Key West

Key West, United States

Historic pastel wooden houses line a quiet Key West street as early morning sunlight casts long shadows.

A laid-back island at the far end of the Florida Keys, where the sea is never far away and the winter weather is at its kindest.

The place

Key West is the island at the far end of the Florida Keys, a chain of low islands that curves south-west from the Florida mainland into the Straits of Florida. It is the southernmost city in the continental United States, and the sea lies close on every side. The city, with about 26,000 residents, takes in a few smaller islets and part of Stock Island, but when people say Key West they almost always mean the main island.

The main island is small enough to walk across in an afternoon and to explore by bicycle in a morning. Streets in the old town run in a loose grid, lined with wooden houses that have deep porches, bright paint and shuttered windows. Most of the well-known sights sit within a short walk of one another, so you can plan a full day without a car. Many visitors arrive by air or drive the Overseas Highway south from Miami, then leave the car parked and go on foot.

Duval Street, the main drag, is busiest from late morning into the night, with bars, restaurants and souvenir shops. Quieter streets a few blocks away feel residential and slower. Summer is hot and humid, though the trade winds and sea breezes stop the heat from building the way it does further inland. Winter is the easiest season: sunny, drier and comfortable for walking. Whatever the month, the water is never far away, and the sunsets draw people to the western end of the island most evenings.

Its story

Long before European ships reached the Florida Keys, people related to the Calusa and Tequesta lived on the island. The Spanish name Cayo Hueso is usually translated as 'bone island', a reference to remains reportedly found there, left by earlier inhabitants who used the island as a burial ground. It was also one of the few places in the chain with a reliable supply of fresh water, which made it a useful stop for passing boats.

Juan Ponce de León sailed past in 1513 and charted the Keys, but no permanent settlement followed. For much of the next period, the island passed between Spanish and British control, and neither nation governed it closely. Cuban fishers came to catch fish, Bahamian fishermen worked the reefs, cut timber and salvaged wrecks, and smugglers and privateers used the scattered cays to hide. The last Native American residents were taken to Cuba in 1763, when Florida changed hands.

After Florida passed to the United States in 1819, Key West grew quickly. Its position on the sea routes between the Gulf and the Atlantic made it a natural base for shipping, and the wrecking trade, which salvaged cargo from ships lost on the reefs, brought in much of its money. Cigar making became another major industry. By the late nineteenth century the town was among the wealthiest in the country, and the mix of Cuban, Bahamian and American families that built it still shows in its food and its cemeteries.

In the twentieth century the island drew well-known visitors. Harry S. Truman used a house here as a retreat, and the novelist Ernest Hemingway lived on the island for about a decade. Today the AIDS memorial near White Street Pier recalls a more recent chapter, when the epidemic took more than a thousand local residents.

What to see

Culture

Key West's identity grew out of a small, mixed community of fishers, cigar workers, wreckers and merchants, and people here still talk about that past with pride. Cuban and Bahamian food and music are part of everyday life in the old town rather than a show put on for visitors. The island's pace is relaxed, and locals tend to be happy to answer questions about the buildings and the families who built them. Remembrance matters here as well: the City Cemetery reflects a blend of African, Hispanic, Anglo and other heritages, and the AIDS memorial honours people who died in the epidemic. Many families have lived here for generations, so a friendly question about the island's history is usually welcome. Late-night life on Duval Street is part of the appeal, but noise should drop as you move toward these quieter places. At the cemetery, keep to the paths, do not climb on tombs or lean on headstones, and ask before photographing anyone at a service.

What to wear

Key West has no single traditional dress, but its older clothing followed the same practical logic as other hot coastal places: light cotton and linen, loose cuts and wide-brimmed hats. Cuban and Bahamian families brought their own styles, among them the guayabera, a pleated shirt associated with Cuban men that is often made in cotton or linen. What people wear now is relaxed. Shorts, sundresses, linen shirts and sandals are everywhere, and bright prints and tropical colours are common. Many people change into swimwear for the beach, but a shirt and shoes are expected inside restaurants and bars. For a visitor, pack light, breathable clothing in cotton or linen, plus a hat, sunglasses and sun protection. Wear closed, flat shoes for old brick paths and wet pavements, and bring a light layer or cover-up for churches, the cemetery and the memorial, where modest dress shows respect. Sandals work on the beach and boat decks, but a sturdier pair will serve you better for walking the old town.

What to eat

Plan it

Best time. November to April is the best window: sunny, drier and easier for walking. Summer is hot and wet, and the trade winds ease the heat without making it cool.

How long. 2–3

Getting there. Key West International Airport is closest to the old town; alternatively, drive the Overseas Highway south from Miami, a long scenic route through the Keys.

Budget. high

Tips

Etiquette

Nearby

Sources