Charter Operator
Headshaker Sportfishing LLC

Member since October 2017 Islamorada, United States
Background
Captain. Jerry Sondag was born and raised in the Chicagoland area and learned to love fishing at an early age. Over the years, he developed a lifetime of experience fishing in both freshwater and saltwater. His professional fishing career began in 2002, guiding charters both in Florida and Minnesota. He now runs charters year-round in the Florida keys. Headshaker Sportfishing LLC is based out of beautiful Islamorada

Hey, we're Headshaker Sportfishing LLC

Islamorada, United States
Background
Captain. Jerry Sondag was born and raised in the Chicagoland area and learned to love fishing at an early age. Over the years, he developed a lifetime of experience fishing in both freshwater and saltwater. His professional fishing career began in 2002, guiding charters both in Florida and Minnesota. He now runs charters year-round in the Florida keys. Headshaker Sportfishing LLC is based out of beautiful Islamorada
46
Reviews
25
Fishing Reports

My Charter Listing

Headshaker Sportfishing LLC

Excellent
4.9 / 5
(46 reviews)
Islamorada
 Instant Confirmation
Trips from US $550

Fishing Reports

Hot spring bite!
Hot spring bite!
Apr 18, 2024 Islamorada
The inshore / backcountry bite has been red hot lately! Everything from tarpon & sharks to snook, permit, pompano, trout etc etc. lots of multi species action!
Continue reading
Hot temps solid fishing!
Hot temps solid fishing!
Jul 17, 2023 Islamorada
Lately the water temps have been spiking moving a lot of the fish around. Still some tarpon remain in the area, many of the permit that were spawing off the reef are making their way back inshore, snappers, cudas and sharks are plentiful. Some snook and trout action in the back sprinkled in with some reds, jacks, and small tarpon. Cโ€™mon down! Lets get bit!
Continue reading
Great multi species around the keys!
Great multi species around the keys!
Apr 22, 2023 Islamorada
Fishing up and down the keys and up to the everglades is wxperiencing a really good bite with a variety. With Tarpon being the hot ticket right now thru June, there is a lot of fun by catch with sharks, cudas, jacks, and grouper. In the backcountry, snook, bonefish, etc are on the chew!
Continue reading
Big bites in the gulf
Big bites in the gulf
Feb 9, 2019 Islamorada
Been having bang up trips in the back and the gulf. Mackerel have been going crazy, Redfish snook, ladyfish, and trout, Continue to bite. Sharks and Tarpon are showing up regularly Now if the water is warming. Days available.
Continue reading
A whole lot of bites.
A whole lot of bites.
Feb 7, 2019 Islamorada
In the back country trout, reds, snook, layfish and snapper are thick. Shark start to pick up now that were warming back up! Inshore The patch reefs are holding a variety of snapper, macks and other various critters.. Offshore the sails tuna and kings Are biting. Come on down to the keys and get bit.
Continue reading
ISLAMORADA FISHING IS RED HOT!
ISLAMORADA FISHING IS RED HOT!
Jan 16, 2019 Islamorada
Backcountry is hosting a great Snapper, Trout bite with days of good Snook and Trout. Not to mention theres still a few tarpon around. Inshore / gulf the Snapper, Macks, and sharks are chewing and word is the cobia have been coming into the slicks. The other day we switched gears on a calm day and went a few miles offshore for some awesome large blackfin tuna action. Tuna up to 25 pounds on the deck with some seen on the 30-35 pound range. Sails have been biting as well as a bevy of snapper and bottom fish are cranking. C'mon down!
Continue reading

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 46 reviews
See details
Boat
Excellent
4.9 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.9 / 5
Photos & videos by reviewers (41)
Great experience
Great Day on the water
Limited out on Mangrove Snapper
+38
Angler rating
39
5
0
0
0
Anglers claimed
Good experience
97%
Friendly captain
100%
Recommend this charter
96%
Appropriate for children
91%
Satisfied with the boat
100%
Caught fish
87%
Sort by:
Featured  
Showing:
5 of 46 reviews
Lori K.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great experience

VERIFIED   Half Day Trip (AM) on April 15, 2025
We had a great experience today on a four hour fishing trip withJerry. We caught a bunch of barracuda, 100 pound plus tarpon!...
Lori K. recommends Headshaker Sportfishing LLC
Mark review as helpful
You found this review helpful
Lori K. recommends Headshaker Sportfishing LLC
Mark review as helpful
You found this review helpful
Read more
Brian R.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great day

VERIFIED   Half Day Trip (AM) on March 20, 2025
Had a great time- family of 4 - targeting Tarpon.ย  Capt Jerry knew the spots, even tho a bit early in season and landed my...
Brian R. recommends Headshaker Sportfishing LLC
Mark review as helpful
You found this review helpful
Brian R. recommends Headshaker Sportfishing LLC
Mark review as helpful
You found this review helpful
Read more
Todd S.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Day on the water

VERIFIED   3/4 Day (6 Hour) Trip on June 24, 2024
Great time on the water. Captain was waiting for us at the dock and ready to go when we arrived.ย  Worked some good spots and...
Todd S. recommends Headshaker Sportfishing LLC
Mark review as helpful
1 person finds this review helpful
You and 1 other person found this review helpful
  Headshaker Sportfishing LLC Charter Operator replied
Read more
Matthew P.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Jerry

VERIFIED   2 Hour Trip โ€“ Captain's Choice on March 11, 2025
Great trip caught a bunch in only 2 hrs definitely coming again
Matthew P. recommends Headshaker Sportfishing LLC
Mark review as helpful
You found this review helpful
Matthew P. recommends Headshaker Sportfishing LLC
Mark review as helpful
You found this review helpful
Norma D.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Fishing with Jerry

VERIFIED   Half Day Trip (AM) on January 29, 2025
Norma D. recommends Headshaker Sportfishing LLC
Mark review as helpful
You found this review helpful
Norma D. recommends Headshaker Sportfishing LLC
Mark review as helpful
You found this review helpful
  • Settings