Bourbon Street Pub

Old Town

The Bourbon Street Pub is an obviously New Orleans-themed, multi-bar, men-only night spot. Its clothing-optional garden has a pool and jacuzzi. The hot "Men of...

  • For Men
  • Nightclub

La Te Da Tea Dance

Old Town

The La Te Da Sunday tea dances are a Key West tradition with resident DJs Rude Girl and Molly Blue, cocktails and martinis. Each week has a different theme. You...

  • LGBTQ
  • Party

Virgilo's Martini Bar

Old Town

Martini purists will like Virgilio's lounge, tucked in the garden behind La Trattoria on Duval. Around for a decade, it has the largest martini menu on the island...

  • LGBTQ-friendly
  • Lounge

801 Bourbon Bar

Old Town

For over 25 years, 801 Bourbon has been home of Sushi and her 801 Girls. You may have seen the drag diva on CNN being ceremoniously lowered in a six-foot red high...

  • For Men
  • Bar

Alabama Jack's

Card Sound

The place to stop to break that long drive to or from Key West, Alabama Jack's is a lively bar with cold beer, conch fritters, live music and mangrove swamp views....

  • LGBTQ-friendly
  • Bar

Aqua

Old Town

Aqua has nightly drag shows with the Aquanettes performing on the stage and in the audience. Cover is $15. The 2-for-1 Happy Hour happens every day from 3 pm - 8 pm....

  • LGBTQ
  • Music Venue

Bobby's Monkey Bar

Old Town

Bobby's Monkey Bar is a local hangout where Happy Hour is really Happy Day, stretching from noon to 7 pm. The gay-friendly dive bar has other specials like karaoke...

  • LGBTQ-friendly
  • Bar

Bull & Whistle

Old Town

The Bull, the bar on the ground level has live music all day, all night, every day of the year. One flight up is The Whistle with a creative drink menu that includes...

  • LGBTQ-friendly
  • Bar

Captain Tony's Saloon

Old Town

Captain Tony's Saloon, famous in its own right, is on the site of the original Sloppy Joe's, the one where Hemingway hung out. Other celebrities like Tennessee...

  • LGBTQ-friendly
  • Pub

Chart Room

Seaport

The Guardian calls it "a dive hidden in the middle of a fancy hotel, " and that's just what the Chart Room is in The Pier House. It has been there since the late...

  • LGBTQ-friendly
  • Bar

Fat Tuesday

Old Town

It's always Mardi Gras at the Key West outpost of the Fat Tuesday chain, that's known particularly for its frozen daiquiris, which are $4.50 during the weekday 4-7...

  • LGBTQ-friendly
  • Bar

Garden of Eden

Old Town

Garden of Eden, on the upstairs deck of Bull & Whistle, is a clothing-optional bar that also offers body painting. Drinks only but food can be delivered. It

  • LGBTQ-friendly
  • Bar

Green Parrot Bar

Old Town

The Green Parrot, around since 1890, has a juke box, some of the best life music in town and free popcorn. Happy Hour 4 pm - 7 pm. Mon-Thurs, Fridays from 4 pm -

  • LGBTQ-friendly
  • Bar

Hog's Breath Saloon

Old Town

Besides a great name and great T-shirts, Hog's Breath Saloon delivers tasty Key West bar food, raw bar, live music and dancing on an outdoor covered patio. It's been...

  • LGBTQ-friendly
  • Bar

Irish Kevin's

Old Town

Not for the inhabited, Irish Kevin's is more than an Irish bar. It's a high-energy entertainment center with live entertainment day and night, good grub (try corned...

  • LGBTQ-friendly
  • Pub

Jack Flats

Old Town

With its laid back atmosphere, long bar and 19 big screen TVs, Jack Flats is a late-night option when you want to keep the party going but need a late-night

  • LGBTQ-friendly
  • Bar

Lazy Gecko

Old Town

With 25 jumbo flat screens, the Lazy Gecko has sports events covered, but be advised that the owners are Red Sox fans. It has live music, DJs, Trivia competitions...

  • LGBTQ-friendly
  • Bar

Little Room Jazz Club

Old Town

Known for its live jazz and blues, often by well-known artists, the Little Room Jazz Club hosts all genres and an occasional comedy night in its jazz atmosphere.

  • LGBTQ-friendly
  • Music Venue

Margaritaville

Old Town

Jimmy Buffett, who now calls Palm Beach home, keeps a foothold where it all began in his Margaritaville, the original launched in 1985. The recorded Jimmy plays all...

  • LGBTQ-friendly
  • Pub

Rick's Bar

Old Town

Rick's Bar is really eight bars, offering a little bit of everything, including a house band named DurtBags, a black-leather martini bar, nude exotic dances, hot...

  • LGBTQ-friendly
  • Bar

Rum Barrel

Seaport

Pat Croce, TV personality, motivational speaker and former professional sports club president, opened the Rum Barrel in 2006 with more than 150 rums plus specialty...

  • LGBTQ-friendly
  • Pub

Schooner Wharf Bar

Seaport

What started on a schooner is an open-air bar and grill with three happy hours a day (the first from 7 a.m. to noon), live music, $2 drafts or bottles, 40-foot boat...

  • LGBTQ-friendly
  • Bar

Sloppy Joe's

Old Town

If you've heard of Key West, you've heard of Sloppy Joe's, which opened in 1933 when Prohibition was repealed and Hemingway was living in town. Hemingway, a loyal...

  • LGBTQ-friendly
  • Bar

Smokin' Tuna Saloon

Old Town

The open-air Smokin' Tuna has two bars, local seafood and live music nightly on the courtyard stage. The streaming mobile bar and stage cams refresh every eight...

  • LGBTQ-friendly
  • Pub

The Porch/The Other Side

Old Town

The Porch in the old Porter Mansion may not be haunted but looks as though it should be. It's a craft beer and wine bar that has 18 beers on draft that change week...

  • LGBTQ-friendly
  • Bar

The Smallest Bar

Old Town

The world's smallest bar - or close to it - is in The Old Customs House Inn. All of 72 square feet - about the size of the jail cell we're told - it's tucked away...

  • LGBTQ-friendly
  • Bar