A Guide to Key West’s Unkitschy Side

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

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Brunch at Salute! On the Beach


Julian Cousins for The Wall Street Journal

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.,


Staple Slice

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.,; 725 Caroline St.,

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.,

Fort Zachary Taylor Beach

Superior Fort

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.

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The Curator: Cori Convertito

Curator of the Key West Art and Historical Society

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The Sunset Experience at the Key West Lighthouse Museum & Keeper’s Quarters includes a bottle of wine or bubbles.


Julian Cousins for The Wall Street Journal

Off the Hook Bar & Grill

Top Tacos

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.,

Key West Island Books

Writer’s Room

There has been a bookstore in this location since the 1920s and they have continually focused on local authors. 513 ½ Fleming St.,

Uva Wine Shoppe

Wine O’Clock

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.,

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.,

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The Restaurateur: Jose Diaz

Owner of Cuban restaurant El Meson de Pepe

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Duval Street, the main drag in Key West.


Julian Cousins for The Wall Street Journal

Mallory Square Pier

Sundown Soiree

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.,

Snipes Point

Private Island

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.

Duval Street

Street Sweep

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.

Blue Heaven

Heavenly Creatures

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.,

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The Hemingway Expert: Jacque Sands

General manager of the Hemingway Home & Museum

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A bucci at the Best Coffee in Town.


Julian Cousins for The Wall Street Journal

Santiago’s Bodega

Tapas Time

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.,

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

Due West

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

Morning Glory

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…
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Higgs Beach


Julian Cousins for The Wall Street Journal

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,

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.,

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.,

Tropic Cinema

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.,


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.,

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