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
    Half Day Trip
    In demand! Last booked: 2 days ago
    FREE Cancellation 1 day notice
    4 Hour Trip, starts at 7:30 AM
    US $900
    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.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Fishing techniques
    Trolling
    Targeted fish
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    King Mackerel (Kingfish)
    King Mackerel (Kingfish)
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Snapper (Mangrove)
    Mangrove Snapper
    Grouper (Black)
    Black Grouper
    Grouper (Red)
    Red Grouper
    Snapper (Mutton)
    Mutton Snapper
    Snapper (Yellowtail)
    Yellowtail Snapper
    Tuna (Blackfin)
    Blackfin Tuna
  • Private trip
    3/4 Day Trip
    In demand! Last booked: 2 days ago
    FREE Cancellation 1 day notice
    6 Hour Trip, starts at 7:30 AM
    US $1,200
    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?
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Fishing techniques
    Trolling
    Targeted fish
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Snapper (Mangrove)
    Mangrove Snapper
    Grouper (Black)
    Black Grouper
    Grouper (Red)
    Red Grouper
    Snapper (Mutton)
    Mutton Snapper
    Snapper (Yellowtail)
    Yellowtail Snapper
    Tuna (Blackfin)
    Blackfin Tuna
  • Private trip
    Full Day Trip
    FREE Cancellation 1 day notice
    8 Hour Trip, starts at 7:30 AM
    US $1,500
    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!
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Offshore Fishing
    Reef Fishing
    Fishing techniques
    Trolling
    Targeted fish
    Dolphin (Mahi Mahi)
    Dolphin (Mahi Mahi)
    King Mackerel (Kingfish)
    King Mackerel (Kingfish)
    Sailfish
    Sailfish
    Wahoo
    Wahoo
    Snapper (Mangrove)
    Mangrove Snapper
    Grouper (Black)
    Black Grouper
    Grouper (Red)
    Red Grouper
    Snapper (Mutton)
    Mutton Snapper
    Snapper (Yellowtail)
    Yellowtail Snapper
    Tuna (Blackfin)
    Blackfin Tuna
There are 27 people looking at this charter.

FAQs about Hooked Up Charters

Hooked Up Charters offers the following trips to customers:
  • US $900 per group - Half Day Trip (4 hours)
  • US $1,200 per group - 3/4 Day Trip (6 hours)
  • US $1,500 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

Meet the Captain

Jimmy Bailey
Key West, Florida, United States
ID & license verified
183 Customer reviews
Response time within an 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) Black Grouper
Grouper (Red) Red Grouper
Marlin (Blue) Blue Marlin

Boat specs

Hatterras (Sportfishing) 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

Trip includes

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

Cancellation policy

Free cancellation up to 1 day prior to trip

You can cancel or modify your booking up to 1 day before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

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 30% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 30% deposit to guarantee your reservation.

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
Excellent
4.8 / 5
out of 5 stars from 183 reviews
Boat
Excellent
4.7 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (153)
Hooked up is the way to go
Hooked up is the way to go
Captain Jim and Bonnie
+150
Angler rating
160
12
1
5
1
Anglers claimed
Good experience
94%
Friendly captain
99%
Recommend this charter
93%
Appropriate for children
91%
Satisfied with the boat
98%
Caught fish
84%
Sort by:
Featured  
Showing:
5 of 183 reviews
Amy M.
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 June 21, 2023
Amy M. recommends Hooked Up Charters
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Amy M. recommends Hooked Up Charters
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1 person finds this review helpful
You and 1 other person found this review helpful

Mark W.
Lantana, TX
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

4 great hours with Jimmy and Bonnie

VERIFIED   Half Day Trip on July 6, 2023
The trip started out great and and finished strong! Jimmy did a great job putting us on the fish while Bonnie worked her tail...
Mark W. recommends Hooked Up Charters
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Mark W. recommends Hooked Up Charters
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Todd L.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Hooked up is the way to go

VERIFIED   NEW  Full Day Trip on March 27, 2024
Captain Jimmy put this on the fish and Bonnie was amazing with the rods and keeping the deck clean and the rods refilled. What...
Todd L. recommends Hooked Up Charters
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Todd L. recommends Hooked Up Charters
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Regina S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fantastic trip!

VERIFIED   NEW  3/4 Day Trip on April 2, 2024
Great 3/4 day charter. Bonnie and Jimmy hustle and are a great team. We had a great day and caught what we were looking for…a...
Regina S. recommends Hooked Up Charters
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Regina S. recommends Hooked Up Charters
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Shawn M.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Captain Jim and Bonnie

VERIFIED   Half Day Trip on March 16, 2024
We had a great experience.  Tried catching tuna in the morning   The other half captain jJimmy got us so we were catching...
Shawn M. recommends Hooked Up Charters
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Shawn M. recommends Hooked Up Charters
Mark review as helpful
You found this review helpful