Headshaker - An Islamorada Fishing Charter

The Headshaker fishing charter is a Florida Keys fishing charter located in Islamorada in the Florida Keys. Headshaker fishes the warm waters of the middle and upper Florida Keys year round for an array of backcountry, inshore, and offshore species. We use a variety of different methods and techniques to fish for these species of fish. Whether you are looking for table fare or a trophy catch, we have you covered! We offer fully guided charter fishing trips for both inshore and offshore game fish.

The Headshaker fishing charter captained by Jerry Sondag is a part of the prestigious Florida Keys fishing Company based out of Islamorada. Headshaker, Catchalottafish, and All Lit Up Charters of The Florida Keys Fishing Company are some of the best in the business. With award winning captains and the best boats and equipment available, you can’t possibly go wrong. Add that to being located in Islamorada, and you have a recipe for your dreams to come true.

Islamorada is called the “Fishing Capital of the World”. It is so named because of the massive variety of record fish found in its waters. You will find no better fishing with such a wide array of species anywhere else in the world. When it comes to fishing, this is the place to be!


Review 2-9-2022

“Had a excellent trip with captain Jerry. Already talking about booking another trip.”

Ron & Roger G.

Fishing Charter Trips Available...

Gulf of Mexico

We have three completely different bodies of water including the Florida Bay & Everglades, Gulf of Mexico, and the Atlantic Ocean. These bodies of water intersect to create an absolutely amazing fishery. It creates an incredible place to fish and is unique to Islamorada and the Florida Keys.

These waters contain a very diverse selection of fish including Groupers, Cobia, Kingfish, and Permit!  There are also Snappers, Bonita, Spanish mackerel, sharks, and Barracuda. Fishing these bodies of water is always an exciting experience. For more information about booking this amazing charter trip, check out our Gulf of Mexico Fishing Charter Trip.


The Florida Keys contain one of the largest coral reefs on the planet! This living reef has a huge variety of fish species and the perfect habitat to sustain a great fishery! When on charter with Capt. Jerry, you will be targeting many species such as Yellowtail Snapper, Mangrove Snapper, Mutton Snapper, Mackerel, Sailfish, and huge Grouper just to name a few! If you want to book an awesome trip, take a look at our Reef Fishing Trips.

Everglades & Back Country

Captain Jerry is also quite experienced at fishing back country waters including areas of the Everglades located off the Florida Bay. These waters possess an array of amazing fish species including Redfish, Snook, Tarpon, Bonefish and more. You don’t want to miss out on this experience of a lifetime! Get a closer look at our Everglades and Back Country Fishing Charter Trips.

Our Rates

  • A 1/2 Day Trip is $750.00
  • A 3/4 Day Trip is $950.00
  • A Full Day Trip is $1150.00
  • A deposit of $300.00 per day is required.

All deposits are 100% refundable if the trip is cancelled 30 or more days prior to the booked date.

Captain Jerry Sondag

Captain Jerry was born and raised in the Chicago area.  Jerry’s family oddly enough, spent an exuberant amount of time on the water from the Great Lakes to offshore in multiple oceans.  He gained a love and respect for fishing at an early age, which continued through his life as he grew as an angler and as a professional.  Becoming a professional fishing guide, Capt. Jerry focused on providing a first class experience.  As a tournament angler, he was driven to bring home the hardware. As a father, now residing in the Florida Keys, he understands the importance of patience and sharing the experience with those closest to you.  Educating anglers as well as entertaining are Jerry’s greatest joys of his chosen path as a guide and captain. Book now for a trip you won’t soon forget. 


Capt. Jerry has participated and earned top spots in many tournaments in both freshwater and saltwater.  He’s been featured on several TV programs such as The Next Bite as well as The Hunt for Big Fish with Larry Dahlberg.  He has also been featured and published in many magazines as well as appearing on several covers. 



The Florida Keys offers some of the best tarpon fishing in the World! It is a common to see them over 100 lbs. swimming and rolling right around the boat. These fish are some of the most sought after fish in the angling world. They bring an exciting fight to every outing and keeping them away from the sharks to land them is a true and tough challenge. Check out our Tarpon Charter Fishing Trip.


The beautiful blue waters surrounding the Florida Keys are loaded with a variety of fish species. This is also true of our sharks. There are a multitude of shark species around Islamorada and the Florida Keys. These species include everything from several species of reef sharks to Lemon Sharks and huge Tiger Sharks. If you’re looking for a fight with bite, check out our Shark Fishing Trips.

In-Shore & Bridges

The main islands throughout the Florida Keys are connected by a series of bridges. These bridges have created an excellent habitat for many species of fish particularly migrating species. These fish include Tarpon as well as multiple species of sharks such as Bull Sharks, Tiger Sharks, and Hammerhead Sharks just to name a few. Fishing the inshore areas and bridges of the Florida Keys is an awesome experience you will not soon forget! For more information, check out our In-Shore and Bridges Charter Trips.


Islamorada and the Florida Keys have many wrecks. The wrecks also contain a variety of fish species including snappers and groupers as well as several species of tunas, jacks, Mackerel, Wahoo, and sharks.  Wreck fishing is an incredible type of fishing. It is a very visual type of fishing with live chumming while drifting or on anchor.  The methods used will greatly vary depending on conditions but with so many species to target, there is always opportunity for a great catch. Don’t miss out! Come see our Wrecks Charter Trip.


Q: Where are you located?

A: We are based at Mile Marker 81.5 on the bayside at the World Wide Sportsman’s Bayside Marina (Bass Pro Shops) in Islamorada in the Florida Keys.

Q: Is my deposit refundable if I need to cancel my charter trip?

A: Yes. The deposit for your trip is 100% refundable if you cancel 30 or more days from your booked date. If you need to cancel within 30 days of your scheduled trip, we may be able to reschedule to a later date.

Q: Do you ever have to cancel a charter trip?

A: Yes. If we need to cancel a trip for unforeseen circumstances, we will refund your deposit the same day. Examples of such circumstances would include but are not limited to the weather and unforeseen mechanical issues.

Q: How many guests can I bring on my charter trip?

A: We allow a maximum of 4 guests on board the boat.

Q: What charter gear do you provide and can we bring some of our own gear?

A: We provide top of the line rods, reels, and tackle. We also have an onboard cooler which is at your disposal. You can bring your own gear, but we will assess if it is suitable to use on your charter trip.

Q: Is food and drink provided or do I need to bring my own?

A: We do provide a cooler with ice on board for your food and beverages as well as your fish, but clients are responsible for providing their own food and drink. Alcohol is allowed, but please do not bring any glass beverages.

Q: What safety gear is on the boat?

A: Safety Gear on board includes life jackets, throw able floatation device, flares, and first aid kit. The safety gear required by the Coast Guard is on board. We also have a marine radio and GPS.

Q: What is the customary tip for a fishing charter?

A: It is customary to tip 20% for any fishing charter. A tip above the customary 20% would be complimentary if you receive extraordinary service. All tips are greatly appreciated.

Q: If I get sea sick and need to cut the trip short, will I still have to pay for the full day?

A: This is done on a case-by-case basis. It depends on the type of charter trip you booked and what time of the day the trip has ended. We strive to be as fair as we can.

Q: Can we keep the fish we catch?

A: Most of the fish caught can be kept for table fare; however, some species such as Sailfish, Tarpon, and many species of sharks are 100% catch and release by law. There are also species of fish that have a catch and keep quantity limit.


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