Filled with mix of local characters and visitors-in-the-know, "The Parrot," is not your typical dive bar. As the oldest watering hole in Key West, they've got nothing to prove, and their motto, "No Snivelling," illustrates their no-nonsense approach to slinging stiff drinks. Tropical breezes and ceiling fans keep the open-air bar cool, and the old-school jukebox mixes B.B. King with The Temptations and New Orleans Funk. While they only have popcorn to munch on, the BBQ joint next door, Charlie Mac's, will send over a waiter who'll bring you a to-go order. At night, bands from around the country up the ante with a heady mix of gritty blues, rock and funk. Just to keep things interesting, the Green Parrot Ukulele Association plays once a month. If you're not a late-night person, at 5:30 pm the bands do an early sound check set.
Recommended for Best Nightlife because: "The Parrot" is best dive bar to enjoy colorful characters, strong drinks and the best live music in town. Remember, "No Snivelling."
Claudia's expert tip: Try the Root Beer Barrel Shot, a Green Parrot tradition for over 20 years. Drop a shot of root beer schnapps into a highball glass of light beer and toss it back. It's refreshing and addictive.
While there are several drag shows in Key West, you'll truly be wowed at The Cabaret at La Te Da, which has been a Key West landmark for over 30 years. Talented singers (there's no lip-syncing) and impersonators like Randy Roberts and Christopher Peterson take the stage, transforming into legendary stars like Marilyn Monroe, Bette Davis, Tina Turner, Barbra Streisand, Liza Minnelli, Judy Garland, and Cher. These classy performers know how to captivate an audience, get them involved and leave them laughing until they cry. The stars usually leave Key West in the summer and return in the fall.
Recommended for Best Nightlife because: There's no lip-synching at this cabaret where true drag divas will wow you with their impersonations.
Claudia's expert tip: There is a two-drink minimum that is not included in the admission.
This all-welcome, gay night club has creative events every day of the week from afternoon to evening. Stop in for no-limit Texas Hold'em poker tournaments, Aqua's American Idol karaoke with proceeds that go to charity and dueling bartenders who sing as they shake and stir their cocktails. Their nightly drag shows, featuring the Aquanettes, get rave reviews from locals and tourists alike for the caliber of the performances and the hilarity that ensues. The performers get the audience involved, so if you don't like to be in the limelight, choose a seat away from the walkways. After the shows, the bar becomes an all-out dance party that is not to be missed.
Recommended for Best Nightlife because: This all-welcome, gay night club features over-the-top drag performances and non-stop dancing til 2:00 am.
Claudia's expert tip: Tickets are for the shows are $15.00, and reservations are recommended.
The intimate ambience of Tropic Cinema makes for a perfect date night away from the hustle and bustle of Duval Street. With its dazzling marquee sign and streamlined Art Deco decor, the theater evokes a sense of nostalgia. The cozy lounge even features vintage photography and an exhibit space for local artists. With three screens, they have something for everyone from Indie and foreign films to Hollywood blockbusters and documentaries. Cinephiles will love the expertly curated selections that highlight movies that are well-made with artistic value and sometimes even provocative. Run by friendly volunteers, the screening rooms are small with comfortable seating. Patrons tend to be members who appreciate a quiet, courteous viewing experience. You can sip on wine or beer from the concession stand. The fresh popcorn has real butter and a fixings table where you can add cheese, salts and other seasonings. Candy, grilled items, ice cream and fresh baked cookies round out the menu.
Recommended for Best Nightlife because: The intimate ambience and upscale vibe makes Tropic Cinema for a perfect date night away from the hustle and bustle of Duval Street.
Claudia's expert tip: They even have something for the young ones at their Kid's Saturday Movie Club. Perfect for any budget, kids under 12 are a mere $1, and adults pay $2 per ticket.
Tucked behind La Trattoria restaurant, Virgilio's (named after the founder of the restaurant) is an elegant indoor/outdoor cocktail bar popular with the swanky over 30 crowd. Perfectly mixed martinis are the house specialty in yummy flavors like mint chocolate chip and Key lime pie. If you have trouble choosing from their extensive selection, the bartenders can help you find the right drink to fit your mood. Kick back either on the outside patio or at the second bar under the roof. Every night people hit the dance floor for live music, usually jazz, blues or Latin. If you're feeling peckish, you can order Italian fare from a full menu until 10:30pm, and from a limited menu until close.
Recommended for Best Nightlife because: For a more upscale experience, Virgilio's is an elegant indoor/outdoor bar with live music, dancing and the best martinis on the island.
Claudia's expert tip: Be there when it opens on Martini Mondays. Their delicious concoctions are only $5, and the place gets packed.
The Little Room Jazz Club & Wine Bar is a refreshing change amidst the Duval Street Troprock scene. Find a new favorite glass of wine from the extensive listing, as you listen to live jazz, blues and even Cuban-fusion bands. If you're feeling peckish, they have light snacks, as well as meat and cheese plates. A 70-inch television has a feed from the Atlantis aquarium, and all the furnishings have an elegant, polished look. Both indoor and outdoor seating are available, and the music starts early every day. Happy Hour includes 2-for-1 specials on hand-crafted specialty cocktails.
Recommended for Best Nightlife because: For a change of pace, mellow out at the snazzy Little Room Jazz Club with a glass of wine and top-notch live music.
Claudia's expert tip: The music starts early every day, so get there ahead of time for the best seat.
When you liver needs a night off from margaritas and rum runners, head on over to Key West's theater scene for live entertainment. The Waterfront Playhouse is a not-for-profit, professional theater that has been operating in Key West for 70 years. Located in an old 1880's ice warehouse, the intimate theater seats 150 people and hosts a wide range of comedies, dramas, musicals, concerts and world premieres. Recent hit productions at the Playhouse include "Dirty Rotten Scoundrels," "Glengarry Glen Ross," "Twelve Angry Men" and "The Full Monty." While not part of the regular season, Key West Burlesque also performs at the venue.
Recommended for Best Nightlife because: Want a more cultural evening on the town? Head to a show at the Waterfront Playhouse off Mallory Square.
Claudia's expert tip: Check their website for a listing of upcoming shows. The regular season runs from December to May, but they have other events throughout the year like Key West Burlesque.
Steps from the controlled chaos on Duval Street, The Porch is a craft beer lovers refuge tucked into the front of a 1839 Victorian mansion. They have 18 brews on tap and plenty more in bottles with selections changing with the seasons. Wine aficionados will also be pleased with their full wall of wine, interrupted only by a flat screen TV playing B-movies (ironically of course). The décor mixes historic architectural details like pressed tin ceilings and chandeliers with 80s music, a Buddha statue and an R2D2 in a Santa hat. It's been likened to "Cheers" on acid. Sit at the small bar where friendly bartenders like "Grubby" will guide you through their selections, or on the namesake porch--a perfect perch for people watching. Happy Hour is ideal for anyone who wants to try a new brew or wine without breaking the bank. Watch their schedule for theme parties.
Recommended for Best Nightlife because: Hidden just steps from Duval Street, The Porch is a craft beer lovers refuge tucked into an emerald 1839 Victorian mansion. "Cheers" on acid, anyone?
Claudia's expert tip: They don't serve food, but they'll happily provide you with delivery menus from local restaurants.
At Irish Kevin's, hilarious entertainers (particularly Pauly from New York) persuade patrons from the street with a chant of "come on in!" The live performers have patrons dancing, singing and entering drinking contests. Music starts most mornings by 10:30 a.m. and goes non-stop until closing time. Most people stop by for a song or the comedy act and end up staying the night. You have to a have a thick skin to go – they do heckle the audience a bit, so be prepared to be a target of a joke or two. Don't forget to pick up a souvenir shirt with their famous quote: "I came, I drank, I don't remember!"
Recommended for Best Nightlife because: Enjoy the bawdy humor of the musicians at Irish Kevin's where they interact with the crowd, keep the party going and cold beer flowing.
Claudia's expert tip: Bring your sense of humor. If you're easily offended, this is not the spot for you.
Don't leave Key West without seeing the nightly Sunset Celebration on the Mallory Square Dock where the crowd is as colorful as the sky. Entertainers like jugglers, tight-rope walkers, psychics and musicians all compete for your attention and illustrate one reason the island is nicknamed "Key Weird." Be sure to check out Dominique and his talented "flying" cats. Local artists have their wares on display like hand-crafted silver jewelry, painted t-shirts and underwater photography. Vendors sell everything from coconuts with straws to conch fritters, while the real star of the show sets a blazing trail to the horizon. Picture-perfect moments abound, and as the sun takes its final bow into the Gulf of Mexico, the crowd breaks into applause.
Recommended for Best Nightlife because: This carnival-style celebration is a must-do to kick off an evening in Key West. Amidst the revelry, you'll have picture-perfect views of the sunset.
Claudia's expert tip: Make sure you head to Mallory Square at least an hour before sunset for the full experience and pack extra camera batteries.