Key West may look small, but what it lacks in size it makes up for with activities, restaurants, and nightlife. Want to get the most out of Key West in one night? Here are some ideas. 

Enjoy the early evening

Go for a walk along the historic Key West Seaport in Old Town to take in the quiet side of the island. If you arrive early, you can watch the entertaining tarpon feeding near Alonzo’s Oyster House at 4 pm daily. Along the bight you’ll see boats bring in the day’s final catch and dock for the night. You’ll also see sunset cruises embark for the evening. Does a sunset cruise sound good to you? Check out Fury Water Adventures for options.

Dine with sunset

The sun is just about to set, and you have the entire night ahead of you to eat, go for cocktails, dance, listen to live music and get your midnight snack. So, start with a hearty meal and take in that Key West sunset you’ve heard so much about.

The Sunset Celebration at Mallory Square is an event within itself, which starts two hours before the sun goes down. Plan to have dinner before or after the sun sets into the horizon. For a taste of Cuban food and live salsa music every evening, get a table at El Mesón de Pepe. Order a mojito and an entree to start out your evening. 

Go for an evening ghost tour in Old Town

Maybe ghosts aren’t your thing, but these 90-minute night tours actually offer a ton of history about Key West! They’re led by master storytellers who will provide you with interesting background on different haunts located in Old Town – especially tales from the Key West cemetery. Choose from walking tours, haunted pub crawls, or ghost trolley tours. Read more.

Shop Duval Street

You may be surprised to see lots of shops and boutiques along Duval Street stay open into the night hours. Take advantage of the hour! Use our shopping guide to local boutiques in Old Town.

Have drinks in an intimate setting

Live music and cold drinks are abundant in Key West, but you’ll want to pace your evening just right. Start small. For an intimate environment that serves small plates, cold beer, wine and cocktails, the Little Room Jazz Club at 821 Duval St. is a good place to start the evening. Live nightly jazz and a calm atmosphere is the perfect segue to your evening.

In the same vein, Virgilio’s at 524 Duval St. is a classy martini bar with live music on Friday and Saturday nights. Follow their Facebook feed for upcoming shows and events.

See live music in a casual atmosphere

Key West keeps it casual. Smokin’ Tuna Saloon at 4 Charles St. always books some of the best live music on the island on their outdoor stage. Enjoy raw oysters and a lively crowd any night of the week.

Willie T’s is another good option with most of the restaurant located outside. It’s open until 4 am on Fridays and Saturdays and always draws a crowd. Live music and drink specials daily. Located at 525 Duval St.

For a dive bar that takes its music very seriously, The Green Parrot is a rowdy Key West staple that’s always a good time. Check acts ahead of time to see what coincides with your visit. 601 Whitehead St., Old Town 

A late night bite

Sometimes the best way to end a night out on Duval Street is with a late night meal that sops up all the late night spirits. Get in line at Mr. Z’s – it moves fast! Mr. Z’s is open until 4 am every night of the week and specializes in Philly cheesesteaks, pizza by the slice, cannolis, and any other carb-heavy thing you’re craving. Located at 501 Southard St.

For other late night options, refer to our Late Nite Bites guide.

Book for Island Vibes at The Gates Hotel

Floridians can take advantage of their own backyard with our Florida Residents Escape deal at The Gates Hotel Key West, which offers a 20% discount on our best available rate. Guests can enjoy perks like free bike rentals, shuttle access to Old Town, and a 10% discount at Starbucks.