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Florida is terrible. Please tell your friends.The heat is oppressive. The humidity is worse. The mosquitoes are big enou...
09/01/2026

Florida is terrible. Please tell your friends.

The heat is oppressive. The humidity is worse. The mosquitoes are big enough to have their own ZIP codes. Alligators are everywhere. Hurricanes have names. The afternoon sky can go from postcard blue to biblical in twelve minutes.

And whatever you have heard about winter is exaggerated.

Fortunately, there is a volunteer workforce of Floridians distributing this information online every single day. You can find them under almost any post about Florida. Someone writes, "We're thinking about moving down next year!" and within minutes a Floridian arrives to explain that this is a terrible idea.

Part of it is a joke. Part of it really isn't.

Collier County had 38,040 people in 1970. It has more than 400,000 today. Everything those people moved here for has had to make room for them.

And the loudest warning in Southwest Florida history is sitting east of Naples right now.

In the 1960s, a developer carved 55,000 acres of swamp into Southern Golden Gate Estates, meant to be the largest subdivision in the world. The Florida Forest Service says buyers were flown over the land in the dry season and worked over with high-pressure sales tactics, and plenty of them bought lots they never once stood on. Come summer, some of that property needed a boat. The developer went bankrupt.

Florida has been undoing it ever since. The state bought back about 20,000 parcels from 17,000 owners around the world. Crews tore out 260 miles of road and plugged 48 miles of canals so the water could find its old path. This January the Army Corps of Engineers cut a ribbon at a pump station on 64th Avenue Southeast and called the job finished, almost twenty years after it started. It is Picayune Strand State Forest now.

A subdivision the size of a small county, sold to people who had never seen it, now on its way back to cypress.

So yes. The summers are unbearable. The traffic is terrible. Way too many alligators. Honestly, you would hate it.

It ain't much, but it's honest work.

They reached the top of their industries. Traveled the world. Lived in the fast lane. Miami. Los Angeles. New York.Then ...
08/28/2026

They reached the top of their industries. Traveled the world. Lived in the fast lane. Miami. Los Angeles. New York.

Then they landed in Naples.

It's a familiar story here.

Naples has long attracted people who spent decades being seen. Founders, executives, surgeons, attorneys, performers. People who lived by a calendar and measured a good year in deals closed. Then they reached the point where they didn't have to anymore.

You keep the money. You keep the access. You drop the performance.

The corner office becomes a morning tee time. Rush hour becomes a golf cart. Dinner moves from 9:00 to 6:30. A full calendar becomes something to avoid.

Naples was built for that. Collier County has around ninety golf courses, and the Naples area ranks first in the country for golf holes per capita. Whole neighborhoods are organized around a course, a clubhouse, and a gate.

Membership buys the tee sheet. It also buys the dining room, the pickleball courts, and most of the people you will see that week. The club is exclusive. The point of the club is lunch.

The rest of the day is short on friction. Beach at 8. The boat behind the house. Dinner on Fifth Avenue South and a short drive home. In season the roads fill and everybody complains. By June the crowds thin out, and the people who stayed treat that as the reward.

One house on Gordon Drive sold for $133 million last year, the priciest single home sale in the country according to Redfin. Most people driving past it would never guess.

Miami, Los Angeles, and New York reward velocity. Success there is public. People have to know you made it. Naples runs the opposite transaction.

The version of these guys twenty years from now doesn't look out of place on that course. They look like the latest version of a pattern Naples already knows: people who won the loud game and then chose the quiet one.

For someone who spent thirty years moving as fast as the industry required, slowing down is the final flex.

Naples was a resort town before it was much of a town at all.The first two structures built in Naples went up in 1888, a...
08/27/2026

Naples was a resort town before it was much of a town at all.

The first two structures built in Naples went up in 1888, and they were a 600-foot pier and a 16-room hotel facing it. The hotel opened on New Year's Day 1889. The Naples Historical Society records Rose Cleveland, sister of President Grover Cleveland, as the first guest to sign its register. Guests arrived by steamer and stepped off onto that pier, which worked as the town's freight dock and carried the post office out over the water. Rail service reached Naples in 1927 and the Tamiami Trail opened in 1928, connecting the town by road to Tampa and Miami. The Town of Naples was incorporated on December 1, 1923, thirty-four years after the hotel took its first booking.

That order still shows in the numbers. Collier County drew more than 2.8 million visitors in fiscal 2025 and collected $49.83 million from the tourist tax, a 5% charge on lodging rented for less than six months that pays for beach maintenance and destination marketing. Rooms keep getting added to hold them. County room supply grew more than 14.3% in fiscal 2025 and another 3% this year. In December 2025 the average room went for $382 a night.

The newest arrivals sit on the oldest ground. Naples Beach Club, A Four Seasons Resort opened in November 2025 with 220 rooms across the 125-acre beachfront where the Naples Beach Hotel and Golf Club ran for decades. The Olde Naples Hotel opened the first 50 of its 109 rooms on May 15, 2026 at 200 Broad Avenue South, built as an homage to the 1889 original.

Its restaurant starts serving breakfast at 7 a.m., a few blocks from where that first hotel faced the pier.

Wynn's has been selling groceries in Naples since 1938, seventeen years before the name Winn-Dixie even existed.The Wynn...
08/27/2026

Wynn's has been selling groceries in Naples since 1938, seventeen years before the name Winn-Dixie even existed.

The Wynn family came to Florida in the 1880s and eventually made its way to Naples, where it bought a small inn near the city docks at what is now Crayton Cove. Half the building became a grocery and restaurant. Fewer than 150 people lived here year-round.

After World War II, Don Wynn bought the business with a $2,000 GI loan. Naples had two grocery stores. Shopping anywhere else meant driving all the way to Fort Myers and back.

In 1948, he opened Sunshine Super Market at Fifth Avenue South and Seventh Street. It was Naples' first modern grocery store, built when the local phone book contained fewer than 200 numbers even during season.

The family kept expanding. A larger market followed in 1953. The original became Sunshine Hardware in 1958, joined Ace in 1964, and the business his family started now operates 19 hardware stores across Southwest Florida.

Also in 1964, the Wynns built a new grocery store on U.S. 41 at Ninth Street North.

It is still there.

Winn-Dixie took the opposite route to Naples. Its corporate family tree began with a Miami grocery in 1925, expanded through acquisitions, and adopted the Winn-Dixie name in 1955 after Winn & Lovett merged with Dixie Home Stores.

Even the checkmark has a history. It traces back to Kwik Chek, another grocery chain the company acquired.

Today, Collier County is down to two Winn-Dixies.

Wynn's still has one store.

Same block since 1964. Same family since 1938. Sunshine Hardware is still there too, separated from the market by an interior wall.

Drake is from Toronto, home to plenty of Canadians who spend their winters in Naples. In 2023, he revealed his gambling alter ego is "Anita Max Wynn," a play on "I need a max win."

Nobody does gated communities quite like Naples.Some are so large the Census Bureau treats them as census-designated pla...
08/26/2026

Nobody does gated communities quite like Naples.

Some are so large the Census Bureau treats them as census-designated places. Lely Resort had 7,619 residents at the 2020 census, up from 4,646 ten years earlier. Pelican Bay had 6,660. Vineyards had 3,883, Island Walk 2,812 and Verona Walk 2,713. Pelican Marsh, Heritage Bay and Winding Cypress appeared as census places for the first time ahead of that count.

Two of the biggest trace back to the same year. In 1972 a division of Westinghouse partnered with the Collier family to develop 2,330 acres seven miles north of downtown. That became Pelican Bay, now more than 65 individual neighborhoods sharing one name.

That same year, a Dutch inventor bought roughly 25,000 acres east of Naples and planned 10,500 homes. His golf courses opened in 1990, 1991 and 1997, but much of the land remained undeveloped until Stock Development bought into the project in 2001. Lely Resort now has roughly 4,500 residences across more than 40 neighborhoods.

The model kept evolving. Collier's Reserve opened in 1994 on 450 acres along the Cocohatchee River with just 224 homes. In 1996 the state created two community development districts at Fiddler's Creek. Together they cover roughly 2,400 acres, with authority over roads, lakes, landscaping and other infrastructure.

Inside some of these communities, the median age runs around 69 to 71. Collier County's is 53.3.

Then there are the lakes. Much of what looks like waterfront in these communities was excavated as part of the drainage and stormwater systems that made the development possible. Once there was permanent water, alligators had habitat.

So behind one Naples gate can be thousands of people, dozens of neighborhoods, golf courses, restaurants, roads, lakes and, in some cases, another layer of government.

The alligators have adapted to the infrastructure.

Florida is full of two things: alligators and HOAs.An HOA governs through documents recorded against the land, and those...
08/24/2026

Florida is full of two things: alligators and HOAs.

An HOA governs through documents recorded against the land, and those documents bind every owner who buys in later. Florida puts these associations under Chapter 720, and over the past two sessions the Legislature rewrote large parts of it.

Scale varies enormously. Collier's Reserve has 224 homes on 450 acres along the Cocohatchee. Pelican Bay covers 2,330 acres and holds more than 65 individual neighborhoods. Lely Resort has roughly 4,500 residences in more than 40. In the big ones an owner often answers to a master association and a neighborhood association at once. Fiddler's Creek adds a third layer, since the state created two community development districts there in 1996 that own and operate the roads, lakes and landscaping.

Since 2023, an association cannot restrict items on a parcel that are out of sight, including artificial turf, boats, flags and RVs. The Legislature widened it in 2024. Vegetable gardens and clotheslines went on the list, and the visibility test now reaches past the frontage and the next parcel to the common area and the community golf course. The statute names the golf course. That tells you who it was written for.

Fines got harder to levy. A fine caps at $100 per violation unless the governing documents allow more, and anything under $1,000 in total generally cannot become a lien. The owner gets at least 14 days written notice of a right to a hearing. An independent committee holds that hearing, and if it says no, the fine dies.

The paperwork opened up. Associations with 100 or more parcels had to run a website carrying their official records by January 1, 2025, and kickbacks to board members and managers became a crime.

None of that means the neighborhood lake is open for swimming. Communities routinely keep those off limits, and the reason is currently standing in the shallow end.

Nobody in Naples shops at all four...Wynn's has been selling groceries in Old Naples since 1938, when the Wynn family bo...
08/23/2026

Nobody in Naples shops at all four...

Wynn's has been selling groceries in Old Naples since 1938, when the Wynn family bought the Bayview Inn at what is now Crayton Cove and ran a grocery out of half the building. Fewer than 150 people lived year-round in Naples then. Don Wynn opened Sunshine Super Market at Seventh Street and Fifth Avenue South in 1948, for a town of about 600. The family built the market's present block at 141 Ninth Street North in 1964.

Publix multiplied with the people. Collier had 321,520 residents in 2010 and 375,752 in the 2020 census, and the Census Bureau estimated 417,131 in 2025, up 11.0%. Even after all that, only 16.1% of the county is under 18. The Neapolitan Way store on Ninth Street opened in 1986 and was the oldest Publix in the county that had never been rebuilt. It came down anyway, and reopened this July at 48,388 square feet.

Seed to Table opened on Immokalee Road in November 2019, 75,000 square feet in a former Albertsons that Oakes Farms bought for $5 million, with produce from 3,500 acres in Immokalee. As of August 1 the Collier County rolls carried 262,213 registered voters: 145,410 Republicans and 50,422 Democrats.

Super Latina Food Mart is at 2164 Santa Barbara Boulevard in Golden Gate, with Rose Food Mart down the street at 1808 and 7 Food Mart and Tortilleria up it at 2332. Flamingo Mini Market is over on Golden Gate Parkway. All four carry Latin American groceries.

Golden Gate is 69.6% Hispanic against 30.5% for Collier County, and 53.0% of the people there were born outside the US. Only 8.9% of Golden Gate is 65 or older. Across the county that number is 34.8%.

Golden Gate is the young end of an old county, eight miles northeast of Naples.

Real estate is the business Naples runs on, and the paperwork behind a sale carries more risk than most buyers realize. ...
08/22/2026

Real estate is the business Naples runs on, and the paperwork behind a sale carries more risk than most buyers realize. Under Johnson v. Davis, the 1985 Florida Supreme Court ruling, a seller has to disclose known facts that materially affect a home's value and are not readily observable to the buyer. Florida Statute 475.278 puts the same duty on the agent, and an as-is clause does not erase either one.

Most of the water behind Naples homes is a stormwater retention pond, dug so the streets have somewhere to put the rain. The City of Naples calls them retention areas that collect runoff and clean it before it reaches the bays, and notes they double as a waterfront amenity. The view is the second job of a piece of drainage infrastructure.

Alligators don't care what it was built for. Florida has around 1.3 million of them across all 67 counties, so a warm pond with fish, ducks and a sloped bank gets found.

That is usually where a disclosure claim dies, on one word: observable. A ten footer sunning on the bank is about as observable as a property condition gets.

Suing the community is harder. Florida courts apply ferae naturae, meaning a landowner generally owes no duty to protect people from native wildlife unless the animal was possessed, harbored or introduced. Alligators are native. In February 2026 a Sarasota County judge threw out a wrongful death case over a woman killed by alligators in a canal behind her Englewood home.

Plaintiffs get at it by arguing the community crossed into harboring. Feeding a gator, naming it, setting a bench at its bank, never calling the state hotline about an animal everyone knew. Those cases are still hard to win.

Before anyone dials 866-FWC-GATOR: a nuisance gator is four feet or longer and believed to pose a threat, and the ones taken under that program are killed. More than 8,700 were removed statewide in 2024, and the state pays the trapper $50 per animal.

The photo is satire. Everything else comes from Florida law, court records, FWC data and the City of Naples lake management plan.

"The phone eats first."Photographing dinner stopped being strange at some point, and nobody marked the day. Now a restau...
08/21/2026

"The phone eats first."

Photographing dinner stopped being strange at some point, and nobody marked the day. Now a restaurant opens knowing the plate and the room will be shot before anyone takes a bite, by customers, for free.

Southwest Florida has a concrete version of that. Sizzle Dining, this region's month-long prix fixe event, keeps a roster it calls the Sizzle Squad: more than 70 local micro-influencers, food accounts and parenting accounts and car accounts and fashion accounts, who shoot and post about participating restaurants. Sizzle markets the Squad to local businesses to hire year-round.

It runs September 1 through 30 in 2026, its tenth year, with a record 140 restaurants across Collier, Lee and Charlotte counties: Marco Island, Naples, Bonita Springs, Estero, Fort Myers, Fort Myers Beach, Cape Coral, Babcock Ranch. Naples alone is split four ways on the event's own map: downtown Naples, midtown, East Naples, North Naples. For every meal sold, the restaurant sends a dollar to Blessings in a Backpack of Southwest Florida.

That dollar does something quietly useful. Last year 127 restaurants sold 87,483 of those meals, and the check handed over at the wrap party on Fifth Avenue South was $87,483. The charity total is also a headcount. Very few places publish a figure like that, and this year the goal is to clear 100,000 meals.

Which leaves the question of why it all happens in September.

Sizzle's founder told Florida Weekly he started it ten years ago to "put butts in seats during the slowest month of the year."

Here is what that month looks like. Collier County's tourist tax is charged on hotel and vacation rental stays, so it is a monthly read on how much visitors are paying for lodging. Last September it brought in $2.37 million. This March it brought in more than $7.93 million. Same county, roughly a third of the collections.

The rent and the insurance run all twelve months.

The phone eats first. September is the month the restaurant needs it to.

In 1885 Thomas Edison sailed down the Gulf coast looking for somewhere warm and stopped at Fort Myers. He bought 13 acre...
08/20/2026

In 1885 Thomas Edison sailed down the Gulf coast looking for somewhere warm and stopped at Fort Myers. He bought 13 acres on the Caloosahatchee River for $2,750 and built a winter house he called Seminole Lodge. Henry Ford came to visit in 1914, liked it enough that in 1916 he bought the property next door and named it The Mangoes.

Fort Myers had 349 residents that year, which made it the second largest town on Florida's Gulf Coast south of Cedar Key.

Naples was barely there. A Kentucky senator and a Louisville newspaper publisher formed the Naples Town Improvement Company in the fall of 1886. About 80 people lived here by the summer of 1888. Rail service reached Naples in 1927 and the Tamiami Trail opened in 1928, four decades later.

The two most famous industrialists in America picked Fort Myers, and they picked it while Naples was still a plat map and a pier.

The modern picture is off too. The city of Naples had 19,115 residents in the 2020 census against 375,752 for Collier County, so the Naples in the postcards is about five percent of the place.

United Way of Collier and the Keys, working from 2023 data, puts 43 percent of Collier households below the ALICE threshold: earning above the federal poverty line and still short of the basics. The survival budget for two adults with two kids in child care is $105,660 a year in Collier. The county's median household income is $90,072. That budget is higher than what the typical household here earns.

Florida's overall rate is 47 percent, and United For ALICE finds households below the threshold in every county in the country. The spa and the pothole are in the same economy.

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