Key West Entertainment

Entertainment in Key West offers something for everyone, with the islands nightlife particularly laid-back. However, for the more discerning the Tennessee Williams Theatre offers some classic plays and several cocktail lounges feature live jazz and blues.

Nightlife

Key Wests notoriously boisterous nightlife is, for the most part, centred around the numerous bars and nightclubs that line Duval Street, the citys main drag in Old Town. Here, youll stumble on bar after bar serving up neon-coloured frozen drinks to revellers who hop from one bar to the next from noon till dawn. Bands and crowds vary from night to night and season to season. A good place to start your pub crawl is at Truman Avenue and then head up to Duval. Duval Street is lined with the most famous bars in Key West, including Sloppy Joe's, Fat Tuesdays and Jimmy Buffets Margaritaville. Cover charges are uncommon, except in gay clubs, so peep into as many as you like and see which you fancy. Key West is mostly a late-night town and bars and clubs usually stay open until around 03:00 or 04:00. In the Keys, there is no dress code as such and most people consider shorts and a t-shirt dressing up.

Theatre and music

Key West is home to a vibrant music scene, while also offering plenty of choices for those interested in the performing arts. The Tennessee Williams Theatre is not just a theatre. It doubles as a performing arts centre, a civic centre and a community centre. It hosts conferences, parties, fundraisers, workshops and live performances. The Red Barn Theatre features live comedy, drama, musical theatre and cabaret shows in a small, intimate setting. The Waterfront Playhouse is Floridas oldest continually operating theatre, where the magic of live theatre has been presented for 65 years. The Crystal Room at La Te Da on Duval Street offers a fun and glitzy atmosphere and stages a different cabaret show every night.

The Tennessee Williams Fine Arts Center offers a variety of music concerts and other performing arts events. During the winter season, Sebrina Alfonso directs the Key West Symphony. Watch for free pre-concert lectures at libraries and other venues. Bourbon Street Pub features 10 video screens along with male dancers grooving to the latest music spun by DJs. Bands play nightly at Capt. Tonys Saloon, where Jimmy Buffet once strutted his stuff. Theres live music nightly at the famous Sloppy Joes, which also features a cigar room and martini bar. The cocktail lounge Virgilios, part of the La Trattoria restaurant complex, serves chilled martinis to the soothing beat of live jazz and blues nightly.

Festivals

Key West hosts a number of lively, colourful and exciting annual street festivals, with the fishing and gay pride festivals proving particularly popular.

  • House and Garden Tour (January) opens a number of important, private houses and gardens to the public.
  • Civil War Heritage Days (February) features a colourful Civil War re-enactment at historic Fort Zachary Taylor. Highlights include fort tours, living history demonstrations, artillery demonstrations and a sea battle.
  • Key West Fishing Tournament Kick-Off Event (March) sees anglers target multiple species in an event that starts a season-long tournament that awards certificates for outstanding catches and prizes in a host of categories.
  • Conch Republic Independence Days Celebration (April to May) features parades, parties and fun events.
  • Annual Schooner Wharf Minimal Regatta (May) is held at the Schooner Wharf, with each participating team building and sailing their own boat.
  • Gay Pride Week (June) offers many celebrations and parties throughout the district.
  • Hemingway Days Festival (July) commemorates the famous author with readings and competitions, including a fishing competition and a Hemingway look-a-like challenge.
  • Lobster Fest (August), featuring famous crustaceans, is held on Duval Street.
  • Fantasy Fest (October) is themed Freaks, Geeks and Goddesses and is a 10-day spectacular with parades and sights with wacky costume competitions.
  • Key West Old Island Days (November) celebrate Key West culture and history with an art festival, crafts show, conch shell blowing contest and house and garden tours.
  • Key Wests Annual Holiday Parade (December) is a parade featuring general holiday celebrations.

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