36 Hours in Key West

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“It’s the best place I’ve ever been any time, anywhere,” Ernest Hemingway wrote of Key West. “Flowers, tamarind trees, guava trees, coconut palms. … Got tight last night on absinthe and did knife tricks.” Now as then, Florida’s southernmost key offers the delights of a tropical paradise matched by spectacular night life. The writer’s favorite pastimes in the 1930s — catching big fish, eating well and drinking hard — still define the island’s appeal today. This historic allure persists in the decades of memorabilia on saloon walls, “conch-style” homes inhabited by famous writers and the never-ending diversion of the omnipresent pale-blue sea. Dip beneath the surface in the Conch Republic, and you’ll find something for everyone in the family. You may also find that, in Key West, everyone feels like a kid.

Friday 3pm | Literary Landmarks
Wallace Stevens said in the 1930s, “Key West, unfortunately, is becoming rather literary and artistic.” Grab a rental bike from WeCycle and enjoy Key West the way so many literary legends lived (and currently live) from Ernest Hemingway, Robert Frost, Tennessee Williams, Elizabeth Bishop, James Leo Herlihy, Richard Wilbur, Ralph Ellison, Shel Silverstein, Judy Blume, Meg Cabot, and more!

Friday 5pm | Dinner Al Fresco
On the southwest side of Whitehead is Bahama Village, where Blue Heaven resides in a one-time bordello and site of boxing matches refereed by Hemingway himself. Make reservations to secure an outdoor table. Breakfast, lunch and dinner are served in the courtyard with a water tower tiki bar, Ping-Pong table, live music and resident chickens and roosters, all beneath white lights and the branches of a colossal 90-year-old Spanish lime tree.

Flicks and Concerts | 7pm
Today, the new “Old Key West” can be found at Coast Projects, a collective of craftsmen, artists and musicians hosting monthly fund-raiser concerts (with the likes of Mason Jennings), workshops and outdoor film screenings at a funky lot on Stock Island (see coastprojects.com for events). Back in town, the old Tropic Cinema has been restored into a multiplex theater and locals’ hub by the Key West Film Society, spearheaded in part by George Cooper, husband of the author Judy Blume.

Saturday 8am | Coffee and Art
Many a book was born in a coffee shop, and the Coffee Plantation is a good place to settle into a couch or on the front porch with a laptop and organic Blue Moon blend house brew or café con leche. Owned by the husband-wife team Diane and Theo Glorie, both artists, the cafe features their paintings as well as art shows, author readings and even a real estate desk run by Theo — just in case you find the need for a home of your own.

Saturday 10am | Angler Central
Renowned as a sport-fishing destination since the days of Hemingway’s marlin conquests, the draw is now catch-and-release fishing for tarpon, bonefish or permit. Nathaniel Linville at the Angling Company can set you up with the appropriate Hardy, Sage and Hatch gear and Simms clothing. Call well ahead to assure a full-day booking. Ask after Capt. Justin Rea, of Sting Rea Charters, a sought-after tournament-winning guide who specializes in fly and light-tackle charters into the backcountry flats, including expeditions to the Marquesas, an intriguing ring of reef islands 20 miles away by boat.

Saturday 11am | Waterfront Walkabout
The Key West Historic Seaport boardwalk weaves along the bight from the ferry terminal on Grinnell to the end of Front Street. Explore the charters, tour operators and schooners for hire (look for the beautifully restored two-masted 1920s Hindu and book a sunset sail), plus gift shops, restaurants, bars and views.

Saturday 1pm | Adventures Afloat
Rob Oliverio of Mellow Ventures Backcountry Outfitters, docked on the Key West Historic Seaport’s Harbor Walk at the end of William Street, organizes full- or half-day private eco-charters to Marvin Key and the Marquesas for up to six passengers on a Twin-Vee catamaran sport boat. His captains will take your family or group to the best spots for paddleboarding in the mangroves, fishing for snapper, snorkeling around shipwrecks and reefs, picnicking on a private island and dolphins watching.

Saturday 4pm | Oyster Happy Hour
At the Harbor Walk, happy hour begins at 4 to 4:30 p.m. — though some would say much earlier. Head to the Half Shell Raw Bar at the end of Margaret Street for Texas oysters on the half shell and a locals-meets-vacationers scene, or go a block farther to Pepe’s, a venerable dining establishment, where Gulf Coast oysters are shucked on demand. The Rum Runner goes down easy and packs a punch.

Saturday 7pm | BYO Catch of the Day
Game fish may be catch-and-release, but snapper, mahi-mahi and grouper are good eating. Bring your own filleted catch to Café Solé, and they’ll serve it grilled, blackened or sautéed with sides for $25 a person. The chef John Correa, with his wife, Judy, and a friendly staff has been offering seafood dishes with French and Caribbean influences since 1995 in the comfortable, candlelit setting.

Saturday 10pm | Famous Night Life
Anything goes and everyone is welcome at most bars in Key West, and there’s no shortage of options. Start the night on Duval Street at the Other Side with a craft cocktail. Next: Capt. Tony’s Saloon, the original location of Sloppy Joe’s, where Hemingway met his third wife, Martha Gellhorn, and where you can check out the decades of dollar bills and other memorabilia (bras, license plates, photos) on the walls and ceiling. After that, perhaps a visit to the Garden of Eden, the clothing-optional bar on the rooftop of the Bull and Whistle. You can always blame the Rum Runners.

Sunday 9am | Beach It
Tennessee Williams liked to swim at the end of White Street, but Fort Zachary Taylor Historic State Park is the place to make a day of it. Though the entrance may suggest the abandoned fort it is, the beach has a clean span of white sand, deep water for swimming and snorkeling, a cafe and picnic tables under the Australian pines. Smathers Beach, though more exposed along South Roosevelt Boulevard to the east, has the benefit of the Sunset Watersports Beach Pass, offering parasailing, sailing, kayaking, tubing, paddleboarding and windsurfing.

Sunday 1pm | Lunch With a View
The best way to end a trip to Key West is lunch on the deck at Louie’s Backyard, noted for its gentle breezes, views of the Atlantic and high Zagat rating, as well as easy proximity to the airport.