When people picture the first Thanksgiving, they usually imagine New England in the 1600s: cold air, roasted turkey, corn, buckles on hats. What almost no one imagines is Southwest Florida — mangroves, mullet nets, citrus groves, and a Gulf sunset.
But long before Naples was luxury beachfront condos and stone crab happy hour, this coast was home to powerful Native communities, rugged fishing families, and a few visionaries who looked around and said, “This could be paradise.”
Let’s talk about how early life here actually worked, what people were living on, and what “gratitude for the land” meant in this part of Florida.
Before Naples Was Naples: The Original People
Centuries before anyone called it “Naples,” Southwest Florida was home to the Calusa — a complex, coastal civilization that dominated much of South Florida for over 1,500 years. The Calusa weren’t small, scattered fishing camps. They built large communities with engineered canals, massive shell mounds, and large-scale fish capture systems that could feed tens of thousands of people.
At their height, the Calusa influenced or controlled an estimated 20,000–50,000 people across the southwest coast, from what is now Charlotte Harbor down through the Ten Thousand Islands and the Keys.
Some of the shell mounds they built are still standing today in places like Pine Island, Estero Bay, Marco Island, and Cayo Costa. These mounds weren’t just trash piles — they were architecture. Layers of shell and bone were intentionally built up to create higher, drier ground for living, ceremonies, and defense. In some places those shell ridges rise more than 20-30 feet above the surrounding water.
So if you’re imagining “the first Thanksgiving in Southwest Florida,” pause the turkey. Picture this instead:
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Fish pulled in from hand-built water enclosures (yes, they engineered literal fish corrals).
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Oysters, whelk, and conch taken from the estuaries and cooked over fire.
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Tropical fruits, roots, and plants gathered from coastal hardwood hammocks growing on those elevated shell mounds.
In other words: seafood feast, waterfront dining, no reservations needed.
Gratitude for the land here wasn’t about surviving a frost. It was about understanding the tides.
Then the Pioneers Arrived (And Realized “Wait… This Place Is Different”)
Fast forward to the late 1800s.
What we now call Naples started coming together in the 1880s, when two men — Kentucky businessman Walter N. Haldeman and former Confederate General John Stuart Williams — looked at this stretch of coast and decided to turn it into a winter retreat for wealthy northerners.
They formed the Naples Company, built a hotel on the Gulf, and in 1888 built the first Naples Pier — which immediately became the town’s lifeline. Steamboats would pull up to the pier, cargo and guests would come ashore, and luggage was rolled from the pier straight to the hotel on little rails. This wasn’t just a fishing pier; it was the airport, grocery store, and social hub of early Naples.
By the 1890s, Haldeman had purchased thousands of acres in and around Naples — reportedly including the hotel, the pier, a transport steamer called the Fearless, and about 8,600 acres of land — for around $50,000 at auction. He basically bought “future Naples” in one deal.
So what did life look like for those first settlers and seasonal visitors?
Not fine dining… yet. Think:
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Fishing off the pier for dinner.
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Smoking and salting fish to preserve it through the heat.
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Gathering oysters and mullet from the back bays.
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Citrus, coconut, and whatever you could grow in sandy soil and keep safe from raccoons.
It was Florida rustic. If you wanted something that wasn’t local — flour, coffee, sugar, canned goods — it had to come in by boat.
That “Thanksgiving table” in 1890 Naples? Much closer to Gulf snapper than roasted turkey.
What Gratitude Looked Like in Old Naples
When you live on the Gulf in the 1880s–1920s, thankfulness sounds different than it does in a northern farmhouse.
Up north:
“We made it through the harvest and the frost hasn’t killed us. Pass the potatoes.”
Down here:
“The pier survived the last storm, the fish are still running, the mosquitoes didn’t carry us away, and the steamer actually showed up this week. Pass the mullet.”
There was gratitude for:
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Access. Without the pier, early Naples was basically cut off. The pier meant medicine, lumber, news, people.
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Mild winters. Wealthy visitors from Louisville, Chicago, etc., came down to escape brutal cold and praised the “balmy climate and beautiful bay,” which is a big part of why the town was named Naples — it reminded them of Naples, Italy.
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Abundance from the water. The Gulf and back bays weren’t just scenery. They were survival. For both the Indigenous people here for millennia and the early settlers, seafood was the main protein on the table.
In other words, “thanks” in Southwest Florida was always tied to the water.
The Shift From Outpost to Community
By the early 20th century, Naples started evolving from a seasonal camp into an actual community. The hotel, the pier, the fishing economy, and later land investment from people like Barron Collier in the 1920s (yes, Collier County is named after him) pushed the area from “hidden winter escape” toward “real town.”
Still, it stayed small and tight-knit for decades. If you lived here, you knew everyone. If you were here for the winter, everybody knew you were here for the winter.
So when modern Naples does Thanksgiving now — long tables, friends who aren’t technically related but might as well be, a mix of traditional turkey and fresh-caught stone crab — that’s not a new social pattern. That’s the original Naples rhythm: people gathering around what the water gave them.
Bringing It Back to Today (Why Buyers Love This Story)
Here’s why this matters if you’re thinking about moving to Naples or buying a winter place here:
1. Gratitude is built into the lifestyle.
In most of the country, “Thanksgiving season” is a pause. Here, that feeling — warmth, fresh food, outdoor sunsets, slower pace — is daily life for a lot of residents from November through April.
2. Our sense of community is not an accident.
Naples grew up as a place where people relied on each other because there wasn’t anyone else. That small-town, “Hey, how are you settling in?” energy is still absolutely here in certain neighborhoods, buildings, and boating communities.
3. The water still feeds us.
We might not be spearing fish in shell-built water enclosures anymore, but seafood is still culture here. The Calusa harvesting fish from coastal estuaries 1,000+ years ago and someone in 2025 cracking local stone crab at sunset? Same storyline, different chair.
If I Could Sum Up “Thanksgiving in Naples,” It’s This:
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Up north, Thanksgiving is about the harvest.
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Down here, Thanksgiving is about the coast.
From the Calusa building shell islands and feeding tens of thousands using the estuaries, to the first settlers hauling supplies down the Naples Pier, to families today having dinner outdoors in November — Southwest Florida’s version of gratitude has always been simple: the water, the weather, and the people around your table.
Happy Thanksgiving from Naples.
And if you’re thinking about making this your winter table, I know a few homes you’re going to love.
Thinking about buying or selling in Naples?
Protect your investment with a trusted local expert by your side.
📞 Call Brian J Giacomello at 239-281-5269
📧 Email: [email protected]
William Raveis Real Estate | 720 5th Ave S. #201 Naples FL 34102
