Bright lights, big city, big fish and big smiles. San Juan, Puerto Rico, doesn't seem to top the charts for trophy tarpon fishing destinations, but there's plenty of marine life swimming around amid all that nightlife. Within a cast of downtown lie hidden lagoons filled with local chrome, and the Tarpon Nest Lodge sits right on their shores.

With a lingering winter still bottoming out the bikini-meter in Vermont and Canada, a long weekend of tropical kayak fishing for tarpon is an easy sell. Captain Omar is our local expert and guide through this urban jungle. James 'Indiana' McBeath is my Team Grey Beard wingman. We have tricked out chariots to cruise for the ladies.

We find ourselves floating within sight of the San Juan skyline, watching the tarpon roll into the lagoon like all around us. We came prepared with pick-up lines made up of flashy flies, but these city girls see right through them. When I think I have one in the bag, she shakes me off with Latin sass. Feeling lonesome, I look to my wingman for sympathy. He just laughs.

Captain Omar however knows the local tricks to adapt and overcome, even for us pale gringos. It's a little hard for a dedicated flyfisherman to chuck bait, but action is action, and these are desperate times. Never underestimate the power of the local lingo. Time to pony up and close the deal and take one of these girls for a ride.

Getting down to business doesn't take long, and the transition from anticipating hooking up to actually hooking up is brief. Part rodeo, part race, tussling with a chrome queen is a workout. One minute I'm sitting in my kayak, talking smack with the boys. The next I'm accelerating across the bay, watching the water explode and wondering where this crazy ride is going to take me. I'm covering uncharted waters, at times I don't know what to do, but a huge smile is plastered on my face.


Tangles with 'poon aren't brief. Early aerial antics lead to a screaming run and muscle-numbing tug-of-war. I settle into the seat and tell myself to let the tarpon and kayak do the work, slowing runs by turning the kayak from side to side. I steer her where I want to go and keep her close. I don't want her to break off. Whatever you do, don't flip over, I remind myself.

All relationships must come to an end, and when she's ready, my silver date comes in to say goodbye. Breakups are never easy. This is the most dangerous part cause she's so sensitive. Keeping my balance and composure, I lean over, bringing her into my lap with one swift motion. I cradle her gently, but don't prolong the breakup. That's not good for anybody.

Tired and weary afterwards, I'm also thankful and satisfied. The shaking and lack of coordination is normal. I text my buddies. If I try to talk, I'll probably mumble. Back at the Tarpon Nest Lodge, hot tub therapy and tequila IVs await—an ancient, proven remedy. Time to get some rest, the weekend is just starting.