The parade of colonial powers across Amelia Island reads like a compressed history of European expansion in the Americas. Spanish Franciscans built the Santa Maria de Sena mission here in 1573, naming the island Isla de Santa Maria. The British came and went, trading Florida for Havana in the Treaty of Paris of 1763. Lord Egmont claimed a 10,000-acre plantation that covered almost the entire island. Then the Spanish returned, loyalists fled, and by 1785 a woman named Mary Mattair, her children, and a single enslaved worker were the sole occupants left on the island after the British evacuation. The Spanish Crown let Mattair stay, granting her land within what is now Fernandina Beach. Georgia's colonial governor James Oglethorpe gave the island its current name, honoring Princess Amelia, daughter of George II of Great Britain, even though Spain still held the territory.

The early nineteenth century brought the island's most colorful chapter. In 1812, American insurgents calling themselves the Patriots of Amelia Island seized Fort San Carlos with the tacit approval of President James Madison, who wanted to annex East Florida. Congress balked, fearing war with Spain during the War of 1812, and the scheme collapsed. Then came Gregor MacGregor, a Scottish soldier of fortune who stormed the fort on June 29, 1817, with 150 men recruited from Charleston and Savannah. He raised the Green Cross of Florida over the ramparts and proclaimed the Republic of the Floridas. By September, broke and outgunned, MacGregor sailed for the Bahamas. French pirate Louis-Michel Aury moved in next, claiming the island for revolutionary Mexico and establishing a Supreme Council of the Floridas. The United States finally ended the revolving door on December 23, 1817, when a naval force captured the island and held it, as President James Monroe put it, in trust for Spain.

Spain formally ceded Florida to the United States through the Adams-Onis Treaty in 1821. The island settled into a quieter era of plantation agriculture, its fields worked by enslaved people. Then the Civil War arrived. Confederate sympathizers seized the still-unfinished Fort Clinch on January 8, 1861, two days before Florida officially seceded. Robert E. Lee himself visited in late 1861 to survey coastal defenses. Union forces took the island back on March 3, 1862, arriving with 28 gunboats under Commodore Samuel Dupont. The island became a magnet for freedom-seekers. By 1863, twelve hundred freedmen and their children lived on Amelia Island alongside just two hundred white residents. Chloe Merrick, an abolitionist teacher from Syracuse, New York, established a school and orphanage for the freedmen in 1863, later marrying Florida's Governor Harrison Reed and continuing her educational mission across the state.

Today Amelia Island moves at a pace that would mystify the filibusters and privateers who once fought over it. The communities of Fernandina Beach, Amelia City, and American Beach occupy this slender barrier island, the southernmost of the Sea Islands chain that stretches from South Carolina and the northernmost barrier island on Florida's Atlantic coast. The Amelia Island Trail connects to the East Coast Greenway, a 3,000-mile system of paths from Maine to Florida. Five golf courses wind through the live oaks and palmettos. Fernandina Beach Municipal Airport, designated KFHB, sits on the island itself, a former military airbase once used by the Navy, Coast Guard, and Florida Air National Guard. From 1980 to 2008, the island hosted a Women's Tennis Association tournament. Since 2009, it has been home to the annual Petanque America Open, bringing the French game of boules to a place where the French flag first flew more than four centuries ago.