top of page

Upcoming Events

  • An Evening with Sunny Jim White
    An Evening with Sunny Jim White
    An Evening with Sunny Jim White
    Sat, Nov 02
    The Drunken Octopus
    Nov 02, 2024, 6:00 PM – 9:00 PM
    The Drunken Octopus, 4 Aster Terrace, Key West, FL 33040, USA
    Nov 02, 2024, 6:00 PM – 9:00 PM
    The Drunken Octopus, 4 Aster Terrace, Key West, FL 33040, USA
    Join us under the stars for this rare opportunity to see Sunny Jim here in Key West. Suggested Donation $75.00
  • An Evening with Cameron Havens
    An Evening with Cameron Havens
    An Evening with Cameron Havens
    Sat, Aug 10
    Key West
    Aug 10, 2024, 7:00 PM – 10:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Aug 10, 2024, 7:00 PM – 10:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Join us for an evening under the stars with Cameron. You won't be able to see him long in a setting like this. He'll soon gracing MUCH larger venue stages. Don't miss this one.
  • A Father & Sons Evening with Robby, Luke & Levi Hopkins
    A Father & Sons Evening with Robby, Luke & Levi Hopkins
    A Father & Sons Evening with Robby, Luke & Levi Hopkins
    Sat, Jul 20
    Key West
    Jul 20, 2024, 8:00 PM – Jul 21, 2024, 10:00 AM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Jul 20, 2024, 8:00 PM – Jul 21, 2024, 10:00 AM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
  • An Evening with Carrie Welling
    An Evening with Carrie Welling
    An Evening with Carrie Welling
    Wed, Jun 19
    Key West
    Jun 19, 2024, 7:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Jun 19, 2024, 7:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Join us for a solo show under the stars by none other than the amazing Carrie Welling.
  • An Evening with Donny Brewer
    An Evening with Donny Brewer
    An Evening with Donny Brewer
    Sat, Feb 17
    Key West
    Feb 17, 2024, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Feb 17, 2024, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Join us for an evening under the stars with an amazing musician and songwriter.
  • A PRIVATE EVENING @ THE DRUNKEN OCTOPUS FOR THE RED GUITAR CAMPAIGN
    A PRIVATE EVENING @ THE DRUNKEN OCTOPUS FOR THE RED GUITAR CAMPAIGN
    A PRIVATE EVENING @ THE DRUNKEN OCTOPUS FOR THE RED GUITAR CAMPAIGN
    Mon, Jan 29
    Key West
    Jan 29, 2024, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Jan 29, 2024, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Join us this evening for a private event to benefit the Red Guitar Campaign. We promise you will not be disappointed with the evening we have in store for you. Lets kick off 2024 right.
  • Christmas at The Drunken Octopus with Cory Young
    Christmas at The Drunken Octopus with Cory Young
    Christmas at The Drunken Octopus with Cory Young
    Tue, Dec 12
    Key West
    Dec 12, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Dec 12, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Join us tonight for a FREE Christmas Party Celebrating the amazing year you have all allowed us to have. This is an open house and there will be food, drinks, friends and of course MUSIC!! Tonight we will be collecting toys again for The Boys & Girls Club of Big Pine Key FL.
  • An Evening with MISHKA SOLD OUT‼️ No admittance without a ticket. No exceptions.
    An Evening with MISHKA SOLD OUT‼️ No admittance without a ticket. No exceptions.
    An Evening with MISHKA SOLD OUT‼️ No admittance without a ticket. No exceptions.
    Mon, Nov 20
    Key West
    Nov 20, 2023, 6:00 PM – 9:00 PM
    Key West, Key West
    Nov 20, 2023, 6:00 PM – 9:00 PM
    Key West, Key West
    Join us under the stars for another amazing evening of great music.
  • An Evening with Roger Bartlett and Emily Randle
    An Evening with Roger Bartlett and Emily Randle
    An Evening with Roger Bartlett and Emily Randle
    Fri, Nov 03
    Key West
    Nov 03, 2023, 6:00 PM – Nov 04, 2023, 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Nov 03, 2023, 6:00 PM – Nov 04, 2023, 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Join us for an evening under the stars with two amazing musicians. Tonight will benefit The Bahama Village Music Program.
  • An Evening with The Sauce Boss
    An Evening with The Sauce Boss
    An Evening with The Sauce Boss
    Sat, Oct 07
    Key West
    Oct 07, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Oct 07, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Join us for a night of great music, fun, friends and of course GUMBO! Tonight will benefit the Florida Keys Outreach Coalition.
  • An Evening with Aaron Scherz
    An Evening with Aaron Scherz
    An Evening with Aaron Scherz
    Sat, Sep 09
    Key West
    Sep 09, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Sep 09, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Come enjoy and evening with Aaron Scherz. Tonight will benefit The MARC House.
  • An Evening with Scott Sean White
    An Evening with Scott Sean White
    An Evening with Scott Sean White
    Sun, Jul 30
    Key West
    Jul 30, 2023, 5:00 PM – 8:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Jul 30, 2023, 5:00 PM – 8:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Join us for an Evening with Scott Sean White to benefit the MARC House.
  • An Evening with Mick Fury
    An Evening with Mick Fury
    An Evening with Mick Fury
    Wed, Apr 12
    Key West
    Apr 12, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Apr 12, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Enjoy and evening with Mick Fury. Tonight will benefit The Wesley House.
  • An Evening with Eric Erdman & Carrie Welling
    An Evening with Eric Erdman & Carrie Welling
    An Evening with Eric Erdman & Carrie Welling
    Fri, Mar 24
    Key West
    Mar 24, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    Mar 24, 2023, 6:00 PM – 9:00 PM
    Key West, 4 Aster Terrace, Key West, FL 33040, USA
    TICKETS ON SALE FEBRUARY 1ST, 2023
bottom of page