Will Kimbrough to Perform First-of-Its-Kind Concert Inside Key West’s Legendary Chart Room8/31/2026
KEY WEST, FL — More than half a century after a young Jimmy Buffett played the Chart Room for tips and drinks, acclaimed singer-songwriter and longtime Buffett collaborator Will Kimbrough will play the first official tribute concert ever staged inside the tiny Key West bar.
The show is a highlight of the 2026 Just a Few Friends festival marking the third anniversary of Buffett’s passing. Kimbrough will echo the way Buffett began: one songwriter, one guitar and a small group gathered within arm’s reach. Live in the Chart Room with Will Kimbrough will take place on Labor Day Monday, Sept. 7, from 10 a.m. to noon at Pier House Resort & Spa, 1 Duval Street. Due to the size of the room, capacity is limited to just 40 people, including the bartender. Guests will begin with brunch by the beach before moving inside the Chart Room for the intimate acoustic concert. “This is not a show that could simply be moved to another venue and still be the same experience,” said Just a Few Friends organizer Jill Snodgrass. “Will is returning to the place where Jimmy started, bringing the story full circle.” When Buffett arrived in Key West with gonzo songwriter Jerry Jeff Walker in November 1971, Walker was already famous for his hit “Mr. Bojangles.” Their first stop was the Chart Room at the then-new Pier House Motel. The funky, unpretentious gathering place soon became Buffett’s home base and the site of his first Key West gig. It was there that bartender, author and later collaborator Tom Corcoran served Buffett his first Key West beer and Buffett spied Jane Slagsvol, his future wife, at a payphone in the lobby. He also befriended legendary bartender Phil Clark, whose tales of smuggling, sailing and Caribbean adventures helped inspire “A Pirate Looks at Forty.” Little about the Chart Room itself has changed. Tucked inside the now-luxurious Pier House Resort & Spa, it remains small, weathered and wonderfully unpolished—a rare surviving piece of the Key West that Buffett first discovered. That continuity took on new significance in July, when the 142-room Pier House sold for $190 million to a global investment firm. The price placed an extraordinary value on the five-acre oceanfront resort surrounding one of Key West’s smallest and most culturally significant bars. General Manager Robert “Bob” Spoto, who will remain at the helm under the new ownership, stressed that the Chart Room would continue as a Key West institution. “The Chart Room has never tried to clean up its act, and hopefully it never will,” Spoto said. “People’s ashes are buried in that bar. You shell your peanuts onto the floor. It’s gritty, funny, a little irreverent and full of ghosts—in the best possible way. That’s what we promise to protect.” Kimbrough was one of Buffett’s most trusted creative collaborators during the final two decades of his recording career. His songwriting and session work appeared on every Buffett studio album released during that period, from License to Chill through Buffett’s final album, Equal Strain on All Parts. Among their best-known collaborations is “Bubbles Up,” released posthumously as the first single from Buffett’s final album. Inspired by the diving practice of following bubbles toward the surface when disoriented underwater, the song became a message of hope, perseverance and finding one’s way home. Paul McCartney praised it as one of Buffett’s finest vocal performances. Kimbrough also recently completed a tour with Buffett’s Coral Reefer Band, helping carry the music forward to fans. “I’ve played Jimmy’s songs on a lot of stages, but the Chart Room is different,” Kimbrough said. “That room is part of the reason those songs exist. Sitting in that little bar with a guitar, playing songs I wrote with Jimmy and sharing the stories behind them will be incredibly special.” Live in the Chart Room is just one of the events to be held at the legendary water hole as part of Just a Few Friends, an annual Labor Day gathering taking place Sept. 2–7, 2026, throughout Key West. The festival celebrates Buffett’s life and legacy through the places, people, music and stories that shaped him, inviting guests to experience his Key West through historic locations, songwriter performances, walking tours, storytelling and community traditions. For additional information and tickets, visit JustAFewFriendsKeyWest.com. Just a Few Friends is not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises. KEY WEST, FL - AUGUST 28, 2026 – Keys Medical Group Psychiatry welcomes Amanda DeBoer, MSN, APRN, PMHNP-BC, psychiatric mental health nurse practitioner, effective September 1, 2026.
DeBoer is a graduate of Milwaukee School of Engineering where she earned her Masters of Science in Nursing specializing in Psychiatric Mental Health. She will provide diagnostic evaluation, individualized treatment plans, individual and family psychotherapy, pharmacotherapy, family support services, crisis intervention and referrals to community resources. DeBoer joins Lynda Woods, licensed clinical social worker, at Keys Medical Group Psychiatry at 1200 Kennedy Drive, Suite 1041, First Floor in Key West. Appointments may be requested at 305-293-1299 or online at KeysMedicalGroup.com. About Keys Medical Group: Keys Medical Group is a multi-specialty physician practice offering primary care, cardiology, gastroenterology, obstetrics and gynecology, orthopedics and sports medicine, otolaryngology, psychiatry and pulmonology Sponsorships open for Fantasy Fest 2026’s “Musical Icons and Iconic Musicals” themed extravaganza8/31/2026
Fantasy Fest invites businesses, organizations and brands to join the 2026 “Musical Icons and Iconic Musicals” themed magic. There’s a level for everyone to get in on the dream and be seen by tens of thousands of festival-goers leading up to and through the Oct. 16-25 revelry. Sponsorships help fuel the festivals iconic events which in turn support charities, celebrate creativity, and build community.
Sign on for a customizable partnership, or select from a ready-made sponsorship menu for these perks and more:
Fantasy Fest 2026 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For all the details e-mail [email protected]. To download the partnership form visit https://fantasyfest.com/pdf/FF2026-Partnership-Opportunities.pdf FDOT Ongoing Construction Activities Sunday August 30, through Saturday, September 5, 20268/31/2026
    Monroe County, FL – Monroe County Commissioner Holly Merrill Raschein was appointed as chair of the Florida Association of Counties’ (FAC) Water & Environmental Policy Committee. She has served on the committee since 2021. The association’s president, Pinellas County Commissioner René Flowers, appointed the committee’s policy leaders.
FAC’s policy committees are responsible for proposing, debating, and adopting policy positions that focus on improving and preserving home rule of Florida’s counties. The chosen proposals will be entered into FAC’s Legislative Action Plan, which will guide the association’s advocacy efforts over the next year. “Water quality, resiliency, and environmental protection are not abstract policy issues for Monroe County. They directly affect our residents, our economy, and the future of the Florida Keys,” said Merrill Raschein. “I’m honored to continue representing Monroe County on this committee and to help shape statewide policies that recognize the unique needs of coastal communities.” The Water & Environmental Sustainability Committee deals with public policies that encompass the following: • Water Quality • Water Quantity • Water Infrastructure • Funding Issues • Interstate Issues • Waste and Pollution • Utilities and Energy • Resiliency KEY WEST, FL — Artists of all experience levels are invited to grab their brushes, pencils, pastels or favorite medium and capture a piece of Key West during Painting Paradise: A Guided Plein Air Experience, part of the 2026 Just a Few Friends celebration honoring the life and legacy of Jimmy Buffett.
Co-sponsored by Keys Framing & Art Supplies, two intimate outdoor painting sessions will take participants to locations with their own connections to Buffett’s Key West story: Shrimp Boat Sound on Friday, September 4, from 8:00 to 10:00 AM, and Louie’s Backyard on Saturday, September 5, from 9:00 to 11:00 AM. The Shrimp Boat Sound session offers a particularly timely opportunity. With significant repairs to the historic waterfront building expected to begin, this may be one of the last chances for artists to capture the familiar structure as it appears today. Each session is limited to just 20 participants and offers the opportunity to paint en plein air—outdoors and from life—surrounded by the scenery, history and island atmosphere that have long inspired artists, musicians and writers. Participants may work in the medium of their choice, with paper/board provided. Finished works will be eligible for a $100 cash prize and will have an opportunity to be included in a special exhibit during the weekend celebration. Registration is $20 per session, and space is limited. Painting Paradise is part of Just a Few Friends Key West, taking place September 2–7, 2026, with concerts, storytelling, tours, gatherings and special experiences celebrating the music, places and people connected to Key West’s favorite son. For event information and registration, visit justafewfriendskeywest.com. More information: www.justafewfriendskeywest.com Link to printable schedule: https://bit.ly/JAFF2026Schedule “All events not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.” First Bubba Look-Alike Showdown and Historic Landsharks Concert Coming to Duval Street Sept. 48/25/2026
Free street celebration will introduce a new Key West tradition before Gary Roland and the Landsharks recreate the spirit of their legendary 1998 concert KEY WEST, Fla. — The first Bubba Look-Alike Showdown, presented by Hogfish Bar & Grill, will take over the 200 block of Duval Street on Friday, Sept. 4, before Gary Roland and the Landsharks return to recreate the spirit of the legendary 1998 Meeting of the Minds street concert.
Hosted in partnership with Sloppy Joe’s, Irish Kevin’s and Rick’s, the free outdoor celebration will run from 5:30 to 9 p.m. and bring together two tributes to Jimmy Buffett’s enduring connection to Key West: a new look-alike tradition inspired by one of his longtime local friends and a return to the Duval Street stage by the band that backed Buffett during one of the most memorable surprise appearances in Parrot Head history. A Homage Rooted in Friendship The Bubba Look-Alike Showdown was inspired by Hogfish Bar & Grill founder Bobby Mongelli, whose friendship with Buffett began more than 35 years ago. Mongelli first entered Buffett’s Key West circle through Sunshine Smith, J.L. Jamison and the musicians working at Shrimp Boat Sound. The friendship continued through the late-night years at PT’s and, later, over seafood lunches at the picnic tables beside the shrimp boats at Hogfish. Mongelli found inspiration for the contest in Key West’s Hemingway Look-Alike Contest and the way that tradition has introduced new generations to Ernest Hemingway. He believes a Jimmy Buffett look-alike event can do something similar—not simply by finding someone wearing the right mustache, sunglasses or flowered shirt, but by celebrating the many versions of Jimmy people remember. Contestants may portray any age or era: the young musician who arrived in Key West in the early 1970s, the mustached pirate with a guitar, the barefoot island storyteller or the older troubadour who quietly returned to town, climbed onto his rusty red bicycle and revisited his old haunts. Mongelli hopes the Showdown will grow into an annual Key West tradition celebrating the music, personality and sense of place Buffett shared with the world. Local Buffett impersonator Caleb Hogan, creator of the daily tribute and cheeseburger show A Pirate’s Look Back, will open the program at approximately 5:30 p.m. and serve as emcee for the Showdown, which begins at 6:30 p.m. Each contestant will introduce himself, pick up the guitar provided onstage and perform lip sync to a randomly selected Buffett song. A panel of local judges including Mongelli, Kit Carson (Sit With Kit), winner of last year’s Pencil Thin Mustache Contest and Tim Stockwell, 2024 Hemmingway look-alike champion, will narrow the field to three finalists before the Duval Street audience takes over and chooses the winner through live QR-code voting. The first official Bubba will leave Duval Street with the Golden Coconut Trophy, ultimate festival bragging rights and a $1,000 cash prize. (register at www.justafewfriendskeywest.com) Recreating a Legendary Duval Street Night Following the Showdown, Gary Roland and the Landsharks will headline the evening with a concert honoring the night that forever connected the band to Jimmy Buffett and the Parrot Head world. During the 1998 Meeting of the Minds convention, rumors once again traveled through Key West that “Jimmy’s in town.” That year, the whispers were true. Buffett made a surprise appearance during the Landsharks’ Duval Street concert, stepped onstage with the band and turned the street into one enormous Key West sing-along. He famously told the crowd, “I told you I was here.” Nearly three decades later, Gary Roland and the Landsharks will return to the Duval Street stage to recreate the energy and spirit of that historic performance. Gary will also be joined by special surprise guests for a concert that Buffett fans will not want to miss. Admission is free, standing only. Food and beverages will be available for purchase from host bars Sloppy Joe’s, Irish Kevin’s and Rick’s. No outside coolers or alcoholic beverages are permitted. The Duval Street celebration is part of Just a Few Friends Key West, held Sept. 3–7 to honor the life, music and Key West legacy of Jimmy Buffett. More information: www.justafewfriendskeywest.com Link to printable schedule: https://bit.ly/JAFF2026Schedule “All events not affiliated with or endorsed by Jimmy Buffett’s Estate or Margaritaville Enterprises.” Key West Womenfest, the ultimate celebration for women in paradise, returns Wednesday, Sept. 2 through Sunday, Sept. 6, 2026, with the theme “Lost Women in the Arts” — a festival that invites women to reclaim and celebrate their creative power, individuality, and sense of belonging in the island’s legendary “One Human Family” spirit.
Events kick off 6:00 PM on Wednesday at Key West’s storied American Legion Post 168 on Emma Street, a National Register of Historic Places venue that has provided a stage for musical icons such as B.B. King, Etta James, and Otis Redding, along with many of Key West’s homegrown legends. Dance to live music, mingle with local artists, and enjoy raffles, live portraits, and plenty of opportunities to make new friends and reconnect with old ones. Thursday, festival-goers can get competitive at the 6th Annual Cornhole Tournament and Indoor Games, attend a romantic Words and Wine Happy Hour featuring the love poems of Elizabeth Bishop, master stage-worthy moves at Drag King Bootcamp, cheer performances by acclaimed drag kings and bootcamp graduates, and sail into the sunset aboard the luxury vessel Argo Navis. Friday brings activities that start early with a Plogging the Keys Waterfront Cleanup, and continue with a clothing optional sandbar snorkel trip onboard the Blu Q, a sparkling pool party at the Bourbon Street Pub, a tasty Key lime pie walking tour, a wildly outrageous Jell-O wrestling event, a live concert, and The Hush Hush Theatre presenting “PLAYGIRL,” an original, femme-focused cabaret featuring burlesque, comedy, drag, song and cirque. On Saturday, trek out and discover compelling art and artists with the Lost Women, Found Art gallery trolley tour, make a splash at the official Womenfest Pool Party at the Lighthouse Hotel, and gussie up for the Womenfest ‘80s, ‘90s, and Today’s Prom, where attendees can channel the aura of their favorite era. Sunday brings an uplifting morning at MCC Church with Rev. Gina Durbin, a wild and flavorful Drag Brunch at The Key West Cooking Show, food and games at Hot Dog Church, and the iconic Tea Dance at La Te Da. “Womenfest has always been about creating a space where women can come together, celebrate who they are, and feel a genuine sense of community,” said Womenfest Executive Director Fritzie Estimond. “This year’s ‘Lost Women in the Arts’ theme allows us to have a lot of fun while also shining a light on women whose creativity, talent, and influence haven’t always received the recognition they deserved. From poetry and visual art to music, performance and drag, we’re celebrating the women who helped shape our culture and the women who are still shaping it today. That feels especially meaningful here in Key West, a place with such a rich creative history and long tradition of welcoming people exactly as they are.” Key West Womenfest is presented in part by the Monroe County Tourist Development Council and the Key West Business Guild. For ticket links and information, including an extensive list of available daily activities, visit www.gaykeywestfl.com/womenfest/ He wrote and performs the local anthem “I’m From Key West,” and has been reeling in a following from island stages and streaming platforms for about half a decade. Now, Mike Stack will bring his supercharged energy to the front of the line as Grand Marshal of the 2026 Deep Eddy Vodka Fantasy Fest Parade, set to roll down Duval Street in Key West, FL, on Saturday, Oct. 24.
Possessing a knack for creating catchy, sing-along songs with his unique island-vibe, hip-hop and country blend sound, Stack has cultivated a devoted audience by serving up the salty spirit of life in the Conch Republic with “I’m From Key West,” and other hits like “I Want My Beer,” and “Boat Days,” turning everyday moments into sing-along anthems. We caught up with Mike ahead of Fantasy Fest to ask a few questions: Q: This year’s Fantasy Fest theme is “Musical Icons and Iconic Musicals.” If your life were a musical, what would it be called, and who’d play you? A: This might be too obvious, but if my life were a musical, I’d have to call it “I’m from Key West.” I was born and raised here, and so much of what I do and the music I make comes from growing up on this island. And I’d have my buddy Arron Kutner play me. He’s been preparing for the role his whole life. Q: What are your top three (or four, or five) annual Fantasy Fest events, and why? A: A few of my favorites are Goombay because of the culture and food; Tutu Tuesday is just one of those nights where everybody gets after it and has a good time. The parade is always incredible… the floats, the energy, and this year I hear they’ve got a pretty cool Grand Marshal. Honestly, the people watching might be my favorite event of them all. You never know what you’re going to see during Fantasy Fest! Q: Name three musical icons, living or dead, that you would most love to see in the crowd, cheering you on during this year’s Deep Eddy Fantasy Fest Parade. A: Bob Marley, Toby Keith, and Mac Miller. Three completely different artists, but all three have influenced the kind of music I love and the music I make. If I saw those three standing together on Duval Street cheering me on, I’d probably have to stop the float and go hang out with them. “With this year’s Fantasy Fest theme of ‘Musical Icons & Iconic Musicals’, we couldn’t think of a better person to lead the biggest night of Fantasy Fest,” said festival director Nadene Grossman Orr. “Mike has spent years bringing music, energy, and pure Key West spirit to performance stages, and now he’ll be bringing that same energy straight down Duval Street!” Fantasy Fest 2026 runs Oct. 16-25 and is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events, a parade entry form, a downloadable mobile APP and other information including ways to get involved, visit http://www.fantasyfest.com. |
|
Greater Key West Chamber of Commerce. All Rights Reserved.
510 Greene St., First Floor | Key West, FL 33040 [email protected] | sitemap |
|