Annual Islamorada Trip ‘Redfishfest’ 2014

The time finally came. Last week was my annual trip to Islamorada with my girl and the skiff. This just so happens to be my favorite week of the year, not because it’s a vacation- but because it’s a vacation where I get to take my skiff and enjoy beautiful scenery each day out on the water.

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My girl and I went last year for our first trip and it was awesome. This year we went back with more knowledge and planned accordingly for the entirety of the trip. Our accommodation this year was at the Cheeca Lodge, a four star hotel right on Islamorada and within walking distance of the Lorelei and other restaurants like Kaiyo Sushi & Grill. I HIGHLY recommend staying at Cheeca Lodge if you can foot the bill (check for frequent 20% off coupons from online booking sites). I have nothing but great things to say about staying at Cheeca, from the on-site restaurants to the gigantic rooms…it truly is one of the best places to stay at in Islamorada. It’s a gated hotel, and they even have a special gravel lot for storing your trailers if you need to use your car to visit other keys or restaurants!

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This trip was also exciting for me as it was my first long-range trip with the newly restored Hell’s Bay DevilRay I picked up last year.

Let’s recap so far: My favorite place, my favorite skiff, and my favorite girlfriend (If you’re reading this, babe, that was a joke!). We booked the hotel for 5 days which is obviously not enough time. As soon as we checked in, I had us out on the water and heading to the first spot.

Day 1

Tuesday was the first day out and it was nice. We actually had beautiful weather the entire trip which was surprising. Only on one of the days out, Wednesday I think, did we have really high wind and had to dodge a few storms in the bay. Right away we found a nice pod of tailing Islamorada redfish (or silverfish if you will). See the below crappy photo for the best I could do with a back sticking out of the water from one of the half dozen fish in this school.

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Unfortunately, these fish didn’t come to the boat. My girlfriend was able to make a perfect cast to them, but she put her gulp on ‘super weedless’. Her idea of a ‘weedless’ hook was to bury the hook tip and barb into the gulp that essentially teased the redfish within 10 feet of the boat before they spooked off across the flat. Oh well…it was off to the Lorelei for lunch.

Day 2

Wednesday was much better. We hit the same flat and didn’t see much so I moved the skiff over to a bank and some islands across the bay where I could normally find some silver Islamorada redfish on the prowl. This paid off again.

I quickly hooked up with one tailing red on fly in literally 5″ of water (I was pushing the skiff on the ground) and the next set of islands allowed my girl to finally catch her first red of the trip.

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After this action the weather got super hot and we headed into Lorelei once again for an ice cold Kalik and fish sandwiches.

Day 3

Thursday gave us storms and wind- but it was Flamingo day! I always try to run into Flamingo and fish some primo flats while down in Islamorada. We were dodging small cloud cells all morning, and by the time they passed my spot for the day the wind had also kicked up. I was basically playing ‘guide’ for my girl on the bow on this day. We motored up and hit one of my all time favorite spots in Flamingo and she manages to pull out another red from a school of two dozen tailing redfish.

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After this we were greeted with a surprise! Bonefish! All of a sudden a huge wave pushed onto the flat we were on and I didn’t think anything of it. “It’s just redfish!” I exclaimed. As I’m pushing us towards it in what felt like 15MPH winds- I see black tails. These aren’t redfish, they’re Flamingo bones moving into the flat and there’s no way I can catch them on fly.

That was depressing.

Day 4

The last day of fishing, Friday, was the best day on the water. Just like last year the last day always produces the most fish for some reason. I tried my hand at permit fishing early in the morning, only to find just a school of microperms on the bank flat as well as a nice medium sized permit that I smacked on the head with my crab. He didn’t like that one bit.

After that ifasco I went back to my spots in Flamingo and poled around not ten minutes before we were hooking up on redfish left and right.

The best part of these fish wasn’t the small pods, but the GIGANTIC school that was in the distance coming right at us! I couldn’t believe the size of this school of redfish and how skinny in the water they were getting. The tide was at the end of slack and beginning to go out, these huge redfish were moving so fast and so shallow that they were actually leaving a trail of white bubbles in the water like an outboard would.

I instructed my girl to “CAST! CAST! CAST! WAIT- ONE MORE PUSH! CAST!” and it was on for her again. She managed to pick off a nice big red from the school before they hauled ass down the flat.

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This year’s trip was a success just as the year before. I hope to come back to Islamorada every single year for the rest of my life to fish this beautiful sanctuary between the keys and the mainland.


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