • Fishing License

Hooked Up Charters offers the following types of fishing:
  • Inshore Fishing
  • Nearshore Fishing
  • Offshore Fishing
  • Reef Fishing
  • Wreck Fishing
  • Backcountry Fishing

Hooked Up Charters offers the following fishing techniques:
  • Light Tackle
  • Heavy Tackle
  • Bottom Fishing
  • Trolling
  • Spinning
  • Deep Sea Fishing

Top targeted fish species with Hooked Up Charters include:
  • Dolphin (Mahi Mahi)
  • Grouper (Black)
  • Grouper (Red)
  • Marlin (Blue)
  • Marlin (White)
  • Sailfish
  • Snapper (Mangrove)
  • Snapper (Mutton)
  • Snapper (Yellowtail)
  • Tuna (Blackfin)
  • Wahoo