On January 21, 1912, Henry Morrison Flagler boarded his private rail car in Palm Beach, Florida, for a history-making southbound journey. The oil tycoon, hotel developer and rail magnate was 82. Seven years earlier, he’d decided to extend his existing Florida East Coast Railway from Miami – over land, swamp and open water – to Key West, terminus of the Florida Keys. On January 22, Flagler arrived in the island city to a hero’s welcome. “My dream has been realized,” he said to the assembled crowd. Though the Key West extension was lost to a hurricane in 1935, the railway sparked the transformation of a tropical wilderness into Flagler’s vision of paradise: commerce, sunshine and palm trees. Follow the historic rail route for a stunning look at continental America’s southernmost state.
Leg One: Palm Beach to Miami (145 km)
Flagler left for Key West from Whitehall, a mansion of marble and gold in Palm Beach, where he and his wife wintered. Now known as Flagler Museum (One Whitehall Way, off Cocoanut Row), it houses original furnishings, Flagler’s original railcar and other exhibits (561-655-2833; Flagler Museum).
But don’t leave pretty Palm Beach without a look at another Flagler masterpiece, The Breakers Palm Beach (888-273-2537; The Breakers). Turn left from Whitehall Way onto Cocoanut Row, right on Royal Poinciana Way and right again onto North County Road. The hotel is on the left. Modelled after Rome’s Villa Medici and opened in 1926, The Breakers sits amid manicured tropical gardens, rows of ancient palms, a sparkling private beach and Florida’s oldest 18-hole golf course. Splurge on a night’s stay, or at least a bite at The Seafood Bar. From here, carry on along County Road, then turn left onto Royal Palm Way and right onto beach-bordered South Ocean Boulevard, which becomes the A1A and runs parallel to Flagler’s tracks (still in use as a freight line).
Follow the A1A to Miami through an unbroken chain of bustling resort towns. After passing the stunning, Mediterranean-inspired mansions south of Palm Beach, the road turns inland slightly, skirting cities that owe much to Flagler’s efforts in the late 19th century. As it pushed south to Miami, the railroad gave rise to colourful, vibrant Delray Beach and brought agricultural pioneers to Boca Raton, now a ritzy city of Moorish architecture, palm trees and white beaches. It also sparked growth at Fort Lauderdale, known today as the Venice of America because of its canals.
The City of Miami shares a similar history. It was incorporated in 1896, just months after the first train’s arrival. Flagler built the port, established the water and electricity systems, laid out streets and even established the first newspaper. For all this, he refused the city’s offer to rename itself in his honour.
The A1A offers a charming introduction to this city of 2.5 million. As Collins Avenue, it passes the beautifully preserved early to mid-20th century buildings of the Art Deco district. From there, it heads downtown into quadrants of numbered roads that ascend in all directions from, appropriately, the intersection of Flagler Street and Miami Avenue.
Good Eats: Overlooking Miami River, Casablanca ( Casablanca; 305-371-4107) serves seafood with a Latin-American flavour. From the patio, watch fishermen call it a day at sunset.
Good Sleeps: The Miami River Inn ( Miami River Inn; 800-468-3589) once charged 50 cents a night for a room. This charming spot, just outside downtown, is still a steal, starting at US$89 a night.
Leg Two: Miami to Islamorada (130 km)
From Miami, leave the A1A for the US1 south to Homestead. Just beyond the latter, the highway rises above serene and grassy marshlands. After Lake Surprise, which Flagler’s engineers crossed via a bed of clay dredged from the Atlantic, you’ve entered the Keys, a coral archipelago that curves southwest from just off Miami’s south shore to the open water 145 km north of Havana, Cuba. On Key Largo, largest of the Keys, begins a stretch recognized by the U.S. Department of Transportation as the Florida Keys Scenic Highway, which traverses the islands via former railroad bridges to Key West.
Dense stands of tropical hardwood (and a fair amount of roadside retail) soon give way to patches of mangrove, a scrubby tree that rises from the water on spidery roots. Henry Flagler would have steamed past the same forests in January 1912. But the 1935 Labour Day hurricane obliterated much of the track in this area, and the line was never rebuilt. Instead, the right-of-way and remaining bridges were sold to the State of Florida for a highway.
A coral limestone memorial at mile marker 81.5 in Islamorada depicts, in art deco relief, that powerful storm – one of the worst to ever hit the U.S. Today, Islamorada, a village of five islands, is otherwise revered for sport fishing along North America’s only coral reef, just offshore in the crystal-blue waters of the Florida Straits.
Good Eats: Open since 1947, the Green Turtle Inn (305-664-2006; Green Turtle) is a casual but classy roadside diner offering uniquely Keys fare, including turtle chowder.
Good Sleeps: With its beach and inviting pool, the Islander Resort (800-753-6002; Islander Resort) epitomizes laid-back Keys culture.
Leg Three: Islamorada to Key West (130 km)
Roughly 50 km south, Seven Mile Bridge spans open water – the Atlantic at left, the Gulf of Mexico, right – between Knight’s and Little Duck Keys, and runs alongside Flagler’s original viaduct, a chain of brick arches that bolstered the railroad’s reputation as the eighth wonder of the world.
Turn left at mile marker 37 into Bahia Honda State Park. Here, Flagler’s original trestle bridge, no longer in use, crosses the deepest waters encountered by the builders – sometimes 10 metres. After a dip in warm waters, continue southward for Key West, hopping bridge-by-bridge over more than a dozen islands in less than 50 km.
A century ago, 10,000 citizens and dignitaries greeted Flagler’s train with fanfare. A celebratory atmosphere still defines the island, particularly touristy Front and Duval streets. As you arrive, veer right onto North Roosevelt Boulevard and right again onto Palm Avenue, which turns into Eaton Street. Make a left at Whitehead Street, where the US1 ends (Mile 0), at Fleming Street. Carry on to South Street and turn left, then go right at Reynolds Street to the end of the road and the Mediterranean-style Casa Marina, the Key’s largest resort and the last Flagler hotel built in Florida.
In the end, Flagler’s railroad extension never turned a significant profit. “I would have been a rich man,” he once said, “if it hadn’t been for Florida.” The quip raises a question: what might Florida have been without him?