Day 1 - Key West, FL to Vero Beach, FL

294 Miles

I can’t ever listen to the sound of the alarm I used on the Pan-American again. The memories of misery and sleep deprivation that are tied to that sound are so vivid that I have a visceral reaction to the noise. I must select a new sound for my alarm on every long bikepacking trip now. If perhaps I run out of iPhone alarm preset sounds one day, it will be a sign that I am to retire from “competitive” speed-focused bikepacking. For this journey, I have settled on the “canopy” alarm tone. When the sound of “canopy” rings through my motel room at 3 am, it does not elicit misery and begrudging acceptance that a new day is here; it brings forth excitement as I leap out of bed and hop onto my bike. I bike across town to the southernmost point on the island of Key West, marked by a concrete sign, where I snap a selfie and push off at 3:24 am on August 31, 2025. Remarkably, exactly one year ago, I set off from Prudhoe Bay, Alaska, on my Pan-American cycle. Hopefully, August 31st will continue to bless me with good tithings. 

For the first 100 miles, I ride along the Overseas Highway between the Florida Keys. A slight tailwind helps me over the long bridges–the longest of which is 7 miles. At Key Largo, I turn due north to stay on Highway 1, which I will largely remain on until Madawaska, Maine, 2,140 miles from Key West. The tailwind becomes a sidewind, then flips to a headwind when I get onto mainland Florida in Homestead. Would it really be a Bond Almand IV world record attempt without headwind?

Mainland Florida is busy, and the road is an incessant stream of start/stop traffic. It’s too hot to bike, but when I stop, I realize just how suffocating the heat really is without any wind. I sweat like I’ve never sweated before. Through Miami, I feel strong and my average speed stays north of 21mph, but as the afternoon heat breaks me down and the wind pushes me back, and the traffic starts to wear me thin, I ride slower and find the first hardship of my journey. Frequent stops for rehydration are essential. I crawl into walk-in beer caves at every gas station I stop at, licking ice cream while I sit on 30 racks of bud light, letting the sweat cool on my skin.

The inevitable afternoon thunderstorms finally catch me, cooling down the air, but doing nothing to improve my sweaty discomfort. The road is like a steam bath as wispy fog pours from the hot asphalt. 

I was planning on camping, but the thunderstorms are closing in from all directions, promising to dump rain all night, so I find a cheap motel and nod off at 9:30, logging a solid 294 miles on my first day.