Hooked Up Charters 

4.8
(302 reviews)
 
Federally permitted
 North Roosevelt Boulevard, Key West, FL 33040, United States–

Hooked Up Charters 

Key West, FL, United States
–
36 ft
6
4.8
(302 reviews)

Booked with us before? You may qualify for a Loyalty Discount. Sign in to check.

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!

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!

Jimmy Bailey
Captain
Jimmy Bailey
54 years of experience
ID & credentials verified
responds within an hour

Select date to see availability

Trip date:
Group Size:
October 2026
SuMoTuWeThFrSa
Loading...
Group Size
2 adults • 0 children
Change
Almost there...
Half Day Trip
FREE Cancellation 1 day notice
4 hour trip starts at 7:30 AM
Dolphin (Mahi Mahi)
Marlin (Blue)
Marlin (White)
Sailfish
+7
US $1,000
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 1 day notice
6 hour trip starts at 7:30 AM
Dolphin (Mahi Mahi)
Sailfish
Wahoo
Snapper (Mangrove)
+5
US $1,200
Entire boat: up to 6 people
Full Day
FREE Cancellation 1 day notice
8 hour trip starts at 7:30 AM
Dolphin (Mahi Mahi)
King Mackerel (Kingfish)
Sailfish
Wahoo
+6
US $1,500
Entire boat: up to 6 people
There are 5 people looking at this charter.

Customer reviews

Loading...

Rating

4.8
302 reviews
4.8
Boat & equipment
4.9
Captain & crew
4.8
Fishing Experience

Anglers' gallery (280)

What anglers say

95%
Great experience
90%
Family friendly
98%
Friendly captain
98%
Good boat
94%
Recommended
89%
Caught fish

All reviews (302)

Frequently mentioned
Showing 1 – 5 of 302 reviews
John Carlson
John Carlson
Repeat angler
us
Iowa, US
Member since 2025
2 trips
5.0
Verified
Hooked Up Charter does exactly that!
3/4 Day Trip on August 25, 2026 • 2 adults

We caught my bucket list fish thanks to Captain Jimmy & Bonnie's quick read and response! I wasn't even thinking Sailfish,but caught the fish ive been after right at the start of our trip! We also caught numerous Mahi mahi and also a bonus barracuda! Super personable team and they definitely work well together! Very helpful and patient with my son who hasn't done this very much! We both had a Awesome memorable Day catching fish and meeting 2 new friends! The boat was Awesome also! Great chairs and also shade to sit under if you want to get away from the sun! Very clean and well maintaned! Awesome 5 star trip ! Definitely recommend!

Jimmy Bailey
Response from Captain

Thanks John 🙌

Allison Williams
Allison Williams
us
Ohio, US
Member since 2026
5.0
Verified
Incredible Experience
3/4 Day Trip on April 9, 2026 • 2 adults

We had an incredible experience with Hooked Up Charters thanks to Captain Jimmy and First Mate Bonnie! Even though the weather didn’t cooperate and the big fish weren’t biting, they made sure our trip was still a huge success—we caught several yellowtails and had an absolute blast the entire time. Jimmy and Bonnie are truly some of the nicest, most genuine people we’ve met in the 11 years we’ve been coming to Key West. Their positivity, knowledge, and dedication to making sure everyone has a great time really set them apart. You can tell they genuinely love what they do, and it shows in every part of the experience. We can’t wait to come back, head out with them again, and give those big fish another try. Highly recommend this charter to anyone looking for an unforgettable day on the water! 🎣

Reported catch:
Yellowtail Snapper
Jimmy Bailey
Response from Captain

Thanks guys 👏

Cameron Whitcomb
Cameron Whitcomb
Repeat angler
us
Missouri, US
Member since 2025
3 trips
5.0
Verified
Only Charter at the Dock that caught fish
Full Day on June 28, 2026 • 3 adults

amazing day on the water. ive done a few charters now and this was the best one by far. at the end of the day all the other charter captains nearby had caught nothing all day. We came back with a nice wahoo, blackfin tuna, mahi, and other fish that we threw back throughout the day. awesome day on the water, i wont use any other captain in Key West

Reported catch:
Dolphin (Mahi Mahi)
Wahoo
Blackfin Tuna
Nicki Rice
Nicki Rice
us
Florida, US
Member since 2026
5.0
Verified
got my first Mahi
3/4 Day Trip on July 9, 2026 • 2 adults

Captain Jimmy and first mate Bonnie made us comfortable from the moment we got to the boat. it was very rough seas and choppy out there which Jimmy made sure we knew bedore going out- he gave us a choice to still go or cancel. We felt very safe and enjoyed the morning. I highly recommend them! we will book with them again next time.

Reported catch:
Dolphin (Mahi Mahi)
Jimmy Bailey
Response from Captain

Thanks Nicki 😊

David Fritz
David Fritz
us
Florida, US
Member since 2026
5.0
Verified
an awesome trip
Full Day Trip on April 17, 2026 • 5 adults

5 of us went out happy and excited and 5 of us came back to shore the sameway. weather didnt permit us for what fish we wanted but jimmy and bonnie didn’t disappoint. they put us on fish, let us be us on boat and bonnie never stopped. after a great day with my family, i think the best part was watching jimmys grand kids( his legacy) welcome him back to the dock. genuine and true people who love what they do . definitely coming back for more trips with HOOKED UP CHARTERS

Jimmy Bailey
Response from Captain

👏

FAQs about Hooked Up Charters

Hooked Up Charters offers the following trips to customers:
  • US $1,000 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 (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 (Customary tip is 20 percent )
  • 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

Your captain

Jimmy Bailey
Jimmy Bailey
Key West, Florida, United States
1 Fishing Report
ID & license verified
302 Customer reviews
Typical response within an hour
Member since June 2017
Angler's Choice
The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.
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!
Jimmy Bailey
Jimmy Bailey
Fully verified
Angler's Choice
1
reports
302
reviews
2017
member since
~1h
response
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!

The fish you can target

Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Black Grouper
Black Grouper
Red Grouper
Red Grouper
Blue Marlin
Blue Marlin
White Marlin
White Marlin
Sailfish
Sailfish
Mangrove Snapper
Mangrove Snapper
Mutton Snapper
Mutton Snapper
Yellowtail Snapper
Yellowtail Snapper
Blackfin Tuna
Blackfin Tuna
Wahoo
Wahoo
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Black Grouper
Black Grouper
Red Grouper
Red Grouper
Blue Marlin
Blue Marlin
White Marlin
White Marlin

Real catches by this captain

  • Hooked Up Charter does exactly that!
    John C.
    John C.
  • Multi species trip, My son caught a nice Sail fish, I caught a couple Barricuda one decent size.. and My son and daughter both cuddle some Mahi Mahi!!
    Jim G.
    Jim G.
  • Words can’t explain how much fun this trip was… Jimmy and B were truly amazing to fish with… we were able to catch plenty of dolphin and Bonita… looking forward to coming back next year… everything was truly top notch !!!
    Jimmy O.
    Jimmy O.
  • Captain Jimmy and Bonnie are 10/10
    Kate B.
    Kate B.
  • Capt Jimmy and Bonnie are The Best
    Dustin P.
    Dustin P.
  • Big Wahoo
    April M.
    April M.
  • Only Charter at the Dock that caught fish
    Cameron W.
    Cameron W.
  • Very Nice trip!
    Brian S.
    Brian S.
  • 10/10 experience
    Michael P.
    Michael P.
  • June fishing trip
    Kevin M.
    Kevin M.

What is the boat like?

Boat image
Boat category
Sportfishing boats
Capacity
6 persons
Boat length
36 ft
Year built
1968
Restored in
2017
Boat manufacturer
Hatterras
Boat type
Sportfishing
Engine model
New Cummins installed September 2024
Powered by
2 x 350HP
Max cruising speed
21 knots

What kind of fishing will you do?

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

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning
Deep Sea Fishing

Which amenities are available onboard

Toilet
Fighting chair
GPS
Fishfinder
Flybridge
Live bait well
Outriggers
Ice box
What's included in the trip price
Rods, reels & tackle
Live bait
Lures
Catch cleaning & filleting
First mate
Customary tip is 20 percent
Fishing license

How cancellations work

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.
More details

What the listing policies are

Pickup not included
Transfer to/from departure site is not included in trip rates.
Child friendly
You keep catch
Catch and release allowed

How you can pay

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

What’s biting in Key West right now

Dolphin (Mahi Mahi)Dolphin (Mahi Mahi)
Grouper (Black)Grouper (Black)
Grouper (Red)Grouper (Red)
Marlin (Blue)Marlin (Blue)
Marlin (White)Marlin (White)
SailfishSailfish
Snapper (Mangrove)Snapper (Mangrove)
Snapper (Mutton)Snapper (Mutton)
Snapper (Yellowtail)Snapper (Yellowtail)
Tuna (Blackfin)Tuna (Blackfin)
WahooWahoo

Compare similar fishing charters

Current
Hooked Up Charters
Hooked Up Charters
Federally permitted
4.8
(302)
36 ft
Group size 1 - 6
1 - 6
Fish 1
Fish 2
+9
4 hour trip • 6 persons
US $1,000