Hooked Up Charters
Hooked Up Charters
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!
Select date to see availability
Trip availability and prices
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
Customer reviews
Rating
Anglers' gallery (280)
What anglers say
Reviews (302)
John CarlsonRepeat angler•
Iowa, US•Member since 20252 trips5.0VerifiedNewHooked Up Charter does exactly that!
3/4 Day Trip on August 25, 2026 • 2 adultsWe 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!
Allison Williams•Ohio, USMember since 20265.0VerifiedIncredible Experience
3/4 Day Trip on April 9, 2026 • 2 adultsWe 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! 🎣
Steve JohnsonRepeat angler•Michigan, US•Member since 20194 trips5.0VerifiedMahi Mania!!
Full Day Trip on April 5, 2026 • 5 adultsCaptain Jimmy and his amazing mate Bonnie were absoute pros. Ive been on several charters and this team was first class. The boat is set up perfectly for deep see fighting. We got into a nice school of Mahi and some Skip Jack tuna. Filled the cooler and had enough meat for 20 people. Seas were rough and we were very comfortable. Cant wait tk come back and get on the bite again.
Cameron WhitcombRepeat angler•Missouri, US•Member since 20253 trips5.0VerifiedOnly Charter at the Dock that caught fish
Full Day on June 28, 2026 • 3 adultsamazing 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
Jim Grady•New York, USMember since 20265.0VerifiedMulti 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!!
Full Day on July 31, 2026 • 3 adultsIt was a swealtering hot day, Capt Jim capt us cool by zig zagging thru the crosswinds a a best he could , first mate Bonnie worked her ass off keeping us ready willing and able to real in some good ones.. I’d use them again!
Michael Pitulej•Syracuse, NY, USMember since 20265.0Verified10/10 experience
3/4 Day Trip on June 21, 2026 • 2 adultsHad a great 6 hours of fishing! The Sargasm was an initial worry but the team took us all over and we ended up with several catches producing a lot of meat!! very professional, personable and fun! we will 100% be coming back!
Kate Baylor•Des Moines, IA, USMember since 20265.0VerifiedCaptain Jimmy and Bonnie are 10/10
3/4 Day Trip on July 29, 2026 • 4 adultsthis is the second time we have fished with Captain Jimmy and Bonnie! i would recommend them every time as they are knowledgeable, fun and know the Island. we will be back for a third for sure!
Brian Smith•Virginia, USMember since 20265.0VerifiedVery Nice trip!
Full Day on June 27, 2026 • 3 adults • 1 childCapt Jimmy and Mate Bonnie worked super hard in Summer conditions to put us on a few fish. Tons of Sargassum had Bonnie working way too hard but it paid off! Thanks for putting the little one on some fish !! Smith’s
J Schopbarteld•
NetherlandsMember since 20255.0VerifiedAmazing fishing experience!
3/4 Day Trip on May 3, 2026 • 2 adultsBooked a 6 hour trip with Jimmy and Bonnie. These guys know how to make a trip to a succes. Good communication and they know how to convey their experience. Leaving you with a cooler full of fish and a big smile.
- Jeff Gardner•Illinois, USMember since 20255.0Verified
Great day out on thw water!
Full Day on April 25, 2026 • 4 adultsWe had a great day out with Jimmy and Bonnie! They are both so knowledgeable! My son caught a huge barracuda and we caught a few others too! Thanks for the great memories 🐟
Rating
Anglers' gallery (280)
What anglers say
All reviews (302)
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!
Thanks John 🙌
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! 🎣
Thanks guys 👏
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
👏
Captain Jimmy and his amazing mate Bonnie were absoute pros. Ive been on several charters and this team was first class. The boat is set up perfectly for deep see fighting. We got into a nice school of Mahi and some Skip Jack tuna. Filled the cooler and had enough meat for 20 people. Seas were rough and we were very comfortable. Cant wait tk come back and get on the bite again.
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
FAQs about Hooked Up Charters
- 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)
- Toilet
- Fighting chair
- GPS
- Fishfinder
- Flybridge
- Live bait well
- Outriggers
- Ice box
- Rods, reels & tackle
- Live bait
- Lures
- Catch cleaning & filleting
- First mate (Customary tip is 20 percent )
- Fishing license
- Inshore fishing
- Nearshore fishing
- Offshore fishing
- Reef fishing
- Wreck fishing
- Backcountry fishing
- Light tackle
- Heavy tackle
- Bottom fishing
- Trolling
- Spinning
- Deep sea fishing
- Dolphin (Mahi Mahi)
- Grouper (Black)
- Grouper (Red)
- Marlin (Blue)
- Marlin (White)
- Sailfish
- Snapper (Mangrove)
- Snapper (Mutton)
- Snapper (Yellowtail)
- Tuna (Blackfin)
- Wahoo
Your captain
Key West, Florida, United States
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!
Real catches by this captain
What is the boat like?
What kind of fishing will you do?
Which fishing techniques you can try
Which amenities are available onboard
How cancellations work
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.
What the listing policies are
Pickup not included
Transfer to/from departure site is not included in trip rates.
How you can pay
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)
Grouper (Black)
Grouper (Red)
Marlin (Blue)
Sailfish
Snapper (Mangrove)
Snapper (Mutton)
Snapper (Yellowtail)
Tuna (Blackfin)
WahooCompare similar fishing charters
Federally permitted4.8(574)50 ftGroup size 1 - 61 - 6
+104 hour trip • 6 personsUS $1,000
Federally permitted4.8(403)42 ftGroup size 1 - 61 - 6
+24 hour trip • 6 personsUS $1,400
Federally permitted4.8(267)42 ftGroup size 1 - 61 - 6+54 hour trip • 6 personsUS $950
State licensed4.7(122)27 ftGroup size 1 - 61 - 6
+104 hour trip • 6 personsUS $800
