Headshaker Sportfishing LLC

40 reviews
In demand!

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 while fishing, snorkeling, sandbar soaking, bar hopping, and much more!

You will enjoy a comfortable ride on a fully loaded 24’ vessel, custom built in 2017 by Islamorada Boatworks. 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. St. Croix rods and Shimano reels are ready and waiting on board. Capt. Jerry does his best to make sure the live bait well is fully stocked when you arrive.

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, 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.

If you’re looking for a little relaxation rather than a hard-fighting catch, Capt. Jerry has something for you, too. Try snorkeling by nearshore patch reefs, visit Islamorada’s famous sandbar, or come aboard for an eco tour through the mangroves. Can’t decide what sounds best? You can ask Capt. Jerry for a combo trip, with plenty of time both for fishing and your choice of fun.

Headshaker Sportfishing provides a fishing license, gear, and snorkeling equipment. 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
    Full Day Trip
    FREE Cancellation 7 days notice
    8 Hour Trip, starts at 8:00 AM
    Seasonal trip (Lun, Mar, Mie, Jue, Vie, Sab)
    $950
    price breakdown
    $950
    This full day of fishing gives you a chance to target inshore and nearshore species such as Spotted Seatrout, Jack Crevalle, Spanish Mackerel, Ladyfish, a variety of Sharks, and much more. You can also choose to split your time between fishing and snorkeling, a sandbar visit, or an eco tour. Top of the line gear and snorkeling equipment are included.
  • Private trip
    3/4 Day (6 Hour) Trip
    FREE Cancellation 7 days notice
    6 Hour Trip, starts at 8:00 AM
    Seasonal trip (Lun, Mar, Mie, Jue, Vie, Sab)
    $800
    price breakdown
    $800
    You have many options for on the six hour trip. You can base the trip around light and/or tides for optimal fishing. Reef, wreck, backcountry etc.
  • Private trip
    Half Day Trip (AM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 8:00 AM
    Seasonal trip (Lun, Mar, Mie, Jue, Vie, Sab)
    $650
    price breakdown
    $650
    This half day trip is a chance to target species like Ladyfish, Spanish Mackerel, Jack Crevalle, and much more, without spending all day on the waves. A fishing license and gear are provided.
  • Private trip
    Half Day Trip (PM)
    FREE Cancellation 7 days notice
    4 Hour Trip, starts at 1:00 PM
    Seasonal trip (Lun, Mar, Mie, Jue, Vie, Sab)
    $650
    price breakdown
    $650
    This afternoon trip includes four hours of fishing for Spotted Seatrout, Jack Crevalle, Snapper, Ladyfish, Spanish Mackerel, a variety of Sharks, and more. A fishing license and top of the line gear are provided. Starting time may be flexible depending on your request, weather conditions, and the captain's schedule.
  • Private trip
    2 Hour Trip – Captain's Choice
    In demand! Last booked: 1 day ago
    FREE Cancellation 7 days notice
    2 Hour Trip, starts at 8:00 AM
    Seasonal trip (Lun, Mar, Mie, Jue, Vie, Sab)
    $400
    price breakdown
    $400
    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.
There are 11 people looking at this charter.

About the Charter Operator

Headshaker Sportfishing LLC
Islamorada, Florida, Estados Unidos
Angler's Choice
22 Fishing Reports
40 Customer Reviews
Response time within an hour
Member since Octubre 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 in Islamorada year-round. Headshaker Sportfishing LLC is based out of the stunning Angler House Marina. They can also help customers arrange accommodations at the Angler House “Villa Fina,” a gorgeous 50’ 2 bed, 2 bath, houseboat, located on the property with every amenity imaginable! We provide a full service charter to handle offshore, inshore, and backcountry.

About this listing

Targeted Species

Barracuda (Great) Barracuda (Great)
Grouper (Black) Grouper (Black)
Jack Crevalle Jack Crevalle
Redfish Redfish

Shark (Lemon) Shark (Lemon)
Snapper (Mangrove) Snapper (Mangrove)
Snapper (Mutton) Snapper (Mutton)
Snapper (Yellowtail) Snapper (Yellowtail)

Snook Snook
Spanish Mackerel Spanish Mackerel
Spotted Seatrout Spotted Seatrout
Tarpon Tarpon

Boat Specs

Islamorada Boatworks (Bay boat) originally built in 2017. Powered by a 300HP Yamaha engine.

Length
24 ft
Capacity
4 persons

Types of Fishing

Inshore Fishing
Nearshore Fishing
Reef Fishing
Wreck Fishing
Flats Fishing
Backcountry Fishing

Fishing Techniques

Light Tackle
Bottom Fishing
Trolling
Spinning
Popping
Drift Fishing

Amenities

GPS
Life Jackets
Fishfinder
Flybridge
Snorkeling Equipment
Live Bait Well
Wireless Trolling Motor
Ice Box
GPS
Life Jackets
Fishfinder
Flybridge
Snorkeling Equipment
Live Bait Well

Trip Includes

Rods, reels & tackle
Live Bait
Lures
Catch cleaning & filleting
Fishing License

Cancellation Policy

Free cancellation up to 7 days prior to trip

Customers can cancel or modify their booking up to 7 days before the trip date free of charge. If the trip is canceled or modified later, or in the event of a no-show, 100% of the deposit will be charged.

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
You Keep Catch
Catch and Release Allowed
Catch and Release Mandatory

Payment

Book with 20% deposit
When the captain confirms your trip, FishingBooker charges your credit card a 20% deposit to guarantee your reservation.
Pay remaining balance to captain
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, there is a 2.5% fee.

Islamorada Fishing Calendar

Loading Fish Calendar!
Please Wait...

Customer Reviews

Rating Summary
Photos by reviewers (39)
4.87
out of 5 stars from 40 reviews
Boat
Crew
Experience
Limited out on Mangrove Snapper
Fishing with Jerry
Full day with Capt Jerry
+36
Angler Rating
33
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%
Catch intended fish
85%
Sort By:
Featured  
Showing:
5 of 40 reviews
Maria S.

The captain canceled

VERIFIED   NEW  Julio 11, 2020
The charter operator canceled on trip date. This is an automated posting
Mark as helpful
You found this helpful
Mark as helpful
You found this helpful

Jimmy C.

The captain canceled

VERIFIED   Junio 20, 2020
The charter operator canceled on trip date. This is an automated posting
Mark as helpful
1 person finds this review helpful
You and 1 other person found this helpful
Mark as helpful
1 person finds this review helpful
You and 1 other person found this helpful

Mark G.
Tampa, Florida
 5.00
Experience:
Boat
Crew
Overall

Limited out on Mangrove Snapper

VERIFIED   NEW  Julio 29, 2020
Great trip with Captain Jerry! He had a great spot and we were catching fish with virtually every cast!
Mark G. recommends Headshaker Sportfishing LLC
Mark as helpful
You found this helpful
  Headshaker Sportfishing LLC Charter Operator replied

Thomas D.
San Juan
 5.00
Experience:
Boat
Crew
Overall

6 hour trip with Capt Jerry

VERIFIED   Marzo 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...
Thomas D. recommends Headshaker Sportfishing LLC
Mark as helpful
You found this helpful
Thomas D. recommends Headshaker Sportfishing LLC
Mark as helpful
You found this helpful

Rob M.
Windermere, FL
 5.00
Experience:
Boat
Crew
Overall

Half Day am trip

VERIFIED   Marzo 12, 2020
Capt. Jerry was prompt, professional, and put us on the fish.  Beautiful boat, we safely navigated to choppy waters to...
Rob M. recommends Headshaker Sportfishing LLC
Mark as helpful
You found this helpful
Rob M. recommends Headshaker Sportfishing LLC
Mark as helpful
You found this helpful