The 2nd day they woke up to clear skies and cooler air — a much-needed reset.

It took a little time to get going, mostly because the bikes needed a serious cleaning after the sandstorm from Stage 1.

Once on the road, it turned into a beautiful coastal ride. Tailwinds stuck around, traffic was light, and for the most part, drivers were surprisingly courteous… with the exception of one BMW motorcycle rider who had some strong opinions about cyclists using the shoulder.

Jim added another flat to his total (starting a trend that would continue). Ben and Scott were still clean.

The mileage stretched longer than expected — one of those moments where you think you’re close, only to realize you’ve got another 16 miles to go.

They wrapped the day with dinner on the water and took advantage of the time change to settle in early.

Long, flat, straight roads made this one a bit of a mental grind.

To keep things interesting, they turned it into a series of races to city limit signs — anything to break up the monotony.

At one stop in Keaton Beach, things got… unusual. An overweight German Shepherd was being chased by a parrot named Kokomo. Ben ended up holding the parrot, which somehow felt completely normal at that point in the trip.

They eventually rolled into Steinhatchee, where they met up with Scott’s family and settled in along the river.

That night, they celebrated Jim’s 50th birthday with cake (candles relit more than once) and a few cigars by the water.

Not a bad way to spend a birthday.

Sunshine, calm air, and something they hadn’t felt in a while — optimism, encouraged them at the start of stage 4. At just 86 miles, this was officially a “short day,” which felt almost strange after the last few.

Breakfast was simple — oatmeal and scrambled eggs — and by 8:30 they were on the road.

There was a quick thought about stopping at the Lower Suwannee National Wildlife Refuge, but momentum won out.

The ride into Rosewood was smooth, with a quick lunch before getting back at it. By 3:00, they rolled into Crystal River right on time — which doesn’t always happen on trips like this.

With some extra time, they reset: laundry, early dinner, a couple of beers, and the usual recovery plan… Advil.

Lights out by 10:00.

And somehow… no flat tires.

The day started with 26 miles along US 19 before dropping onto the Suncoast Trail — 45 miles of uninterrupted riding with no traffic, just trees, wind, and the occasional wildlife sighting.

Eventually they worked their way toward the Pinellas Trail, navigating cross streets where drivers were surprisingly courteous, often stopping even when they didn’t have to.

Ben finally picked up his first flat near the end of the day. Jim kept his streak alive. Even the trailer got in on the action, shredding a tire before being fixed and sent back on the road.

They rolled into camp just before dark, ready for a reset.

With a 9:00 AM start, the trio headed out along a mix of trails, side roads, and highways.

The Skyway Bridge required a shuttle — one of the few sections they couldn’t legally ride — and probably for the best, considering there was a trooper waiting on the other side.

From there, it was a long stretch down US 41 — fast traffic, constant awareness, and a more stressful ride than previous days.

They made it to Fort Myers by early evening, just in time for dinner at Uncle Paul’s.

The real highlight? Their first massages of the trip.

That alone made the day worth it.

Rain came back and stuck around for about half the ride — cold enough that the spray from the rider ahead became something you really noticed.

Shoulders were tight, roads were busy, and focus was high.

Midway through the day, Ben celebrated his birthday with family, a bottle of his favorite Merlot (that Scot unintentionally chose), and a much-needed break.

They pushed through the weather and wrapped up the day at camp, surrounded by good people and plenty of food.

Stage 8 started with headwinds that didn’t let up for the first 30+ miles.

They leaned into it, navigating traffic, crosswinds, and those reflector-lined shoulders that seemed perfectly designed to keep things interesting.

There were a couple of close calls with drivers along the way — the kind of moments that get your attention real quick.

Then things shifted.

They picked up US 1, tailwinds kicked in, and the miles started to fly. After everything they’d dealt with, it finally felt like the ride was giving something back.

Dinner at The Fish House in Key Largo hit the spot, surrounded by family and support crew who helped make the whole thing possible.

Mile 800 accomplished.

They woke up to sun, light breeze, and the finish line finally within reach.

After everything — the storms, the flats, the long days — this one felt different.

Then the wind showed up again… but this time in their favor.

Tailwinds pushed them fast — really fast. Speeds climbed into the 30s, and on the Seven Mile Bridge, it felt like flying.

They rolled into Key West that afternoon, finishing what started as a crazy birthday idea.

Jim “Flat Tire” Rahman
Ben “The Silver Fox” Anderson
Scott “The Quiet One” Cavin

They made it.

And just like that, it wasn’t just a ride anymore — it was a story.