Oddly, there's no overarching name for the group of mostly-connected-by-bridges islands off the Gulf Coast in the Ft. Myers/Cape Coral area. You sometimes see the term "The Sanibel Islands" but this is usually in reference to just Sanibel and Captiva. For lack of anything better, we'll call them "The Estero Bay Islands" for now. (Similarly, "The Florida Keys" is a pretty terrible and misleading name for those most famous islands at the state's southern tip, and "The Bayway Islands" isn't a very creative name either.)
Your adventure starts in Bonita Springs, where Bonita Beach Road will take you offshore onto the marvelous Little Hickory Island (which isn't so little), a highly populated, swingin' place, very beachy-restauranty-touristy. Like most of these islands, it's crawling with people, so get out here early if you hope to get a parking place for a beach access spot.
Next up is Bay's Island and Big Hickory Island (plus a bunch more accessible by boat only, like Battista Island). Not a whole lot going on here, though there's a fabulous beach on Big Hickory's northern end. Then the road takes you over a couple of unnamed islands (name those islands, dammit!) which is weird because one of them has one of the region's most beloved dog beaches. I've seen no online source that names the island it's on - they just say "Estero", which is the city that owns these keys.
Long Key is next, and Black Island - which is where you can turn off and drive over to Lovers Key and Inner Key at the Lovers Key State Park. Black Island is a strangely shaped squiggle of land that has tendrils coming off it that almost make it three different islands - and when you're standing on one arm of it looking way over at another, it might as well be so. Other islands, like Charlie Key, Monkey Joe Key, Davis Key, Little Davis Key, and Mound Key loom in the distance, inaccessible by automobile.
Estero Island may not come first to mind - if at all - when you think of party-tourist hotspots in Florida, but let me tell you, this place is hoppin'. After the mangrove nature trails of the last few islands, you may be shocked to find this one completely built up with resorts, beach cottages, and row upon rows of stores and bars. The beaches here are fantastic, and I suspect a lot of people, fed up with trying to find a place to park down the road at Sanibel, just say to heck with it and make camp here. There was a biker event going on when I was recently here, and the place had that quintessential good-times-in-Florida feel.
Meanwhile, inside the bay, plenty more islands lie in wait for your exploration via boat. Most are unnamed, but at least three are: Dog Key, Julie's Island, and Starvation Key.
Beyond Estero Island we find San Carlos Island and a community that is partially built on mainland swamp and partially on artificial islands; the maps list it as Siesta V, and about it I can find very little. You cross over these on your way back to the mainland for just a bit before heading back over the puddle to enter Summerlin Road, which quickly changes its name to McGregor Blvd, and then becomes the Sanibel Causeway.
Once on the causeway, first up is Connie Mack Island, a lovely little boating community mostly surrounded by swampland. Then there's Punta Rassa, an almost-island which for some reason has a much more colorful history than some of its neighbors. It was once a thriving shipping port for cattle, was a key site during both Seminole Indian Wars and the Civil War, and its telegraph office was where America first learned of the sinking of the U.S.S. Maine in Cuba in 1898.
Then we have Island A and Island B, two beautiful must-pull-over spots on the causeway. What they lack in imaginative names, they more than make up for in tranquility. Personally, I'd be happy to stop here and kick back on Islands A and B and call it a night. Estero has all the action one needs and A & B have all the tropical peacefulness. But for many tourists, the real goal is still to come: Sanibel Island.
Sanibel's a weird and rather creepy place. You can never really get a grip on it because it's a mishmash of highly touristy places intermingled with deep jungle-like nature preserves. There are long stretches of civilization followed by even longer spooky swampy stretches of "Where the hell am I?"
The reason Sanibel is so popular is because it's regarded as the ultimate place to collect exotic shells on the beach in Florida, and perhaps the entire nation. This is in part because Sanibel is a geographical oddity: a barrier island that sticks out east-west rather than hugging the coast north-south. For this reason, they say, flotsam and jetsam from the sea are more likely to wash up here than elsewhere.
But there's even one more island drivable past Sanibel: Captiva Island. Artist Robert Rauschenberg made Captiva his home and workplace, and his studio still stands today, just as he left it when he died. His estate remains the largest landowner in the area. The photo below was taken at the Green Flash Dock in Captiva, overlooking Buck Key in the distance.
North Captiva Island is not connected to Captiva Island by road, but is home to many rich folks who go get their groceries by plane or boat.
If you're lucky enough to have said boat, there's still loads more islands past North Captiva that properly belong classified with this grouping before you reach the huge mouth of Charlotte Harbor. To name just a few: Lacosta Island, Punta Blanca, Black Key, Wood Key, Josslyn Island, Cabbage Key, Useppa Island, The Panther Keys, Bokeelia Island, Patricio Island, Burgess Island, etc.
And don't forget Pine Island, a massive one that runs parallel to much of Sanibel and Captiva, and is accessible by car from the mainland but it's a very long drive to get back up and around to its entrance. So much so, that it's probably something you'd do on a different day's excursion. But if you go, bring your metal detector.
Me, I just wanna go back to Island A.