Walking Pinellas Beaches: Day 2 – Caladesi Island and Clearwater Beach

Today’s Walk

Start / End: Tarpon Springs – Clearwater Beach

Distance: ~7.3 miles / 19,219 steps

Time: 5 hours, 1 minute

Today’s Listens: “The Campfire Headphase” by Boards of Canada, “Southern Rock Opera” by Drive-By Truckers, Audiobook: “Blue Highways” by William Least Heat-Moon

My day began on Caladesi Island, which is an island in the same sense that ketchup is a vegetable. It may have been that at one point, and people might still sometimes try to tell you that it is, but no one who experiences the real thing would make that argument.

The second of Pinellas County’s two state parks, it’s separated from Honeymoon Island by the aptly named Hurricane Pass. The two were one island until a 1921 storm (sometimes known as the Tarpon Springs hurricane; our home was built in 1922, for what it’s worth) cut the two apart with a channel that’s survived more than a century. Since the late 1980s, however, it’s been connected to Clearwater Beach to the south, as tides filled in the narrow, shallow gap that once existed between the two islands. This is good news for me, otherwise I’d be doing a good bit of backtracking, or a very ill-advised swim.

Still, the now-inaccurate name is a testament to the powers of tropical storms to completely reshape barrier islands of this size. The good thing is no one would ever think to put dozens of high-rise condos and hotels on the same eternally shifting barrier island just a few miles south.

Anyway. Caladesi Island is mostly undeveloped, other than the ferry terminal where I was dropped off, which has a few services. The inaccessibility and unspoiled gulfront has been enough to earn the park accolades as one of the country’s best beaches multiple times from the (self-declared) Dr. Beach.

The only (official) way to get to this gorgeous place is by boat, either private or the public ferry. If you call the state park office, they will strenuously discourage you from walking. In a rare case of not trusting park rangers working out, I ignored them and thrived instead of ending up falling off a cliff or in the stomach of some animal.

The 20-minute boat ride over was beautiful, if slightly longer than necessary after someone’s bag got caught by the wind and blew off into the water. From the ferry drop-off, I headed north on what I thought was a nature trail; hey, why not see some inland areas before I spent the rest of the day on the beach? However, I learned this was decidedly not the case from signs only upon reaching the beach. Oh well – it seemed pretty to me!

I might be a professional writer, but I’m going to struggle to find ways to describe how beautiful some of these places are by the end of this. The north end of Caladesi is particularly notable because you can be, and most likely are, the only person around for miles.


Only person, of course. My walk companions this morning were several hundred birds of varying species, surprisingly few of which I’d seen the day before. Today’s Birds of the Day™ are the Caspian tern, the black-bellied plover, and the black skimmer, which was apparently nesting in large numbers right now.

Although I would have liked to linger at the north end a little longer, time was ticking away, and it was more important than usual today. That’s because, as fake as Caladesi’s island status is, it can still get a little dicey on the walk to Clearwater. This is what that it looks like with a rising tide and a strong onshore wind.

The upshot is that, due to timing and weather issues beyond my control, I ended up walking about a third of a mile to the park boundary in knee-deep water with a heavy pack on. I do not recommend this as a matter of enjoyment, but I was able to cross safely and relatively easily. With the only real question mark of the walk behind me, I set up my umbrella and had my lunch with Clearwater in the distance.

It was around here where I had my strangest encounter of the day. I was starting to wonder if I wasn’t going to encounter the same class of characters I’d run across on the Jersey Shore. Then I remembered: I’m in Florida.

As I was relaxing after eating, struggling to (and ultimately failing at) keep my umbrella from blowing away, a middle-aged guy with no shirt and soaking wet cargo shorts who was walking up the beach gestured to me to get my attention. Because I still haven’t learned my lesson with this kind of thing, I went over.

”Do you see that thing?,” he asked me. He pointed out toward where the azure shallows turned a more emerald green. I could see what he was talking about. It was big, maybe 10-15 feet long, dark in color, and moving along at what appeared to be a steady, deliberate pace north. “Are you from around here? What is that thing?,” he asked.

I answered that I was, and that I couldn’t say – maybe a dolphin, or a manatee, or even a shark? Maybe it was even just a big piece of driftwood caught in a strong tide. None of these suggestions satisfied this man, who stood next to me in silence for a minute before announcing he was going to keep following it. I warned him the tide was coming up and the beach was already underwater further north, but he was undeterred. I wonder what happened to that guy. And I wonder what that thing was. Because he was right, it probably wasn’t anything I’d suggested.

From here, it was an easy few miles logistically and beachwise. But the overall vibe could not have been more different. Clearwater Beach is easily among the most developed and most tourist-heavy parts of the entire Gulf Coast. Miles of empty sand were replaced by dozens of perfectly aligned chair-umbrella combos and hordes of southerners and midwesterners wading into the Gulf, mostly clustered around the famous Pier 60.

Still, deceptively quickly, the island came to abrupt end. All in all, I was ready. I’d had enough sun, enough people, and enough walking. My Airbnb was a short walk away, and after a shower and a nap, I took in the sunset from Jimmy’s Crows Nest, a rooftop bar that would have provided one of the best sunset experiences of all time if not for the choice in music (“Wonderwall” at sunset for a bunch of boomers? What are you guys doing?).

Another day down, and the only main wildcard now settled. From here on, all I’ve got to do is walk. I’ll be doing plenty of that tomorrow on Day 3, where I’ll tackle some of the lesser-known Pinellas County beach communities, and likely spend a good deal of time wondering why they are named so similarly.

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