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.
Sep01Double 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 - December 31, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Sep03Just a Few Friends, Favorite Son Celebration
Just a Few Friends is a one-of-a-kind festival celebrating music, community, and island life in beautiful Key West over Labor Day Weekend.
Date: September 3 - 11, 2026
Time: Varies by event
Location: Key West (multiple venues)
Sep03Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - December 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Sep03Ocean 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 - December 31, 2026
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
Sep03Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Sep04Snorkel 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 - December 31, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Sep05Sunset Sails
There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier, of course) is out on the water.
Date: May 9, 2026 - December 31, 2026
Time: Saturday's, Varies (sunset)
Location: Off-Site (Key West waters)
Sep06The Wheeland Brothers Private Poolside Concert
Join us for a Just A Few Friends, exclusive Ocean Key Resort poolside concert.
Date: September 6, 2026
Time: 12:00 pm - 1:30 pm
Location: LIQUID Pool Bar & Lounge
Sep06World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarpon or bonefish or in the deeper waters of the backcountry, on the hunt for snapper, grouper or tuna.
Date: May 10, 2026 - December 31, 2026
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)
Oct16Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
