September marks the peak of hurricane season along Florida's Gulf Coast. It's a season I think about differently than most, because it isn't only something I follow on the Weather Channel. It's part of my family's story on these islands, going back more than a hundred years.

This month I want to share a piece of that story, along with a few practical lessons I've picked up over a lifetime on the water, for boaters and waterfront homeowners heading into the heart of the season.

What My Grandmother Remembered

My great-grandfather, Gus Cole, settled on what's known today as Boca Grande North in the early 1900s. My grandmother, one of his daughters, was born and raised there on Cole Island. She grew up and spent her life along the same shores that I did, except her childhood came with something mine didn't: no bridge, no causeway, and no road off the island. In her early years, the only way on or off Cole Island was by boat.

She used to talk about a storm from the 1921 hurricane season that passed along our coast and brought serious flooding to our area. As a little girl with nowhere to go but the water around her, that storm stayed with her.

Her memory lines up with what's recorded in the Boca Grande Historical Society's archives. According to accounts collected by the Society, the 1921 hurricane washed away nearly all of the homes on Cole Key — the last key before Gasparilla Island. One longtime resident of the fishing village recalled the water being so high that she had fishing boats tied to her front porch. Another remembered it as the highest water he'd ever seen on Gasparilla Island, driven less by wind than by an enormous tide. That same storm also destroyed the original bathhouse at the Gasparilla Inn, which had only opened its doors about eight years earlier.

I can't tell you with certainty every detail of what my grandmother and her family went through that day. What I can tell you is that her memory of flooding from that storm, and the documented history of what happened on Cole Island, point to the same event. And by her account, nothing in her lifetime — and nothing in mine, until recently — ever matched it.

Before the Bridges, and After

It's easy to forget, looking at today's causeway and bridges, that this kind of access to Gasparilla Island is relatively recent. The Boca Grande Causeway didn't open until 1958. Before that, getting on or off Gasparilla Island meant a boat, a rail line, or nothing at all. Cole Island was boat access only. When my grandmother's family faced that 1921 storm, there was no bridge to cross and no dry storage options for the boat at the marina. Whatever they did, they did it on the water or they stayed put. My grandmother wasn't the only one in my family who lived that reality. My mother and father did too, for years before the causeway finally connected the islands to the mainland.

Today, of course, we have the causeway, and for most of us on Gasparilla Island that means a real road off the island when a storm approaches. But for Little Gasparilla Island, Cayo Costa, and Useppa Island, that older reality never fully went away. These are still boat-access-only islands. There's no bridge, no car, and no shortcut. If you own property on one of them, your evacuation plan has to account for that from the start, not as an afterthought once a storm is already in the forecast.

Even once you're off the island, the evacuation isn't over. Southwest Florida has grown enormously, and when a storm approaches, everyone along this coast is trying to move inland at the same time, on the same roads. More development means more cars and slower going than it used to be. That's one more reason not to wait until the last minute. Getting off the island isn't the only concern.

Even on Gasparilla Island itself, the causeway doesn't behave the same way for every kind of traffic. The swing bridge stays open to car traffic, but it closes to boat traffic once winds reach a level set by the Coast Guard and the bridge tender monitoring conditions. If you're planning to move a boat ahead of a storm, don't assume you'll have until the last minute. Check current conditions and closure information directly with the Gasparilla Island Bridge Authority or the bridge tender on VHF Channel 09, and plan your timing well ahead of the forecast winds, not against them.

Getting the Boat Ready

After years on the water, both personally and professionally, I've seen what tends to hold up in a storm and what doesn't. A few things I always come back to:

Decide early: haul out, or stay in the water. If you're hauling out, don't wait until the yards are full. Boatyards fill up fast once a storm is in the forecast, and the ones that will take you get more particular the closer the storm gets.

If staying in the water, double your lines and add chafe protection everywhere a line touches a fitting, cleat, or piling. Chafe is one of the most common reasons boats break free in a storm, and it's one of the easiest things to prevent ahead of time.

High water isn't the only concern. Most people planning for a storm think about flooding and storm surge, and that's real. Lines that look plenty long on a calm day can come up short when the water rises several feet, so give yourself extra scope. But hurricanes can cause both extremes. Extreme low water is just as possible, sometimes low enough to ground a boat, restrict your draft, or close off a channel you'd normally run without a second thought. Plan your lines, your timing, and your escape route for both extremes, not just the high water everyone expects.

If you're considering anchorage or a haul-out at one of the South Gulf Cove yards, plan around the lock. The South Gulf Cove lock, operated by Charlotte County Public Works, also serves as a flood-control gate for that canal system, and its operating schedule can change or close entirely around a storm. Don't assume you'll have normal access on your usual timeline. Check current status and any storm-related advisories directly with Charlotte County Public Works before you commit to a plan that depends on getting through the lock.

Remove anything that can become a sail or a projectile. Canvas, cushions, electronics, and anything loose on deck should come off the boat, not just get tied down.

Waterfront Home Prep

For waterfront homeowners, a few practical, general items are worth checking well before a storm is on the radar:

Know your dock and lift. Understand how your lift is rated and what, if anything, the manufacturer or installer recommends for high-wind conditions.

Understand your flood zone. Knowing your property's flood zone in advance gives you a much clearer sense of what to expect and how to prepare, rather than trying to figure it out as a storm approaches.

Secure or remove exterior items. Furniture, potted plants, and anything else that can move in high wind should be brought inside or secured well ahead of time.

Review your insurance coverage before the season, not during it. I'm not able to advise on specific policies or coverage questions, but I'd encourage every waterfront owner to have that conversation with their insurance professional early in the season, well before a storm is approaching.

Looking Ahead

A hundred years ago, my grandmother rode out a storm on an island with no bridge and no road, and the flooding she remembered stayed with her for the rest of her life. For a century after that, nothing came close to it, until Helene and Milton arrived within weeks of each other. Storms like these are part of life on these islands, the same as they were for the Cole family in 1921. The best thing any of us can do is stay prepared, stay informed, and take the season seriously every single year, whether or not the last one was quiet.

Next Month in The Waterfront Advantage

Waterfront & Island Insight #003

Sailing into Fall. As the season turns, I'll share what changes on the water this time of year, and what it means for boaters, anglers, and waterfront owners along our coast.