Oh, the contradictions of Florida.
It’s seen as a young state, more recently settled than, say, those in New England, but it contains North America’s oldest city.
It seems more northern than Louisiana or Mississippi, but remnants of our plantation past linger.
So do whispers of the Native Americans whose mysterious mounds still line a section of the Gulf of Mexico not far from the modern casinos of the only tribe never to sign a treaty with the American government.
Centuries of hardship have been obscured in our most notorious party city, while secrets of our Cold War history have recently been uncovered in the Everglades.
They’re all part of the perplexing, captivating puzzle of Florida.
Here are eight places to visit to reconnect with Florida’s history:
Step aside, Jamestown.
Pedro Menendez de Aviles founded St. Augustine in 1565, 42 years before the British colony at Jamestown and 55 years before the pilgrims landed in Massachusetts.
Today, the oldest permanent European settlement in North America retains its Spanish charm, with an assist from its years as the “14th Colony” during British rule in the 18th century.
Castillo de San Marcos, North America’s only existing 17th century fort, squats on the city’s eastern edge, complete with a moat, daily cannon firings and regular re-enactments. Walk in the footsteps of pirates, a trio of signers of the Declaration of Independence and Seminole Chief Osceola, who was imprisoned here at the end of the Second Seminole War.
Henry Flagler created Florida’s tourist industry by opening the spectacular Ponce de Leon Hotel, now Flagler College in 1888. The mammoth building’s terracotta Spanish Renaissance architecture and 79 Tiffany windows reflect the luxe fantasy that’s been part of Florida tourism from the beginning.
Part of the original colonial town plan, the narrow brick Aviles Street is the city’s oldest, with several house museums, restaurants, shops and a quaint European look. Don’t miss the 1798 Ximenez-Fatio House.
The Colonial Quarter is a Williamsburg-like living history compound, depicting the city in the 16th through 18th centuries. University of Florida historians ensured the accuracy of artisans’ shops selling period items, blacksmith and military demonstrations as well as the popular Taberna de Gallo restaurant.
Long before it ran North, the Underground Railroad for runaway slaves aimed South, to the marshes of Spanish St. Augustine. Here, the first free black settlement of former slaves in what became the U.S. was founded in 1738. Although there are no remains of the earth and wooden structures, visitors to Ft. Mose State Park can still view the land where the settlement stood.
The Battles of Loxahatchee, Loxahatchee River Battlefield Park, Jupiter
The last great battles of a vicious war waged against native Americans took place in what is now Palm Beach County.
In January, 1838 during the Second Seminole War, Seminole Indians and the escaped slaves they sheltered won a clash with American troops. Nine days later, the largest army assembled during the seven-year war marched to the river. Under Major General Thomas Jesup, 1,500 soldiers faced about 300 Seminoles. After inflicting more casualties than they received, the Seminoles faded back into the Florida jungle.
Later, Jesup wanted to allow the Seminoles to return to the Everglades south of Lake Okeechobee, but his government forced him to capture 500 Seminoles camped at Ft. Jupiter.
The site of the battle today is an Old Florida expanse of pine woods, cypress swamp and oak hammock.
This Amelia Island town near Jacksonville in the only city in the country to have flown eight different flags. Beginning in 1562, the old port city has been part of France, Spain (twice), England, a smugglers’ resort under the Patriots of Amelia Island, the Green Cross of Florida, Mexico, the Confederacy during the Civil War and finally, the U.S.
Today, the former Gilded Age summer resort remains a pristine village of restored 19th century homes, with a historic waterfront downtown lined with restaurants and shops.
Key West and Ft. Jefferson at Dry Tortugas National Park
When the rest of South Florida was still uninhabitable swamps before the Civil War, Key West became the richest city per capita in the country, thanks to residents’ penchant for salvaging valuable cargoes from the ships wrecked on nearby reefs. Shipbuilders constructed the quaint 19th century wooden Conch houses that decorate the city’s leafy Old Town neighborhoods. The 1830 Audubon House, whose 1970s restoration started the island city’s preservation movement, is one of the prettiest.
From the old Custom House, the 1848 Lighthouse and Ernest Hemingway’s house, all now museums, to the island’s historic inns, Key West is a lively timeline of Florida’s unique story.
Seventy miles offshore, the mid-19th century Ft. Jefferson in the Dry Tortugas was once part of a chain of forts built from Maine to California to protect a young nation. Isolated and sun-blasted, the fort housed Union deserters during the Civil War. Its most famous resident was Dr. Samuel Mudd, who set the broken leg of John Wilkes Booth after he assassinated Abraham Lincoln.
Accessible only by boat or seaplane, today the waters around the fort contain some of North America’s best snorkeling and diving spots.
Nike Missile site, Everglades National Park
For nearly 50 years after the Cuban missile crisis, this Cold War site remained a secret deep in the sawgrass swamps. Now open for public tours, Missile Base HM-69 demonstrates how close we once came to nuclear annihilation.
Built in 1964 as one of 240 Nike missile bases across the country, the base housed 150 soldiers whose barracks was painted pink, to fool the Soviets into thinking it was a civilian building.
Tours, which are given from November through April only, take visitors to the missile stands once bristling with nuclear warhead-topped missiles. Bunkers in which Americans prepared for the possibility of World War III still stand, as do the barns that contained the Nike Hercules surface-to-air missiles, designed to take down supersonic aircraft. There’s even a real Nike missile to see.
Big Cypress Indian Reservation/Miccosukee Indian Village
Hunted down, chased into the Everglades and forced onto the Trail of Tears, the Seminoles and Miccosukees had the last laugh.
The now-prosperous Seminole tribe never signed a treaty with the U.S. government and today runs casinos and tobacco shops at six reservations around the state. West of Fort Lauderdale, the Big Cypress reservation includes a rodeo entertainment complex, an airboat tour operation, RV resort and the Ah-Tah-Thi-Ki heritage museum.
Today’s Miccosukee people are descendants of about 100 who hid in the Everglades during the 19th century Indian Wars. Just west of Miami, the tribe owns the Miccosukee Resort and Gaming complex.
Farther west at the reservation on Tamiami Trail, the tribe sells examples of traditional arts and crafts at its Indian Village, where a restaurants serves Indian fry and pumpkin bread as well as frog legs and gator from the ‘Glades. An airboat ride into the Everglades takes visitors to a 100-year-old hammock camp.
Pineland Indian Mounds and Randell Research Center
For 1,500 years, the powerful and fierce Calusa Indians lived in a large city on Pine Island Sound, north of Ft. Myers. Tall shell mounds dot the 67-acre complex, where the remains of a 2.5-mile canal the Calusa dug to the Sound can still be seen. The Calusa were abducted for slaves or died of disease not long after contact was made with the Spanish in the 1500s. Ponce de Leon died after being injured during a skirmish with Calusa in Southwest Florida.
Such shell midden mounds, built by Florida’s first inhabitants including the Calusa, Jeaga, Hobe and Tequesta, once lined the state’s coastline before most became fill for roads and subdivisions. The Pineland area contains the most extensive remaining site.
Gamble Plantation Historic State Park
The last surviving antebellum plantation remaining in peninsular Florida, the Gamble Plantation began in 1844, when Virginia sugar planter Robert Gamble arrived on the rich lands near the Manatee River, near what is now Bradenton.
Built and maintained by Gamble’s 200 slaves, the plantation eventually spread to 3,500 acres, including a wharf from which he shipped sugar and molasses. With 2-foot-thick tabby walls and a large cistern, the mansion, fronted with a line of white columns, is thought to have hidden Confederate Secretary of State Judah P. Benjamin while he sought safe passage to England. The United Daughters of the Confederacy saved the house and donated it to the state in 1925.