Also called the Florida Keys Scenic Highway, this water-flanked road began life as an elevated railroad line, transformed into a hurricane-proof highway in the 1930s.
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Route: Miami to Key West
Distance: 151 miles
Start: Southern Miami
Drive Route 1 (63 miles), stopping to snorkel or take a glass-bottom boat tour at John Pennekamp Coral Reef State Park, with its incredible underwater gardens. Snorkelers will also love Windley Key Fossil Reef (16 miles) and its ancient limestone quarry remains.
Pit stop on Marathon Key (29 miles) for lunch—try the raw bar or seafood enchiladas at Castaway Waterfront Restaurant & Sushi Bar—as well as an afternoon of boating or seaside golf. You can also walk the original Seven Mile Bridge, part of the Florida Keys Overseas Heritage Trail.
Check in to Little Palm Island Resort & Spa (shown here; rates start at $690, see our review) from the passenger ferry and relax on a private 5½-acre island of palm trees and plush bungalows. Take a dip in the sea the following morning.
Finish your casual island-hopping drive in Key West (27 miles)—visit the Ernest Hemingway Home and Museum, try the sautéed pink shrimp at Blue Heaven, and enjoy the Duval Street nightlife.