Familiar Key West

Charles Greenfield Visits Home


Charles Greenfield is a Miami-based travel writer who has contributed to Travel & Leisure and regional magazines/ newspapers. He also is Cultural Arts Contributor to Artsbeat on WLRN 91.3 FM, South Florida’s NPR affiliate, a producer for WLRN Ch. 17’s Artstreet, and writes on classical and jazz musicians for the Miami Herald.



Indisputably, Key West is family. Since the 1880s, the Wolkowskys, my mother’s people, have laid claim to that six-square-mile island at the end of the Florida Keys, a mere 90 miles from Havana. Great-grandfather Abraham first came with his peddler’s pack and started his dry goods store. His son Isaac once kicked Ernest Hemingway out of his bar on Greene Street. My mother Ruth was born on South Street across from the southernmost house in the continental U.S. And Uncle David’s renovating magic would re-create, nearly single-handedly, historic Key West around Mallory Square, Pirate’s Alley, Captain Tony’s Saloon on Greene Street, the Pier House (formerly, the Havana Ferry Docks), the Sands Beach Club (now The Reach Resort), and the Kress Building on Duval, home today to popular Fast Buck Freddie’s Emporium and Jimmy Buffet’s Margaritaville Café.

My youthful summers in the 1970s and 80s were spent in Key West’s hippie hedonism where one Fourth of July parade consisted of two separate fires (quickly extinguished), floats and majorettes, bearded Vietnam Vets and the strong scent of cannabis. An afternoon boating foray off the harbor often produced more grouper and lobster than a month’s worth in South Florida today. From the Hamptons to Hollywood (CA), Cayo Hueso (Ponce de Leon’s “Bone Island”) became a buzzword for lazy island living, sexual freedom, and cute $100,000 “conch” houses-to-convert. However, in the last two decades, the island paradise has slowly relinquished some of its ineffable tropical charm for gentrified resorts, trendy eateries, cruise ship day-trippers, and a boisterous downtown night scene.


The good news remains that tasteful compromise with the past does exist, especially with accommodations in a town where parking is scarcer than sandy beaches. Southernmost on the Beach, newly built on the Atlantic beachside of Duval and Simonton, is grouped together with its historic sister properties La Mer Hotel and Dewey House (famed educator John Dewey). With hard-to-find free parking and convenient walking to the Hemingway House, my brand new lodgings at Southernmost on the Beach had a tasteful plantation-style mahogany king bed and paddle fan, spacious tile shower, and neat ocean-view balcony. Besides a cute private pier, convenient lap pool and tiki bar, compact fitness facility, customized spa services and gracious concierge desk, the hotel complex offers meals in their funky Southernmost Beach Café. Overall service is attentive and hospitable. Not surprisingly, Southernmost on the Beach has just received the Travelers’ Choice 2010 second ranking for Top 10 Hotels for Romance in the United States from TripAdvisor.

Touring in Key West can seem like a confusing maze. While visitors take nocturnal treks to track down house “ghosts” or meander the eccentric above-ground coffin cemetery (epitaph: “I told you I was sick.”), the town crawls with alleys and side streets filled with renovated gingerbread-trim mansions, quaint

museums, a vibrant waterfront, and century-old churches. To help sort out the abundant activities I spoke to long time islander, arts enthusiast and travel planner Tracy Ahearn and daughter Tara about their agency.

“I take the stress out and become your own personal assistant for offbeat boutiques, hip bars, sunset sails, female impersonator shows, local dining favorites, or eco dolphin trips and reef dives,” she laughed. Ahearn’s one-stop service and advice proves invaluable especially during annual festivities like Key West Fantasy Fest, Goombay, and Hemingway Days.


If time is limited try a quick self-tour. Across from Southernmost on the Beach, hop on Old Town Trolley Tours (stop #10) that rolls down South to Whitehead and Truman to The Ernest Hemingway Home and Museum. Here you find the iconic refuge of the Nobel-prize author with gardens, swimming pool, sun-filled writing room, memorabilia, and the wandering progeny of his six-toe cats. Across the street the 88-step Key West Lighthouse Museum, built in 1847, is remarkable as the city’s best observation tower and worth the admission alone for its gorgeous glass Fresnel lens. Around the corner at 1316 Duval marvel at The Key West Butterfly & Nature Conservatory, a glass enclosed, climate controlled habitat with 60 species that flutter overhead.


Down Duval’s row of shops and eateries lies Mallory Square, the town’s historic nexus. Here sit venerable tourist institutions: the Conch Tour Train depot and at the end of David Wolkowsky Lane the Key West Aquarium with its turtle kraals, touch tanks, and shark feedings. Around the corner the massive redbrick and terra cotta trim U.S. Customs House (1891) now houses folk artist Mario Sanchez’s vibrant painted woodcarvings of early 20th century Key West daily life as well as striking Hemingway photos and letters. In fact, Whitehead and connecting streets offer a treasure chest of historic venues: the Mel Fisher Maritime Museum containing his 1985 gold and silver salvage from the Spanish galleon, Nuestra Señora de Atocha (1622); Audubon House & Tropical Gardens and its unique bird prints and lovely gardens; and the Truman Little White House, the 33rd President’s winter residence.


After a few days of sightseeing I moved lodgings literally across Simonton to The Reach Resort, which along with its sister property down the beach, the 90-year-old Casa Marina Resort, belong to Hilton’s newest brand, The Waldorf Astoria Collection. The Reach’s 150 guest rooms (76 suites) sport ocean view balconies, a Nespresso coffee machine, home radio with I-pod docking station, and clean, beige wood interiors. Outside a life-size chess set highlights a smart avenue of royal palms leading to the swimming pool, the natural sand beach, and prominent gazebo-domed pier originally built by my uncle David. The next morning I walked over to the 311-room, Mediterranean-style Casa Marina for a tranquil terrace breakfast overlooking the beautifully landscaped grounds, twin pools and enormous 1,100-foot beachfront.

After breakfast I joined several guests at Barefoot Billy’s, The Reach Resort’s water sports concession. With our guide Brian we had an exhilarating two

hour adventure jet skiing 27 miles around the Atlantic and Gulf sides, exploring former submarine pens and a mangrove island, and whizzing past Mallory Square, Sunset Key, and Fort Zachary Taylor State Park, Key West’s best beach. Later, I drove to Garrison Bight marina and boarded the 65-foot Gulf Stream III (10am-4pm) to fish the Atlantic reefs for snapper and grouper. Owner Jamey Snediker maintains a tidy boat with a large enclosed cabin, snack bar, and wide fishing benches. (On the drive to Key West dedicated fishermen should definitely try sand balling for large yellowtail on Captain Chan’s Gulfstream at Mile Marker 99.5 in Key Largo.)

Happily, Key West is synonymous with fresh fish and key lime pie. A five-minute walk from The Reach Resort, Camille’s Restaurant at 1202 Simonton may be the locals’ favorite breakfast spot - her eponymous eggs Benedicts and lobster omelets are served until 3pm. Camille’s eclectic all-day menus change every two days and include yummy house dips, fresh yellowtail in a macadamia nut crust, and a Zagat “best key lime pie” designation. Over on Duval at Nine One Five owner Stuart Kemp combines global lounge music, a sleek menu of top-grade ingredients, a compact wine list, and a wide-open Victorian mansion and patio setting. Signature items include: tuna dome (Dungeness crab, Ahi tuna, avocado sushimi), steamed clams and chorizo, and butter-smooth Black Angus filet mignon with homemade fries.

Across town on Simonton the Hyatt Key West Resort & Spa has just opened Shor, their American seafood grill. The dining room has a spare, minimalist look that enhances the outstanding harbor and Gulf of Mexico panorama. Instead of over-served and often mushy yellowtail, I selected one of my favorites, a beautiful, firm slab of mutton snapper with a choice of four sauces including pomegranate molasses glaze. A few blocks back on Simonton and Fleming the Café Marquesa has stood out since “New World Cuisine” chef Norman Van Aken dazzled its kitchen 20 years ago. For a romantic dinner the scene is readymade with its amber walls and trompe l’oeil painting across the back wall. Popular dishes by executive chef Susan Ferry include seafood potstickers with spicy peanut sauce, herb dusted black grouper with blue cheese gnocchi, and a key lime napoleon. The adjoining 27-room Marquesa Hotel has received an AAA 4-Diamond award for 18 consecutive years.

Back in Miami I told Aunt Edna Wolkowsky about my stay. She replied, “Why didn’t you visit Abraham’s house around the corner on Whitehead?”

Key West is such a familiar town.