The drive from Miami to Key West on US-1 covers 160 miles and crosses 42 bridges over open water — the final 110 miles on the Overseas Highway after the mainland ends at Florida City. Before the Keys start, two stops in Homestead are worth a half day each: Coral Castle, where one man carved 1,100 tons of limestone solo over 28 years without any witnesses or explanation; and Everglades National Park, where the Anhinga Trail puts alligators and wading birds within a few feet of a paved path. Jonathan Dickinson State Park in Hobe Sound, 90 miles north of Miami on US-1, is the natural overnight stop for anyone driving the route from central or northern Florida.
Jump to: Before Miami: Staging From the North · Homestead: Gateway to the Keys · Key West · Planning Notes
Before Miami: Staging From the North
If starting from Orlando, Jacksonville, or anywhere on Florida's east coast, Jonathan Dickinson State Park sits 90 miles north of Miami on US-1 — a full-day stop or natural overnight before the push south to the Keys.
Jonathan Dickinson State Park Must-see
Martin County · Hobe Sound
Jonathan Dickinson State Park covers 11,500 acres on Florida's Treasure Coast between Stuart and Palm Beach Gardens — a stretch of US-1 otherwise defined by strip development and condo towers. The Loxahatchee River running through the park is one of only two nationally designated Wild and Scenic Rivers in Florida; twice-daily manatee-watching boat tours depart from the park marina year-round ($32/adult, 2 hours). Nine miles of the Florida National Scenic Trail pass through the park with access to river paddling, pine flatwoods, and scrub habitat. Kayak rentals at the marina launch onto a river corridor with no visible development for miles in either direction. The park has 135 campsites and cabin rentals, making it a viable overnight if staging the Keys road trip from the north. It's at mile marker 0 of US-1 in Hobe Sound — 15 miles north of Stuart, 90 miles from Miami.
Homestead: Gateway to the Keys
Homestead sits 30 miles south of Miami and 8 miles north of Florida City, where the Overseas Highway begins. Both stops below are within 10 miles of each other and can be done in a single day before continuing south.
Coral Castle Must-see
Miami-Dade County · Homestead
Coral Castle at 28655 South Dixie Highway is a 1.1-acre compound built from 1,100 tons of oolite limestone — carved and moved entirely by Latvian immigrant Edward Leedskalnin between 1923 and 1951, alone, at night, without powered machinery or any recorded construction method. Leedskalnin died in 1951 without explaining how he quarried, shaped, or moved stones weighing up to 30 tons; the engineering methods remain genuinely unknown. The compound includes a 28-ton obelisk, a 9-ton swinging gate balanced so a child can push it with one finger, a crescent fountain, a working sundial accurate to within 2 minutes, and stone furniture scaled to precise measurements. Allow 90 minutes. Admission is $18/adult; open 8 a.m.–6 p.m. Sunday–Thursday, 8 a.m.–8 p.m. Friday–Saturday. The site sits directly on US-1, adding zero detour to the drive south.
Everglades National Park Must-see
Miami-Dade County · Homestead
Everglades National Park's Ernest F. Coe Visitor Center entrance is at the south end of Homestead on SR-9336 — 8 miles from Coral Castle, right before the Keys turn-off. The park covers 1.5 million acres of subtropical wilderness: sawgrass prairie, mangrove forest, coastal lowlands, and Florida Bay. The Anhinga Trail at the Royal Palm Visitor Center (4 miles from the entrance) is the most productive 0.8-mile walk in the park — anhingas drying wings, great blue herons stalking the waterway, and alligators resting within 3 feet of the paved path year-round. The Flamingo Visitor Center, 38 miles inside on Florida Bay, has kayak rentals for the mangrove backcountry creeks. Dry season (December–April) brings fewer mosquitoes and concentrated wildlife around receding water. Park admission is $35/vehicle; the America the Beautiful annual pass ($80) covers re-entry and national parks beyond Florida.
Key West
Key West is 110 miles from Florida City on the Overseas Highway — 42 bridges over open water, the longest of which (the 7-Mile Bridge near Marathon) has no gas stations or exits midspan. The island is 4 miles long and 1 mile wide; the entire Historic District is walkable.
Key West Historic District & Duval Street Must-see
Monroe County · Key West
Key West's Historic District covers the northwest quarter of the island — a dense grid of Victorian conch houses, two-lane streets, and the westernmost point in the continental US. Duval Street runs the full north-south length of the district and concentrates the bars, restaurants, and shops; it's an easy 20-minute walk end to end. Mallory Square at the western waterfront hosts a free nightly sunset celebration with jugglers, musicians, and fire performers beginning 2 hours before sunset — a Key West tradition since the 1960s. The Hemingway Home on Whitehead Street ($16) tours the house where he wrote A Farewell to Arms and For Whom the Bell Tolls; 40+ six-toed cats descended from Hemingway's original cat roam the property. The entire district takes a full leisurely day to explore with meals and stops.
Blue Heaven (Key West) Must-see
Monroe County · Key West
Blue Heaven on Thomas Street in Bahama Village operates in a former bordello and cockfighting arena — open-air tables on a gravel patio shaded by a banyan tree, roosters and chickens wandering between chairs, and a live reggae band playing from a small raised stage. The menu runs to lobster Benedict ($28), shrimp and grits, banana pancakes, and a scratch-made Key lime pie that regulars order by the slice. Weekend brunch waits run 1–2 hours on busy mornings; arrive before 8 a.m. or after 2 p.m. for the shortest lines, or book the 5–8 p.m. dinner shift a week ahead. Blue Heaven is 10 minutes on foot from Duval Street, at 729 Thomas Street — look for the hand-painted sign at the corner of Petronia.
Planning Notes
Plan your visit: Miami is the natural staging city for the southern end of this trip — see our Miami guide for hotel zones and same-day options in the city before heading south. For Key West planning, including where to stay and what else to see on the island, see the Key West guide. Traffic on the Overseas Highway can add 60–90 minutes southbound on Friday afternoons and northbound on Sunday afternoons when Keys residents commute; leave Miami before noon on Fridays or plan to drive the last stretch after 7 p.m.
