FMBGN-EIHS-From Sand To Skyline: How Early Developers, Casinos, And Storms Shaped Fort Myers Beach

A fifty-cent toll changed the fate of Fort Myers Beach. When early developers Thomas Phillips and Jack Delisle couldn’t get county funding for a bridge, they sold bonds, built their own, and rolled open a brand-new future in May 1921. From that moment on, everything accelerated: beachside casinos, bathhouses, and a handful of hotels welcomed the first waves of visitors, while locals still steered work around the tides. You’ll hear how cars once drove along the wide, hard-packed sand to reach the southern stretches, and why the first traffic jam arrived almost as soon as the toll booth did.

We dig into the storms that reshaped the map and the mindset. Hurricanes in 1921, 1926, and 1928 damaged roads and spans, yet the island pushed ahead with big, distinctive ideas. Phillips’s Arches rose in 1925 as a ceremonial gateway to a waterfront vision called San Carlos on the Gulf, supported by seawalls you can still spot. A new direct road from Gladiolus and McGregor to the beach slashed travel time and supercharged tourism. The 1928 swing bridge—hand-cranked into the 1950s—became both a bottleneck and a beloved landmark, pivoting open for shrimp fleets and stalling cars in long, salty lines. It’s an unforgettable picture: arches framing a low steel span, masts bristling in the channel, and a community learning to share space between leisure and labor.

We also chart the working water’s heartbeat. Before shrimp took over, mullet powered the economy, smoked and dried into hearty staples that fed families and markets. As hospitality grew—Gulf Shore Grill, Silver Sands, and other early names—the island balanced grit with charm. A few 1921 cottages still stand as proof of sturdy craft and stubborn hope. The larger pattern becomes clear: a cycle of boom and bust, progress and pause, that carried Fort Myers Beach from the roaring 20s into the quiet rebuild of the 30s and the demands of the war years. It’s not just history; it’s a guide to resilience and smart access, the forces that still decide how this shoreline lives.

If this story sparked a memory or a question, share it with us, then subscribe, leave a quick review, and send the episode to someone who loves coastal history. Your notes help us decide which corners of the island’s past to open next.

Estero Island Historic Society
161 Bay Road Fort Myers Beach, Florida, 33931
esteroislandhistoricsociety.org

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Transcript

Setting The Stage: The 1920s

Intro/Close 0:00

Welcome to the Fort Fire Speed Fitness Podcast and the Asteroid Island Historic Side area, where we preserve an extra story that state Fort Fire Speed. So settle in and look closely. Because on this island, you can de-breeds have a story to tell.

SPEAKER_01 0:26

Welcome back to the uh Estero Island Historical Society series. We're moving along in the history here, and we're moving into the 20s, I believe, right?

Building The First Bridge

Casinos, Bathhouses, And Early Hotels

Ellie Bunting 0:36

Exactly. The 20s were uh I think a funny moment in the history of our island because it was when most of the early development occurred. Um, the Florida land boom was going on at that time. People were coming down, the Dixie Highway opened up from the Midwest to get people down here. People had money, they had cars, so everything was happening, particularly on the East Coast, and the coastal areas were the first ones to develop. But the problem with Fort Myers Beach was we didn't have a bridge. Little details, right? Little details. You can't get here, you can't develop, right? So uh Thomas Phillips and Jack Delisle were two of the early developers on the island, they saw the potential of what it could be, and um they went to the county and asked for money for a bridge, and they were turned down. So they didn't let that stop them. They formed their own bridge company, they sold bonds and stocks or whatever. They earned enough money that they finally got a bridge built in 1921. Wow, it opened in May of 1921. 100 cars went over the first day, 50 cents a car. Yeah, that was a lot of money. Exactly, right? So the beach had finally opened up, and um Delisle and Phillips were ready for it because they both had a casino. Yeah, I don't know if it was built on that day, but I'm sure they were they were already they were ready. So there was a he had his casino was where the Gulf Shore Grill is, yeah, yeah. And then um the Lyle's was down at the end of Connecticut Street.

SPEAKER_01 2:17

Interesting.

Driving On The Beach

Ellie Bunting 2:18

So they were casinos, bathhouses, kind of thing, and the restaurants make an indentination for this drive. Right. So once people could get here, you could drive on the beach. The road went eventually, the road went to the beach hotel. Okay, it stopped there. Okay, so if you wanted to go further south, like down to Connecticut, you had to go on the beach, and the beach was large enough. It was wide enough. I think I noticed something back there where you could have three or four lanes of traffic on the beach. Wow, right, a lot of beach room, yeah. Without renourishment, exactly. Yeah, we're gonna renourish having it that much. So the bridge was built, you know, like I said, in May, and then there was a hurricane in October, so it damaged it, but didn't knock it out completely. Um and then in 1926 we had another hurricane. And we will do a uh a session with you on hurricanes in this area. So that that hurricane did quite a bit of damage to the road and to the bridge, but they patched it back together. Um in 1928, another hurricane. Wow, and that pretty much sounds like what we were gone through recently. Yeah, we needed to get a new bridge. So in 1928, a new bridge was was put in.

SPEAKER_01 3:34

Was there a lot of dam? Well, I mean, we'll get in there with the hurricanes. Yeah, yeah.

Janet Gottlieb 3:38

Oh there weren't you gotta remember there weren't there was nothing here, so there wasn't a whole lot to develop, yeah, and it was all at the north end of the island.

Ellie Bunting 3:46

Okay, so yeah, everything was there. But I don't think the beach hotel was was damaged very much.

Janet Gottlieb 3:52

Um it was set back somewhat.

Ellie Bunting 3:55

Yeah, there were some cottages at Red Coconut that were damaged. Um so there was some, yeah, but the development started then. We had the casinos, there was um all kinds of hotels. I mean, three or four hotels. Port Washington Hotel opened up down where Margaritaville is. Okay, and then we had the beach hotel and Phillips did Silver Sands Cottages. Remember those? Yeah, yeah. They were a hundred years over a hundred years old when Ian took about.

SPEAKER_01 4:26

Yeah. And pig shell came later. Yeah, pig shell didn't come until the 60s.

Hurricanes Test The Island

Ellie Bunting 4:31

Yeah, um, but these were the first. He did that, he did the Gulf Shore Grill. What was the Gulf Shore Grill? And his big thing was the um the arches. They were built in 1925, and he started them earlier. Um, and they were the entry to what he thought would be a wonderful development called San Carlos on the Gulf.

SPEAKER_01 4:51

So, and for our listeners that aren't familiar with that, where exactly is that?

The Arches And San Carlos Vision

Ellie Bunting 4:56

That is right where Bonita Bills is now, okay, and the and the marina diversified yachts. That's where the arches, and there's there's even a plaque right there now that shows you these were where the arches were. You had to go through the arches to get to the bridge. But Phillip's point was San Collars Island was not part of the beach, it was uh part of the mainland until 1926 hurricane that separated it. So his idea was he would have this wonderful development, every lot would be on the waterfront. He built the sea wall, which still exists on places, you can still find it. Yeah, so he had a seawall there. He had wonderful plans, and he was instrumental in getting a road because originally the road to get to the beach, you had to go down McGregor to John Morse Road. You had to take John Morse Road to Bunch Beach, then you got on the beach if there was low tide and drove to the bridge. So it was not an easy way to get here. So Phillips wanted he was bound to determine to get a road from well, we call it Miners Corner. Now it's the intersection of Gladiolis and McGregor. Okay, where K More um is what's there now? I don't know. Things have changed. Yeah, things have changed. It's that intersection there where Summerlin hits, where McGregor hits. Uh it's before that. It's yeah, right. Rondeos is there, the pizza place, and yeah, yeah. Right by Target, I guess that's right. Yeah, yeah. That was so he built the road from there straight to the beach, or he had it built. The town he did help on that one, and that's what really opened the whole area up because you could get here in 30, 40 minutes from Fort Myers, which you can't do that.

Janet Gottlieb 6:47

And I think from the time the first bridge opened in 1921, very shortly thereafter, we had our first traffic jam. And as much as people complain today about, oh, the traffic is so terrible in season, there were always traffic issues pretty much from the beginning on the beach. Whether it was because there wasn't much infrastructure and there weren't that many roads, you couldn't go very far, but it's been a perennial problem. And I think one of the themes of Fort Myers Beach is cycles, boom and bust, you know, sudden influxes of tons of people, and then a very quiet off-season. That's kind of a theme. The other theme I think from the beginning has been fishing, because before the shrimp were discovered, there was mullet fishing. That was probably the that was the first major fishing industry, and um it was a big business. Now, mullet is a very strong-tasting fish and it's bony, right?

Ellie Bunting 7:44

It's yeah, I not my favorite.

Carving A New Road To The Beach

Janet Gottlieb 7:47

No, but usually they smoked it, and I don't mean they smoked it, they put it on racks, smoked it and dried it, and then it was palatable and they made it into I guess fish cakes, mullet dip. It was a popular, um, popular item, and it was the industry in the early years in the 20s, probably 30s, and for a few years after that. That and tourism. Yeah, yeah.

Ellie Bunting 8:12

Tourism came in the 20s, as early as the 20s. As soon as that bridge came in, people started coming down here. And so when did the when did the toll go away? I think the toll went away in 1928. They replaced that bridge with a swing bridge, right? All right, and um it was built in Germany. There's rumor that it was secondhand from Jacksonville, but I'm not sure that's true.

SPEAKER_01 8:36

Like a lot of bridges up there, yeah.

Traffic Jams Since Day One

Ellie Bunting 8:38

So they brought that bridge in, and it was uh kind of an interesting bridge because it swung out, it didn't swing up, it wasn't like the drawbridge went up, this went out, and um it was there for 50 years. Wow, and it was a great, I think it was uh you know, the entrance to the island with the arches and then that bridge and the shrimp boats over there. It was just iconic fishing building, and you're coming in the paradigm with an entrance, leave the fishing building. But the bridge would get stuck. It took two, it wasn't electrified until eight 1950. So it took two men to physically push it open. Wow, they had a crank, I think. Yeah, they cranked it. The bridge tender had a little place to live, yeah. Right at the end of the bridge, but it would get stuck, and imagine it costs. Shrimp boats would go come and go whenever they wanted. I mean, there in the 50s we had 250 shrimp boats on St. Carlos Island. Yeah, so that bridge was ugly and closing, and every time it opened, it was a half-hour wait because it had to open bridges, they had to be cranked open, cranked closed, and yeah, traffic would back up.

Janet Gottlieb 9:54

Yeah, yeah. So I think the the hotels and casinos were going to be the mainstay of tourism, and that's why the the Gulf Shore and the Silver Sands and places like that, the casinos that then got wiped out. But the um the Gulf Shore continued on until Hurricane Ian in various forms. And it started as a casino, and then they rented uh they rented rooms, there was a bathhouse. There were rumors um which are unsubstantiated that maybe they rented rooms by the hour for other purposes at some time, but it was a very popular place, and the restaurant, as we all know, was a main stage until right up until where it came in.

SPEAKER_01 10:39

There were plenty of times, yeah. Over a hundred-year-old building, wasn't it?

Ellie Bunting 10:44

Right, absolutely.

SPEAKER_01 10:45

Yeah, yeah.

Mullet, Shrimp, And Working Water

Ellie Bunting 10:46

I think there were four buildings. This was 1921. This cottage, this cottage was 1921, Silver Sands was 1921, Gulf Shore was 1921, and then there was another cottage at the end of Madison called the Pine Cone that was 1921. And uh I think we're the only one left.

Janet Gottlieb 11:07

Yes, that's right. And this was probably the fifth between the fifth and the seventh building built on the island, and it's still here. Incredible, yeah, pretty great after all we've been through.

SPEAKER_01 11:19

Yeah, good construction, right?

Janet Gottlieb 11:21

Yeah, built solid. Original floors and walls, yeah.

Ellie Bunting 11:26

So the three hurricanes and the Great Depression pretty much put a kibosh on the on the growth, on the bus, on the boom, it became a bus, and things just stopped. So next time we'll talk about the 30s and the 40s, which were a time of reconstruction, regrouping. It was a quiet time, yeah.

Janet Gottlieb 11:47

Right, and then we had the war years, so the cycles, the eternal cycles, just like the tide.

SPEAKER_01 11:54

Exactly.

Janet Gottlieb 11:55

It goes down.

SPEAKER_01 11:56

Yeah, yeah. That's where we live here, but it's funny that a lot of things haven't changed on the island.

Janet Gottlieb 12:05

The density has changed, yes, but uh yeah.

SPEAKER_01 12:08

Very good. Any last words for uh the 20s?

Ellie Bunting 12:12

Well, we will are going to be doing uh a little more in-depth discussion of the 20s on March 21st for our uh diving into the decade series. So come by and and view it. We've got all the pictures and stuff up to whatever we had left is now on display. So come and uh and see what we got.

The 1928 Swing Bridge Era

SPEAKER_01 12:36

I love it. I love it. I'm just fascinated by you know learning about this and being able to share with the with our listeners, but it's just it's it's good stuff. And thank you guys for doing this and putting it together and presenting it to all of us. So we will see you next time in the 30s, right? Hopefully our temperatures will be a little lower. It doesn't feel like a traffical paradise, but soon, soon. And I'll be playing uh complaining it's too hot, right?

Intro/Close 13:02

Thanks for spending this time with the Astero Island Historic Society, where every story is a tide that brings our island past back to shore. If today's episode sparked a memory or a question, we'd love to hear from you. And we hope you'll visit us at the museum and check out our events on Fort Myers Beach as during the journey together. So we meet again with the island history. One footprint.