Chapter 3: Take the Long Way Home

In August 2017, Aaron and I were on a 12-hour drive back from a two-day enduro race in Southern Colorado.

“Someday I’d like to run Romaniacs,” I said.

“Man, that would be fun,” Aaron replied. “Not sure how we could pull it off.”

When I got home the next day I downloaded the entry regulations for the longest hard enduro race in the world. Five days in Transylvania, Romania. I was far from being a pro rider, or even an expert, but could usually place in the top three of the Super Senior (over 50) class at regional enduro races. What I lacked in skill, I made up for in fitness and grit.

When registration opened in November, I found myself at my computer at 2:00 AM, clicking confirm on a $2,000 entry fee. The following eight months were all about training. Think it, plan it, do it.

I entered a class too high and couldn’t finish. A different year, a different class.

If you are reading this and wondering, “Where’s the context?” you may have missed the prior chapters. Go to Anymajordude.co to read everything that came before! I hope you enjoy it - Shaun.

* * *

Almost immediately after finishing the Ecuador adventure, I started researching the LatAm. Bike shipping, routes, timelines, logistics, and import permits. Every topic related to planning a self-supported Andean motorcycle adventure.

Most of what I found was oriented toward riding the Pan-American highway, made famous by Che Guevara’s Motorcycle Diaries. The route was now entirely paved, four lanes for most of the way, and heavily trafficked by trucks. Not the adventure we were looking for.

I kept searching for routes down the spine of the Andes. High up, two-lane, unpaved, two-track, remote. The bikepackers had the most useful information, but only for the popular areas — around Cusco, Chilean Patagonia. We wanted to see all that, and everything in between.

Joe told me about a woman vlogger who had done a solo south-to-north route during COVID on a Honda. Watching her narrate her every move, tip over, and map discussion made me feel sorry for her. It annoyed me that she was out there doing it, and I wasn’t. I watched two episodes and stopped.

There were still wild places in this hemisphere. I was drawn toward the unknown, the exploration, the rawness. I knew the satisfaction of figuring it out on our own would be half the payback.

* * *

I reached out to Tucker, who had ridden the Mexico adventures with Doug and me. Tucker was the fun, go-lucky kind of guy that most guys like to hang around. “Mother Tucker,” as we affectionately call him. On any given day, when asked if he wanted to ski, fish, bike, or go to the lake, the answer was always “yes, but I’ll be 30 minutes late.” He was a core part of the trip before I even approached him with the idea.

It was unlikely everyone would be able to commit to a trip of this scale and duration, so the invite list was longer than the ideal three- or four-person group. No assholes, only capable riders, and no whiners. Tucker was high on the list because I also knew there was a 90% chance he would blow off whatever he had going at home to make sure he didn’t miss it.

“Aaron and I are thinking about shipping some bikes to South America later this year and riding the continent. What do you think?” I asked. “Want to go?”

Without hesitation, “hell yeah! Who else is going?”

“My friend Joe might, and possibly my buddy Todd from Denver. I’m going to see if Rob wants to go.”

“What about Doug?” he asked.

“He’s out. I already asked him, and he didn’t want to do it.”

Soon after, Doug sold his dirt bike, then his 690, then his snowmobile. He was just done riding. And so ended my twelve-year riding relationship with my go-to riding buddy. We were already missing a core crew member.

* * *

Shipping motorcycles to Argentina, where Ushuaia is located, was virtually impossible due to customs restrictions that no one could fully explain. Santiago would work, but that was more than 3,000 miles from Ushuaia and 9,000 miles from Bogota. Starting in the middle of the continent wasn’t an option — we’d spend weeks backtracking if we wanted to do top-to-bottom. We needed to start at the top.

I found a freight forwarder in Bogota through an overlander chat, a woman named Veronica. I reached out to her on WhatsApp. She was back to me within hours with a detailed quote and a list of follow-up items she needed to start the customs paperwork. The bikes could be crated and flown from Miami to Bogotá for about $3,500 each. Shipping from Jackson to Miami, $850.

* * *

I love maps and navigation. When I was in the sixth grade, our PE teacher, Mr. Workman, introduced us to orienteering. A speed competition, usually in the mountains, that goes from point to point off-trail using only a compass and a map. I was the smallest kid in the class with no future in football or basketball. Finding my way with a map and compass while competing on foot helped build my confidence. What I lacked in athletic ability, I more than made up for with spot-on navigation.

For adventure riding, my planning process starts with Google Maps — city-to-city routing, basic mileage, and natural stopover points. Good for the big picture. Useless for finding the real adventure.

That’s what we use Gaia for. A topographic backcountry mapping app that finds roads and even towns that don’t appear on Google Maps. The real goods. Two-tracks, fire roads, unmarked stream crossings, slope angles. This mile-by-mile route plotting takes hours. Mapping immersion ignites my imagination.

I mapped the first leg — Bogotá to Quito. Shared a spreadsheet and a folder of GPS routes with Aaron, Joe, and Tucker. Nobody responded. I felt the silence equated to consent.

Tucker was already planning the sightseeing in Colombia. I appreciated that. I had a hard time with guidebooks. Someone else’s ratings of places I plan to judge for myself. Tucker read every entry, and he was good at it. He had a good idea of the main things to see in central Colombia and on our way to Ecuador. The problem was that my mapping and his site planning didn’t match up.

He and I got together for a dirt bike ride behind his place in August and met afterward for beer and to talk through specific sites in Colombia. He had already poured himself into the Lonely Planet guidebook and identified enough places to fill a summer’s worth of travel. I broke out the spreadsheet and Gaia on my laptop in his kitchen, our opportunity to reconcile the trip.

We worked together, linking places on the map, with him reading descriptions and me entering endpoints into a spreadsheet with mileages. Not knowing the terrain or road conditions, I was cautious on distances, trying to keep them under 150 miles per day.

“We need to be careful on mileage, I’m thinking 150 a day,” I said. “It will take us 10 riding days to get to Quito if we can keep to that.”

“I know, but I really want to see as many of these places as possible while we’re there,” he replied. “Some are north of Bogota, I think we should do a loop before heading south.”

I let it slide, knowing the calendar would be the constraint and would set the tempo once we sorted things out on the road.

I shared the spreadsheet with the group. Daily destinations, mileage, potential lodging, elevation gains. I wanted more input before locking the plan.

A few days passed, and nobody had commented. We went back and forth on potential dates and settled on late November for the trip from Colombia to Quito, right after Thanksgiving. I began nailing down shipping details with Veronica in Bogotá.

* * *

I knew which bike I wanted to bring with me, the Tiger I had appreciated so much in Ecuador. I did a little research on the dealer network in South America to feel confident in my ability to source parts or service when needed; every major city seemed to have a dealership.

I just needed to find one for sale online. I eventually found a new 2023 Triumph Tiger 900 Rally Pro, white, with a $3,500 end-of-year rebate at a dealer in Phoenix. Shipping included, I could have it sitting in my garage for about $14,500. I knew this was a lot of money to spend on a bike I was sending halfway around the world, but I wanted something I could trust. I was planning on selling my 690 and a snowmobile, which would cover most of the cost. I pulled the trigger and wired the cash to the dealership the same day.

I was determined to get the bike set up with the same gear and configuration I would be riding it in LatAm. Same phone and GPS mounts, luggage, and suspension tuned for my weight and offroad riding.

I built a packing list from my Mexico trip lists and expanded it for the LatAm. My goal was full self-sufficiency — tools, a tire repair kit, spare parts, camping gear, first aid, and a survival kit. We standardized where it mattered — tubeless tires, intercoms, and GPS units.

I wasn’t going to be reliant on anyone.

I shared my list of riding gear, tools, supplies, and camping gear on the WhatsApp group. Tucker replied with a few questions; the others were silent.

For luggage, I did what I always do — ordered everything, multiple brands and configurations, to see what would fit my gear and the bike. I settled on soft side panniers with dry-bag inserts and a dry-bag top duffel. Waterproof, durable, and a tight fit to the bike. Then I returned the rejects for refunds.

* * *

Brand new 2023 Triumph Tiger 900 Rally Pro in my garage… so cool!

One hot day in early September, the last of the Summer, we were coming home from a day on the lake. Sun-baked and tired, we pulled into the driveway. There was a truck and an enclosed trailer parked in front of the house. Betty scarcely noticed it until the driver hopped out and approached me.

“Are you Shaun?” he asked.

Betty looked confused, “Who is this?”

“This is my bike I’m taking to South America.”

Her expression went from confusion to cold anger. No jaw drop, just clenched teeth. She rushed inside. The relaxation I brought home from the lake evaporated as the tension in my throat rose. I knew what was coming.

I helped unload the Triumph and rolled it into the garage. I signed the bill of lading receipt, and the driver was off. I rolled the bike to my workshop side of the garage, behind my workbench, futilely trying to conceal its existence as much as possible. I had been busted.

“What is that?” she asked, “When were you going to tell me?”

“I did tell you,” I responded defensively.

“That’s bullshit, we never talked about this in detail,” her anger rising, “how do you intend to pay for it?” The last part a jab, and a question I never had the chance to answer.

“We did talk about it,” at that point, knowing that I had been too afraid to explain the plan to her in detail.

She was pissed and didn’t speak to me the rest of the evening.

The next morning, over coffee, she broke it to me, “I’m not OK with you doing this South America trip.”

“What are you not OK with?” I asked.

“The whole thing. Your escapism, your neglecting our relationship, the danger. None of it,” she continued. “When were you planning to tell me?”

Again, I sucked myself back into defensiveness, “I thought we talked about it.”

She interrupted, “You mentioned it, but we never talked about it.” She was right.

I was already committed. I had three friends ready to go. Tucker and I were already planning stops and lodging. I had almost cracked the code on getting the bikes to South America. And, I had a brand new Triumph Tiger 900 Rally Pro sitting in my garage.

“I’m doing the trip, not sure how long it will take, but it’s important to me.”

“What about me, us?” she stated. “You think it’s OK to leave me for weeks at a time. What about your work?”

“Come on, you’re the one who is gone weeks at a time on business trips.”

“That’s bullshit,” she interrupts again,” I am the only one around here with a predictable income and health insurance, a real job.”

I had a real job. CEO of three medical imaging centers, a land development in Driggs, and Executive Chairman of a geospatial software company in Denver. I had jobs, three to be exact. But, no health insurance, no 401k, no fixed salary. Those were ours because of her job.

“Doing this trip won’t change any of what I am doing. I don’t see how it will affect us financially now or in the future.”

“That’s what you always think and look where it’s gotten us,” she accused. “More escapism, I’m tired of this rollercoaster you have put us on. You say you love me, you say you care about me, but you don’t include me in the decisions that affect us both.”

She left me to stew as I finished my cold coffee, while she got ready for work. She was right about more than I was willing to admit. I just didn’t see it yet.

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