Feb/March 10 | City Portrait

The Weird Magic of Key West

Always eccentric and wildly beautiful, the southernmost city has long beckoned adventurous souls, whether they’re dropping in or dropping out

EAT
Blue Heaven
The old blue building has seen a little bit of everything in its 100-year history. It’s been an artist commune, a gambling house, an ice cream parlor, and a bordello, not necessarily in that order. But today it’s probably the most laid-back fine-dining restaurant you’ll ever visit. Don’t miss breakfast—eggs Benedict with lobster and key lime hollandaise, Key West shrimp and grits, and banana bread that’s its own little slice of paradise. 729 Thomas St.; blueheavenkw.com

El Siboney
Tucked away in the heart of Old Town, this unpretentious family-owned eatery specializes in one thing: good Cuban food. It starts with butter-soaked Cuban bread piled high in a red plastic basket. Then, you order numbered dishes like “1. Roasted Pork” or “24. Breaded Shrimp.” Yellow rice, black beans, and sticky sweet plantains crowd every plate, perfectly accompanied by the homemade sangria. 900 Catherine St.; elsiboneyrestaurant.com

Louie’s Backyard
The food lives up to the scenery at this converted oceanfront home on Waddell Avenue, which also boasts one of the best views on the island. Chef Doug Shook joined the staff twenty-four years ago, and his talent has made Louie’s an enduring favorite. The specials each night reflect the fresh seafood collected at the dock that day—grouper, snapper, swordfish, shrimp, and lobster, depending on the season—and the lower deck is a perfect spot for a happy-hour cocktail. 700 Waddell Ave.; louiesbackyard.com

Mangia Mangia
Key West is a lot more Little Havana than Little Italy, but don’t let that dissuade you from a stop at Mangia Mangia (“Eat! Eat!”). The trattoria’s marinara sauce and semolina pasta are made fresh daily, though you’ll also find some inventive nods to local tradition (like the conch minestrone). And the forty-four-page wine list will blow your mind. 900 Southard St.; mangia-mangia.com

Santiago’s Bodega
Big flavors come in small sizes at Santiago’s, a tapas restaurant located in one of Key West’s oldest neighborhoods, Bahama Village. Divine salads and plates like yellowfin ceviche or prosciutto-wrapped dates pair with a fine selection of beer, wine, and ports. The tiny space fills quickly every night, so reservations are highly suggested. 207 Petronia St.; santiagosbodega.com

DRINK
Captain Tony’s Saloon
In the 1930s, Ernest Hemingway spent many an evening sidled up to this Greene Street bar (the original location of Sloppy Joe’s bar before it moved down the street in 1937). In 1958, local fishing legend Tony Tarracino bought the place, renaming it Captain Tony’s Saloon. He sold it in 1989, the same year he became mayor, but he was still a regular until his death in 2008 (fittingly, it was the site of his funeral reception). 428 Greene St.; capttonyssaloon.com

Green Parrot
On any given night, the Green Parrot is stuffed with folks huddled underneath a draping parachute hung above the bar. Some are there for the music—jazz, blues, and rock—but others are there for the company and the crew of friendly bartenders who remember your name year after year. The Parrot never closes, not even during hurricanes. And recently, the unthinkable happened. It started accepting credit cards. 601 Whitehead St.; greenparrot.com

Schooner Wharf
Schooner Wharf calls itself the “last little piece of Old Key West,” and it looks that way, too. Names are etched into the thick wooden pub tables. There are no walls or a proper roof—just a few dried palm fronds thatched to overhead beams over the dirt and gravel floor. Located waterside at the Historic Seaport, Schooner is on island time. It opens at 7:00 a.m. for the “breakfast club” and often keeps it going until 4:00 a.m., with a rotating cast of local bands and even a house magician. 202 William St.; schoonerwharf.com

Virgilio’s
Though it’s just off Duval Street, Virgilio’s is hard to find, so it often escapes the attention of tourists. You have to look for the small white sign that leads you through a black iron gate into the courtyard. Once inside, you’ll be treated to the widest and best selection of martinis on the island, and live jazz almost every night. 524 Duval St.; virgilioskeywest.com

SLEEP
Key West Bed and Breakfast
This colorful boutique B&B goes by another name, the Popular House, and for good reason. It’s immensely more charming than most of the island’s other moderately priced alternatives (read: fleabags). Each of its eight rooms is unique—the King Room, the Pink Room—and gallery-worthy local art hangs throughout. Ask for a room with a balcony. 415 William St.; keywestbandb.com

Marquesa Hotel and Cottages
The Marquesa Hotel is one of the most beautiful and celebrated old hotels in Key West. It’s a collection of four classic Conch-style homes transformed into luxurious guest rooms, all surrounding a tropical courtyard and two pools. It’s hard to believe the quiet enclave is just a block from the bustle of Duval Street. And the new Marquesa Cottages, six long-term vacation rentals a few blocks east, offer modern-island living for guests planning to stay awhile. 600 Fleming St.; marquesa.com

Victoria House
Heading down with a group of your closest friends? Check out the five-bedroom Victoria House, which rents by the week for $6,000. Its history is traced to cigar man William Otis Johnson, and you can see the care that’s gone into maintaining the home and outdoor gardens for a century. Inside is a mix of comfy furnishings and antique fixtures, and it’s all just a few blocks from the seaport. 806 Truman Ave.; victoriahousekeywest.com

SHOP
Bésame Mucho
While you’re out fishing, send your better-smelling half to Bésame Mucho. The selections at this gorgeous home/apothecary/beauty/bath/garden store in Old Town fit one criterion: They’re the best. TOCCA perfumes, Mason Pearson brushes and combs, Libeco linens, and Antica Farmacista home scents are some of the luxurious finds at this quaint yet elegant shop. 315 Petronia St.; besamemucho.net

Key West Island Bookstore
A sign at the door reads “80,000 books (and we even know where some of them are),” and you can smell the decades of writing as you enter the Island Bookstore. New and used paperbacks fill floor-to-ceiling bookcases and every space in between. The real reason to go, though, is the collection of hundreds of works by Key West authors, from today and years past. You can find a copy of almost everything Ernest Hemingway wrote, including some rare short stories and poems, along with books by local legends like Elizabeth Bishop, John Hersey, and Thomas McGuane. 513 Fleming St.; 305-294-2904

Saltwater Angler
You can hardly take a step in Key West without overhearing some kind of fish story, but if you want to hook up with a knowledgeable guide, head to the Saltwater Angler at the Westin Marina. The staff—including head guide Tony Murphy—are happy to help you plan an excursion or simply answer questions at the store while you scope out the rod racks. Heck, they might even tell you the truth. 243 Front St.; saltwaterangler.com

Upper Duval Arts District
Key West is made for walking, and on Duval Street between Truman and United avenues, you can meander through a close-knit cluster of diverse art galleries. South Pointe Gallery sells original vintage posters (mostly French), while the Alan S. Maltz Gallery features Maltz’s venerated Florida Keys wildlife photography. Other galleries worth a stop: Joy Gallery for original watercolors and oils from Key West artist Irma Quigley, and Island Arts Co-Op Gallery for a selection of work by local artists in all media.

SEE & DO
Audubon House & Tropical Gardens
Long before tourists began flocking to Key West, ornithologist and artist John James Audubon paid a visit in the 1830s, documenting a number of bird species, many of which he is said to have painted on the property of this historic home. It was saved from demolition in 1958 and now houses twenty-eight first-edition Audubon works, along with prints and books in the adjoining gallery. 205 Whitehead St.; audubonhouse.com

Ernest Hemingway Home and Museum
Hemingway and Key West will forever be intertwined, which is why his Whitehead Street home, where he lived for most of the 1930s, is pretty much a must-see for Papa’s admirers. The home itself isn’t particularly remarkable, but Hemingway fans love its haphazard collection of books, photos, and newspaper clippings. You can also get a look into his carriage-house writing studio, where his Royal typewriter and Cuban cigar-maker’s chair still sit. 907 Whitehead St.; hemingwayhome.com

Fort Zachary Taylor State Park
Key West isn’t known for its beaches, but Fort Zach is the exception. While it doesn’t boast the sugary white sand you find in the Caribbean, it does boast beautiful views as well as swimming and snorkeling in clean, clear waters. Pack a lunch and enjoy a picnic under the casuarinas that shade the park for a peaceful afternoon away from the crowds. fortzacharytaylor.com

Key West Butterfly & Nature Conservatory
When you’re looking for a place of respite after a long night, slip into the butterfly conservatory. Inside the walk-through atrium live fifty to sixty species of butterflies—emerald swallowtails, blue morphos, black-and-yellow zebra longwings—from all over the world, sharing the space with tropical birds and plants. An attached gallery features the butterfly artwork of part-owner Sam Trophia. 1316 Duval St.; keywestbutterfly.com

Marquesas Keys
Anglers the world over dream about a trip to the Marquesas Keys (often called the Golden Donut by locals), a ring of mangrove-encrusted islands about thirty miles west of the southernmost city. Located in the protected Key West National Wildlife Refuge, the pristine waters offer anglers an incredible amount of diversity, from bonefish and permit on the flats to grouper and snapper off the nearshore reefs and wrecks. If you’re short a boat, plenty of guides offer trips to the Marquesas, running upwards of $600 a day, but the fishing—and the views—are worth it.

Mel Fisher Maritime Museum
Everybody hunts for treasure in Key West, whether it’s marlin or the best margarita. But Mel Fisher found the real deal, $450 million in loot from the 1622 wreck of the Spanish galleon Nuestra Señora de Atocha, in 1985. A portion of that bounty now rests at the Mel Fisher Maritime Museum, including gold and silver bars, contraband emeralds, and Atocha coins. Self-guided tours tell the story of the Keys’ turbulent maritime history. 200 Greene St.; melfisher.org