Florida Keys Retreat: Discover Laid-Back Island Charm

The Florida Keys remain a celebrated escape for travelers craving a tropical retreat: endless water vistas, swaying palms and warm trade winds. This 125-mile chain of islands extends from just south of Miami to Key West and sits between three bodies of water—the Atlantic Ocean, Florida Bay and the Gulf of Mexico.

Henry Flagler, often called the “inventor of modern Florida” for establishing tourism as a cornerstone of the state’s economy, extended his Florida East Coast Railway’s Over-Sea Railroad from Miami to Key West in the early 1900s. After a 1935 hurricane destroyed the railroad, the Florida Keys Overseas Highway was built along the former rail route and completed in 1938. Stretching roughly 113 miles and connecting the islands via 42 bridges, the road—often called the Highway That Goes to Sea—was designated an All-American Road in 2009. Driving the Overseas Highway is one of the best ways to experience the entire island chain.

The Florida Keys are commonly described in five distinct regions, each with its own character. Below is an overview of those regions and what to expect when you relax in the southernmost reaches of the continental United States.

KEY LARGO

Known as the “Dive Capital of the World,” Key Largo is the first major island you reach when heading south from Miami and offers exceptional underwater experiences. Divers and snorkelers of all levels will find vibrant coral, schools of tropical fish and clear water at John Pennekamp Coral Reef State Park, the nation’s first underwater preserve.

Islamorada is renowned for sportfishing and is often called the “Sportfishing Capital of the World.” Backcountry fishing and saltwater fly-fishing have deep roots here. Expert captains navigate the Atlantic, Florida Bay and the offshore Gulf Stream to target seasonal species such as mahi-mahi, sailfish, kingfish, tuna, wahoo and marlin. The surrounding waters are also ideal for standup paddling, kiteboarding, snorkeling and scuba diving.

Built as part of Flagler’s railroad construction—workers famously said, “This is getting to be a real marathon!”—Marathon covers about 23 miles and is a family- and boating-friendly stretch of the Keys. Hawks Cay Resort is a popular place to stay for families and groups.

Perhaps the most iconic spot in Marathon is the Seven Mile Bridge, one of the world’s longest segmental bridges. Its 2.2-mile Historic Old Seven Mile Bridge has reopened for walking, running and cycling. Beneath the bridge lies Pigeon Key, once home to railroad workers; its historic buildings and education center are well worth a visit.

The Lower Keys, often called the Natural Keys, invite travelers to slow down and explore wildlife and scenic parks. This region includes two national wildlife refuges—the National Key Deer Refuge and the Great White Heron National Wildlife Refuge—along with Bahia Honda State Park, known for its sandy beaches and clear water.

Just before reaching Key West, Stock Island offers an intriguing mix of commercial shrimping activity and a vibrant arts community, where painters, sculptors and other artisans create and exhibit their work.

Key West, also known as the Conch Republic, is the southernmost city in the continental United States. Its relaxed, tropical atmosphere has inspired writers and artists such as Ernest Hemingway, Tennessee Williams and Jimmy Buffett. With a strong Bahamian and Cuban influence, Key West also hosts the largest historic district of wood-frame buildings in the country; many have been converted into inns, galleries and restaurants like The Gardens Hotel and Blue Heaven.

From historic landmarks to lively bars and daily sunset celebrations, Key West welcomes visitors with a carefree spirit and a variety of cultural and recreational offerings.