***Author’s note: Sometimes I’m having such a good time, I’m not very good about taking pictures. This trip was one of those situations. The only real pictures I snapped were while I was snorkeling. Unfortunately, even those are mediocre at best. I had a very difficult time getting my usually reliable underwater camera/housing to focus on the subjects. Please forgive the lack of pictures, and the low quality of those I did include with this post.

I spent the long Labor Day weekend in the Upper Keys with my girlfriend, Susanna – who has made previous appearances in my posts. Our initial trip plan didn’t have fishing in the cards, so you can imagine my surprise and excitement when a week before we were set to leave, Susanna actually ASKED to go fishing. She wanted to do a simple half day and catch some dinner. I started scrambling to find a last minute guide in the Upper Keys that fished for snapper or grouper. I narrowed the choices down and started sending some emails and making calls for availability.

Several guides had trips, but I picked Captain Rick Killgore after chatting with him on the phone. Rick was so easy to talk to and loved to share stories about fishing in general. You could tell this was a guy that loved every minute of his job. I booked the half day trip, planning to meeting in the afternoon. Rick had also mentioned he also leads snorkeling, lobstering, and spearfishing trips – even scuba diving if he can get a divemaster to come along. After talking with Susanna and my friend Kyle, who was joining us for the trip, I called Rick back up to change to a full day combo trip.

Barracuda on the reef

We met up with Rick at the docks in the morning and watched some big tarpon swim under the boat as Rick was putting the final preparations on the boat. Rick pushed off and we made our way to our first stopping point. We were starting off the morning with some snorkeling on a shallow reef while we enjoyed the scenery and looked for lobster. As soon as we jumped in, I was greeted by a barracuda patrolling the reef. He casually looked at us before moving along. Swimming around the sea fans, I finally saw a couple antennae sticking out from beneath a coral head. I dove down to check it out, and sure enough, there was a nice lobster relaxing. I called over Rick who explained what technique we used, then suggested he show me how to catch the first one and he’ll hand everything over for the second. We dove down, and Rick set up the net and used the tickler to coax the lobster out of his hiding spot. As Rick expected, it went speeding out into the net. He was a quarter inch bigger than legal size, so we knew we’d at least have some good eating for dinner!

Hiding spiny lobster

We swam around for a while looking for more lobster, but around this time the purple moon jellyfish started moving in. I spent a little more time in the water, but I felt like I was getting to the point where I was spending more time dodging the jellyfish than I was looking for lobster. Susanna had already bailed on the snorkeling, so I decided to join her on the boat while Kyle finished up looking for lobsters with Rick. Kyle and Rick managed to put one more keeper lobster in the bag before Kyle gave up on the jellyfish too. While I was on the boat watching, I was wondering if I’d regret not staying out there. My mind was very quickly changed when I saw the welts on Kyle’s back from jellyfish stings. Maybe he should’ve taken Rick up on his offer of a spare protective lycra shirt…

After we got on the boat and out of our snorkel gear, we headed off to a nearby wreck to try to pull up some mutton snapper or grouper. Rick hooked on a live pinfish and dropped the bait. Kyle manned the rod as we drifted across the wreck. We see a tap-tap-tap on the rod, then suddenly it doubles over as Rick tells Kyle to reel. Unfortunately, the line didn’t stay tight. Drop number two, however, had different results. The rod doubled over again, and this time Kyle got tight. A few minutes later, the leader broke the water, and Rick pulled up the fish. It was a shark – not our targeted quarry, but still a fun fish. The next drop, I was on the rod with the same result: another bite, another shark. Even Susanna had the same luck. Rick kept us tight on fish the whole time. In fact, we never even had a drop that didn’t result in a bite. Sharks were king that day though and we probably got eight of them to the boat. I pulled up one very good size bonito that made a very strong run, but nothing that we were planning on eating. All our suspected grouper or snapper bites ended up freeing themselves before we could get them to the gaff.

After a little while of fighting the sharks, Rick moved us on to some slow trolling over the reef for some cero mackerel. Almost immediately, one of our baits got nervous. Suddenly, there was a big blow up behind the bait, but the fish missed our hook. Like the sharks, this became a repeated pattern. We’d have the fish blow up on the bait, but would just miss it. Finally, Susanna’s line actually held tight, and she fought the cero mackerel to the boat where it would become dinner in a few hours.

We kept on trolling, and Rick told us a few stories about fish he’s caught on the reef. He said it wasn’t uncommon for him to hook into mahi mahi, blackfin tuna, or even sailfish. Less than three minutes after, I see my bait starting to get nervous. Suddenly, I see what looks like a dark triangle behind the bait. As I’m trying to get the words out of my mouth to describe what I’m seeing, Rick yells, “SAILFISH!!!!!” Rick jumped in to help feed the bait to the sail, sets the hook, and the line stays tight. He immediately handed over the rod, and I started the battle. A big sailfish (easily 6 feet or more) makes his first appearance above water and goes on a tear in the opposite direction of the boat. The reel is screaming as my smile is growing. The sailfish was clearly unhappy being hooked as it unleashed another beautiful tail walk. Unfortunately, the sailfish got its wish and threw the hook, but the exhilaration didn’t go away.

Rick tried to get us on another fish before the light was gone, but the fish just wouldn’t cooperate. After a good 9 or 10 hours on the water, we headed back to the dock. Rick says he always likes to make sure his clients get at least 8 hours actually on the water. It’s a nice differentiation between other guides that consider a full day 8 hours dock to dock. Rick also doesn’t hesitate to stay on the water for some extra time if you are hot in the action, or in our case where he’s trying to get you that one last fish. We got back to the dock and Rick cleaned and prepped the Cero and the lobsters for us to bring off to get cooked.

Ready to book with Captain Rick Killgore? He can be reached at rick@fish-killgore.com via email or by phone at (305) 852-1131. Rick is a versatile captain based out of the Upper Florida Keys (Islamorada) that has both a 23′ Center Console for some reef, wreck, and offshore fishing, as well as a flats skiff for hitting the flats and the backcountry. Rick guides for everything from snapper to bonefish to tarpon to sailfish, and uses either spinning gear or the fly rod. Rick will do everything for you on your trip, or is more than happy to teach you everything you need to know. I’ll be booking Rick again for some flats fishing next time in the Keys. Make sure you leave Rick a review if you get out with him!