Share : It was a busy Thursday. I was scrambling to finish up the rest of my work in preparation for my Monday flight to Central America for a week of factory work in Nicaragua and Honduras. The luscious tobaccos from each country's first harvests were being prepared for the curing barns and I wanted to monitor quality control. Suddenly, my phone rang and I grinned when I saw the familiar number, my good friend Nestor Plasencia.I've written about Nestor several times before but for those not familiar, he and his family are the largest growers of premium Cuban-seed tobacco in the world. In fact, 90% of all cigars sold in the United States contain at least one leaf of tobacco grown on the Plasencia farms. Upon answering, Nestor immediately said enthusiastically, "Primo, can you change your flight and come tomorrow?" Nestor and I know each other very well. We traveled quite a bit together and last year we even spent a week in Canada hunting black bear and fishing for Northern Pike. He explained that he'd chartered a boat to fish in Rio San Juan for the weekend and requested my company. If there's anything I enjoy in life as much as cigars, it may very well be fishing and hunting, so I immediately called the airline and made the arrangements.I've traveled all over the world in the name of cigars and tobacco, and on many occasions I've had the privilege of exploring some of the world's most remote areas. I've explored all of Nicaragua, from the Pacific coast to the Caribbean, including the rarely accessed island of Ometepe. However, Rio San Juan has been in my scope for quite some time for a multitude of reasons, not least its historical significance. The area connects the Caribbean on Nicaragua's East Coast with the Pacific to the West by way of Lake Nicaragua. Hundreds of years prior to the construction of the Panama Canal, Rio San Juan was the preferred route for crossing the Americas by boat.The lake itself, Lake Nicaragua, is located in Nicaragua's interior and was the central hub for trade and shipping in the new world. Due to its centralized location, not only in the country of Nicaragua but Latin America in general, the Spanish Conquistadors brought their gold, tobacco, and other booty from El Salvador, Guatemala, Honduras and Costa Rica to the lake city of Granada - North America's first colonial city - where it was loaded onto ships and sent back to Spain via Rio San Juan. Given the value of shipments going up and down Rio San Juan, it didn't take long before piracy took over, sacking ships and the city of Granada itself on several occasions. In the 19th century, Rio San Juan provided safe passage for early settlers looking to get to California during the gold rush. The river provided passage for over 200,000 people who moved to the US.In addition to its historical contributions, Rio San Juan and Lake Nicaragua are ecological, scientific anomalies which attract fishing enthusiasts from across the world. The river is home to tarpon (weighing in as much as 300 lbs), bull sharks, and snook, and even marlin and tuna from Lake Nicaragua. Although many of these types of fish are commonly found in fresh water areas, those areas rarely exist 120 miles inland, such as Lake Nicaragua. Not only are these rare fish located in the center of the country, but they are massive! Here's my account:Friday, 3:00am: Woke up early and still have the taste of Johnny Walker Black Label in my mouth. I quickly start to regret that extra glass of whiskey I had several hours earlier. My bags were ready and the driver was outside. Here we go!Friday, 11:45am: A long flight from Chicago. Passing through Miami, I finally land in Managua, Nicaragua where I meet Nestor and his cousin. We walk to the south terminal of the airport where Nestor's Cessna 183 is fueled up and ready to go. The three of us pile in the prop-job and put our gear in the back.Friday, 1:30pm: A beautiful sight as we fly over Lake Nicaragua and Ometepe Island where some of Nicaragua's finest and most rare tobaccos are grown. Nestor, who's flying the plane, told me the route from Granada to the Caribbean was the first route ever used by traders transporting tobacco from Central America to Spain. I love Nicaraguan tobacco and as I listened to Nestor talk about its history, I imagined the first bale of Nicaraguan tobacco making its way back to Spain and earning its first following among tobacco lovers. Facing strong crosswinds, Nestor calmly lands on a dirt runway as we finally touch-down in San Carlos. A small quaint town situated where the river meets the lake. We board a boat and head to the fishing camp.Friday, 4:00pm: We make our way down river from San Carlos, exploring the river's most remote areas. After an hour of exploration, we are officially off the map. We are literally in the middle of nowhere. I never thought I'd ever reference this particular movie, but it feels like I'm in "Anaconda." Small fishing villages appear on both sides of the river from time to time and the occasional water taxi or fishing boat passes by about every thirty minutes. Our camp is a small lodge with about a half dozen rooms – all built over the water. It's quite comfortable and I even found a small bar and restaurant, as well as hot water. Booze, food, cigars and a hot shower…what more does a fellow need?Friday, 4:30pm: We take advantage of the day's remaining sunlight and begin boarding our boat as another group of fishermen pull in. They landed a 200lb tarpon – a fine catch indeed - but my eyes are drawn to these two beautiful women fishing with them. World Fishing Network was there shooting their hit show, "Hookin' Up with Mariko Izumi." Mariko is as beautiful in person as she is on the show. She was joined by special guest Lauren Alvarez who, at just 23 years old, is a world class professional fisherman. We exchange hellos before heading out on our first set.Saturday, 4:00am: With a long travel and slow fishing day behind us, we're ready to shake off the bad luck. The fishing here seems cursed as we've had no action as of yet. It's now 11am. I just picked up my thermos and poured myself a cup of hot coffee. Naturally, right as I put my lips to the cup, I hear the unmistakable sound of my fishing line unspooling. Our guide shouts out in Spanish, "Fish on!" I jump from my seat, spilling my coffee all over my feet, and grab the rod. I immediately feel the heft of the 150 pounder on the end of my line. My fishing skills, at this point, are limited to light tackle. I've never went fishing for big game like tarpon and man, am I in for some work. After 30 minutes of fighting this fish, I thought my arms were going to fall off, but as the fish breached the water multiple times, I took on a renewed sense of excitement. My arms now feel numb so I hand the rod off to Nestor to bring us home. After another 30 minutes of fighting this massive fish, we painfully lose it, but we don't care. This was an exciting, big fight and we talk about it for an hour.Saturday, 1:00pm: We're starving so we start motoring toward the town of El Castillo. Castillo in means castle but in this case, the town was named for a stone fort built high on the bluffs to protect the trade route of Rio San Juan from pirates. We make our way down river and see the other group from World Fishing Network again. Lauren has a huge tarpon on her line. We stop to watch her fight the monster fish for more than an hour. Here is a petit girl, weighing maybe a little more than 100 pounds, working this fish like a pro. Thinking back to my 30-minute fight and how soar I was, let's just say it was a humbling experience.Saturday, 3:00pm: We pull into El Castillo for a late lunch. The menu for the day is fresh water river shrimp – a species of shrimp only found in Nicaragua and very few other places in Central America. These tasty shrimp are found in Nicaragua's Rio Frio River (cold river) and are a cross between shrimp, lobster and crawfish (if you can imagine what that looks like). They aren't cheap but boy are they tasty. After lunch, we walk to the top of El Castillo, touring the fort and museum. Amazingly, there's some interesting information regarding tobacco and the tobacco trade from Nicaragua. I even see a quote from Mark Twain about the tobacco from Nicaragua's southern region as Twain himself made a journey to the west coast on one occasion.Saturday, 4:00pm: Back on the boat, we throw our lines back in the water and troll for another four hours without success. With no luck on our side, we retire back to camp where food is waiting. We spend the evening enjoying cigars and drinking rum with Mariko and Lauren as well as their film crew. I will say, the only thing more attractive than seeing a beautiful woman reel in a huge fish is watching her smoke some incredibly full-bodied cigars. We drink glass after glass of 18-year-old Flor de Cana rum as she made light work of Diesel Unlimited and Cu-Avana Intenso.Sunday, 4:00am: Another early start - we set out hoping to hook a fish before our departure. Our coffee must bring us luck because as I sat in the boat pouring my morning cup, only an hour into trolling, we finally heard those famous words, "fish on!" Sergio, Nestor's cousin, sprang to life and grabbed the pole for a 15-minute fight before losing the fish as it sprang into the air shook from the hook. Close, but no cigar.Sunday, 12:00pm: We work our way back up river to San Carlos. Felipe treats us to lunch at his other lodge where he also resides. Two Labradors made their way in and out of the water as we shovel down some chicken and rice.Sunday, 1:30pm: Back in the plane, we took to the air off the dirt runway back out over the lake toward Managua. Monday means back to work and I had a long week of traveling ahead of me between Northern Nicaragua and Southern Honduras.I love these little adventures I find during my travels, especially when it gets me outside. I fancy myself an avid hunter, but fishing is growing on me, especially hooking monsters like Tarpon. One thing I didn't expect was the amount of history I learned about the region and the role it played in facilitating the tobacco trade in all of Latin America. One thing for sure, I will be back to Rio San Juan soon. While there, Nestor and I discussed the various aspects of the soil and cloud cover that could one day make the region a hotspot for tobacco. In fact, Nestor already set plans in motion to experiment with some small crops. With already four distinct growing regions in Nicaragua, a fifth may open the door for even more complex blends than what we're already seeing out of Nicaragua, one of my favorite cigar producing nations.