LOCATED AT the end of Florida’s 113-mile Overseas Highway, Key West inspires unabashed revelry, even in the steamy summer. Maybe that’s because, as one of the southernmost points in the contiguous U.S., it feels more Caribbean than continental. Or perhaps it’s because raucous, sun-bleached bars flank Duval Street, its main drag. But don’t dismiss this city of around 24,000 as a party town. Countless writers have yielded to its tropical magnetism over the years—Ernest Hemingway stayed for a decade, and Tennessee Williams, Robert Frost and Wallace Stevens all spent time here. Stevens once complained that his frequent winter escape was becoming “furiously literary.” Here, we ask four locals, including one noted scribe, for their favorite aspects. The intel they share goes beyond frozen daiquiris and Papa Hemingway look-alike contests to reveal hidden beaches, hole-in-the-wall coffee shops, and three contenders for the “best” vantage point from which to watch the sun set. Which wins? Go judge for yourself.
For the Real Key West, Follow the Locals
From seafront restaurants with dinner ‘theater’ to a lighthouse that you can have all to yourself, here are a few hidden treasures recommended by discriminating locals
Higgs Beach Pier in Key West,
Julian Cousins for The Wall Street Journal
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The Author: Judy Blume
Author and co-founder of Books & Books at the Studios of Key West
Salute! On the Beach
Serve and Volley
I love going to this place on Higgs Beach for early dinners with beach volleyball and, if the winds are right, ocean kite boarding as dinner ‘theater.’ 1000 Atlantic Blvd., saluteonthebeach.com
The best pizza in town. We enjoy it every week, in the Old Town garden or at the newer, bigger Grill. 613 1/2 Duval St., onlywoodkw.com; 725 Caroline St., onlywoodgrill.com
The Studios of Key West
Deco the Halls
There are performances and exhibits, the building is an iconic piece of Miami-style art deco and the roof garden offers the best views in town. 533 Eaton St., tskw.org
Fort Zachary Taylor Beach
There’s a Civil War fort here to entice the kids and my favorite beach in Key West, with picnic tables under swaying Australian pines. floridastateparks.org
The Curator: Cori Convertito
Curator of the Key West Art and Historical Society
Off the Hook Bar & Grill
The fish tacos are the best I’ve ever eaten and I can never go wrong with their lobster mac n’ cheese. 920 Caroline St., offthehookkeywest.com
Key West Island Books
There has been a bookstore in this location since the 1920s and they have continually focused on local authors. 513 ½ Fleming St., keywestislandbooks.com
Uva Wine Shoppe
I love to frequent this family-owned business. They also deliver wine, artisanal cheeses and meats directly to your door the same day. 519 Fleming St., uvakeywest.com
Key West Lighthouse Museum & Keeper’s Quarters
Ray of Light
One of my favorite Key West experiences is taking in the sunsets from the top of this lighthouse. You need to book in advance but you’ll get it to yourself. 938 Whitehead St., kwahs.org
The Restaurateur: Jose Diaz
Owner of Cuban restaurant El Meson de Pepe
Mallory Square Pier
Crowds gather at Mallory Square to enjoy the most beautiful sunsets anywhere. Vendors and a variety of street entertainers fill the square giving it a very “boardwalk” feel. 400 Wall St., mallorysquare.com
This small island beach, which can only be reached by boat, is a local hot spot. It’s just a quick 20-minute ride from Key West.
You can find something for everyone here: restaurants, nightclubs, bars and various shows. My personal favorite is the drag show at Aqua. It’s extremely entertaining.
The Caribbean-accented food is amazing, particularly the lobster Benedict at breakfast. The mostly covered outdoor space is a nice place to eat and see wild roosters walk around. 729 Thomas St., blueheavenkw.com
The Hemingway Expert: Jacque Sands
General manager of the Hemingway Home & Museum
It’s a short walk from the museum so we will stop over for lunch or their unbeatable happy hour. The saganaki and sangria make a notable duo. 207 Petronia St., santiagosbodega.com
Boca Grande & Woman Key
Birds of Paradise
These two islands sit side-by-side about 15 miles west from Key West and are home to beautiful beaches and a bevy of bird activity and marine life.
Truman Waterfront Park
The oceanfront park sits at the far west end of the island and provides some of the best sunset views in the country. Southard St.
The Best Coffee in Town
A hole-in-the-wall the locals call Felix’s after the owner. I start my day there with a bucci or two (a straight shot of Cuban coffee) and a bacon, egg and cheese on a roll toasted to perfection, with a side of gossip from the early birds. 1222 White St.
Plus, Don’t Miss…
Key West Food Walking Tour
This isn’t just a gluttonous introduction to the snacks and sips of this compact key, but also an intriguing outing through the history of the island. Guides lead small groups to sample Cuban cuisine, fried conch fritters, rum cocktails and Key lime pie. Tours start at $75 per person, keywestfoodtours.com
Fort East Martello Museum & Garden
With exhibitions on early sponge fishing and the Cuban influence on Key West, this museum gives visitors a deeper sense of the history and culture of the area. 3501 S. Roosevelt Blvd., kwahs.org
Books & Books at the Studios of Key West
Founded by author Judy Blume and her husband, George Cooper, this bookshop housed in an erstwhile Masonic temple is a fun place to browse for new reading material. 533 Eaton St., booksandbookskw.com
This movie house has four comfy screening rooms in which to beat the heat for a few hours, plus you can sip wine while catching a flick. 416 Eaton St., tropiccinema.com
SHARE YOUR THOUGHTS
What are your favorite places to visit in Key West? Join the conversation below.
Hemingway Rum Company
You can’t escape Hemingway when in Key West so you might as well drink to him. Take a short tour of the distillery and then sample the rum, named Pilar for his Key West fishing boat. 201 Simonton St., papaspilar.com
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