Waterfront playhouse

1. Waterfront Playhouse

In the site of a former warehouse that stored wrecker’s loot confiscated from ships gone aground, today this historic structure just off Mallory Square, houses one of the finest live theater venues in the South, the Waterfront Playhouse. Each season tourists and locals alike are treated to performances that rival Broadway productions. Drawing from exceptional local talent and attracting seasoned veterans of the stage, Executive Director, Danny Weathers does not disappoint. You’ll rave at the quality of the acting, the professionally crafted sets and the enthusiasm of the volunteers that greet you at the theatre. The Waterfront Playhouse is one of the many things that keep you coming back to Key West.




Tennessee Williams

Tennessee Williams Fine Arts Center

2. Tennessee Williams Theater

The namesake author and playwright may never have laid eyes on this impressive auditorium, but his reputation for first rate entertainment lives on. Adjacent to the Florida Keys Community College, this modern facility is host to a wide variety of performances including the South Florida Symphony Orchestra, the Keys Chorale, performances by Coffee Mill Dance Studio, generous fund raising presentations by amazing local talent, as well as numerous internationally acclaimed concerts. So much talent on such a little island keeps you coming back.





hog music

Kenney Chesney at the Hog’s Breath Saloon

3. Music in the Air
On any given evening in Key West, music fills the air. The length of Duval Street, the strident sounds of country, folk, jazz, rock and reggae tunes leave a dizzy resonance in your ears. But don’t forget the side streets for more cozy settings and discover a new musical talent or to hear a favorite crooner. Through the Applerouth Lane entrance of Virgillios you’ll hear a different sound experience every night of the week. Or Southard Street’s funky Green Parrot is a favorite for local performers. Music of every variety in Key West keeps you coming back.






Key West Pink Shrimp

4. You Don’t Have to Be Hungry to Eat
Eating for sustenance is what you do everyday. In Key West, you eat for the adventure of it. If you eat out every day of the year, you may get to sample all the gastronomy choices here. Seafood is a must, especially the famous Key West Pinks, delectable fresh shrimp like no other. You’ll find these lovelies paired with pasta, jasmine rice with mango salsa, or as garnish for a steak. Try them once and they’ll keep you coming back.






Ft Zach

Fort Zachary Taylor State Park Beach

5. Reborn As a Water Baby
Yes, Key West is surrounded by water. That’s why it’s called an island. So don’t delay one more minute- get in the water! Whether you dip your toes off the shore of Higgs Beach or glide across the waves on a sunset cruise, being in or on the water is a comfort and a blessing. Blissful water, see it, feel it; it keeps you coming back for more.