Headshaker Sportfishing LLC
+31For 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!
Charter Operator
Headshaker Sportfishing LLC
Most popular features:
Trip availability and prices
Customer reviews
Rating summary
Photos & videos by reviewers (41)
+38Angler rating
Anglers claimed
Good experience
97%
Appropriate for children
91%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
96%
Caught fish
87%
Experience:
Boat
Crew
Overall
Great experience
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! 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.
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.
Experience:
Boat
Crew
Overall
Great day
Half Day Trip (AM) on March 20, 2025
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
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
Experience:
Boat
Crew
Overall
Great Day on the water
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. Worked some good spots and put us on some fish. Boat was well equipped and comfortable. Would recommend to anyone doing some inland/back country fishing.
Great time on the water. Captain was waiting for us at the dock and ready to go when we arrived. Worked some good spots and put us on some fish. Boat was well equipped and comfortable. Would recommend to anyone doing some inland/back country fishing.
Experience:
Boat
Crew
Overall
Fishing with Jerry
2 Hour Trip – Captain's Choice on March 11, 2025
Great trip caught a bunch in only 2 hrs definitely coming again
Great trip caught a bunch in only 2 hrs definitely coming again
Experience:
Boat
Crew
Overall
Fishing with Jerry
Half Day Trip (AM) on January 29, 2025
FAQs about Headshaker Sportfishing LLC
What are the trip rates for Headshaker Sportfishing LLC?
Headshaker Sportfishing LLC offers the following trips to customers:
- US $550 per group - 2 Hour Trip – Captain's Choice (2 hours)
- US $750 per group - Half Day Trip (AM) (4 hours)
- US $950 per group - 3/4 Day (6 Hour) Trip (6 hours)
- US $1,200 per group - Full Day Trip (8 hours)
Which amenities are available onboard with Headshaker Sportfishing LLC?
When you book a trip with Headshaker Sportfishing LLC, you can expect the following amenities onboard:
- GPS
- Fishfinder
- Live Bait Well
- Wireless Trolling Motor
- Ice Box
What's included in the trip price with Headshaker Sportfishing LLC?
Trips booked with Headshaker Sportfishing LLC include:
- Rods, reels & tackle (St. Croix rods and Shimano reels)
- Live Bait
- Lures
- Catch cleaning & filleting
- Drinks (Water on board)
- Fishing License
What types of fishing does Headshaker Sportfishing LLC offer?
Headshaker Sportfishing LLC offers the following types of fishing:
- Inshore Fishing
- Nearshore Fishing
- Reef Fishing
- Flats Fishing
- Backcountry Fishing
What fishing techniques does Headshaker Sportfishing LLC offer?
Headshaker Sportfishing LLC offers the following fishing techniques:
- Light Tackle
- Bottom Fishing
- Trolling
- Spinning
- Popping
- Drift Fishing
Which fish species can I catch with Headshaker Sportfishing LLC?
Top targeted fish species with Headshaker Sportfishing LLC include:
- Barracuda (Great)
- Bonefish
- Jack Crevalle
- Redfish
- Shark (Blacktip)
- Shark (Bull)
- Shark (Lemon)
- Snapper (Mangrove)
- Snook
- Spanish Mackerel
- Spotted Seatrout
- Tarpon
Your operator
Islamorada, Florida, United States
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
The fish you can target
What is the boat like?
What kind of fishing will you do?
Inshore Fishing
Nearshore Fishing
Reef Fishing
Flats Fishing
Backcountry Fishing
Which fishing techniques you can try
Light Tackle
Bottom Fishing
Trolling
Spinning
Popping
Drift Fishing
Which amenities are available onboard
GPS
Fishfinder
Live Bait Well
Wireless Trolling Motor
Ice Box
What’s included in the trip price
Rods, reels & tackle
St. Croix rods and Shimano reels
Live Bait
Lures
Catch cleaning & filleting
Drinks
Water on board
Fishing License
How cancellations work
Free cancellation up to 7 days prior to trip
You can cancel or modify your booking up to 7 days 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 agreed upon reservation
Transfer to/from departure site may be available and included in price depending on your location and distance from the dock.
Child Friendly
Kids are always welcome
You Keep Catch
Client's choice
Catch and Release Allowed
Some species
Catch and Release Mandatory
Some species
How you can pay
Book with 15% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 15% 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
PayPal
When paying the remaining balance with a credit card, an additional 3.5% charge will apply.
What’s biting in Islamorada right now
Barracuda (Great)
Bonefish
Jack Crevalle
Redfish
Snapper (Mangrove)
Snook
Spanish Mackerel
Spotted Seatrout
Tarpon