Growing up, most of my summers were spent in Englewood and Boca Grande, Florida. It's true what they say... most Floridians just vacation in other parts of Florida. Why wouldn't we? We already live in paradise.
Anyway, when I was in my late teens, my parents bought a small manufactured home just off Boca Grande island. We'd drive one block to the Boca Grande bridge, pay our fare to cross over, and spend the day on the beach, eating ice cream and poking around the little shops. Once I turned eighteen, I'd bring friends along and we'd party late into the evening at a bar and restaurant called South Beach. Those really were the best days of my life. Between Christmas and New Year's, the island would buzz with excitement whenever the George H.W. Bush family came to visit. I can still picture the stream of black Secret Service vehicles rolling down the main stretch—George H.W., George W., and Jeb all had their own details. During the day, we might catch a glimpse of Barbara Bush walking her dogs along the golf cart path.
I paint this picture so you get how very exclusive this island really is. We were there because my dad loved the fishing and made friends with one of the founding families who still owned a modest marina on the island. That was more our speed of people. Most of the million-dollar homes are occupied by part-time residents who winter here. The folks who work in the marinas and boutique stores can't afford to live on-island. It's a playground for the very, very wealthy.
Recently, though, the residents have gotten a bit angsty about outsiders visiting. It's gained more acclaim because Tucker Carlson bought a home there, and social media has broadcast its hidden beauty to the world. So the wealthy residents pushed through some very strict parking restrictions that make it tough to plan a casual day trip—think 3-hour limits in the few non-residential spots during daytime hours, no visitor parking in residential areas, and some beach access points off-limits without permits. It's basically squeezed out the easy, drop-in vibe we used to have.
Lee County Sheriffs Office will begin enforcing a massive new parking regulation fully on Boca Grande this weekend. While it reduces the number of public spaces considerably, there is still plenty of parking and space at State Park. Just look where you park the car.
— Garland Pollard (@GarlandPollard) January 30, 2026
Now we are… pic.twitter.com/5uMZ8IRd2x
That's why I found it utterly hilarious (if not a bit baffling) when I heard these same people who don't want even their fellow Americans to shop on their island hosted and participated in a parade protesting ICE.
About 125 Boca Grande residents came out to protest immigration and ICE enforcement today led by a Minnesotan Karin Birkeland here on island. pic.twitter.com/xt0neCU5fh
— Boca Beacon: Weekly Newspaper of Boca Grande (@BocaBeacon) January 27, 2026
Boca grande FL is an island with a swing bridge and millions of dollars out here I just caught the end of the march about 100 people with signs to save democracy and MN and the killing of Pretti . There are more liberals out here than I thought but they are all old and very… pic.twitter.com/tW65x2sGmK
— Corey Wilkinson (@Coreywi40858429) January 27, 2026
This is the Florida version of Martha's Vineyard. There isn't a poor person who lives on the island. If Ron DeSantis shipped a plane full of illegals to Boca Grande, much like Martha's Vineyard, they'd panic and have them off the island before the sun rose again.
These are the ultimate NIMBYs. It just highlights the utter hypocrisy of the people protesting. They make it next to impossible for American families to enjoy the island, they've placed the shop and restaurant owners in terrible financial travail with these parking rules, yet they'll protest ICE protecting American borders. The only explanation is they're terrified of losing their cheap domestic workers and gardeners. What utter fools.
