This island used to be a little self-sufficient 1800s town, complete with a bowling alley. Now its ruins are a state park (closed until fall 2026 though).
This island used to be connected by a drawbridge to Marathon. They blew up the moving part of the drawbridge in 2010 because it was too expensive to maintain safely. Kayak over and see the old overgrown roads and radio transmission tower.
If you’re kayaking over to Boot Key, why not stop at West Sister Rock near its southeast corner. There’s nothing here except one of those signposts with distances to other famous landmarks. East Sister Rock, on the other hand, is taken up by a multimillion dollar home.
Somebody tell me what is going on here. Google Maps shows that the Niles Road Trail, a little walking path from the northern end of Niles Road to the water’s edge, used to (?) connect to the little island across the water. One guy I talked to said there used to be a wooden foot bridge but I cannot find any evidence of this.
Mr. Perky thought if he built a big house for bats, they would move in and eat the mosquitoes that bothered him. He had this built in 1929, any bats that were once there were gone by 1930, it blew down during Hurricane Irma in 2017, and John Oliver mentioned it on his show in 2025.
The old seven mile bridge had a rotating swing span to let boats through, with a little control room above the traffic level. Peter Fancher was on duty in March 1981 when a catastrophic explosion on the swing span killed him instantly. There’s a plaque in his memory embedded in the side of the new seven mile bridge, but good luck spotting it at 55 mph.
Replicas of the original Lourdes, France grotto exist all over the world. But the one at The Basilica of St. Mary in Key West is credited with protecting the island from direct hurricane hits since it was dedicated in 1922.
This manmade channel on the bay side of Islamorada is demarcated by posts, and Hurricane Donna deposited a toilet seat on one of them in 1960. Now, instead of leaving a lock on a bridge, people leave a toilet seat on an empty post for anniversaries and celebrations.
Patron saint of the Florida Keys, Jimmy Buffett, played his first gig in this bar in 1971. The hotel around it has gotten nicer since then, but you can still grab a free hot dog from the crockpot next to the popcorn machine.
Sloppy Joe’s bar in Key West draws the big Duval Street crowds and is often mentioned along Ernest Hemingway’s name. The original Sloppy Joe’s is now called Captain Tony’s Saloon, holding on to more of the old Key West feel. Ask about the ghost story around the tree growing inside the bar.
A lot of this bar’s original kitsch was about being out of the way and hard to find, but everyone has GPS now. It’s also hard to miss the dollar bills stapled to the walls. The key deer in the area are a little more elusive!
Everyone loves Fred, the (invasive) Australian pine tree somehow growing out of the asphalt of the closed-off part of the old seven mile bridge. Fred even survived hurricane Irma! But it is trespassing to climb up on the bridge to say hi.
Sure they’re cute, but yeah don’t do this.