Key West Travel

Here’s a handy general guide to Key West travel. This is an introduction to help you get started in planning your next visit to our Southernmost City. Key West, America’s southernmost city, is a seductive combination of vintage architecture, mild climate and tropical vegetation coupled with a live-and-let-live ambiance; all having long made it a favorite vacation retreat. Key West travel is very popular amongst cruise passengers these days, and this force has had a large impact on the island. However, Key West is still a paradise destination for so many visitors each year. There are countless activities, attractions and services for visitors to Key West, making it a great place to go on vacation. Over the last decade, Key West’s growing popularity with wealthy snowbirds and investors has pushed property values skyward, generating fear among locals that Key West may be losing its small-town flavor and bohemian lifestyle to gentrification and over-commercialization.

Visitors can take a look and decide for themselves aboard the Conch Train (pronounced “Konk,” the nickname for a native resident of the Keys) on a breezy 14-mile journey around the island. On its 90-minute circuit, the train (four canopied cars pulled by a propane-powered Jeep) winds through commercial and residential areas of the historic district with a foray to the beaches and newer developments along the city’s southern border.

Another easy way to get around is on foot or on rented bikes with the help of Sharon Wells’ definitive “Walking & Biking Guide,” which leads along Whitehead, Caroline and Eaton streets with its rarefied Conch architecture. You will find the Heritage House Museum on leafy Caroline Street where poet Robert Frost wintered in the back cottage; and, on Whitehead Street, the handsome Classic Revival Audubon House with its lush gardens where the famed ornithologist once briefly visited.

Also, the Octagon House on Eaton Street, owned for a time by designer Calvin Klein, with encircling verandahs and turquoise-trimmed shutters; and, at the intersection with William Street, the two well-traveled Bahama Houses, distinguished by their unusual beaded clapboard siding.

Many of these graceful, wood-frame buildings date from the early 1800s, when maritime trade thrived along the treacherous Florida Straits and town seafarers-turned-wreckers grew wealthy off the spoils from foundered ships.

Others were constructed later in the century when the sponging and cigar-making industries muscled their ways to the economic forefront. About 3,000 historic structures are spread haphazardly across Old Town’s maze of streets, lanes and dead-end alleyways.

Some of the prettiest are found in the quiet neighborhoods along Olivia, Frances, Angela and Margaret streets where palm, frangipani, mango, kapok and flame trees vie for attention with hibiscus, oleander, bougainvillea and night-blooming cereus.

Ships’ carpenters designed and built these Conch beauties mixing architectural influences from the Bahamas, New England, New Orleans and the Caribbean. Just blocks away is the 15-acre Key West Cemetery. Its above-ground vaults — because much of Key West is located zero feet above sea level — marble statues and famous epitaphs (“A Devoted Fan of Singer Julio Igelsias,” “The Buck Stops Here” and “I Told You I Was Sick”) have made it a favorite pilgrimage for sightseers. Key West travel books will almost always mention this famous and beautiful graveyard.

There are memorials to victims of the USS Maine explosion in 1898 in Havana Harbor and to Cubans lost in a failed 1868 coup attempt to free their homeland from Spanish domination. In the latter’s aftermath, Cuban political refugees flocked to Key West, finding work as tobacco strippers, rollers and trimmers in the booming cigar industry.

The three-room shotgun cottages that prosperous manufacturers once built to house their employees are still in evidence. Many have survived in style, showcasing fresh coats of paint, but over time the old factories, leveled or refitted to other uses, have fared less well.

Key West has long been a magnet for writers, artists and assorted eccentrics, but none has left a more indelible imprint than the legendary Ernest Hemingway, who moved to the island in 1928 with his second wife, Pauline. Sightseers meander past his Whitehead Street address or line up to tour the Moorish-influenced Hemingway museum/home with its swimming pool and gardens. The Nobel Prize-winning author wrote several of his best-known stories while in residence, including “To Have and Have Not” and “The Snows of Kilimanjaro.”

A different Key West emerges along breezy Atlantic Boulevard, where sandy beaches and azure seas are on dramatic display. The White Street Pier with its poignant AIDS Memorial is a much-visited spot, as is the restored Casa Marina Resort Hotel, a Spanish Renaissance gem that originally opened in 1920.

Classy Upper Duval Street is the place to browse in chic galleries and stop for snacks in a patio cafe. Nearby is the San Carlos Institute, a cultural center where patriot José Marti rallied forces in the fight for Cuban independence.

The sea is a heady presence in Key West, and many visitors succumb to its charms on a sunset cruise aboard one of the charter sailing vessels plying the harbor’s deep waters.

Seaside Mallory Square plays host to another ritual, in which crowds gather for the daily sunset celebration. This 1960s-style lovefest features craft booths and street performers who juggle, do tightrope walking and delight onlookers with other feats of derring-do. Then, as the sun slips below the horizon, the crowds clap and cheer before deserting the docks for Duval Street and still more explorations.