Festival highlights include "Henry Flagler's Welcome Party" on January 28, on the beach at the Waldorf Astoria's storied Casa Marina, a sponsor of the event. The sunset shindig will take guests back to the early 1900s, when railroad tycoon Flagler completed the Florida Keys Overseas Railroad—an engineering marvel initially referred to as "Flagler's Folly" and then as the "eighth wonder of the world" following its stunning completion—and conceived the storied hotel.
On Saturday, oenophiles will converge on Key West's renowned main drag for "Duval Uncorked UnDone," a tasting event showcasing stellar vintages and flavorful bites, along with "Sip & Stroll," a free pop-up tasting at galleries along Caroline, Greene, and Simonton Streets. Rounding out the five-day itinerary are a variety of brunches, cocktail classes, dinners, and kitchen tours across the island.
Whether or not you make it to the festival this year, Key West's list of exceptional eateries (over 300 and counting) and inspired watering holes gets longer seemingly by the minute, while tried-and-true local favorites turn residents and tourists alike into regulars. Meanwhile, recently launched ventures like Key West Food Tours offer a tantalizing taste both of the island's singular specialties (think stone crabs, pink shrimp, cracked conch, and, of course, Key lime pie) and its incomparably colorful history. Below are ten must-visit spots for those keen to eat and drink their way through the Conch Republic.
Blue Heaven—Live music and roosters roaming the outdoor dining area create an inimitable atmosphere at this perennial favorite close to the Ernest Hemingway Home & Museum. Sunday brunch is a popular draw thanks to specialties like lobster eggs benedict and banana pancakes, while yellowtail snapper with citrus beurre blanc sauce and Jamaican jerk chicken lure hungry crowds come sundown.
The Flaming Buoy—This low-key hideaway on a charming residential street combines alluringly amber-lit ambience with cuisine that's simultaneously sophisticated and stick-to-your-ribs, including lobster mac-and-cheese, pan-seared hogfish with banana salsa, and beer-battered chicken with spicy waffles.
Kojin Noodle Bar—If your hangover inspires a sudden hankering for authentic Japanese noodles, head straight to this friendly spot, which consistently earns rave reviews for its steamed pork belly buns, house ramen, and other satisfying dishes.
Latitudes—You'll have to hop the free shuttle boat from the Westin Marina (one block from Duval Street) to reach this fine-dining restaurant on Sunset Key, but the idyllic location overlooking the Gulf of Mexico, coupled with a thoughtful seasonal menu, makes the brief trip well worth it. Menu highlights include delectable tuna tartare, grilled Florida lobster tail, and tenderloin you can practically cut with a fork, while tiki torches and palm trees swathed in white lights add to the rarefied island vibe.
nine one five—This laid-back eatery in a Victorian house on Duval Street is a study in understated elegance and irresistible fare. Grab a table on the porch and while away the evening over starters including asparagus with pancetta and pine nuts and clams with chorizo and cherry tomatoes, along with can't-miss homemade pastas like oven-roasted tortellini with ricotta, spinach, pancetta, and parmesan.
Pepe's—Established in 1909, this local favorite across from the historic waterfront is the oldest "eating house" in the Keys, serving up a bustling patio scene along with specialties like baked oysters "Rudi Style" (with parmesan, butter, and garlic), hand-cut steaks, and quite possibly the best homemade coconut cream pie on earth.
The Porch—There's always something fun and funky happening at this Caroline Street bar in the historic Porter Mansion, where you can sample an ever-changing array of 18 beers on tap and 12 wines by the glass. Upcoming events include a "courtyard boogie" (with an all-vinyl music lineup) and a Girl Scout cookie and beer pairing.
2 Cents—On a quiet lane just a few steps from Duval Street, this unassuming spot with a roomy outdoor patio elevates comfort food to whole other level. Don't miss the bacon-wrapped jalapeno poppers, chicken-fried oysters, or colossal B.L.T. at lunchtime. And speaking of bacon, here it's thick-cut, delicious, and served gratis at happy hour, when you roll the dice (literally) to determine how much you pay for your poison.
The Waterfront Brewery—This newly opened bar/restaurant is a lively seaside option where beer aficionados can sample a rotating selection of exotic ales made on-site, including a peanut butter brew that's as tasty (and unusual) as it sounds. Hearty fare like Bahamian white conch chowder and Lower Keys fish dip help the suds go down easy.
Wine-O—A recent addition to the historic La Concha Hotel & Spa (whose location is unbeatable if you want to stay in the heart of the action on Duval, and whose airy rooftop spa is an oasis ideal for recovering from too much overindulging), this sleek bar-and-wine-store hybrid features over 200 bottles from around the world. Wine flights served by the friendly and knowledgeable staff let you sample a few vintages before choosing your favorite.
The aforementioned Casa Marina, a Waldorf Astoria property, is a sprawling, casually luxurious option for visitors coming for the festival or just a tropical escape. Opened in 1920 to accommodate wealthy customers of Henry Flagler's celebrated Overseas Railroad, it was designed by architects Thomas Hastings and John M. Carrere, whose other esteemed credits include New York's Metropolitan Opera House and the New York Public Library. Listed in the National Register of Historic Places, the landmark boasts over 300 rooms and suites, an incomparable location on Key West's southern edge complete with the island's largest private beach, and gorgeous pools and public areas.
With a full roster of inspired spirits programming—including the memorably monikered seminars, "To Have and Have Another (Rum)" and "Death In the Afternoon Absinthe" on January 29 and January 30, respectively—festival visitors with a hankering for the harder stuff will be well served at Casa Marina and its neighboring sister resort, The Reach.
Those driving to Key West from Miami should consider breaking up the four-hour trip halfway with a stay at Cheeca Lodge in Islamorada, which is celebrating its 70th anniversary this year. The resort's lush setting, atmospheric elegance, and distinct sense of place is rivaled only by its long and illustrious history, during which it's hosted countless boldface names including Paul Newman and former President George H.W. Bush.