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How to Have Old-School Fun in Key West

Key West gets more gentrified every year. But it's still a fun place for visitors, who don't have to worry about the long-term changes that drive locals crazy.

Key West gets more gentrified each year -- it can't help itself. The glory that was -- meaning the funky place at the end of the road where escapees from "normal" life joined up with writers, artists and musicians -- made for a laid-back ambiance where almost anything went, and frequently did. Gay men and women flocked here, as did husbands fleeing alimony, wives running from wrecked marriages, debtors hiding from creditors, and a few felons escaping the law, with, of course, some people with no problems other than wanting a warm place in the sun. Dressing as they pleased, maintaining their abodes in a casual manner (or not at all), many honed their eccentricities sharply. Key Westers were, well, something else. And the old establishment welcomed them all with open arms.

But a flood of money raises all boats, apparently, and as the likes of Banana Republic and Coach replaced mom and pop stores, and BMWs and Porches roamed the streets instead of bicycles and Beetles, the funkiness began to grow thinner. As the number of locals has declined, second home ownership has jumped by 27 per cent over the past five years, and the number of rental units has dropped nearly 22 per cent. It's still a fun place, though, especially for visitors, who don't have to worry about the long-term changes that drive locals crazy.

There's plenty of music in dozens of venues, tons of art in the many galleries, good and expensive food in a couple dozen restaurants (with so-so food in many more), and every kind of water sport and activity you can think of. The artists and writers who continue to gather here in disproportionately large numbers mean dozens of cultural attractions for you to attend. But along with gentrification has come the reality of higher prices for nearly everything, of course.

Cultural Events

This spring, the calendar is full of things to do. Here's just a sampling:

The 13th Annual Robert Frost Poetry Festival & Contest takes place from April 11 to 15 at the Heritage House Museum, with poets Michael Wyndham Thomas, Rosalind Brackenbury, Barry George and Charles Trumbull. You can submit poetry and haiku by March 20 if you want to enter. Check out

Also along literary lines, but with fine arts, too, are the programs of newly-formed Studios of Key West, which opened in February and continue through May, with workshops by eight outstanding artists and writers, such as Robert Stone and Roxana Robinson (writing), William Welch and Skip Lawrence (painting). Costs range from $50 to $950, according to their brochure. More info at tel. 305/296-0458 or

Also part of the Studios of Key West program is its free "Speakers Series," with overviews of the history and role of artists and writers in the community. This spring, Robert Faggen, author of The Notebooks of Robert Frost, speaks on March 21; Thomas H. Pauly, author of Zane Grey: His Life, His Adventures, His Woman, lectures on April 12; and Randall Jarrett, author of Winslow Homer: An American Vision, speaks on May 16. In autumn, speakers will talk about John Dewey, the poet Elizabeth Bishop and Florida folk artists. More information at

From now through April 14, you should try to visit Sculpture Key West, a huge show (over 80 sculptures, many outdoors) in three historic settings, including two old small fortifications (the East and West Martellos) and Fort Zachary Taylor itself (the latter is a National Landmark and dates from 1866). More info at More on the artwork at

The other Big Deal event is the showing by J. Seward Johnson, Jr. of his fantastic Impressionistic sculptures and paintings, into which you can walk and pose as part of the artwork itself. Featured are his interpretation of such works as Van Gogh's The Bedroom (you can even sprawl on the bed) and Renoir's Dancers series. Some of the work is in bronze, some in mixed media. This is at the historic Custom House daily until June 1, and is called "Impressionism Revisited: Beyond the Frame." Admission is $10 and the Customs House is at 281 Front St.; tel. 305/295-6616; Johnson, a scion of the Johnson & Johnson band-aid family, has his own website, too:


Old Key West can be visualized easily in the "Historic Homes Museum Walk," made up of five marvelous buildings and gardens, the first four very close to one another. I suggest starting at the Harry S. Truman Little White House (c.1890, National Register of Historic Places), where the former president spent a lot of time during his term of office, then going to the Audubon House & Gardens (c. 1846), where you can view some of the ornithologist's original art. Your next stop is just around the corner at the Heritage House Museum & Robert Frost Cottage (c. 1834), with its beautiful collection of furnishings from the China Trade and other artifacts of an early sea captain's home, as well as the cozy rooms where poet Frost spent many of his winter vacations. The orchid collection here is especially valuable.

Farther along Caroline Street is The Curry Mansion (c. 1905), beautifully restored with artifacts from the lives of Tiffany, Audubon and Hemingway, among others, and the only widow's walk in Key West open to the public. The fifth house, the Hemingway Home & Museum (c. 1850), is a bit farther away, about six blocks south on Duval, then right on Olivia to Whitehead. Ernest wrote several of his greatest novels and short stories here, earning the place recognition as an Historic Landmark and himself a Nobel Prize for Literature. (A sixth place, The Oldest House, has been closed by its owner, the State of Florida, because of its decrepitude and may or may not be reopened anytime soon.)

Two of the above (Audubon House and Heritage House), plus Casa Antigua, a marvelous wreck of a building where Hemingway first lived in Key West, are on a Three-Museum tour for a price of $15, self guided. Otherwise, individual admission prices are noted below:

An unusual way to see Key West is with the Orchid Lady, who leads tours to gardens featuring orchids (including the Heritage House display), the cost $25. Contact her at tel. 877/747-2718 or visit A more lugubrious pleasure would be Key West's Ghosts & Legends Haunted Tour, which takes in the old city morgue, the oldest graveyard (including the famous tombstone reading "I Told You I Was Sick!"), some voodoo talk, pirate lore, haunted mansions and enchanted dolls. Admission is $18; tel. 866/612-3890 or 305/294-1713, website


Over 60 inns, guesthouses and B&Bs are members of the Key West Innkeeper's Association, with establishments ranging from elegant mansions to Conch cottages. Check out their offerings on or phone them for information at tel. 888/KEY INNS, and make reservations at tel. 800/492-1911.

L'Habitation boasts a French ambiance, with private rooms (including bath) starting at $109 up through $179, depending on season, including a continental breakfast with freshly baked pastries. You're in the heart of Old Town here, close to all the historic attractions and a short stroll to the sunset celebration. My sister greatly enjoyed her stay here. 408 Easton St.; tel. 800/697-1766 or 305/293-9203, website

Westwinds Inn has rooms starting as low as $80 in low season (May 30 to December 21), $115 in middle season (April 23 to May 29) and $165 in high season (December 22 to April 22). The prices include continental breakfast beside the pool, and all rooms are non-smoking. One caveat, according to their website: "For the benefit of our writers and readers, TV is limited purposefully to designated units." Nice neighborhood in Old Town, near Historic Seaport (two blocks), no pets or children under 12. At 914 Eaton St.; tel. 800/788-4150 or 305/296-4440, website

Angelina's Guesthouse is conveniently located at 302 Angela Street, right in Old Town, and serves up homemade cinnamon rolls at breakfast. There are several types of rooms, ranging from those with shared bath to a honeymoon suite. The house was once a bordello (in the 1920s) and gambling spot. Rates for rooms with shared bath range from $69 to $99, depending on season, while rooms with private bath run from $89 to $169. No one under 18 is allowed, and no one under 21 may check in (Spring Break is not popular at this establishment). Contact them at, and tel. 888/303-4480 or 305/294-4480.

Dining Out

Be sure to try seafood while you're here. The Key West Seafood people say this is the best place in the world to sample a wide variety of local produce from the ocean, including stone crab claws (mid October to mid May), Florida lobster tails (August 6 to March 31), Key West pink shrimp, grouper, yellowtail snapper, tuna, mahi-mahi (sometimes called dolphin), wahoo and mangrove snapper.

Many locals and visitors call Square One the best restaurant in town, and it has won several awards, including those from Wine Spectator and People's Choice Key West. Among its signature dishes, I like the aromatic baked garlic ($8) and the locally-caught sautéed Gulf shrimp scampi ($22). Owner Michael Stewart is everything you want a good host to be, and can suggest other favorites to you as well as discuss wine with authority. Dinner nightly, breakfast and lunch or brunch daily except Mondays. 1075 Duval St., tel. 305/296-4300.

For really good Japanese food, including sushi, check out Ambrosia, which I have visited several times. In addition to fresh fish (tuna sushi order $2.50, for instance), I enjoyed the tempura dinner at $16.95. Authentic, for sure (I lived in Japan for nine years). Open daily, lunch and dinner. 1401 Simonton St., tel. 305/293-0304.


You might like to help the ambiance of Old Town by biking around Key West when you can, rentals at the Moped Hospital, 601 Truman Ave., tel. 305/296-3344, $1 an hour, $6.99 per day.

More tourist information at or tel. 800/FLA-KEYS. The most objective Visitors Information spot in Old Town is the Chamber of Commerce office right at Mallory Square, 402 Wall St., tel. 800/527-8539 or 305/294-2587, website

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