My wife, seated facing me on the bench directly opposite, gave me a confused, uncomfortable look. She has never been a fan of boating trips where land isn’t readily visible, and I initially chalked up her expression as a reaction to the rather sizable waves slapping against the side of the boat. She noted that I wasn’t getting it and sent her eyes downward to draw my attention.

I quickly saw the wrinkled hand of the elderly, local woman seated next to my wife. The elderly woman’s hand right hand clutched my wife’s left knee in a death grip. Her free hand was cupped beneath her mouth, catching most, but not all, of the vomit that was now coming out in regular intervals before tossing it over the gunwale and into the water just in time to make it back for another batch.

This was far from the first sign of trouble on this trip — which was instigated by a deal on Continental Airlines where a round-trip ticket to Nicaragua cost only $17,500 frequent flier miles. At the time I had accumulated several hundred thousand miles from my 4+ days of weekly work travel, so there was little ammunition at hand to shoot down the notion using 35,000 of them for a journey to Central America.

Our flight in to Managua in a regulation jet the night before was uneventful. Our taxi ride shortly thereafter to the secure zone — roughly four blocks of buildings where affluent locals and gringos roamed and played whilst guards with machine guns occupied every corner — was odd in that the ambient lighting came not from street lights, which didn’t exist, but instead from the ongoing fire in the sewer system. As the reddish flames reached out from the storm drains I wondered what exactly we’d gotten ourselves into.

The general sense of uneasiness remained in place when we returned to the Managua airport the following morning for our connecting flight to our ultimate destination, Little Corn Island. At the time, there were two local airlines operating in Nicaragua. All flights for these two purported competitors left within 15 minutes of each other, and all ultimately involved airline A’s plane following closely behind airline B’s as if we were all participating in some sort of on-the-job training program. Presumably the pilot in the lead plane had some idea where he was headed. Presumably.

Uneasiness soon capitulated to genuine fear as our plane (the lead plane in the 2-plane parade) dive-bombed the airfield on Big Corn Island to compel movement on the part of the cows and the sleeping locals that had taken up residence on the landing strip.

From the airport, which featured the local equivalent of the Trainspotting bathroom, we were steered towards a nearby dock. We watched semi-interested as a long boat tied off to the dock was filled with a large pile of bananas, water jugs and other odds and ends. Our interest ramped up a bit when we, and about 20 other people, were then directed to climb aboard this same wooden boat and find a place to perch.

We clambered aboard with the others, trying our best to avoid stepping on anyone else, or a banana, whilst dealing with the added weight of our fancy bags, which doubled as unwieldy backpacks. When we eventually sat down on the benches, surrounded by people, and bananas, I thought back to the many fishing trips I’d taken in the Gulf of Mexico where the Captain had announced before boarding that bananas — the ultimate bad luck charm — were not allowed on his vessel. Bananas were bad. Very bad. And we were surrounded by bananas.

Eventually, under the power of a single, aged outboard, and with the combined weight of the occupants and bananas threatening to compel the water in over the gunwales, we chugged off to try our luck against the four-plus miles of open water that separated us from our destination.

With all of this as a backdrop I found myself smiling at the horrified look on my wife’s face as the old woman again tightened her grip to better throw another handful of vomit over the side. Sure, I’d agreed to this discount adventure but, to be completely honest, I took a lot of comfort knowing that besides providing the frequent flier miles I’d had nothing to do with it. Moreover, I’d been good throughout the travel required to get this far. I hadn’t even said anything about the fact that our Buddy Holly local plane had Russian labeling/instructions (the proxy war fought by the super powers, to the exclusive detriment of the local people, had concluded not that long before and the plane, which resembled a john boat with wings, was not valuable enough to make the return trip to the USSR).

The tension and the vomiting only mounted when the outboard soon died, twice, whilst roughly halfway to our destination. As the large waves buffeted our small vessel I took additional, nihilistic comfort in knowing that bananas weren’t going to be useful as a flotation device and, especially post super-power proxy conflict, there was no coast guard or navy that would come to our rescue. We, the bananas, and our pukey comrade were going to make it — or we weren’t.

We did, as it turns out, survive this crossing as well as the equally harrowing return trip. We then had the hubris to repeat this event the following year — the island is amazing. It’s worth pointing out that since our last trip to Little Corn Island, which was roughly 13 years ago, Nicaragua has seen an explosion in the way of retirees from the U.S. and Western Europe. There are no longer decommissioned Soviet troop carriers ferrying gringos about, but there are plenty of gringo enclaves up and down the coast lines where machine gun touting guards have been replaced by waiters serving cheep beer.

While some things have definitely changed, and gentrified, it’s also worth noting that other things have oddly come full circle. The Russians have returned — and they’re visiting their old buddy, Daniel Ortega. Unfortunately, and tragically, I was recently reminded about all of this via news of a failed open water crossing to Little Corn Island that proves it remains the same treacherous expanse. I hope that one day very soon these open water crossings in overloaded long boats join the rest of this amazing country’s troubled past.