Solo Travel: The Friendliest Bars in Key West
Key West has a reputation of being a friendly, welcoming place - hence our motto, “one human family.” Just because you’re traveling without friends doesn’t mean you’re alone.
Navigate nightlife in Old Town to see which bars are most comfortable if you’re flying solo. Here’s a look at your options – see which best matches your taste.
Little Room Jazz Club
821 Duval St., Key West
If you’re looking for a more posh environment with a focused, intimate setting, the Little Room Jazz Club on Duval Street may be your cup of gin tea. See live jazz every evening at 8pm and enjoy some of the best cocktails in Old Town.
801 Duval St., Key West
For a night of laughs, entertainment and performers hamming it up with some camp, 801 Bourbon is a your friendly neighborhood gay bar. Nightly drag shows and cabaret are raunchy, good-humored fun for adults from all walks of life. Bring cash to tip performers!
Sloppy Joe’s Bar
201 Duval St., Key West
Sloppy Joe’s has live musical entertainment (almost) always and there’s usually ample space to grab a seat at the bar and enjoy the set. It’s also the most iconic bar on the island, so attracts lots of tourists. You can meet people from all around the world at this humble watering hole.
3824 N. Roosevelt Blvd., Key West
Of course we’re partial, but our friendly bartenders and sophisticated cocktail list – which features locally distilled rum – make a drink or two at Rum Row a relaxing, laid-back experience. You can lounge poolside, and if you get hungry, the nearby Blind Pig food truck serves food until 10pm. Check out our Rum & Reggae Saturdays as well as our regular Yappy Hours, which features live entertainment, drink specials, and benefits the local SPCA. Pets welcome.
The Bull & Whistle Bar
224 Duval St., Key West
Do you like to people watch? The Bull is your place. With views of Duval Street and live entertainment on the mainstage, the old-school watering hole provides endless action. Head upstairs to The Whistle and take in the view of Duval Street from the balcony. The Bull is an open-air bar without air conditioning, so make sure to order something cold!
If you’re thinking about a visit to Key West, don’t delay! It’s always summer in the Conch Republic. The Gates Hotel is a Condé Nast award-winning hotel located in New Town, which offers free hourly shuttle service to Old Town. Exciting onsite amenities – like a food truck, cigar lounge, and a spectacular swimming pool – puts The Gates in its own special category. Check out our special offers online.