A certain anxious excitement comes with traveling to a foreign country—especially one so close to the U.S. yet so vastly different from anything we know at home. Arriving in Cuba feels like stepping back in time. The sight of vintage cars sharing the streets with horse-drawn carriages and the colonial architecture standing proudly despite the wear of time immediately immerses you in a nostalgic and unique world. From the moment you land, it’s clear—you’re in for an experience unlike any other.
As we stepped out of the airport, we were immediately greeted by Boris, a smile on his face and a torch in hand. “Brother, you want a cigar?” he asked, the rich scent of Cuban tobacco lingering in the air. Behind him, a fleet of gleaming classic cars, their chrome accents catching the sunlight, stood ready as we loaded our luggage and headed to the hotel.
Once we had settled in and refreshed from our travels, we piled back into the classic cars and made our way to Boris’ house.
The evening began with a spectacular feast—roast pig, freshly caught lobster, and smooth Cuban rum. A live band filled the air with infectious rhythms, and dancers moved to the beat, their energy pulling everyone into the celebration. The combination of music, laughter, and incredible flavors created an undeniably authentic Cuban atmosphere.
Though I’m not much of a cigar smoker, watching professional cigar rollers at work was fascinating. Their hands moved with expert precision, crafting each cigar with the skill of artisans who had spent a lifetime perfecting their craft. They shared stories of Cuba’s deep-rooted cigar history as they worked, offering insight into the tradition and prestige that make their cigars world-renowned.
With plates emptied, glasses refilled, and music playing late into the night, it was clear that this was more than a meal. It was an experience, a true immersion into the heart of Cuban culture.
On the first day of fishing, everyone set out with different goals. With a mix of first-time fly fishermen and seasoned traveling anglers, each of us had our own ambitions for the day.
Although flats fishing isn’t the easiest place to learn how to fly cast, some of the group returned to the marina with impressive numbers—landing large snapper and jacks from deep “blue holes,” along with a few juvenile tarpon and aggressive barracudas.
The rest of us spent the day chasing after large bonefish and permit, taking advantage of the crystal-clear waters and expansive flats. Throughout the day, we had a good number of shots at permit, though, as always, their elusive nature kept us on our toes.
The following two days were particularly calm, with the water like a mirror reflecting the blue sky. Such conditions present a dilemma on the flats. Today was dedicated to permit fishing, and without any wind, I could see their black tails breaking the glassy surface from hundreds of feet away. However, these fish were highly wary, often sensing our presence long before we were in casting range. It was both beautiful and cruel to see so many fish only to spook them before getting a chance to make a cast.
During our fourth attempt to approach a permit in these conditions, I could tell my guide, Yilbert, was setting the pole as gently into the white sand as possible, slowly sliding the skiff in its direction. “Get ready,” he said. After what felt like an eternity but was really just a couple of minutes, we inched closer to the fish, its massive tail flopping out of the water as it happily dug for crabs, blissfully unaware of our presence.
“Okay,” Yilbert said calmly. My heart raced as I laid out a cast that, to my surprise, landed accurately on the fish’s head. It took an immediate interest in my crab pattern, curiously bringing its face so close to the fly it felt destined to connect. Trying to remain calm, I slowly stripped the line back to me, but suddenly, the fish became aware of our scheme. It was gone in the blink of an eye, leaving us heartbroken yet in awe as we watched its wake speed across the expansive flat.
Following the calm conditions, the wind had switched directions and arrived with a vengeance. While we walked to the marina, struggling to keep our hats on our heads, we braced ourselves for a choppy day on the water. While battling the wind was tough for casting, it also provided the necessary cover to approach unsuspecting permit and bonefish. The gusts ripped across the surface, creating noise that masked our movements, allowing us to sneak up on these elusive fish in their natural habitat.
A fishing highlight emerged when angler Mo ventured onto a shallow flat, hunting for bonefish on foot. After landing several bonefish in the first couple of hours, Mo and his guide decided to focus solely on the largest fish in the schools they encountered. Rather than casting at every school that passed by, they patiently waited for the right opportunities. Their patience paid off when they successfully landed two trophy fish in quick succession, with the largest estimated by his guide to weigh around 9 pounds. The thrill of the chase and the satisfaction of landing such impressive fish made for an unforgettable experience on the water.
Good fishing continued through our final day on the water, with everyone getting multiple shots at permit and landing some impressive bonefish. As the clock approached 5 PM, I decided to call it a week, feeling satisfied with the great opportunities I had experienced. As our skiff sped across the ocean-facing flat, we spotted angler Matt and his guide, Elder, waving at us in the distance. We waved back, our minds drifting toward the cold mojitos waiting for us at the marina.
However, as we drew closer, we realized they weren’t just saying hello but calling us over. Matt, rod in hand, was connected to a fish that had taken a significant amount of line. “It’s been on for 30 minutes!” he exclaimed, igniting our excitement as we anchored the boat at a safe distance to watch the action unfold.
Fifteen grueling minutes later, Elder waded into the water, expertly tracing the leader with his left hand while reaching out with his right to snatch the tail of a large permit. Celebration erupted as Yilbert and I congratulated the pair and moved in for a closer look. The fly had already slipped from the fish’s mouth the moment the tension was released, and we all let out a sigh of relief, soaking in the incredible moment together.
While keeping the fish submerged, we quickly jumped out of the skiff to photograph the excited angler and his proud guide before sending the fish back to its salty home.
As our time in Cayo Cruz came to a close, we reflected on the unforgettable experiences we had shared on the water. Each day brought new challenges and triumphs, from battling the wind– and lack of, while experiencing the high stakes of permit fishing to celebrating trophy catches. The friendships we made, the expertise of our guides, and the serenity of the flats made for a fantastic blend of adventure and relaxation. We left Cayo Cruz with our hearts full and spirits high, already dreaming of our next escape to this tropical paradise.
