Where To Stay

11 Things To Do On Your Next Key West Trip

A balcony overlooking Oceanside Marina from Stock Island's first hotel Ocean's Edge.
A balcony overlooking Oceanside Marina from Stock Island's first hotel Ocean's Edge.

Look—either you get Key West’s quirky, magical charms.

Or you don’t.

If you fall into the former camp, chances are you’re as madly in love with the island’s penchant for day drinking on Duval Street as you are riding bikes through quiet side streets lined with conch cottages and palm trees punctuated by bougainvillea. It’s equal parts sporting life and cultural hallowed ground with boundless offshore pleasures and a legacy as artist and writer haven.

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Oh yeah, and it’s always an unadulterated good time.

You’ve probably got the spots you hit on every visit, but read on to learn about the locals who are shaping the island into an ever-fascinating place to explore. From a new bookstore owned by Judy Blume to the gentrification of Stock Island (and, yes, plenty of new bars and restaurants), here’s where to go and what to do on your next trip to Key West.

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5. A Different Kind of Duval Crawl

The Key West Library's facade flanked by palms on Fleming Street.

The island’s rich literary history is stoked every January with Key West Literary Seminar‘s (305-293-9291) program of panel discussions, parties and author readings. Celebrating its 36th annual seminar in 2018, the theme is “Writers of the Caribbean.”

For new executive director Arlo Haskell, one of his missions is to bring more year round programming to the island. This is being realized with February’s introduction of Literary Walking Tours. Departing from the Key West Library on Fleming Street every Friday and Saturday, the 75-minute tour ($25) led by Sarah Thomas, will explore the former homes and favorite haunts of famous writers including Tennessee Williams, Shel Silverstein, Elizabeth Bishop and Robert Frost, as well as highlight tales of the island’s lesser-known literary talent.

700 Fleming St., Key West, FL

9. Craft Beer Game

When in Key West, drink the Crazy Lady... and get crazy!

After more than five years in the making, the Waterfront Brewery (305-440-2270) opened its doors in 2015 inside the old Waterfront Market made unmistakable by the enormous Wyland mural painted on its warehouse-like facade. The vast, open-air space with views of the Historic Seaport serves a full menu of bar fare, from burgers to conch fritters. Start with a flight of their onsite brewed craft beers, like the Crazy Lady Honey Blonde, Key Lime Witness and Truman Double IPA.

201 William Street, Key West, FL