Johann Hunt
Island towns in the U.S. often carry a rhythm that feels far removed from the mainland. Days move slowly, surrounded by water that shifts in color from soft green to clear blue. It is here that the scenery and climate echo something many associate with the Caribbean. Let’s highlight 20 islands where that feeling comes alive in unexpected ways.
Key West, Florida
Turquoise waters surround Key West and give it a distinctly Caribbean look. Winter temperatures average 75°F, so the island is warm year-round. Mallory Square is very famous for its daily sunset gatherings, while Ernest Hemingway’s former home remains a historic landmark closely tied to the island’s cultural identity.
St. George Island, Florida
Unlike busier beaches, St. George Island offers over 20 miles of sand with little interruption from crowds. Its barrier island setting supports a slower rhythm of life. Each year, loggerhead sea turtles nest on its shores. The oyster harvest also highlights another vital local tradition.
Ocracoke Island, North Carolina
Getting to Ocracoke requires a ferry, boat, or small plane, but the effort pays off. Soft, secluded beaches feel worlds away from the mainland, and the island’s history echoes with stories of Blackbeard the pirate, who made Ocracoke Inlet his favorite hideout in the early 1700s. Today, wild ponies managed by the National Park Service remain the island’s most iconic residents.
Tybee Island, Georgia
Only 18 miles from Savannah, Tybee Island charms with sandy beaches, winding salt marshes, and dolphins that frequently visit the shore. Anchoring its historic vibe is the Tybee Light Station, first built in 1736 and restored to its 1916 design. The island is where natural beauty meets a rich maritime past.
South Padre Island, Texas
Migratory birds fill the skies above South Padre Island, using it as an important seasonal stop. Sea turtles also return here, where rescue and release programs help protect them. These natural rhythms unfold against the backdrop of a subtropical island that sees over 300 days of sunshine annually.
Catalina Island, California
A short ferry ride from Los Angeles brings travelers to Catalina, where sparkling coves recall the bright palette of the Caribbean. Wildlife thrives in unusual ways, as buffalo roam freely across the island’s interior. Beneath the water’s surface, glass-bottom boats reveal marine life in a dazzling underwater world.
Hilton Head Island, South Carolina
Palm-lined beaches shape Hilton Head into something distinctly tropical. Yet this island offers more than scenery: golf lovers find themselves spoiled by over 70 courses nearby. Nature makes its mark, too, as sea turtles return to the shore from May through October.
Martha’s Vineyard, Massachusetts
Martha’s Vineyard has long carried layers of history, including visits from former Presidents who favored it for vacation. The island’s sandy shores rival southern beaches in summer, and it is accessible only by boat or plane. Gingerbread cottages add another distinct element to this island’s character.
Anna Maria Island, Florida
Anna Maria Island delivers the perfect Florida experience with brilliant blue waters and amazing sunsets that stretch for seven protected miles. The community fought hard to keep skyscrapers out, so it still feels like classic Old Florida. Dolphins appear regularly near the coast, and manatees arrive seasonally for warmer waters.
Block Island, Rhode Island
Reaching Block Island means boarding a ferry, and that journey preserves its quiet atmosphere. White sand and clear waters welcome visitors, while dramatic bluffs rise to frame the horizon with striking views. Over 300 bird species have been found here, proof of the island’s importance as a natural stopover and sanctuary.
Molokai, Hawaii
Known as the “Most Hawaiian Island,” Molokai preserves traditions without spectacle. Its climate stays warm year-round, resembling the Caribbean. The island is also home to some of the world’s tallest sea cliffs. With few crowds, Molokai maintains a small-town character and an unhurried natural setting.
Kiawah Island, South Carolina
Palm-studded beaches stretch 10 miles across Kiawah to form a tropical-like canvas that’s both natural and serene. Golf courses here rank among the world’s best, which merge greenery with ocean views. Wildlife, too, thrives: deer move freely through the island’s interior, and bottlenose dolphins patrol the waters nearby.
Jekyll Island, Georgia
Jekyll Island used to be a private playground for wealthy families like the Rockefellers and Morgans during America’s Gilded Age. Today, everyone can enjoy its beautiful beaches and historic areas. Driftwood Beach showcases amazing weathered trees and otherworldly scenery created by natural erosion. And the pleasant weather makes visits enjoyable anytime.
Islamorada, Florida Keys
Anglers know Islamorada as the “Sportfishing Capital of the World,” but it offers far more than rods and reels. Caribbean-clear waters invite snorkelers, and a diving museum preserves underwater history. The town’s annual seafood and arts festivals bring both locals and visitors together in a lively, colorful celebration.
Fire Island, New York
Energy on Fire Island shifts as summer arrives, when neighborhoods come alive with beach culture. Long sandy shorelines frame the island, while deer move easily through dunes and yards. With no cars allowed, ferries and bicycles set the rhythm of transportation here.
Sanibel Island, Florida
Half of Sanibel Island is set aside as a protected wildlife refuge to ensure the environment shapes its identity. Its beaches (covered in shells) invite the familiar “Sanibel Stoop” collecting pose. The Gulf waters shimmer in turquoise shades that resemble those found in the Caribbean.
Sand Key, Florida
The character of Sand Key is shaped by light, water, and sand. Clear Gulf waters border barrier island beaches, where sea turtles lay their eggs seasonally. Activity comes in many forms, such as kiteboarding high above the waves and slow shelling walks across the shoreline.
Dauphin Island, Alabama
People call Dauphin Island the “Sunset Capital of Alabama,” where evenings light the Gulf in golden tones. It’s a stopover for migrating birds, which draws countless watchers each year. Moreover, Fort Gaines, a historic brick fortress, continues to overlook the shoreline.
Bald Head Island, North Carolina
The island’s most enduring symbol is “Old Baldy,” a historic lighthouse that still stands tall. Surrounding it are wide beaches where sea turtles nest seasonally. Bald Head Island avoids car traffic altogether, relying on ferries and private boats to preserve its atmosphere.
Nantucket, Massachusetts
Nantucket sits 30 miles from Cape Cod and once dominated the global whaling industry during the late 1700s and mid-1800s. Today, the Whaling Museum, historic Brant Point Lighthouse from 1746, and beautiful Quaker buildings tell that story. Ferry rides or flights preserve the island’s secluded feel with stunning beaches and charming cobblestone roads.