Postcards from the Island
Stories from
Key West.
History with the varnish scraped off — hurricanes, cigar factories, secessions, and sunset rituals older than the tourism. Written for people who want to understand the island, not just walk it.
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Labor Day 1935 — the hurricane that unmade the railroad
By MDKW editors · July 4, 2026 · 8 min
The strongest Atlantic hurricane to make landfall in the United States tore into the Middle Keys on September 2, 1935. It killed hundreds, ended Flagler's railroad in a single afternoon, and rewrote what the Keys would become.
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Cigar City — when Key West rolled a hundred million cigars a year
By MDKW editors · July 2, 2026
In 1885 Key West was the largest city in Florida, richer per capita than Chicago, and the cigar capital of the world. Two hundred factories, ten thousand Cuban rollers, and a hundred million cigars a year. Then Tampa poached the industry in one decade.
The Conch Republic — the day Key West seceded from the United States
By MDKW editors · July 1, 2026
On April 23, 1982, the U.S. Border Patrol set up a checkpoint on US-1 at Florida City that treated everyone coming out of the Keys as a suspected foreign national. Key West's response: declare independence, wage a one-minute war, and immediately apply for foreign aid.
The Hemingway House and the sixty-something-toed cats
By MDKW editors · June 30, 2026
Ernest Hemingway lived at 907 Whitehead Street from 1931 to 1939 — his most productive decade. The house is a museum. The cats descend from a six-toed white tom named Snow White given to him by a ship's captain in the 1930s.
Mallory Square Sunset Celebration — the nightly ritual
By MDKW editors · July 5, 2026
Every night, two hours before sunset, Mallory Square fills up. Buskers, jugglers, a bagpipe act that's been running since the 90s, conch shells blowing when the sun hits the water. It's free, it's older than the postcards, and it's still the best free show on the island.
Dry Tortugas — Fort Jefferson, 70 miles west, and the reef nobody talks about
By MDKW editors · July 6, 2026
Seventy miles west of Key West, in the middle of open Gulf water, sits a massive unfinished Civil War fort on a coral island. Getting there takes a day. The snorkeling on the moat wall is the best in the continental United States. Almost nobody goes.
Fort Zachary Taylor — the island's best beach hides behind a Civil War fort
By MDKW editors · July 7, 2026
Everyone goes to Smathers or Higgs. The locals go to Fort Zach. Six dollars to enter, the cleanest sand on the island, deep water 15 feet offshore, shade from the pines, and a Union fort attached that's older than the Civil War.