Islamorada

Islamorada isn't one island. It's a village of islands — Plantation Key, Windley Key, Upper Matecumbe, Lower Matecumbe, plus Indian Key and Lignumvitae offshore. Eighteen miles of highway with water on both sides, a fishing fleet that is genuinely without equal, and more history per mile than anywhere else in the chain.

Why the fishing is different here

Geography again. Islamorada sits between Everglades National Park and the Florida Straits, directly on the migration route of an enormous number of large fish species. Step off the dock and within twenty minutes you can be in three completely different fisheries:

• The backcountry and flats — skinny water on the Florida Bay side for bonefish, permit, tarpon, and redfish. Sight fishing: you pole the flats and cast at fish you can see. This is where saltwater fly fishing and backcountry sport fishing were born.
• The patch reefs and the reef line — snapper, grouper, cobia, and the everyday bread-and-butter fishing that feeds families.
• Offshore, past the reef — the Gulf Stream edge for sailfish, mahi, tuna, wahoo, and marlin.

Islamorada is said to host the largest fishing fleet per square mile in the world, and fishing legends including Ted Williams, Jimmy Albright, and Cecil Keith made their homes here. Albright in particular is a name every fly angler knows — the knot is named after him.

The purple island

The name comes from Spanish and translates roughly as "purple island." There are competing explanations and locals will argue about them cheerfully. One holds that it's from the purple sea snails that gather offshore and occasionally wash up in numbers, tinting the shoreline. Another credits crushed conch shell mixing into the sand and giving the shore a purple cast. A third simply points at the sunsets. Take your pick.

The history stops

The Hurricane Monument (MM 81.6)

Right on the highway, and the most important thing to stop for in the Upper Keys. Dedicated in 1937, it commemorates the hundreds who died when the 1935 Labor Day Hurricane — the most intense storm ever recorded to strike the United States — came ashore right here. A crypt beneath the monument holds the ashes of many of the dead. Ten minutes and it will change how you see the drive.

Indian Key Historic State Park

An island you can only reach by boat or kayak, and one of the strangest places in Florida. In the 1830s this eleven-acre key was a thriving wrecking settlement — a town with streets, a hotel, and warehouses, serving as the county seat. It was destroyed in an 1840 raid during the Second Seminole War and never rebuilt. What's left is a grid of streets in the scrub, cisterns, and foundations. Walking it is genuinely eerie.

Lignumvitae Key Botanical State Park

Also boat-only. One of Florida's few remaining tropical hardwood hammocks — an intact West Indian forest that shows you what these islands looked like before everything was cleared. There's a 1919 house on it and guided walks. Bring bug spray; this is not optional.

Windley Key Fossil Reef Geological State Park (MM 85.5)

An old quarry that supplied "Keystone" building material and cut stone for Flagler's railroad. The quarry walls are polished cross-sections of ancient coral reef — you're looking at fossilized reef structure at eye level, with the saw marks still visible. Quiet, cheap, and unlike anything else.

Florida Keys History & Discovery Center (MM 82)

The best small museum in the Upper Keys, with permanent exhibits on the wreckers, the railroad, the 1935 hurricane, and the pioneer families.

The rest of it

• Theater of the Sea (MM 84.5) — one of the oldest marine parks in the world, opened 1946, in a former quarry.
• Robbie's Marina (MM 77.5) — feeding the tarpon off the dock is the most reliably delightful five dollars in the Keys, and the boats to Indian Key and Lignumvitae leave from here.
• Anne's Beach (MM 73.5) — a shallow, soft-bottomed public beach on Lower Matecumbe with a boardwalk through the mangroves. Free, and excellent with small children.
• Founders Park (MM 87) — beach, pool, and marina; the village's main public park.

Practical notes

• Feel: more polished and more expensive than Key Largo, with genuinely good restaurants and resorts. It's the fine-dining stretch of the Keys.
• Drive time: about 1.5 hours from Miami; about 1.5 hours on to Key West.
• Best base if: you want to fish seriously, or you want a comfortable middle-of-the-chain home for exploring both directions.
• Sunday afternoons: the northbound highway backs up with Miami weekenders heading home. Plan around it.