Key West is an island of drifters, dreamers, free spirits and those simply drawn to the sea and the end of the road. The southernmost city in the Continental United States—and geographically closer to Cuba than it is to mainland Miami—Key West has always played to the beat of its own drum. Only eight square-miles with a melting pot of 25,000 residents, it’s an inclusive place with the motto, One Human Family, so come as you are. You’ll quickly realize it’s hard not to be lured by the salt breeze, the endless horizon and the laidback locals on this anything-goes, Bohemian island.
Start your day on the right foot with breakfast at Help Yourself. This open air, organic restaurant and market occupies a former laundromat with communal bench seating on a covered patio surrounded by freshly potted plants. With a menu of all natural, sustainable and local ingredients, opt for a cold brew with coconut milk, the fruit parfait made of house-cultured coconut yogurt, homemade granola and seasonal fruit, and the rise and shine bagel with cashew cream cheese, tomato and avocado.
Take your cold brew to go and cruise down Margaret Street toward the Historic Seaport. You’ll spy fishermen getting their boats ready for the day, early morning boozers already at it at Schooner Wharf and slips lined with elegant schooners and luxury yachts. Back on Caroline Street, duck into the backyard at Pepe’s for screwdrivers at the small bar. This is Key West, after all, and you’re just not doing it right without a drink before noon. At Pepe’s, the pours are long and the oranges are fresh-squeezed at the bar.
The best way to get around Key West is by bicycle, so rent yours from Eaton Bikes and do as the locals do. Grab a map from the shop as a reference point, but set your sights on getting lost through Old Town. You’ll pedal amid blooming bougainvillea and banyan trees and past charming conch cottages in a palette of pretty pastels with white gingerbread latticework.
Photo by Shayne Benowitz
Stay on your bike and cruise by these points of interest: the historical Key West Cemetery with one salty epitaph that reads, “I told you I was sick;” the Southernmost House, a fabulous Victorian hotel in sea foam green and conch shell pink that has hosted presidents, royalty, and famous figures like Ernest Hemingway (pictured above); and the Southernmost Buoy emblazoned with the claim, “90 Miles to Cuba” for your obligatory photo-op.
Photo by Shayne Benowitz
Pedal toward The Hemingway House where the Key West Lighthouse is just across the street for impressive bird’s eye views. A guided tour of the Nobel and Pulitzer Prize-winning author’s home is well worth your time where one of the knowledgeable guides will impart all manner of amusing anecdotes about Papa’s time on the island during the 1930s.
Stop for lunch at organic Bad Boy Burrito, a hole in the wall joint on Simonton Street run by a husband and wife duo. From fresh caught Key West pinks to ground Kobe beef to tofu, top your burrito (rice and beans come standard) with a variety of fresh ingredients and homemade sauces, like a roasted pineapple habanero or chipotle red chili.
The sunset is celebrated every night in Mallory Square, but the best place to marvel at the sky’s changing colors is on the water. Embark on a two-hour sunset sail aboard the Schooner Hindu, a 79-foot, square-rigged wooden boat originally built in 1925 and restored by the Rowan family in 2012 (check the schedule to make sure the boat is in Key West when you are). Glide peacefully through Key West Harbor with the engine switched off and the sails filled with wind, while enjoying fine wines, craft beer, artisan charcuterie and small batch chocolates as the sun makes its nightly journey past the western horizon.
Photo by Michael Marrero
Disembark and head to dinner at 2 Cents, a funky gastropub with steampunk light fixtures and intergalactic mural art. Pull up a chair at the bar or grab a table on the outdoor patio for a dinner of elevated mix and match pub grub. A few standout selections: nachos with duck confit, bacon-wrapped jalapeno poppers and the royale with cheese on a brioche bun.
Key West is a hard drinking town famous for its nightlife, so don’t plan on going to bed early. Inside a historic Victorian mansion on Duval Street, you’ll find The Porch (pictured at top) for craft beer and fine wines, as well as The Other Side dedicated to creative mixology. With both bars under the same ownership, patrons breeze between each and gather on the spacious front porch for good times. End your night at the Green Parrot, easily Key West’s most beloved bar. Follow the sounds of a melodious jam band to find revelers spilling onto the sidewalk. Order a round of root beer barrels (their proprietary shot) and find your place in the dimly lit dive amid the throbbing crowd.
Photo by Shayne Benowitz
Up with the roosters and still feeling groggy? Head to the Cuban Coffee Queen, a colorful shack by the Historic Seaport for the perfect pick me up. Order the Sunrise Special, half a Cuban pressed sandwich with eggs, cheese and bacon with a café con leche. Alternatively, the Hangover Helper smoothie does just that.
Photo courtesy of Fury Water Adventures
Take your grub to go and hurry over to the Westin Marina to catch the morning snorkel boat with Fury Water Adventures (pictured above). Departing daily at 9:30 a.m. (if you oversleep, not to worry—just reschedule for the 1 p.m. trip), this three-hour adventure takes you seven miles offshore aboard a 65-foot catamaran to snorkel at the third largest reef in the world.
Venture into Bahama Village for lunch at La Creperie, a restaurant with a sunny wraparound patio dishing up fresh crepes by two loquacious French women. From classic combinations like jamon y fromage to creative concoctions like Le Mexicaine (refried beans, avocado, Swiss cheese), everything is made fresh to order. And don’t leave without sharing a tantalizing dessert crepe. Afterward, cruise Petronia Street with its art galleries and tempting boutiques.
Escape the sun for a late afternoon matinee at the Tropic Cinema. An Art Deco art house theater in the center of Old Town with three small screens, The Tropic is the perfect place to catch an indie flick in an intimate, air-conditioned setting. In addition to reasonably priced popcorn, candy and sodas, the snack bar also sells beer, wine and gourmet munchies.
For dinner, Santiago’s Bodega in Bahama Village serves Spanish tapas with a New American twist. The dining room is intimate and romantic with fresh flowers and bottles of wine as décor, as well as surreal paintings lining the walls. Small plates are meant to be shared with standout items including the seared beef tenderloin topped with blue cheese butter, fennel-encrusted grouper and saganaki, a haloumi cheese flambéed in brandy and served with caper berries and pita. After dinner, head to Point Five for a nightcap with a sophisticated, classic martini like the Vesper at their upstairs wraparound balcony overlooking Duval.
And if the Key West night is calling you, don’t be afraid to answer it. Bars stay open until 4 a.m.
Most airline carriers will route you through Miami to Key West International Airport (EYW). However, Delta flies direct from Atlanta. It’s a three-and-a-half hour drive from Miami down the scenic Overseas Highway.
Where to Stay
A stone’s throw from the Historic Seaport and in the heart of Old Town, The Marker Waterfront Resort opened in December 2014 as the first new hotel in Key West since 1994. They’ve taken great care to ensure that it blends seamlessly into its tropical, historic surroundings. With 96 guest rooms, a courtyard pool and Cero Bodega restaurant, it embodies Old Key West in new lux digs from $489 per night.
Short for Not Your Average Hotel, NYAH is a wallet-friendly guesthouse tucked away behind a charming conch cottage in Old Town. Each of their 36 unique rooms can accommodate up to six people comfortably thanks to flexible configurations. While the rooms are no frills, the hotel boasts a courtyard pool, complimentary Continental breakfast and happy hour in a setting that couldn’t be more Key West. From $40 per person or $359 per night.
Shayne Benowitz is a Miami-based travel writer and former Key West local who still gets nostalgic about island life. Good thing she’s never more than a three-and-a-half hour drive to paradise from her home in South Beach.