When July comes around, I make my annual pilgrimage to Cuba with Stillwater Travel. This year, I will be hosting my own group through Havana and a week of fishing. This week’s group was filled with six first-time flats fishermen, a Florida Tarpon guide, and a die-hard Permit fisherman. The one thing we all had in common was our love for fishing and our desire to have a good time.

At 4: 30 Friday morning in Miami, we learned that the airline computer system had broken down across the United States, planes were delayed, and flights were being canceled. As luck would have it, though, our flight to Havana had zero issues. We made the quick one-hour flight over the Florida Keys to Havana. We cleared customs with no problems and were met by three 1950s-era cars to whisk us to the Airbnb we had for the night. Lunch and Mojitos at a rooftop restaurant got everyone in the right state of mind after an early morning flight.

The city of Havana has an odd feeling to it. If you know your history, you know that pre-revolution Havana was the fashionable spot for Americans to gamble and party. Walking the street, you can still feel that forgotten vibe around you. On the outside, things look run down and unmaintained, but as you get familiar with the surroundings, the city opens up. Fantastic rooftop restaurants are found through hidden doors and excellent dive bars down dark alleyways.  All these places are run by the most gracious Cuban hosts who welcome you and thank you for coming.

But we were here for the fishing, so we took the three-hour bus ride to the port and a five-hour sail to the flats off the coast. We were greeted by low light and thunderstorms the first morning, which slowed the fishing. For our first-timers, getting the hang of spotting fish, casting in the wind, and balancing on the skiff was an eye-opener. The thrill of the chase, the anticipation of a catch, and the camaraderie on the boat were all part of the experience. Stillwater holds “class” on the boat at night to help answer questions and help people understand how to catch these fish. 

As the week went on, the fishing began to pick up, and our group got “fishy”. Their casting came around, and their ability to spot the fish improved. One first-timer caught 37 bonefish this week. Another landed a seven-pound bonefish and nearly caught a Permit if a five-pound bone hadn’t stolen the fly at the last second. We had one client on ten Stillwater trips and finally landed his first Permit. Another first-timer learned a hard lesson in line management. Don’t stand on your line when you hook a Permit because it will instantly break the line and your heart. People fell in love with the chaos of Tarpon fishing, and after a week, we were all ready to sign up for next year. I was lucky enough to get my second Grand Slam, which I attribute to the great fishing, my guide, and me doing my best not to screw it up. The feeling of accomplishment and the shared joy of the group were palpable.

All in all, it was another great Stillwater Cuba trip. Stillwater  has been to Cuba 25 times in the last two and a half years. The program is dialed in, with a perfect balance of adventure and comfort. The staff on the boat are more than accommodating, always ready to assist and share their knowledge. The Cuban flats will deliver the fish, and the experience is one you won't forget. One thing the group could all agree on is to catch these fish: “It all starts with a quality cast.” Flats fishing is a humbling sport for anglers of all levels. Everything must go right even to get that Permit to follow or jump that Tarpon. But it all starts with you being able to deliver the fly. Before I make the journey next July, you better believe I will be practicing my casting because, after two Grand Slams in two years, my luck must run out sometime.