Key West summer nights are their own kind of magic. Whether you want a nocturnal adventure with the family or a night out with your best drinking buddies, try one of these after-dark experiences in Key West.

1. Start with the Key West Sunset

Watch the vibrant color display with thousands of other spectators at Mallory Square, go to Fort Zach on the southern tip of the island for less noise and fanfare, or, take a relaxing Key West sunset cruise with Fury Water Adventures.

2. Do the Duval Crawl - Key West Pub Crawl

A nighttime stroll along Duval Street is a form of free entertainment in and of itself, but if you want to add an adult beverage into the mix, try the Duval Crawl! There are dozens of drinking establishments along Duval, so another option is the Key West Pub Crawl. The guided tour happens almost every night of the week and brings you to five of the best bars on Duval.

3. Catch a Show at the Key West Theater

Watch comedy, variety shows, and live music at the historic performing arts venue in Old Town. Past performers include big names like Jefferson Starship, Arlo Guthrie, and Jimmy Buffett. See upcoming acts on the Key West Theater calendar that coincide with your visit.

4. Go on a Key West Ghost Tour

Key West has a long history and not all of it is sunsets and margaritas. The island’s past has some tales to tell, and they’re best told after-dark. Take a walking ghost tour or hop on the Trolley of the Doomed to explore “one of the top ten most haunted cities in America.”

5. Grab a Drink After Hours - Key West Bars

Looking for the perfect spot for a summer sunset sipper? The best happy hours? The best gay bars? We can direct you where to go. Visit our Key West Bars & Nightlife Guide for more.

6. Have Dinner at Key West’s Best Restaurants

It’s so easy to find good food in Key West, this is the obvious option for a summer’s night. What are you in the mood for? From iconic eateries to hidden gems, eat fresh at local landmarks. Check out our Key West Food & Dining Guide to find your spot. Or, stay right here at The Gates and grab something from our on-site food truck, The Blind Pig, it’s open late!

7. See a Performance at the Key West Amphitheater

The largest performing arts venue in Key West has hosted major artists like The Beach Boys, ZZ Top, and Willie Nelson. See who’s on the schedule and grab a ticket to the grassy grounds to enjoy a show under the stars.

8. Go on a Night Kayak Trip

For an active kind of outing, try a night kayak trip with Key West Paddle. Your nighttime paddle through the mangrove tunnels is done in a kayak outfitted with bright LED lights that illuminate the sea life below.

9. Listen to Live Music in Key West

The Conch Republic and live music go hand-in-hand. Jimmy Buffett even got his start here by playing at local venues! Catch live music every night of the week at places like Green Parrot, Sloppy Joe’s, Smokin’ Tuna Saloon, Hog’s Breath Saloon, El Meson de Pepe, and Virgilio’s.

10. See Sharks and Tarpon Along the Key West Boardwalk

When the sun goes down, the lights come on, including those shining below the surface of the water along the Key West Bight. As fishermen filet their catch and discard the waste overboard, the sharks and tarpon show up to feed. The lights illuminating the underwater scene capture quite the display of hungry sea life. Watch the show! Outside of the White Tarpon is a good place to start.

Seal the summer deal! Book your stay at the Conde Nast award-winning The Gates Hotel Key West. See which of our special offers works for you. We have deals for AAA members, Florida and Georgia residents, seniors, government workers, and more. Now for a limited time, escape to our sun-soaked paradise with the entire family with the Tropical Family Retreat package, which includes all sorts of special extras to create unforgettable memories for you and your loved ones.