ENCORE! Key West Showstoppers
Sat. Nov. 22 - Sun, Nov. 23 - 8PM - $50
ENCORE! will feature over 25 of Key West’s finest singers performing great numbers from hit Broadway shows. Both evenings will include post-performance catered parties. Directed by Danny Weathers with guest Musical Director Robert Strickland. Scheduled to perform are: David Black, Laurie Breakwell, [...]

The Waterfront Playhouse will present “The Red Head Dilemma,” an interactive children’s musical for ages 6 to 12 that has been created by the Key West Children’s Theatre Company. “The Red Head Dilemma” will play Saturday mornings at 11:00, November 8, 15, 22 & 29. Tickets are ONLY $1 for children and $5 for adults! [...]

17th Annual Meeting of the Minds 2008
Bar Stools & Beach Chairs
October 30 - November 2, 2008 (Key West, Florida)
Meeting of the Minds is Parrot Heads In Paradise Inc.’s annual convention. To attend you must be a member in good standing of a Parrot Head Club. There are over 200 chapters in the US, Australia, Canada [...]

Check out the entertainment around town.  Many bars have webcams with streaming video.
Hog’s Breath Saloon Stage Cam
Listen live as bands play on stage at Hog’s Breath.
Schooner Wharf Webcam
Listen live as bands play on stage at Schooner Wharf.
Sloppy Joe’s Webcam
Listen live as bands play on stage at Sloppy Joe’s.
Green Parrot Bar Webcam
Listen live as bands play [...]

Fantasy Fest is a ten day celebration that includes costume contests, parties, balls, fundraisers, body painting, drag queen contests,  lots of drinking, and parades.
This years theme is Pirates, Pundits and Political Party Animals.
The festival kicks off with GOOMBAY on Friday, October 17.  The ten day long party climaxes with the CAPTAIN MORGAN FANTASY FEST PARADE [...]

Get ready to enjoy live theater productions at the Red Barn Theatre in Key West, Florida.
2008-2009 Season:

Pre-season Show Dec. 4,5,6 2008 Laughing Matters Comedy Show
Show #1 Dec 16 - Jan 17, 2009 Wild Women of Planet Wongo, Lyrics, by Ben Budick Book and Lyrics by Steve Mackes, Music and Lyrics by Dave Orgin, Directed By [...]

I see the bikini contest is coming up at Hog’s Breath Saloon during Fantasy Fest time.  I have seen this live as well as online.  It’s not actually ‘G’ rated, but you can check out photos and videos online.
That reminds me that I forgot to get a new black hogs breath t-shirt when I visited [...]

Waterfront Playhouse at Mallory Square in Old Town, Key West
2008/2009 SEASON
Production #1:
Dec. 17 to Jan. 10. 8:00 pm
Regrets Only
by Paul Rudnick
SOUTH FLORIDA PREMIERE
Director: Danny Weathers
A laugh-out loud comedy by the author of Jeffrey and I Hate Hamlet. Rudnick skewers Park Avenue high society in this hilarious exploration of same-sex marriage, friendship and plastic surgery.
An all-star [...]