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DTSTART;VALUE=DATE:20260903
DTEND;VALUE=DATE:20260908
DTSTAMP:20260706T193251Z
CREATED:20251117T205354Z
LAST-MODIFIED:20260706T193251Z
UID:2784-1788393600-1788825599@www.historichideaways.com
SUMMARY:Just a Few Friends - Key West
DESCRIPTION:2026 JAFF SCHEDULE Preliminary schedule — subject to change\nAll information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)\nFull schedule & tickets on sale May 1 \n\nApril 28 for package holders\nApril 30 for badge holders\n\n\nWEDNESDAY\, SEPTEMBER 2 \n11:00 AM — JAFF Headquarters | Key West First Legal Rum \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n6:00 PM — Early Welcome Party at the Chart Room | Pier House \n\nTHURSDAY\, SEPTEMBER 3 \n9:30 AM — Just a Few Friends Walking Tour | Shrimp Boat Sound \n11:00 AM — Cooking Show: Grits n Grunts | Key West Cooking Show \n11:00 AM — Friends of Bubba HQ | Key West First Legal Rum \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n1:00 PM — Truman Waterfront Farmers Market | Truman Waterfront Park \n2:15 PM — Tales from the Chartroom | Pier House \n5:00 PM — Cheeseburger Beach Battle and Tribute Concert | Southernmost on the Beach \n7:00 PM — “Open Mic / No Mic Night” at Andy’s Cabana | Andy’s Cabana \n8:00 PM — After Party | TBD \n\nFRIDAY\, SEPTEMBER 4 \n8:00 AM — Plogging the Keys Waterfront Cleanup | Reef Relief @ the Historic Seaport \n8:00 AM — Painting Paradise: A Guided Plein Air Experience (Session 1) | Shrimp Boat Sound \n9:00 AM — Island Time Brunch Buffett | TBD \n11:00 AM — Key West’s Favorite Son City Proclamation | Shrimp Boat Sound \n11:00 AM — Cliff Cody Performance at Proclamation | Shrimp Boat Sound \n11:00 AM — Friends of Bubba HQ | Key West First Legal Rum \n12:00 PM — Coconut Telegraph Trolley Tour | Pier House \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n1:00 PM — Screening with Panel Discussion | Tropic or San Carlos \n2:30 PM — VIP Special Edition: Jimmy Buffett Tribute Show | Comedy Key West \n3:45 PM — Tales from the Chartroom | Pier House \n5:00 PM — Duval Street Party with the Landshark Band | TBD \n9:00 PM — Outdoor Movie | Southernmost Pint Brewpub \n\nSATURDAY\, SEPTEMBER 5 \n9:00 AM — Painting Paradise: A Guided Plein Air Experience (Session 2) | Louis Backyard \n10:00 AM — Private Distillery Tour with Paul Menta | Key West Legal Rum \n10:00 AM — Coconut Telegraph Trolley Tour | Pier House \n10:00 AM — Just a Few Friends Walking Tour | Shrimp Boat Sound \n10:00 AM — Sails Up: Intro to Sailing Experience | Key West Sailing Center \n11:00 AM — Ultimate Friend’s Private Distillery Tour with Paul Menta | Key West Legal Rum \n11:00 AM — Best Friend’s VIP Live Music Sail | Fury Water Adventures \n11:00 AM — Author/Photographer Book Signing | Books & Books @ Studios of KW \n11:00 AM — Friends of Bubba HQ | Key West First Legal Rum \n11:00 AM — Back to the Island Beach Party | Bourbon Street Pub \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n1:15 PM — Tales from the Chartroom | Pier House \n2:00 PM — Milagro Margarita Historic Seaport Bar Stroll | The Marker Resort \n2:00 PM — Milagro Margarita Duval Street Bar Stroll | La Concha \n5:00 PM — Early Access: Table Seating (JFF VIPs) | Big Stage \n5:30 PM — Early Access: Entry (JFF Badge Holders) | Big Stage \n6:00 PM — Doors Open (GA) | Big Stage \n6:30 PM — Mike Stack & Friends | Big Stage \n6:30 PM — Cruisin’ Tiki Sunset & Music Cruise | Cruisin’ Tikis @ Mac’s Place \n6:30 PM — Latitude Adjustment Sunset Sail | The Dock @ Sunset Pier \n8:00 PM — Changes in Latitudes: Concert ft. the Wheeland Brothers | Sunset Pier \n8:00 PM — Outdoor Movie | Southernmost Pint Brewpub \n\nSUNDAY\, SEPTEMBER 6 \n10:00 AM — Coconut Telegraph Trolley Tour | Pier House \n10:00 AM — Bubbles Brunch Sail | The Dock @ Sunset Pier \n11:00 AM — Book Signing | Books & Books @ Studios of KW \n11:00 AM — JAFF Headquarters | Key West First Legal Rum \n12:00 PM — Wheeland Brothers Poolside Acoustic | Ocean Key Resort \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n1:00 PM — Best Friend VIP Private Show | Margaritaville Restaurant \n1:00 PM — Pool Party at the Marker | The Marker Resort \n1:15 PM — Tales from the Chartroom | Pier House \n5:00 PM — Second Line Memorial Walking Parade | 100 Duval Street \n6:00 PM — Key West Artisan Market at the Party in the Park | Truman Waterfront Park \n6:00 PM — Party in the Park: Tribute to Bubba | Truman Waterfront Park \n\nMONDAY\, SEPTEMBER 7 \n10:00 AM — Just a Few Friends Walking Tour | Shrimp Boat Sound \n10:00 AM — Tin Cup Sailing Adventure | Danger Charters \n11:00 AM — JAFF Headquarters | Key West First Legal Rum \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n2:00 PM — Tales from the Chartroom | Pier House \n2:30 PM — Pencil Thin Mustache Contest | Chart Room \n5:00 PM — Early Access: Table Seating (JFF VIPs) | Sunset Pier \n5:30 PM — Early Access: Entry (JFF Badge Holders) | Sunset Pier \n6:00 PM — Doors Open (GA) | Sunset Pier \n6:30 PM — Come Monday: Cayman & the Mango Men | Sunset Pier \n6:30 PM — Island Tiki Sunset & Music Cruise | Cruisin’ Tikis @ Mac’s Place \n8:30 PM — Last Call | TBD
URL:https://www.historichideaways.com/event/just-a-few-friends-key-west/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Concerts,Festivals,Outdoor Activities
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DTSTART;VALUE=DATE:20261022
DTEND;VALUE=DATE:20261023
DTSTAMP:20260706T194507Z
CREATED:20230629T182247Z
LAST-MODIFIED:20260706T194507Z
UID:1720-1792627200-1792713599@www.historichideaways.com
SUMMARY:Key West Headdress Ball
DESCRIPTION:Key West Headdress Ball\n\nThe Key West Business Guild proudly presents the 43rd Anniversary Edition of the Headdress Ball — one of the most anticipated events of the Fantasy Fest Celebration\, on Thursday\, October 22\, 2026\, at the Coffee Butler Amphitheater at Truman Waterfront Park. Doors open at 6:30 PM\, with the show beginning at 8:00 PM.\n\nThis unforgettable evening of creativity\, glamour\, and entertainment will once again be hosted by legendary Key West entertainer Randy Roberts\, with music by WEOW’s RudeGirl. Guests will experience an extraordinary showcase as twelve to fifteen contestants unveil their stunning Headdress creations\, judged from the shoulders up\, all competing for the coveted $5\,000 grand prize.\nThe evening will also feature performances by some of Key West’s most celebrated local talent\, making this a true highlight of Fantasy Fest. Guests can enjoy full bar service\, specialty wines\, and the convenience of preordered food delivered directly to their tables.\nTicket options: (does not include fees)\n• Premium Table for 4 — $400( includes a bottle of wine of your choice\, non-alcoholic drink option\, or bucket of beer)\n• VIP Table for 4 — $290\n• Chair Seating — $40\n• General Admission (Grass Seating) — $30\n\nThe Headdress Ball continues to celebrate the vibrant spirit\, creativity\, and welcoming atmosphere that makes Key West one of the world’s most unique destinations for visitors from all walks of life.\n\nFor more information\, or to enter the Headdress Contest\, visit gaykeywestfl.com/headdress-ball or call 305-294-4603.\nThis event always sells out\, so book your tickets early.
URL:https://www.historichideaways.com/event/key-west-headdress-ball/
LOCATION:Truman Waterfront Park\, Key West\, FL\, United States
CATEGORIES:Arts,Festivals,Outdoor Activities
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270428
DTEND;VALUE=DATE:20270503
DTSTAMP:20260706T194000Z
CREATED:20230105T194740Z
LAST-MODIFIED:20260706T194000Z
UID:669-1808870400-1809302399@www.historichideaways.com
SUMMARY:Key West Songwriters Festival
DESCRIPTION:The Key West Songwriters Festival.\n4/28/27 – 5/2/27 \n\nThe Key West Songwriters Festival is the largest festival of its kind in the world\, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves\, Florida Georgia Line\, Jake Owen\, Michael Ray\, Randy Houser and Maren Morris. In its 27th year\, KWSF has grown into a top destination for music lovers who flock to Key West for five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers.
URL:https://www.historichideaways.com/event/key-west-songwriters-festival/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Concerts,Festivals
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