2025 Oaxaca Winter Cycling Camp

How being a good tour operator is like being a good manager

Last week, I tried my hand as a cycling tour operator — an experience more challenging than I had ever imagined. More on that below. But it was also rewarding and fun!

By Monday afternoon, 15 American cyclists arrived at our home base, Estancia La Merced, nestled between Oaxaca’s historic center and the artsy Jalatlaco neighborhood.

Getting situated

Manuel, our local bike mechanic, came by to help unpack and assemble bicycles. Meanwhile, Chef Lorena and her crew took over the kitchen to make us tortilla soup, pollo en mole negro, freshly made tortillas, and flan.

Day 1: Agave Route | 77 miles, 3,400 feet

For the first ride, we rolled south out of the city center to Ocotlán, then east through the rolling hills and endless maguey fields to Santiago Matatlán, the “world capital of mezcal.” We stopped by Mal de Amor, a local distillery, to refuel with lunch and some freshly squeezed lemonade. Half the group stayed for a mezcal tour and tasting, while the other half pedaled an extra 20 miles back to base.

Each afternoon, we had a team of physical and massage therapists set up on the rooftop terrace with compression boots, electric muscle stimulation, and good old-fashioned massage. Chef Lorena and her team returned for an all-you-can-eat buffet of tacos de guisado and freshly made tortillas. (Endurance cyclists can eat a lot of tacos!)

Day 2: Cuatro Venados | 50 miles, 5,400 feet

As the cyclists acclimated to Oaxaca’s higher elevation, we climbed up into the Zapotec village of Cuatro Venados at 9,000 feet above sea level. I provoked (motivated?) a group of strong cyclists to compete for the Strava segment while I got to know the more civilized riders toward the back of the pack.

In Cuatro Venados, we regrouped at a roadside eatery, where Cecilia made us fresh memelas, Oaxacan hot chocolate, and cafe de olla. Half the group descended for a tour of Monte Alban, while the masochists continued climbing up a red dirt road through pine forest before descending into the Zaachila Valley.

Two support vans, led by Pedro Martinez, followed us each day. Pedro is one of Oaxaca’s most experienced tour operators and formerly one of Mexico’s fastest cyclists. We were also joined by Ela, a talented photographer and my morning swim partner—until she leaves for Poland next month, abandoning me to the solitude of solo laps.

Day 3: Rest Day | 35 miles, 700 feet

After two big rides, we deserved a “rest day” — a flexible concept with this group. A third of us did a leisurely 35-mile coffee ride past El Tule. Another third climbed up to Ixtepeji. The final third actually rested, exploring the city center. That evening, we convened for tlayudas, beers, churros, and the kind of funny, relaxed conversation that comes out on a rest day.

Day 4: Guacamaya | 45 miles | 4,500 feet

Time for the queen stage: a brutal 10-mile, 3,300-foot climb from San Miguel Etla to Guacamaya at 9,000 feet. I offered mezcalinas as bait for anyone who could summit in under an hour, and three riders took the challenge—and the drinks.

It’s always cooler up there, but this time, it was downright chilly. We layered up and huddled around a traditional comal stove while Doña Liseth served up fresh memelas, hot chocolate, and coffee.

That evening, folks seemed ready for a break from traditional Oaxacan food, so we went out to a nearby pizzeria, then enjoyed some mezcals across the street at Santo de mi Devoción — a distiller and sponsor of a local cycling team.

Day 5: Hierve el Agua | 90 miles, 4,300 feet

For our grand finale, we pedaled through the Central Valley to Mitla before climbing up to Hierve el Agua, a set of natural travertine rock formations with calcium deposits cascading over a cliffside. We changed into our bathing suits and cooled off in the pools (which are not boiling, despite the name). The strong sun dried us off quickly, and we had 45 miles left to wrap up the adventure.

All in, we logged nearly 300 miles and climbed over 18,000 feet in five days. We capped it off with a final group dinner on the terrace of Casa Oaxaca.

Lessons Learned

I learned that being a good tour operator is like being a good manager. Yes, there are some universal principles. And some people are naturally more fit for it than others. But more than anything, you have to learn what kind of manager/tour operator is right for your personality. It takes at least five years to become a great manager—and I suspect the same is true to become a great tour operator. It requires meticulous planning and unrelenting problem-solving, all while staying present to connect with each participant.¹ No matter how hard you work to make the trip smooth, your job is to focus on the problems: delayed luggage, bike malfunctions, forgotten articles of clothing, upset stomachs, and so on.

I imagine the world is full of bad tour operators—and as of now, I am one of them—because the job demands so much.

I’m writing this last paragraph from my standing desk, watching the sun set over the Southern Sierra mountains while Coco wags his tail, reminding me it’s time for our evening walk. Despite the challenges, I’m grateful for the experience. It’s the difficult things that make us grow, that reveal our limits and capabilities. Would I do it again? Probably not—but never say never.

It certainly gave me a new level of respect for tour operators. Which is timely because in just a couple of days, a guide is leading a group of us up Pico de Orizaba, the third highest peak in North America. You know what that means: another trip report coming soon.

Yours,

David

1. Not to mention the 20 hours of intense cycling!