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!



Select date to see available trips and rates:

  • Private trip
    2 Hour Trip – Captain's Choice
    FREE Cancellation 7 days notice
    2 Hour Trip, starts at 7:30 AM
    Seasonal trip (Mon, Tue, Wed, Thu, Fri)
    US $550
    2 hour trip in the Florida keys will keep us near shore and fishing for what's plentiful. Snapper, Barracuda, sharks, and more. It's a great little option for families and kids. Can be combined with a snorkel trip for an additional fee.
    Types of fishing
    Inshore Fishing
    Nearshore Fishing
    Fishing techniques
    Bottom Fishing
    Light Tackle
    Spinning
  • Private trip
    Half Day Trip (AM)
    In demand! Last booked: 17 hours ago
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 7:30 AM
    Seasonal trip (Mon, Tue, Wed, Thu, Fri)
    US $750
    This half day trip is a chance to target species locally like Tarpon, Bonefish, snook, Ladyfish, Spanish Mackerel, Jack Crevalle, and much more, without spending all day on the waves. A fishing license and gear are provided.
  • Private trip
    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)
    US $950
    You have many options for on the six hour trip. You can base the trip around light and/or tides for optimal fishing. 6 hours provides a bit more versatility in how far we can fish, backcountry etc.
  • Private trip
    Full Day Trip
    FREE Cancellation 7 days notice
    8 Hour Trip, starts at 7:30 AM
    Seasonal trip (Mon, Tue, Wed, Thu, Fri)
    US $1,150
    This full day of fishing gives you a chance to target inshore and nearshore species such as Tarpon, Bonefish, Snook, Sharks, Spotted Seatrout, Jack Crevalle, Spanish Mackerel, Ladyfish, and a variety of Sharks.
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FAQs about 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 $1,150 per group - Full Day Trip (8 hours)

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

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

Headshaker Sportfishing LLC offers the following types of fishing:
  • Inshore Fishing
  • Nearshore Fishing
  • Reef Fishing
  • Flats Fishing
  • Backcountry Fishing

Headshaker Sportfishing LLC offers the following fishing techniques:
  • Light Tackle
  • Bottom Fishing
  • Trolling
  • Spinning
  • Popping
  • Drift Fishing

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

Meet the Charter Operator

Headshaker Sportfishing LLC
Islamorada, Florida, United States
25 Fishing Reports
41 Customer reviews
Response time within an hour
Member since October 2017
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

About this listing

Targeted species

Barracuda (Great) Great Barracuda
Bonefish Bonefish
Jack Crevalle Jack Crevalle
Redfish Redfish

Boat specs

Xplor Boatworks (Bay boat) originally built in 2021. Powered by a 300HP Mercury engine.

Length
24 ft
Capacity
4 persons

Types of fishing

Inshore Fishing
Nearshore Fishing
Reef Fishing
Flats Fishing
Backcountry Fishing

Fishing techniques

Light Tackle
Bottom Fishing
Trolling
Spinning
Popping
Drift Fishing

Amenities

GPS
Fishfinder
Live Bait Well
Wireless Trolling Motor
Ice Box

Trip includes

Rods, reels & tackle
St. Croix rods and Shimano reels
Live Bait
Lures
Catch cleaning & filleting
Drinks
Water on board
Fishing License

Cancellation policy

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.

Listing policies

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

Payment

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.

Islamorada Fishing Calendar

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Recent fishing reports

Hot spring bite!
Hot spring bite!
April 18, 2024
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

Customer reviews

Rating summary
Excellent
4.9 / 5
out of 5 stars from 41 reviews
Boat
Excellent
4.8 / 5
Crew
Excellent
4.9 / 5
Experience
Excellent
4.8 / 5
Photos & videos by reviewers (39)
Limited out on Mangrove Snapper
Fishing with Jerry
Full day with Capt Jerry
+36
Angler rating
34
5
0
0
0
Anglers claimed
Good experience
97%
Friendly captain
100%
Recommend this charter
95%
Appropriate for children
91%
Satisfied with the boat
100%
Caught fish
85%
Sort by:
Featured  
Showing:
5 of 41 reviews
Jay F.
Loxahatchee Groves, FL
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

2 Hour Fishing with Guide Jerry

VERIFIED   2 Hour Trip – Captain's Choice on January 12, 2019
My wife and I just wanted a taste of Islamorada fishing as we were passing through on the way to Key West so we took this 2...
Jay F. recommends Headshaker Sportfishing LLC
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Brett M.
Riverview, FL
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half day trip with Capt Jerry

VERIFIED   Half Day Trip (PM) on July 24, 2019
Had a great day with Capt Jerry.  We told him that my son wanted to catch a shark and he was able to get him 3.  Along the...
Brett M. recommends Headshaker Sportfishing LLC
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1 person finds this review helpful
You and 1 other person found this review helpful
  Headshaker Sportfishing LLC Charter Operator replied

Kirk K.
Las Vegas, NV
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Great Trip with Capt. Jerry Sondag!!

VERIFIED   Half Day Trip (AM) on June 29, 2018
Capt Sondag put together a great trip for my girlfriend and I to enjoy some Keys fishing on Friday morning, June 29.  Capt...
Kirk K. recommends Headshaker Sportfishing LLC
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Thomas D.
San Juan, Puerto Rico
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

6 hour trip with Capt Jerry

VERIFIED   3/4 Day (6 Hour) Trip on March 17, 2020
Great day of fishing with Capt Jerry.  Landed us on fish at the start of the day and we caught a lot of fish.  He also recommended...
Thomas D. recommends Headshaker Sportfishing LLC
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Thomas D. recommends Headshaker Sportfishing LLC
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Rob M.
Windermere, FL
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Half Day am trip

VERIFIED   Half Day Trip (AM) on March 12, 2020
Capt. Jerry was prompt, professional, and put us on the fish.  Beautiful boat, we safely navigated to choppy waters to get...
Rob M. recommends Headshaker Sportfishing LLC
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Rob M. recommends Headshaker Sportfishing LLC
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