| Introduction: The Shipwrecked Train | |
1 | A Land Apart | 1 |
| The founding of Key West | |
| Turtling, sponging, and wrecking | |
| Years of prosperity | |
| First proposals for an "overseas" railway | |
2 | Salvage, Starch, and Seminoles | 35 |
| Early life on the Biscayne Bay frontier | |
| The bizarre saga of old Fort Dallas | |
| Seminole Indians and Seminole Indian traders | |
3 | Sails and Rails | 64 |
| The arrival of the "yachting set" in Biscayne Bay, c. 1880 | |
| The life and times of Henry Flagler | |
| Completion of the first railway to Biscayne Bay | |
4 | Dusty Old Town | 91 |
| Cubans and Cuban cigars | |
| Key West's golden age, c. 1890 | |
| Key West's growing economic problems | |
| Revival of interest in an "overseas" railway | |
5 | A Perfect Wilderness | 123 |
| The taming of the Biscayne Bay wilderness | |
| The founding of Miami, 1896 | |
| Miami's violent early history | |
| Dawn of the Miami tourist age | |
6 | Eighth Wonder | 150 |
| The construction of Flagler's marvelous Overseas Railway, 1906-1912 | |
7 | American Frontier, American Riviera | 184 |
| The saga of John Ashley, early Miami outlaw | |
| Everglades drainage and the founding of Moore Haven | |
| Carl Fisher's Miami Beach dream | |
| George Merrick's Mediterranean vision for Coral Gables | |
| The passing of John Ashley and the coming of the boom | |
8 | Castles in the Air | 210 |
| The Great Miami Boom and the bust that followed, 1925-1926 | |
9 | Recurving Disturbance | 238 |
| The Great Miami Hurricane of September 1926 | |
| The destruction of Moore Haven | |
| Casualties and consequences | |
10 | Poverty in Paradise | 274 |
| Key West's economic collapse, 1912-1934 | |
| The Key West hurricane of 1919 | |
| Hemingway in Key West | |
| Contemporary developments in Miami | |
| Down and out in the Florida Keys: tramps and "bonus marchers" | |
| The FERA and the foundations of modern Key West, 1934 | |
11 | No Return | 299 |
| The Labor Day Hurricane of 1935 | |
| The fate of the last train | |
| The death of the Overseas Railway | |
| Epilogue: September, Remember | 335 |
| Index | 339 |