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Any trip can be a bike trip if you’re willing to put the work in. A veteran business traveler shares how to fit in a ride no matter where you are or why you’re there.
Jon began racing in the early 1990s and stopped racing shortly thereafter. After hanging up the bike for a year, he got back in the saddle for the love of riding and ended up taking part in events like RAAM. He’s now looking forward to achieving fewer and fewer PRs on Strava as he gets older.
In February 2023, I was packing for a family trip to Montego Bay, Jamaica. I turned to my wife and said “so … mind if I bring my bike?” By that point, she was used to me making this ask, and the idiosyncrasies and occasional indignities of traveling with someone who will find any excuse to ride somewhere new. Fortunately, my wife is incredibly patient and understanding, and she knew about my cycling problem when she married me.
Two days later, breakfast buffet settling in my stomach, I rolled up to the guard at the front gate of the resort. After a brief back-and-forth with the guard – guests at Jamaican resorts are famously encouraged to remain on-premesis, for safety – I was allowed to pass with an “uh … be careful.”
And I was off. The coastal highway was right outside the gate, but despite its wide shoulder, the constant mid-day truck traffic made it unpleasant. Fortunately, Jamaica is a mountainous island, with plenty of steep, narrow roads with beautiful Caribbean views that wind around hills, farms, villages, and the occasional timeshare complex. Most of the roads had little or no traffic, and the only time I had to brake was for the goats and chickens that would wander across my path. Every time I passed someone – sitting on their porch, working in their garden – they would smile and wave.
I felt incredibly welcome, which is good, because I ended up on a more intense ride than I expected. Flower Hill climbed 1,100 feet in less than two miles (330 m in 3.2 km – roughly 10% average gradient), and the beautifully paved descent on the back side abruptly turned into a jeep track. And yet it was everything I sought in a vacation ride: I had the opportunity to see a part of a beautiful country that most visitors never get to experience.
Topping out on Flower Hill Road, Jamaica, well outside the bounds of the resort.
Two days later, I found myself in an industrial parking lot at 5:30am as the local group ride assembled. I’d found it listed on the local club page on Strava. We rolled out, and Fowlie, Junior, Spider Man and I pacelined down the coastal highway, past sleepy beaches and fish shacks as the sun rose. We chatted, each of us sharing a bit about our lives and our years of cycling. I was even invited to ride in the local club race that weekend, and while I begged off due to the fact that I had not raced since 1998, I did get to watch the race when it passed our hotel.
Scratching the itch
I love riding my bike, I love to travel, and I particularly love riding my bike in new places. Over the years, I’ve tried all sorts of approaches to traveling with a bike, mostly to avoid airline bike fees: a bike with S&S couplers (TSA always messed up my careful packing when they inspected the bike), renting (worked pretty well until Rapha closed their clubhouses), and the Orucase Ninja (I just didn’t love removing my fork to pack my bike). But when United eliminated bike fees in 2021, the question around trip planning changed from “can I bring a bike?” to “is there any reason not to bring a bike?”
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