Key West’s Classic Landmarks & Their Hidden Counterparts

If you’ve crossed off every item on your Key West itinerary – popular landmarks, historic sites, iconic beaches, and noteworthy bars – then you’re ready to graduate to a whole new level of Key West travel and exploration. 

Search “things to do in Key West, Florida,” and find hundreds of guides filled with common tourist attractions, popular restaurants, bars, and island-friendly activities. But what about the secret side of the island? We’ve put together a comprehensive list of Key West’s top attractions that you may already know of and provide a comparable insider-only spot. You might want to book a few extra days, these are too good to pass up.

For the Book Nerds

The Classic: The Ernest Hemingway Home
The Counterpart: Tennessee Williams Key West Exhibit

Hemingway wasn’t the only literary icon who called Key West home. Tennessee Williams – playwright of classics like “A Streetcar Named Desire” and “Cat on a Hot Tin Roof” – lived in Key West from 1949 until his death in 1983. This small but interesting and carefully curated museum on Truman Ave aims to bring his work to life with artifacts including his old typewriter, first edition plays, photographs, rare articles and videos, and more.

For the Beach Bums

The Classic: Fort Zachary Taylor State Park and Beach
The Counterpart: Simonton Street Beach

This small pocket beach is located at the west end of Simonton Street, which, yes, is smack dab in the middle of the heavily visited tourist area near Mallory Square. But because of the marinas that border it, you’d never know it was there. Not only is it well-maintained, but the hidden gem features a small beach bar, Lagerheads, where you can grab a cold beer and some of the best fish tacos in the Keys.

For the Duval Street Done-It-Alls

The Classic: Green Parrot
The Counterpart: Little Room Jazz Club

Despite being located on Key West’s loud and often rowdy Duval Street, this intimate bar is a little-known spot for live jazz music every night of the week. As for the vibe, expect cozy nooks and crannies, silent films projected behind the wall of the bar serving craft cocktails, and “little bite” appetizer options like Jazzy Chicken Bites and Lobster Cakes.

For the Easy Riders

The Classic: Old Town Trolley Tour
The Counterpart: Key Lime Bike Tours

In place of a traditional trolley tour, this bike tour offers a more active alternative and a close-up view of the historical side of Key West. During the close-to three-hour ride, you’ll roll through Mallory Square, White Street Pier, and the Key West Cemetery, to name a few landmarks. Plus, you’ll make a pitstop at the Southernmost Point Buoy – one of the most photographed spots in the area – to take in some majestic waterfront views. At the end of the tour, prepare to be rewarded with a well-deserved slice of Key Lime pie from Key West Key Lime Pie Co.