Headshaker Sportfishing LLC 

4.9/5 (47 reviews)
 81576 Overseas Highway, Islamorada, FL 33036, United States

Headshaker Sportfishing LLC 

4.9/5 (47 reviews)
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81576 Overseas Highway
Islamorada, FL, United States

For fishing and fun in Islamorada, look no further than Headshaker Sportfishing. Captain Jerry Sondag aims to put you on the best bite, which is why many of his customers keep coming back for more. Whether you’re looking for table fare or a trophy, he’s got you covered. Come aboard for a memorable day on the water!

Capt. Jerry has traveled all over the world fishing both fresh and saltwater.  from the Great barrier reef in Australia to the Lakes of Ontario and everything in between, your Capt has tried to learn it all.  The keys have become home where he focuses his attention now. 

You will enjoy a comfortable ride on a fully loaded 24’ vessel, custom built Xplor Boatworks 24. This boat comes equipped with advanced fishing technology and top of the line gear, including GPS, fishfinder, a wireless trolling motor, and a fighting chair.Top of the line rods and reels are ready and waiting on board.

With many trip options to choose from, you can make the most of your time on the waters surrounding Islamorada. Fishing inshore and nearshore gives you a chance to reel in many species, including Barracuda, Spotted Seatrout, Jack Crevalle, Bonefish, Sharks, Spanish Mackerel, and Tarpon when in season. Capt. Jerry provides light and heavy tackle, and he will help you target your catch using the most effective technique. You may also request to fish offshore for an additional charge.

Headshaker Sportfishing provides a fishing license and tackle. You may keep your catch and Capt. Jerry will clean and fillet it for you. Alcohol is permitted, preferably not in glass containers.

Come aboard today for a fishing adventure you won’t soon forget!

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Customer reviews

Rating summary

4.9/5
out of 5 stars from 47 reviews
Boat
4.9/5
Crew
4.9/5
Experience
4.9/5

Photos & videos by reviewers (41)

Great experience
Great Day on the water
Limited out on Mangrove Snapper
+38

Angler rating

40
5
0
0
0

Anglers claimed

Good experience

97%

Appropriate for children

91%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

96%

Caught fish

88%

Showing 1 - 5 of 47 reviews
Showing: 5 of 47 reviews
Keith Williams
Keith Williams
5.0
Verified
Tarpon!!!
Half Day Trip (AM) on June 27, 20252 adults
The captain was honest upfront regarding the tarpon fishing. He said he was only getting 1-3 bites a trip. Well, we took a chance on catching a big tarpon and succeeded. We caught 2 over 100lbs.
0
Lori Keller
Lori Keller
5.0
Verified
Great experience
Half Day Trip (AM) on April 15, 20253 adults
We had a great experience today on a four hour fishing trip withJerry. We caught a bunch of barracuda, 100 pound plus tarpon! And hooked a nurse shark that put up a nice fight for a while. Jerry was great teaching our 13-year-old son exactly what to do to reel the fish in. We will definitely book with him in the future.
Review media 0
0
Brian Rowland
Brian Rowland
5.0
Verified
Great day
Half Day Trip (AM) on March 20, 20254 adults
Had a great time- family of 4 - targeting Tarpon. Capt Jerry knew the spots, even tho a bit early in season and landed my sons first Tarpon along with some jacks- great day on the water
0
Matthew Palasay
Matthew Palasay
5.0
Verified
Fishing with Jerry
2 Hour Trip – Captain's Choice on March 11, 20253 adults
Great trip caught a bunch in only 2 hrs definitely coming again
0
Norma Doyon
Norma Doyon
5.0
Verified
Fishing with Jerry
Half Day Trip (AM) on January 29, 20252 adults
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
November 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
2 Hour Trip – Captain's Choice
FREE Cancellation 7 days notice
2 Hour Trip, starts at 7:30 AM
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US $550 
Entire boat: up to 4 people
Half Day Trip (AM)
FREE Cancellation 7 days notice
4 Hour Trip, starts at 7:30 AM
Seasonal trip (Mon, Tue, Wed, Thu, Fri, Sat)
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US $750 
Entire boat: up to 4 people
3/4 Day (6 Hour) Trip
FREE Cancellation 7 days notice
6 Hour Trip, starts at 7:30 AM
Seasonal trip (Mon, Tue, Wed, Thu, Fri, Sat)
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US $950 
Entire boat: up to 4 people
Full Day Trip
FREE Cancellation 7 days notice
8 Hour Trip, starts at 7:30 AM
Seasonal trip (Mon, Tue, Wed, Thu, Fri, Sat)
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US $1,200 
Entire boat: up to 4 people
There is 1 person looking at this charter.

Customer reviews

Rating summary

4.9/5
out of 5 stars from 47 reviews
Boat
4.9/5
Crew
4.9/5
Experience
4.9/5

Photos & videos by reviewers (41)

Great experience
Great Day on the water
Limited out on Mangrove Snapper
+38

Angler rating

40
5
0
0
0

Anglers claimed

Good experience

97%

Appropriate for children

91%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

96%

Caught fish

88%

Showing 1 - 5 of 47 reviews
Showing: 5 of 47 reviews
Keith Williams
Keith Williams
5.0
Verified
Tarpon!!!
Half Day Trip (AM) on June 27, 20252 adults
The captain was honest upfront regarding the tarpon fishing. He said he was only getting 1-3 bites a trip. Well, we took a chance on catching a big tarpon and succeeded. We caught 2 over 100lbs.
0
Lori Keller
Lori Keller
5.0
Verified
Great experience
Half Day Trip (AM) on April 15, 20253 adults
We had a great experience today on a four hour fishing trip withJerry. We caught a bunch of barracuda, 100 pound plus tarpon! And hooked a nurse shark that put up a nice fight for a while. Jerry was great teaching our 13-year-old son exactly what to do to reel the fish in. We will definitely book with him in the future.
Review media 0
0
Brian Rowland
Brian Rowland
5.0
Verified
Great day
Half Day Trip (AM) on March 20, 20254 adults
Had a great time- family of 4 - targeting Tarpon. Capt Jerry knew the spots, even tho a bit early in season and landed my sons first Tarpon along with some jacks- great day on the water
0
Matthew Palasay
Matthew Palasay
5.0
Verified
Fishing with Jerry
2 Hour Trip – Captain's Choice on March 11, 20253 adults
Great trip caught a bunch in only 2 hrs definitely coming again
0
Norma Doyon
Norma Doyon
5.0
Verified
Fishing with Jerry
Half Day Trip (AM) on January 29, 20252 adults
0

FAQs about Headshaker Sportfishing LLC

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Center console boats
Capacity
4 persons
Boat length
24 ft
Year built
2021
Boat manufacturer
Xplor Boatworks
Boat type
Bay boat

Engine model
Mercury
Powered by
1 x 300HP
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