Key West is fun destination by day and and even more-so at night. After the sun sinks into the western horizon, the sky turns a million different colors before fading into night and the island comes alive with revelers on Duval Street, patrons of the arts heading to the theater and curious travelers delving into the island’s haunted past.
Start your evening with a sunset cruise where you’ll take in Key West’s famous sunset in the most scenic way possible. At Fury Water Adventures, you have multiple distinct cruises to choose from. The traditional sunset sail includes unlimited beer, wine and champagne as you cruise in style through the harbor. The Commotion on the Ocean features a live band with margaritas and appetizers in addition to the spread on the traditional sunset sail. The Glass Bottom Boat Sunset Cruise Combo allows you to experience the reef through glass panels and then toast the end of a perfect day while enjoying views of the sunset. Finally, the Rum & Reggae includes a trip to the reef and an hour of snorkeling. The sail back to Key West is perfectly timed to the sunset where your captain will be blasting reggae music and rum punches will be flowing.
Key West is famous for its raucous nightlife, so bar hopping on Duval Street is a natural pastime after sunset. Lower Duval tends to be wilder with bars and nightclubs like Sloppy Joe’s and Rick’s, while Upper Duval has a more sophisticated side with wine bars and cocktail dens like Grand Vin and Point Five. Smack dab in the middle, you’ll find The Porch and The Other Side for craft beer and cocktails with a cool locals vibe.
Louie’s Backyard is one of the most picturesque restaurants in Key West. Set in a Victorian mansion on the southern edge of the island, the restaurant opens up to a tiered back deck where the Atlantic gently laps the shore. From sunset to dusk to starlight, it’s a gorgeous venue to enjoy some of the island’s most refined, fresh seafood dishes and a slice of key lime pie.
Key West Theater
For a cultured night out in Key West, check the calendar at the Key West Theater. This new venue in the heart of Old Town has opened the island up to touring entertainment acts, from comedians like Tig Notaro to bands and musicians like Donavon Frankenreiter and Sister Hazel. It’s also home to original community theater productions and special film screenings inside a charming, historic setting.
Key West is home to its very own indie movie theater, the Tropic Cinema. Beneath a kitschy deco façade, you’ll find intimate screening rooms to watch the latest documentaries, indie films and critically acclaimed blockbusters. They’ve also got a great snack bar serving wine and beer, as well as reasonably priced candy and popcorn.
Better Than Sex
The name might make you blush, and this dessert-only restaurant is definitely best for a visit after dark. Whether it’s a romantic date or a fun girls’ night out, Better Than Sex is a dimly lit, red-draped restaurant serving generous slices of decadent desserts, like a brie cheese, Belgian chocolate tart, chocolate pumpernickel bread pudding and wine and champagne served in glasses dipped in chocolate, all with funny, naughty names.
Hauntings Ghost Tour
Take a spooky walking tour of the island’s haunted side. Founded by longtime local Dave Sloan, you’ll meander through the island’s haunted houses and learn about the spooky history of the Hemingway House, the lighthouse and the famous ghost Typhoid Mary.
Ghosts & Gravestones Tour
The Ghosts & Gravestones tour takes you through the streets of Key West aboard the trolley of the doomed for a narrated tour of the creepy history of the island’s old wooden homes. You’ll also visit the haunted East Martello Tower, a Civil War fort and barracks that once served as quarantine for soldiers suffering from yellow fever. Here, you’ll meet Robert the Doll, considered the world’s most haunted toy.
A block off Duval down Southard Street, the Green Parrot is Key West’s most beloved bar. Crowds spill onto the sidewalk grooving to the latest jam band in town and the bar serves cheap drinks along with its signature root beer barrel shot. There’s a pool table, darts, a killer jukebox and free freshly popped popcorn—what more could you ask for?
At the end of a night out in Key West, all signs point to Mr. Z’s. This late-night pizza joint always satisfies 4 a.m. hunger pangs with a slice of cheese or pepperoni. If you’re really hungry, go straight to the Philly cheesesteak with onions, peppers and mushrooms.