Key West Nightlife
Duval Street, which runs through the heart of Key West from the Gulf of Mexico to the Atlantic Ocean, is the place to go for exciting nightlife. Paint the town red, indulge in tropical cocktails and take in the many options for live entertainment. Our concierge team is always happy to help point you in the right direction if you need suggestions.
Nightlife - Upscale
Grand Vin Wine Shop & Bar
1107 Duval Street
Phone: 305.296.1020
A wine shop on Duval Street offering excellent company and wines by the glass. You can find a seat on the porch and indulge in people-watching.Nightlife - Upscale
The Cabaret at La Te Da
1125 Duval Street
Phone: 305.296.6706
Have a cocktail in their beautiful garden terrace, listen to tunes in the By George Piano Bar, or catch one of the many great performances upstairs.Nightlife - Upscale
d’Vine Gallery @ The Gardens Hotel
526 Angela Street
Phone: 305.294.2661
You can try more than 32 bottles of wine via the self-serve wine dispensing system for as little as $1.50 per taste. This state-of-the-art wine bar is an ideal location for a classy night out.Nightlife - Dancing
Rick’s & Durty Harry’s
202 Duval Street
Phone: 305.296.4890
With eight different bars in one massive space, you'll find everything and then some. Here you'll find a dance club, martini bar, live music, adult entertainment, karaoke and people watching. Try their frozen drinks.Nightlife - LGBTQIA+
Island House Bar + Cafe
1129 Fleming
Phone: 305.294.6284
Men not staying at the Island House Bar can get a day pass to enjoy all that the site has to offer. Clothing is optional at this Key West café and bar that’s set in lush tropical gardens beside the resort’s pool. An excellent place to mingle, meet and enjoy some delicious drinks, but remember it’s for men only.Nightlife - LGBTQIA+
801 Bourbon Bar
801 Duval Street
Phone: 305.294.4737
The legendary 801 has been part of the Gay Key West landscape for more than 30 years. Enjoy the downstairs bar or night cabaret upstairs, featuring the largest drag house on the island.Nightlife - LGBTQIA+
Aqua Nightclub
711 Duval Street
Phone: 305.294.0555
Aqua Nightclub is the Southermost City’s largest gay dance club, featuring drag shows with the Aquanettes, karaoke, dueling bartends, happy hour trivia, Texas hold ’em and live entertainment. The nightclub includes three bars, one of which is an outside wet bar.Nightlife - LGBTQIA+
Bobby’s Monkey Bar
900 Simonton Street
Phone: 305.294.2655
This straight-friendly gay bar has an old-school vibe that is great for relaxing and enjoying some beers. Expect a smoky atmosphere, some pool tables and the largest book of karaoke songs in Key West.Nightlife - LGBTQIA+
Bourbon Street Pub
724 Duval Street
Phone: 305.293.9800
The hottest video and dance bar in Key West has everything you need for an epic night. Strong drinks, male dancers, a clothing-optional pool area and adult videos make Bourbon Street Pub a favorite spot for the LGBT crowd in Key West.Nightlife - Dive Bars
Green Parrot Bar
601 Whitehead St.
Phone: 305.294.6133
Green Parrot Bar is a famous Key West outpost that features low prices, a large selection and live music on the weekends and was named the #1 live music venue in Florida.Nightlife - Dive Bars
Margaritaville
500 Duval Street
Phone: 305.292.1435
From the enchantingly drinks, fantastic food, and the ongoing dance party, you might want to spend your whole trip at Margaritaville. Jimmy Buffett fans will enjoy the stories from the bartenders, while lovers of the island lifestyle will enjoy the laid-back island feel.Nightlife - Dive Bars
Hog’s Breath Saloon
400 Front Street
Phone: 305.296.4222
Good times and great entertainment are sure to be had at this Key West bar. Check out their live music and don't forget to call your friends from the bar with the Hog Webcam.Nightlife - Dive Bars
Smokin Tuna Saloon
4 Charles Street
Phone: 305.517.6350
Taste some delicious local seafood straight from the grill at the Smokin’ Tuna Saloon. This spacious bar features live entertainment, cheap drinks and the friendliest bartenders in town.Nightlife - Dive Bars
Sloppy Joe’s
1 Duval Street
Phone: 305.294.5717
This famous and infamous Key West saloon is a favorite of locals and tourists alike. Tasty food, generous drinks and live music are served up daily. Known as Hemingway’s watering hole and home of the annual “Papa Look-Alike” contest, this warm and welcoming landmark needs to be on your list of must-sees while in Key West.Nightlife - Dive Bars
Captain Tony’s Saloon
428 Greene Street
Phone: 305.294.1838
Captain Tony was a bootlegger, gambler, and mob affiliate who became the Mayor of Key West. The drinks are tasty, the lighting is low and the band is loud. This Key West bar is the perfect place to hang out in the air conditioning and enjoy some delicious Pirate Punch and local favorites of the Florida Keys.
Nightlife - Dive Bars
Island Dogs Bar
505 Front Street
Phone: 305.509.7136
Visit the Island Dogs Bar in the heart of historic Old Town Key West, where locals and visitors converge over tropical cocktails, one-of-a-kind martinis, live music and top-notch bar food in Key West.Nightlife - Dive Bars
Schooner Wharf Bar
202 William Street
Phone: 305.292.3302
Stop by and pet a rooster while sipping a tropical drink and look out over the ocean in this funky, open-air bar with the best musicians and unique special events.
Explore More
Events Calendar
Good times and good vibes are always on deck. Check out our activities and the local music scene at Ocean Key Resort and Sunset Pier.
Jul21Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.
Date: May 12, 2026 - July 31, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Jul21Live at Sunset Pier - Reggae Lou & The Kind Buds
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: July 16, 21, 23, 28, 30, 2026
Time: 7:00 pm - 9:00 pm
Location: Sunset Pier
Jul22Zero Duval Scavenger Hunt
Experience a one-of-a-kind, interactive scavenger hunt in the downtown area of Old Town, starting at Zero Duval.
Date: May 13, 2026 - July 31, 2026
Time: Wednesday's, 10:00 am – 12:00 pm
Location: Old Town Key West (starts at Zero Duval)
Jul22Live at Sunset Pier – Jerico Rockability Quartet
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: Wednesdays & Fridays | July 1 - 31, 2026
Time: 7:00 pm - 9:00 pm
Location: Sunset Pier
Jul23Hemingway Days
Fans of Ernest Hemingway’s literary greatness and vigorous life – including scores of bearded Hemingway look-alikes
Date: July 23 - 27, 2026
Time: Varies by event
Location: Key West (Sloppy Joe's Bar, 201 Duval St., and other venues)
Jul23Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - July 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Jul23Ocean Key Lime Bike Tour
Sightseeing the Key West way with a leisurely island bike tour that can be done in flip flops!
Date: May 14, 2026 - July 31, 2026
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
Jul23Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - July 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Jul24Snorkel Experience
Dive into the 3rd largest coral barrier reef in the world and the only barrier reef in the continental United States.
Date: May 8 - July 31, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Jul24Live at Sunset Pier - Gi Buxdorf & Jack Wolf
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bites.
Date: July 17, 24, 31, 2026
Time: 1:00 pm - 4:00 pm
Location: Sunset Pier
