If you’ve checked every box next to Key West’s most popular landmarks, these similar – but lesser-known – highlights are as worthy of a look.

It’s easy to find a guide (or a few hundred of them) for what to do in Key West, and be pointed to Key West’s most popular and famous landmarks. But what about the secret side of the island? We highlight a few famous landmarks that you likely already know of, but then offer a comparable insider-only spot that is too good to miss.

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 like 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 get 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. **Please note, Little Room Jazz Club is currently undergoing renovations – including adding a new front deck – that is expected complete in spring 2021. 

For the Easy Riders

The Classic: Old Town Trolley Tour

The Counterpart: Lloyd’s Tropical Bike Tour

Old-Town-Trolley-Tour versus Lloyd’s Tropical Bike Tour

In place of a traditional trolley tour, this bike tour – hosted by local Lloyd Mager for 30 years running – offers a funky alternative and a close-up, tactile view of another side of Key West. In addition to rolling through the neighborhoods of some of Key West’s notable residents and taking in the eclectic mix of homes, you’ll also visit a private beach, try the island’s native fruits (like freshly cracked coconut, mangoes, key limes), and smell and examine some of the island’s most beautiful flowers.


Where to Stay Sunset Key Cottages  | The Laureate Key West | Opal Key Resort & Marina | The Capitana Key West