Magnificent Gulf View Condo in Shipp's Landing
- Free Cancellation
The Florida Keys are a 113-mile chain of islands curving southwest from the mainland to within 90 miles of Cuba. The Overseas Highway (US-1), built on the bones of Henry Flagler's 1912 Florida East Coast Railway, links them with 42 bridges — the longest, the Seven Mile Bridge, opened in 1982 to replace Flagler's original. Key Largo, Islamorada, Marathon, Big Pine Key, and Key West are the five anchor towns; mile markers count down from MM 113 in Florida City to MM 0 at the corner of Whitehead and Fleming in Key West.
The Florida Keys begin at Key Largo (MM 113) and end at Key West (MM 0), a 113-mile drive on US-1 that takes about 3.5 hours nonstop and ten times that with the right stops. Henry Flagler's Florida East Coast Railway opened the original Overseas Railroad on January 22, 1912 — the 1935 Labor Day Hurricane destroyed it, and the state rebuilt the right-of-way as the Overseas Highway four years later. The current Seven Mile Bridge (6.79 miles, 1982) parallels Flagler's original, which is now a fishing and biking pier.
Each segment of the chain has its own personality. Key Largo (MM 113–90) is the dive capital, home to John Pennekamp Coral Reef State Park — the first underwater park in the United States, opened in 1963 — and the Christ of the Abyss statue in 25 feet of water on Dry Rocks reef. Islamorada (MM 90–73) is the sportfishing hub; the Lorelei Cabana Bar at MM 82 sells the most photographed sunset frozen drink in the Keys. Marathon (MM 65–47) hosts the Turtle Hospital and the Seven Mile Bridge access. Big Pine Key (MM 33–29) is the Key deer refuge — a subspecies that grows to about 70 pounds. And Key West (MM 4–0) is the southernmost city in the continental U.S., 90 miles from Cuba, with Hemingway's house, Mallory Square sunset, and Duval Street.
Plan five to seven days to drive the chain end to end with real stops. Book Bahia Honda State Park camping or the Hawks Cay Resort early — both fill 11 months out for the December–April high season. Sunblock, polarized sunglasses, and reef-safe sunscreen (mandatory by Key West ordinance since 2021) are non-negotiable. The Dry Tortugas day trip from Key West — 70 miles further west, only reachable by ferry or seaplane — is the single best day in the Keys for anyone who's already done the standard chain.
A short loop through the exhibits, encounters, and shows that make this stop worth a half-day on its own.
The longest bridge in the Keys at 6.79 miles, opened January 1982 to replace Flagler's 1912 original. The old bridge runs alongside as a fishing/biking pier connecting Marathon to Pigeon Key. Photographable from both ends; the eastbound shoulder pull-off at MM 47 is the standard sunset spot.
The first underwater park in the U.S., opened in 1963, protecting 70 nautical square miles of living reef off Key Largo. Glass-bottom boat tours run three times daily over Molasses Reef ($32 adult); the Christ of the Abyss bronze statue sits in 25 feet of water on Dry Rocks for snorkelers and divers.
Repeatedly named the best beach in Florida. Three swimming beaches plus the old Bahia Honda Rail Bridge — Flagler's surviving steel cantilever you can still walk halfway across for the postcard shot. $9 per car, day-use parking caps fill by 10 AM December–April.
907 Whitehead Street, Key West. Hemingway lived here 1931–1939 and wrote A Farewell to Arms, The Snows of Kilimanjaro, and Death in the Afternoon on the property. The famous descendants of his polydactyl (six-toed) cat Snow White still roam the gardens — about 60 of them, all named after celebrities. $19 adult; 9 AM–5 PM daily.
A nightly festival at the Key West harbor, starting about 90 minutes before sundown. Tightrope walkers, fire-eaters, escape artists, and a guy with a trained-cat circus that's been performing since 1985. Free; cruise ship night's a zoo, walk over from Duval Street fifteen minutes early.
Seventy miles west of Key West, only reachable by ferry (8 AM departure, $220 round trip including lunch) or seaplane. Fort Jefferson — a 16-million-brick coastal fortress begun in 1846 — sits on Garden Key. Snorkel the moat wall (lobsters, parrotfish, the occasional nurse shark) before the ferry leaves at 3 PM.
The Key deer is a subspecies endemic to the Lower Keys, standing about 30 inches tall and weighing 65–80 pounds — fully grown adults are the size of large dogs. The 9,200-acre National Key Deer Refuge is centered on Big Pine; sightings are routine on Key Deer Boulevard at dawn and dusk. Free; do not feed.
Robbie's of Islamorada has fed silver king tarpon off its docks since 1976. $5 dock entry, $5 bucket of bait fish; the 100+ resident tarpon (4–6 feet long) leap clear of the water for handouts. Free pelican photobombs included. Daily 8 AM–5 PM.
The Overseas Highway is open 24/7. Most attractions, state parks, and dive shops run 8 AM–5 PM. Hurricane season runs June–November; the high season (December–April) brings the calmest weather, the best dive visibility, and the highest rates. Sunset at Mallory Square in Key West starts about 90 minutes before official sundown.
Note · Dry Tortugas ferry from Key West (departs 8 AM, returns 5 PM) requires advance booking — drytortugas.com sells out 60 days ahead in winter. Bahia Honda State Park caps day-use parking; arrive before 10 AM December–April.
Per-person admission. Buy in advance to skip the gate line.
Most stops in the Keys are pay-as-you-go — no chain pass covers everything. The Overseas Highway itself is free; budget separately for state parks, dive trips, and the Dry Tortugas ferry. Bring cash for the smaller roadside fish shacks and No Name Pub.
Plan your route