Sailfish Sport Fishing Islamorada

Fishing Charters Florida Keys with Captain Rick Killgore

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Tim Wendelburg with a big Islamorada sailfish he caught off the kite. This sailfish tail-walked around the boat 270* so fast the angler thought we had another sailfish on. We caught this one off the kite.


"While catching sailfish, there are a variety of other fish we catch."

We caught this sailfish, couple dolphin, red grouper, and cero mackerel while kite fishing. That is the nice thing about kite fishing, we can catch numerous types of fish at the same time by putting baits on the surface, at mid-depth, and down on the bottom. There is a photo of our catch at the end of these large photos.

We were also fishing in +20 knots of wind out of the N.N.E., and we were quite comfortable because my boat does not rock much compared to big boats with high towers and deep V's.

Chris and Hope Dorsey came back, but this time instead of trying to best their 10 tarpon released one July 14th they wanted to go offshore to fill the cooler. Hope asked me a couple times about catching a billfish for Chris. I explained it is possible, but not very likely because it is not sailfish season and marlin are even more rare - but still possible.

 Today was his day, and well deserved for this active duty Special Forces soldier on leave.

As we ran out we found a floating pallet, and we caught a couple nice gaffers on it. There were a couple nice triple tail, but we could not keep our baits from the jacks and trigger fish. We gave it a good try, but I knew Chris wanted to catch bigger fish too not just good eating fish so we started trolling again. We caught enough dolphin for the box, but it was slow for the fleet on the radio - lots of undersized fish - same for us. I started my way back in after getting over 20 miles offshore.



Trolling a weed line the left rigger gets knocked down, I turn expecting a dolphin and a billfish comes out of water shaking and jumping all over. I could not see it's dorsal, just it's belly as it charged the boat. I punched the boat to keep the line tight. Then it made a nice run. Chris had the rod, and I directed him up to the bow so we could follow it. It was not more than 50 pounds.

It could be a white marlin or even a small blue this time of year, the suspense was gnawing at me. Then it jumped up again, tail-walking right at the boat 150 yards out. I had to floor it in reverse to help keep the line tight. What was it? I couldn't see clearly, a white marlin? Then it jumped again now just 50 yards out and I see the sail, sailfish, a great fish to catch while dolphin fishing.

I decide to run in to hit a wreck for snapper or amberjacks, because the dolphin fishing was spotty for keepers. That was a good decision. First drop Chris hooks and catches a nice mutton snapper around 14 pounds. Then we dropped a second time for Hope, and she catches another mutton snapper around 12 lbs. In two drops we catch two big mutton snapper at the end of the day. Now a day that started out tough for dolphin just became a GREAT DAY: one sailfish released, two big mutton snappers, and a good box of dolphin. Photos will be up this week.

It could not happen to a better couple. Chris serves on the front lines in the "War on Terror" in the "Special Forces" for around the last 10 years. Thank you so much Chris and Hope for your all's sacrifice for "our safety and freedom" keeping our enemies at bay a long way away from our country. I am so happy you all had another great day fishing down here with me. You all really deserve it, and you all are a pleasure to fish with.

"RED FLAGS" have been used for decades to indicate a released sailfish.

Hall Hicks' boys Hoyt, Harley, and Hunter catch two sailfish and some nice kingfish We also lost one of a double header.

 John Moore and his two boys, Jack and Scott, catch two sailfish and a nice kingfish.

I always try to get a picture in the boat without hurting the sailfish's chances of survival.


The Hicks boys and their Dad catch a sailfish and this nice mutton out of 200' deep. They caught their first sailfish each fishing three days.


Another good day, they caught another sailfish and a black grouper out of 200' deep.




John Moore and his two boys, Jack and Scott, catch two sailfish and a nice kingfish.


What a dream for teenagers and a father!


Talk about a nice variety. We catch mangrove snapper on the patch reefs while netting ballyhoo for bait. Then we go fishing for sailfish, catching one sailfish and cero mackerel.



Sailfish fishing 20 years ago in Costa Rica,

 when I was charter fishing and living down there for five years.




Sailfish on Fly Rod

Old photos from when I ran a charter boat in Costa Rica in the late 1980's. These are some great photos and shows my depth in experience of sailfish fishing.

For clients, friends, family, and personally; I have caught just over 700 sailfish since catching my first one at the age of 8 years old with my Dad on his first open fisherman, an 18' Al Martin plywood boat. Later he bought a 20' SeaCraft, and after that a 34' Norseman. What a great fishing boat that was. As a family we caught over 300 billfish on it.

Just before my 16th birthday, I was off to work as second mate on Bill Hegamyer's boat "Broadbill" in the Bahamas Blue Marlin Tournaments. Here is where I gaffed my first blue marlin, which I think only weighed 142 lbs. - not bad for a fifteen year old. Here I learned the basics of rigging all types of bait: mackerel, mullet, ballyhoo, but Bill insisted on rigging his own squid.


A great series of photos my Mom took of my Dad catching his first two sailfish on fly rod.
My Dad  fights his first sailfish on fly. We discuss strategy on a tough sailfish. My Dad, who has caught hundreds of sailfish, lands his second sailfish on fly

My Mom, a great angler and boats-woman, runs the boat while I tease the sailfish. She puts it in neutral when I call it out, and in forward - and faster! - as I call it out after the sailfish eats the fly, so as to clear the line on the deck after the hook-up.

I fished without a mate most of the time. This was the second year of sport fishing down in Quepos, and there where no qualified mates, they where just essentially boat cleaners. In flamingo you could pick up a more qualified mate.


Jumping in the distance, I fight this very tough sailfish on fly for two hours. This was the second sailfish on fly for the day.  Close to sunset I break him off so we can get back to Quepos, but we get caught by a big storm just offshore.  It was a perilous run along the shear cliffs at night. where if it were not for the lightning we my have been wrecked. This was in the day before GPS and no loran beacons in C.R. Here I catch my first sailfish on fly. Now I had already guided several anglers to sailfish on fly. A total of 13 sailfish on fly, which I'd like to continue here in Islamorada.


  That next Christmas, we fish with a good friend of mine, Luke Hocke. here's my Dad and I with his third sail on fly. In two days we catch two sailfish on fly, and several others on conventional tackle for the rest of the family.