Orlando, St. Pete, and starting the Pinellas Trail

2/4/26

Hello from Tallahassee!

In my last post, I left off as I arrived back in Orlando after roughly a week of bike touring the eastern part of the Florida Coast to Coast Trail.

I spent that first night in the hotel on the edge of Winter Park, and then the next day, rode to the home of my new Warmshowers hosts, Danny and Sarah, in a lovely classic neighborhood in the northern part of Orlando. They were cool hosts, of course interested in bicycling, but also very vegan-adjacent and eco-friendly in their approach to life. (Sarah had recently founded a local nonprofit focused on reducing solid waste, hosting clothing swaps and similar events.)

I used their home as a base for two nights, and explored the nearby neighborhood parks and bikeways in the intervening day.

I decided to give myself a “vegan splurge day” (rare within my extremely low-budget travel style) and treated myself to a decadent “fried chicken” sandwich at an acclaimed local vegan restaurant, Winter Park Biscuit Company.

Then I wanted to continue the splurge, so I pedaled over to the local vegan bakery, Valhalla Bakery. (To my delight, I later learned they have a St. Petersburg location too!) I enjoyed a rich chocolate Biscoff cupcake.

The next morning, I packed up and headed out to the Winter Park Amtrak station for my train-and-bus ride to St. Petersburg. The house was roughly equidistant to both the Winter Park and Orlando stations, so having arrived in Orlando twice already, I thought I would try something new.

The weather was sunny and 71F/22C as I left the house, but the forecast had led me to fear rain, even on this short 20-minute ride. Just as I was starting to sweat from the sun, and feeling foolish for having worn rain pants and my rain jacket, those fears were realized when the skies suddenly opened up.

I took shelter under a school awning for about ten minutes, but the rain continued pouring—for what my weather app seemed to suggest would be just another few minutes—when the timing started seeming urgent for me to get to the station. (I wanted to be careful to arrive at least 45 minutes before departure, since I would be checking my trailer. Some stations are very strict about these cutoff times, and I could not afford to miss being able to check it onto this Viewliner train; there would be no room in the coach cars to store it.) Sure enough, it only rained for a few more minutes, but that was long enough to get both me and my rig thoroughly drenched.

At the station, as I tried the door and found it locked, the attendant regarded me a bit like a drowned rat, and informed me somewhat tersely that the station wouldn’t open for another 15 minutes. (Apparently these folks were less concerned with the 45-minute window at this station—their opening time wouldn’t even allow for it. Guess I could have waited for the rain to stop.)

Dejected and dripping, I did manage to strike up a very friendly conversation with a woman in her 80s (she volunteered her age, as well as the fact that she was beginning to experience some symptoms of dementia, though she was taking the train alone—for her first time ever—to Tampa that day.) She was a retired schoolteacher, and was very taken with my way of travel. It cheered me up to talk with her.

Once I did make it inside, I ran into more hassles with the two staffers. The woman who had closed the door on me outside mostly avoided interacting with me at all—just interjecting disapprovingly a few times—while her male counterpart helped me to get the trailer checked. He seemed pretty accommodating, but he did later walk out to find me to let me know that technically the dimensions of the trailer were large enough that he could charge me for oversized luggage.

“I won’t this time, since you said other Amtrak staff have let you do it… but just so you know, technically you should pay the extra $20 [$30?] for oversized luggage in the future.”

Argh.

It’s always something.

I thanked him politely, but made a mental note never to depart from the Winter Park station again. I’m very glad to know that Orlando is so close by, since I will probably go through that area at least once more this winter.

The train ride to Tampa was pleasant, and I was seated next to a woman who had also founded a nonprofit—this time a global one, focused on an aging world population, and based on teaching people around the world to live more multi-generationally.

At the Tampa station, I transferred to an Amtrak bus to St. Petersburg. I had considered bicycling across the Gandy Bridge—as I had done four years ago—but decided against it, opting for the ease of a bus. And I’m glad I did, because it was a chilly and windy day in the Tampa Bay. I watched the choppy water as we drove under the clouded skies, and was relieved not to be out riding in the wind for those miles.

And sure enough, arriving in St. Petersburg, my weather app showed a “wind advisory,” with some pretty nasty gusting possible. I was glad I only needed to bicycle a few miles to my Warmshowers host’s house.

Unfortunately, the furnace at the house wasn’t working very well, and it got to be a very cold night, dipping down near freezing. I had thought I might be staying in that house for close to a week, since that host had graciously offered “as long as you need!” but fortunately, I found another host who offered a mother-in-law apartment above his garage for nearly a week, so I moved over there the next day.

While in St. Pete, I also got to meet someone really cool!

I had seen one Katherine Price in a few of my Facebook nomad, pet sitting, and Host a Sister groups. She has been living as a traveling pet sitter (mostly dogs, and traveling in her car) around the US for the past six years—about twice as long as I’ve been at it. We finally found ourselves in the same place at the same time, so we met up! It was so much fun to swap stories about our lives these past few years, and share various tips we had each learned. We planned to meet up again, and I’ll write more about that in the next post.

The following day, the weather was still a bit blustery and, although sunny, not terribly warm (high of 53F/12C) but I set out to cycle my first leg of the Pinellas Trail, about 30 miles/48 km from the trailhead in downtown St. Pete to Dunedin, up the coast a bit. The first part of the trail wasn’t all that scenic, and with the subpar weather, it was a bit of a letdown after that perfect last day on the eastern part of the trail.

But the second half was a little prettier, and I was glad to have done it.

I took a total of three buses back to the apartment, which took me more than two hours! But I felt accomplished at the end of that day.

I’ll write more about my time in St. Pete—and my travels from there to Odessa, then Spring Hill, and now Tallahassee—in upcoming posts.

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