I’m back in the saddle again

My last trip to Cuba as a Stillwater Host was in July 2024 to Cayo Largo. This year, I was fortunate enough to co-host a Tarpon Migration trip to the Islands of the Youth, May 2026. I’d seen what Cuba has to offer for Permit and Bonefish in July but had never experienced a trip fully focused on Tarpon. No need to pack the eight weight rods, this would be a big boy game played with ten and eleven weights. I lined up Nautilus reels, Asquith rods and the new Balance line from SA. My casting has improved since 2024, and the flats are the true test of a caster's ability. Everyone thinks they can cast until that first string of Tarpon comes swimming by at 20 meters, one o’clock, then suddenly your cast completely falls apart.

Cuba is currently finding its way into the headlines with food shortages, blackouts, and civil unrest. It’s natural to wonder what that means for a trip like this. Here is the reality on the ground: the U.S.–Cuba dynamic is complicated, but our trip operator has been successfully running logistics on the island for over thirty years. They know exactly how to keep things moving smoothly when things get difficult elsewhere. Our mothership operates on its own independent grid, and there was absolutely no shortage of great food, cold drinks, and fuel on our boat. Don’t let the news cycles keep you from taking advantage of this amazing opportunity to fish some of the best flats in the world.

We now skip the night in Havana, the four hour bus ride, nine hour boat ride and fly directly to Cayo Largo on a private charter. I had only been on small planes a few times as a kid, so this would be a new experience. I admit I was a bit nervous about the flight. Our pilot Zee looked the part right down to the aviator glasses, and I overheard he had flown to St. Croix the day before. When you think of flying privately, your mind takes you to caviar and champagne. The 1981 Turbo Prop Cessna was far from that but gave me the same vibe as a dependable old truck. It may not look like much, but it starts up every time, runs strong, and you would take it anywhere.

Once we got up to 8,000 feet, I settled into my seat and was treated to a spectacular view of the Florida Keys. About an hour later, we got an aerial view of the flats that we would be fishing for the next week. Pristine aqua blue water with zero boat traffic, each of us looking for Tarpon as if we could see them from this high. When we touched down in Cayo Largo, we were the only airplane on the runway and pulled right up to the customs building. We were greeted with warm smiles, and I quickly realized we were the only people in the airport. It took ten minutes for our whole group to clear customs and get our bags. This is what VIP treatment feels like: no lines and warm welcomes. Cuban customs is always a worry for first time visitors, and I have to say there is nothing to be concerned about. Even with the current tensions being what they are, Cubans have always greeted Stillwater travelers with nothing but the warmest of welcomes. Within twenty minutes, we were boarding our Mothership and setting sail for Islands of the Youth.

Over the next week, the group would each have our own adventures. Weather plays a major role in fishing and there is just no way to control it, it can only be dealt with. Our weather was a bit windy, not terrible but enough that you had to factor it into your casting. We had sunlight for most of the trip. All Flats anglers know that you must have sun, and without it, you are playing whack-a-mole. Quick shots, 30 feet from the boat to fish that seem to just appear out of nowhere. Even though Cuba has arguably the best flats fishing in the world, it is still fishing. One realization I had while there is that fishing is not linear. In Cuba we can almost guarantee you a certain number of shots at fish over the week. At times you get zero shots for hours, then bam, here comes the fish and it is shot after shot. One angler who had two shots at Tarpon over a day and a half was suddenly confronted with 60 eats by Tarpon in a three-hour period on the reef. Life on the Flats can feel like a grind at times, until it's not. In Cuba, your patience will be rewarded.

This was a Tarpon Migration trip, and it lived up to the hype with tons of fish around. An angler can expect five to ten Tarpon eats a day, with a great day being twenty plus eats. But nothing tests your sanity quite like catching a Bonefish and a Permit, needing only a Tarpon to complete your Grand Slam, and watching it all go sideways. Another guest was seen having an absolute meltdown on the skiff, yelling and using his fishing partner's Asquith rod like a sword to repeatedly hit the water. When asked at dinner what happened, he painted a tragic picture: he had his Grand Slam Tarpon right to the boat. He recounted how both his guide and partner were just quietly sitting there frozen while he screamed, “someone touch the f@$king leader!” It was at that precise moment that the Tarpon spit the hook and swam off. Fortunately, he was able to catch another Tarpon later that evening to officially seal his Grand Slam.

Sometimes it’s dumb luck. While fishing a channel, the largest Cubera snapper anyone has seen swam out of the mangroves and began following the fly. Our guest saw this big ugly fish and was going to pull the fly away as we were fishing for Tarpon, not big ugly fish. Luckily, this lunker was quicker than our guest and grabbed the fly. As snapper do, it went right back into the mangroves, and it took all three of them to land a snapper that would make the front page of the Miami Herald.

Life on the Mothership falls into a routine very quickly. Because of tides, we split our fishing into a morning session and an evening session. Morning was eggs and coffee, followed by fishing. Then lunch and a nap, followed by fishing. Then rum, cigars, fishing stories aka lies, dinner, then bed for some. For others, dinner was followed by more rum and games of Uno with the guides and ship's crew members. A week flies by when you’re in fly fishing wonderland.

Before we knew it, we were all back at the empty airport in Cayo Largo to go back through exit customs. This process took maybe five minutes and included the high tech process of writing everyone's passport number on a scrap piece of paper. The quick hour and a half flight back to Miami and it was all hugs and handshakes. On all shared experiences like this, bonds are formed and friends are made.

But now it was time to return to reality. Back to a world where we don't start the day with Cuban coffee, end it with rum and Uno, or scream at our boat partners to touch a leader. Cuba has a way of ruining you for ordinary fishing trips, and this migration week at IDJ was proof of that. Whether you are chasing your first Grand Slam or looking to sight cast to massive schools of silver kings, Stillwater Travel can get you there. Just make sure you practice your casting before you step on the plane and remember that even easy tarpon fishing is still hard—that’s why we do it.