A passport-free island odyssey lies within America’s borders, where volcanic craters, pirate lore, and whaling legends mingle with modern-day beach bliss. In 10 Breathtaking Islands in the United States, we sail through centuries of history, spotlight the pivotal moments that shaped each shoreline, and toss in on-the-ground tips so you can live the stories yourself.
From Revolutionary-era forts on the Great Lakes to lavender-scented fields in the Pacific Northwest, these isles prove that the nation’s most gripping narratives often come wrapped in sea mist and seabird song. Grab your flip-flops—or hiking boots—and let’s island-hop through time.
Oahu, Hawaii
Long before Waikiki’s high-rise hotels, Oahu was the seat of the Hawaiian Kingdom; ʻIolani Palace (completed 1882) still stands as the only royal residence on U.S. soil. The island’s destiny shifted on December 7, 1941 when Japanese planes attacked Pearl Harbor, drawing America into World War II—visit the USS Arizona Memorial early to beat the crowds and feel the hush. Surf culture took root here in the 1950s, and winter waves at Banzai Pipeline still crown world champions. Between sessions, hike the old military tunnels inside Diamond Head Crater or sample garlic-shrimp plates on the North Shore food-truck circuit. After sunset, aloha shirts mingle with designer labels along Kalākaua Avenue’s tiki-lit sidewalks.
Key West, Florida
Spain claimed Key West in 1513, but it was the 19th-century wreck-salvage trade that minted fortunes; the Mel Fisher Maritime Museum narrates that golden age with genuine treasure. In 1861, the Union Navy seized the island, making Fort Zachary Taylor a Civil War linchpin. Key West briefly “seceded” again in 1982 during the tongue-in-cheek Conch Republic rebellion—join the April anniversary parade if you love irreverent history. Daylight hours promise reef dives and six-toed cats at Hemingway’s house; nights bloom with roving street performers at Mallory Square. Cap it off with a slice of tart Key lime pie from an old-school bakery on Duval Street.
Santa Catalina Island, California
Tongva peoples fished these waters for millennia before Spanish explorer Juan Rodríguez Cabrillo charted them in 1542. After chewing-gum magnate William Wrigley Jr. bought controlling interest in 1919, he built the red-tiled Catalina Casino (think Jazz-Age ballroom, not blackjack tables). During World War II, the island doubled as a military training base—spot concrete bunkers peeking from chaparral ridges as you hike the Trans-Catalina Trail. Today Avalon’s waterfront shimmers with art-deco façades and fresh-caught swordfish tacos. Snorkel in Lover’s Cove for bat rays, then board an evening flying-fish tour when moonlight turns the channel into liquid silver.
Mackinac Island, Michigan
Fort Mackinac’s stone ramparts have policed the Straits of Mackinac since 1780, trading hands during the War of 1812; reenactors fire muskets every summer hour on the half-hour. The island banned automobiles in 1898, and horse-drawn drays still haul luggage from the ferry docks—saddle up for a clip-clop ride along the eight-mile perimeter road. Victorian vacationers popularized “Mackinac fudge” in the 1880s; watch candymakers marble slabs of molten chocolate before indulging. Lilac Festival in June perfumes every veranda, while autumn paints sugar maples fiery crimson. Cyclists can detour inland to see Skull Cave and the limestone arch soaring 146 feet above Lake Huron.
Amelia Island, Florida
Known as the Isle of Eight Flags, Amelia has flown Spanish, French, British, Confederate, and even pirate standards—most infamously under corsair Luis Aury in 1817. Fort Clinch, begun in 1847, never saw battle but its brick casemates and live-oak campgrounds overlook a shark-tooth-laden beach. Shrimping boomed here in the 1930s; sample a boat-to-table “Mayport pink” at a dockside shack in Fernandina Beach’s historic district. Kayak Egan’s Creek at high tide for spoonbill sightings, then horseback-ride the surf at sunset. Antique shops along Centre Street hide Gilded-Age curios and rumored smugglers’ tunnels.
Martha’s Vineyard, Massachusetts
Wampanoag whalers commanded these waters long before English settlers arrived in 1642; their descendants still steward the island’s western Aquinnah cliffs and the Gay Head Lighthouse. The Vineyard earned America’s first deaf community in the 18th century, developing its own sign language that pre-dated ASL. In 1974, Steven Spielberg transformed Menemsha into Amity Island for “Jaws,” and you can still photograph the famed harbor shacks. Spend mornings pedaling gingerbread-cottage lanes in Oak Bluffs, then slurp “chowdah” at a church fair older than the Civil War. Off-season, storm-watching at Gay Head Lighthouse reveals Atlantic rollers pounding rainbow-striped clay bluffs.
Nantucket, Massachusetts
By 1835, Nantucket captained half the world’s whaling fleet, a saga preserved at the Whaling Museum where a 46-foot sperm-whale skeleton hovers overhead. The Great Fire of 1846 razed downtown, but Greek-Revival mansions rose from the ashes and still line Orange Street today. Cranberry cultivation swept the island in the late 1800s; October bog “floods” create a crimson mosaic visible from the Milestone Road bike path. June’s Figawi sailboat race jump-starts the season, while December’s Christmas Stroll wraps carolers in top hats and wool cloaks. Pack a thermos of chowder for sunset at Steps Beach, where sand-ripple shadows echo the town’s cobblestoned past.
Hilton Head Island, South Carolina
Union forces seized Hilton Head in 1861, turning it into the Civil War’s largest naval base south of Virginia; you can wander earthworks at Fort Howell that once protected freedmen’s village Mitchelville. Developer Charles Fraser ushered in eco-minded tourism during the 1960s, topping it off with Harbour Town’s candy-striped lighthouse in 1970. Today the island’s 100 miles of multi-use trails link 24 championship golf courses and centuries-old live oaks dripping Spanish moss. Kayak skull-creek salt-marshes for dolphin entourages, then catch a Gullah oyster roast where storytellers trace roots to West Africa. Sunrise bike rides on packed-sand beaches feel like floating across a mirror.
South Padre Island, Texas
Once a quiet ranching spit, South Padre’s modern chapter began in 1954 when the Queen Isabella Causeway connected it to the mainland—though Hurricane Beulah in 1967 reminded residents of the Gulf’s muscle. NASA scientists tracked Apollo splashdowns from here, and SpaceX rockets now punctuate the southern horizon. Spring breakers may crowd March, but kiteboarders, birders, and anglers claim the breezy months before and after. Tour Sea Turtle Inc. to meet rescued “cold-stun” Kemp’s ridleys, then sign up for a moonlit sand-castle lesson (yes, they provide glow sticks). Evening bay-front bars serve red-snapper tacos beneath orange sherbet sunsets.
San Juan Island, Washington
In 1859, an errant pig sparked the bloodless “Pig War” border standoff between British and American troops—hike the grassy parade grounds of American Camp where soldiers once squared off. Lime-kiln operations peaked in the 1860s, but the abandoned ovens now flank one of the world’s top shore-based whale-watching sites at Lime Kiln Point State Park. Friday Harbor’s cypress-shaded streets shelter galleries featuring Salish Sea artists; linger over lavender lattes roasted on-island. July’s Lavender Festival blankets Pelindaba Farm in purple blooms, and fall bioluminescent-kayak tours turn each paddle stroke into a comet tail. End the day at Roche Harbor’s 1890 Hotel de Haro, listening for harbor-seal barks echoing off forested bluffs.
