Walking Pinellas Beaches: Day 4 – The “Redingtons”, Treasure Island, and St. Pete Beach

Today’s Walk

Start / End:  North Redington Beach – Fort De Soto Park

Distance: ~11.1 miles / 28,724 steps

Time: 6 hours, 41 minutes

Today’s Listens: “Graceland” by Paul Simon, “Aja” by Steely Dan

On day 3, I did not have a lot of fun. For something I’ve chosen to do voluntarily, and of which I have total control, this was stupid. So for day 4, I decided to change that.

This is no doubt a case of mind over matter, because as soon as I stepped outside, I was struggling. The humidity was borderline unbearable by 9, and there wasn’t even a hint of a breeze. Emergency measures had to be taken. Then, a sign from above that someone actually wants me to finish this trek.

I came upon the Madeira Beach post office, and, despite the general suspicion of the alternately extraordinarily chatty and mean clerk, mailed some of my unneeded stuff back home. This was a trick I’d picked up on the Jersey shore walk, although I still apparently didn’t learn the lesson of not overpacking. A few pounds out of my pack was instantly noticeable, and I suddenly had a new respect for those ultra-light backpackers who measure their bags down to the ounce.

In a minute, I was back on the beach via Archibald Beach Park – yes, a public beach access with public parking and actual amenities like bathrooms, showers, and places to sit. In all sincerity, this felt like a novelty after the inaccessibility of the day before.

Despite this, I was struggling. I spent the entire two miles to John’s Pass bargaining with myself about how much I could or would actually do that day. I was still doing this until a large iced coffee and a drawbridge saved the day, perhaps literally.

The iced coffee came from a relatively nondescript cafe in John’s Pass, an unusual combination of Old Florida and Tourist Florida in the form of a mixed development of commercial and recreational boat slips, large and small restaurants, tacky souvenir shops, and respected local artists and craftsmen. You can rent a kayak and paddle into the mangroves on the back side of the island, followed by a dinner of local seafood, or you can grab a ride on the party boat that looks like an old-time riverboat and eat at the Hooters location with the World’s Largest Chicken Wing. I quite like the area overall.

After dawdling and wandering a bit through the area, I found myself approaching the bridge across the pass as red lights began to flash and swinging arms came down across the roadway and sidewalk. I’d been caught by the John’s Pass drawbridge, which, ludicrously in my estimation, doesn’t open on a designated schedule, but on demand to any boats needing to get through. Supposedly, this has something to do with the speed of the currents in the pass, but I’m not sure that’s much comfort to the looooong line of cars backed up down Gulf Boulevard on a prime beach Saturday.

For me, it was probably the best thing that could have happened. It forced me to stop, finish my coffee, and cool off in the stiff breeze blowing off the water. Why not finish the next island and see how I feel?

And that’s exactly what I did when the bridge (eventually) lowered, and I trekked across to arrive on Treasure Island, a community that, in my estimation, is as charming as its name (even if the entrance sculpture isn’t actually sand).

Part of my second wind upon reaching Treasure Island, admittedly, was leaving the beach for stretches. This is a beach walk, true. But what was sorely missing on the previous day was any sort of connection to the towns I was walking through. For as much as I interacted with the Bellairs and Indians, I might as well have been in New Jersey, or California, or Australia, or anywhere else with sand and water.

I decided to change this with Treasure Island. I didn’t know much about it before my walk, to be honest. But I was completely charmed by the character of the place: small, old-school beach cottages, authentic retro motels, and lots of shops, restaurants, and bars; the first town with a distinctive character I’d encountered since Clearwater Beach. You’re able to take it all in, along with some beautiful beach views, along a paved “Beach Trail” that runs between the expansive sand and the motels.

The one thing they almost all had in common? They weren’t open. It was apparent that one of the back-to-back hurricanes that affected our area in 2024 (who can even tell anymore?) had done some serious damage, and the owners of these august establishments had yet to pull together the contractors, money, or will to fix them. In any case, that’s two winter peak seasons missed now for many of these spots.

I’ve tried not to dwell too much on the doomed nature of a lot of these places as I pass through them. I think a lot about hurricanes, generally, for both personal and family reasons, as well as the general specter they cast over summers here. But as I proceeded further and further south toward Milton’s landfall, and residential development hugged the water closer and closer (victims from the storm surge from Helene), it was hard to ignore.

Despite all this, Sunset Beach, at the southern tip of Treasure Island, still had a lot of charm, even if the differences in style of home and phase of rebuild were stark.

As I walked back onto the beach itself to reach the southern tip of the island, a banner on a tent caught my eye.

It took me a second to parse what this meant, but when I did, I was instantly glad I hadn’t planned this walk for late August. I’d seen enough unwanted and unexpected nudity at Sandy Hook on my last walk. It was this same moment when I realized the extraordinarily large number of men (and only men) around me on the beach, with a far higher speedo quotient than I’ve seen in North America. Go figure – I’d stumbled across the most popular gay beach in Pinellas County, another fact my (apparently quite incomplete) research hadn’t turned up about Treasure Island.

In any case, I had only about a half-mile to go to reach the end of the island, and reach it I did. For future reference, it was also here where I first saw it, looming in the distance.

It, in this case, being the Don Cesar Hotel, which I would spend much of the rest of the day peering at off in the distance like Oz at the end of the yellow brick road. I hopped in an Uber to negotiate the crossing from Treasure Island to St. Pete Beach, and after a brief detour through the charming Corey Avenue corridor, I reemerged on the beach. 5 miles to go.

But it was getting late. Morgan was nearly on the way to meet me, and I very much wanted to finish as close as possible to her arrival to not make her wait, on top of the other sacrifices she’d be making in service of my walk – namely, sleeping outdoors on a hard pile of shells.

So, I set my eyes on the Don Cesar, put on “Aja” by Steely Dan, and walked. It began to creep closer.

And closer.

And even closer still.

Finally, it was here. I’d spent so long staring at it. It beckoned me to come inside and explore (and had been since I first saw it in 2022), but two very important things kept me out: the clock and the fact that my sweaty, disheveled self was increasingly resembling a shipwreck victim who’d decided to take up hiking. Although it was unavoidable, it was nevertheless somewhat disappointing.

1.7 miles to go. There was nothing left to look at other than…the end. Suddenly, the buildings to my left dropped away in the distance, and the uninhabited Shell Key into view. I was going to make it, despite everything else.

With the end of the beach in sight, I caught sight of a guy waving at me as he closed the distance in a light jog. “Where are you going, man?” I described my walk and my destination, now just a stone’s throw away. He asked why I was doing it, and I did my best to explain that I was doing it mostly because it was there to do.

“Just free-willin’ it, huh?” I thought about it for a second. “Yeah, that’s a really good way to put it,” I told him. I guess that was as good an explanation as any. There were so many things I could have gotten up and done this week, and this was what I chose out of all of them. It had been sitting at the edge of my thoughts for a day or so now. I put it out of my mind; I didn’t want to be thinking about it when I reached the end of the beach.

A few more steps of free will, and there I was – at the southernmost tip of the Gulf barrier island chain that stretched from Honeymoon Island to Pass-a-Grille. I wasn’t done. But I was done with something.

I took a few moments to rest as I looked out into the channel before my phone rang. Just like that, my ride was here. Morgan had arrived a few minutes before me and shuttled over to pick me up on my side of the island. “You look so sunburned!” she told me. It was good to see a friendly face. It was good to move from one place to another without walking.

Unfortunately, our challenges for the day weren’t through. My reward for my 11 miles of walking was to sleep on some very hard ground, albeit in a very beautiful place. More on the final day tomorrow.