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DTSTART;TZID=America/New_York:20270107T080000
DTEND;TZID=America/New_York:20270109T170000
DTSTAMP:20260905T202454Z
CREATED:20260905T202454Z
LAST-MODIFIED:20260905T202454Z
UID:3352-1799308800-1799514000@www.historichideaways.com
SUMMARY:Blanche and Beyond
DESCRIPTION:January 7 – 9\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Spotlight Series continues with Blanche and Beyond\, Steve Lawson’s one-man play assembled from Tennessee Williams’s own letters. It’s the sequel to Lawson’s A Distant Country Called Youth\, which drew on the early correspondence; this one covers 1945 through 1957\, the stretch that produced A Streetcar Named Desire\, Summer and Smoke\, The Rose Tattoo\, and Cat on a Hot Tin Roof. \n \nThe letters are by turns funny\, obscene\, and unguarded\, and they catch Williams in the middle of something he never quite adjusted to — going from unknown to internationally famous in the space of a few years. He writes about Brando\, Jessica Tandy\, Elia Kazan\, David O. Selznick\, Laurence Olivier\, and Vivien Leigh\, and about the plays still forming in his head. \nWilliams was living in Key West through most of the years these letters cover. He bought the Duncan Street house in the late 1940s and kept it until his death. \nBlanche and Beyond opened the Tennessee Williams New Orleans Literary Festival in 2006\, in a production directed by Lawson and performed by Richard Thomas. Three performances only in Key West. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/blanche-and-beyond/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270115
DTEND;VALUE=DATE:20270118
DTSTAMP:20260831T184853Z
CREATED:20230105T153545Z
LAST-MODIFIED:20260831T184853Z
UID:592-1799971200-1800230399@www.historichideaways.com
SUMMARY:29th Annual Key West Half Marathon & Runfest
DESCRIPTION:29th Annual Key West Half Marathon & Runfest®\nJanuary 13–18\, 2027 · Race weekend January 15–17 \nKey West offers a multitude of exciting experiences\, from its diverse restaurants and vibrant nightlife to the numerous museums and art galleries. The wide range of water sports options adds an extra layer of adventure\, making it an unforgettable destination. And let’s not forget the intriguing fact of having 400 bars on an island that’s only 2 x 4 miles. Set aside some extra time to explore all that Key West has to offer. \nSchedule of Events\nWednesday\, January 13\nVolunteer Check-In & Party · 11am–1:30pm · Sailfish Bar at Half Shell Raw Bar\, 231 Margaret St \nThursday\, January 14\nRunner’s Meet & Greet with drink specials · 4:30–6pm · Sailfish Bar\, Half Shell Raw Bar \nFriday\, January 15\nRunner’s Expo & Packet Pick-Up · 2–7pm · Outside Half Shell Raw Bar\nLate bib pick-up (bibs only) · 7:15–10pm · Fit2Run\, 211 Duval St\nAll-day drink specials at Half Shell Raw Bar \nSaturday\, January 16 — 5K & 10K\nBag check · 6–6:45am · In front of Salute! On the Beach\, 1000 Atlantic Blvd\n5K start/finish · 7am · Higgs Beach\n10K start/finish · 8am · Higgs Beach\nConcert & Awards Party with Homebred Band featuring Dave Richards · 8–11am · Outside Salute! On the Beach\nOverall winners announced · 9:30am\nRunner’s Expo & Packet Pick-Up · 1–6pm · Outside Half Shell Raw Bar\nPresentation by Dr. Kellee Reed · 3:30pm\nLate bib pick-up (bibs only) · 7–10pm · Fit2Run\, 211 Duval St\nEarly breakfast and all-day food/drink specials at Salute! and Half Shell \nSunday\, January 17 — Half Marathon & 8K\nBag check · 6–6:45am · Lot by the finish line at Waterfront Brewery\nHalf Marathon start · 7am · Caroline St & Trumbo Rd\n8K start · 7:30am · Same start line; finish behind Waterfront Brewery\nConcert & Awards Party with The Cayo Ritmo Big Band · 8:30am–12:30pm · Outside Half Shell Raw Bar\n8K awards 9:30am · Half Marathon awards 10:30am\nPapa’s Pilar Rum Stroll · 1–5pm · Nine stops from the distillery on Simonton to Southernmost Beach Cafe\nBeach ‘N Beer Mile (untimed; four loops\, four beers) · 3pm · Southernmost Beach Cafe\, 1405 Duval St\nCool Down Pool Party\, free entry · 4–6pm · Blue Flamingo Resort\, 3820 N Roosevelt Blvd\nKey West Farewell Party · 4–6pm · Salty Oyster at the Perry Hotel\, 7001 Shrimp Rd\nAll-day Bloody Mary\, mimosa\, and vodka specials at Half Shell \nMonday\, January 18\nMarathon Farewell Party & Happy Hour · 4–6pm · Blu Bistro at Skipjack Resort & Marina\, 19 Sombrero Blvd\, Marathon \nSchedule subject to change. Information courtesy of the event organizers — see their website for registration\, updates\, and complete details.
URL:https://www.historichideaways.com/event/annual-key-west-half-marathon-5k/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270118
DTEND;VALUE=DATE:20270119
DTSTAMP:20260905T192050Z
CREATED:20260905T192050Z
LAST-MODIFIED:20260905T192050Z
UID:3309-1800230400-1800316799@www.historichideaways.com
SUMMARY:The Doo Wop Project
DESCRIPTION:Monday\, January 18\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nAmerica’s premiere doo wop group brings a brand-new show to the Tennessee Williams Theatre stage this January. The Doo Wop Project takes today’s biggest hits and “doowop-ifies” them — reimagining contemporary songs as though they’d been written and recorded in 1958. Familiar melodies arrive wrapped in tight harmony\, walking bass lines\, and finger-snap rhythm\, and the effect is genuinely surprising the first time you hear a modern radio staple come at you in a completely different decade. It’s the reason audiences around the country leave these shows talking\, and the reason the group has built a following well beyond the generation that grew up with the original records. \nAn evening at the Tennessee Williams Theatre is one of the more comfortable nights out in Key West — a proper 480-seat house on the College of the Florida Keys campus\, with easy free parking\, which is not something you can say about most venues on this island. Subscription packages covering the full 2027 season are available at a 15% savings if you’re planning to catch more than one show. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/the-doo-wop-project/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Concerts,Theater
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BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270119T080000
DTEND;TZID=America/New_York:20270220T170000
DTSTAMP:20260905T200725Z
CREATED:20260905T200725Z
LAST-MODIFIED:20260905T200725Z
UID:3336-1800345600-1803142800@www.historichideaways.com
SUMMARY:Dracula: A Comedy of Terrors
DESCRIPTION:January 19 – February 20\, 2027 · Tuesdays–Saturdays at 7:30pm\nRed Barn Theatre\, 319 Duval Street (rear) \nThe Red Barn follows its holiday show with Dracula: A Comedy of Terrors\, the Gordon Greenberg and Steve Rosen send-up that became an off-Broadway hit and has been working its way through regional theaters ever since. The premise is the Bram Stoker story you already know\, played entirely for laughs — a high-camp spoof that borrows its sensibility about equally from Mel Brooks and Monty Python and never slows down long enough for anyone to take it seriously. \nThe whole thing runs on a small cast covering a great many characters\, with gender-bent casting\, quick changes\, and a fair amount of deliberate chaos. Jokes land at a clip\, the physical comedy is broad on purpose\, and the script is happy to break its own logic if there’s a bigger laugh available. If you’ve seen the Red Barn take on this kind of material before\, you know they commit. \nThe Key West production stars Jody Orrigo\, Susannah Wells\, Erin McKenna\, Phillip Cole White\, and Dominic Paolillo\, directed by Mimi McDonald. \nSchedule subject to change. Information courtesy of Red Barn Theatre — visit redbarntheatre.com for tickets and complete details.
URL:https://www.historichideaways.com/event/dracula-a-comedy-of-terrors/
LOCATION:Red Barn Theatre\, 319 Duval Street - Rear\, Key West\, Florida\, 33040
CATEGORIES:Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270121
DTEND;VALUE=DATE:20270122
DTSTAMP:20260905T193128Z
CREATED:20260905T193128Z
LAST-MODIFIED:20260905T193128Z
UID:3312-1800489600-1800575999@www.historichideaways.com
SUMMARY:NoGravity Theatre
DESCRIPTION:Thursday\, January 21\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nOne of Italy’s most inventive performing arts companies makes a stop in Key West this January. NoGravity was founded in Rome in 2005 by artist Emiliano Pellisari\, and it has spent two decades building a form of theater that doesn’t fit neatly into any existing category — part dance\, part visual art\, part outright illusion. Bodies appear to float\, fall upward\, and dissolve into one another. The mechanics behind it are never explained and\, honestly\, are better left unexplained. \nThe company draws its imagery from the Italian Renaissance and Baroque\, translating the compositions of old master painting into moving bodies on a darkened stage. The result is dreamlike rather than technical — surreal tableaux that assemble\, hold for a beat\, and come apart. Since 2010 the dance cast has been led by Mariana Porceddu\, a graduate of the National Academy of Dance who became co-author of the company’s choreography in 2012. \nNoGravity performs annually in major Italian theaters and tours internationally with support from Italy’s Ministry of Cultural Heritage. This is the kind of production that rarely makes it this far south\, and it’s worth seeing on a proper stage rather than in a clip.
URL:https://www.historichideaways.com/event/nogravity-theatre/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270126
DTEND;VALUE=DATE:20270131
DTSTAMP:20260831T193706Z
CREATED:20230105T192332Z
LAST-MODIFIED:20260831T193706Z
UID:638-1800921600-1801353599@www.historichideaways.com
SUMMARY:Annual Mile 0 Fest Key West
DESCRIPTION:Mile 0 Fest Key West\nJanuary 26–30\, 2027 · Truman Waterfront Amphitheater and venues across the island\n10th Anniversary — Red Dirt\, Americana & Texas Country\nNamed the #1 music festival of 2025 by USA Today\, Mile 0 Fest turns Key West into a five-day music vacation each January. Evening shows run at the Coffee Butler Amphitheater at Truman Waterfront\, while daytime sets spill out across more than ten stages — beaches\, pools\, piers\, bars\, boats\, the historic Key West Theater\, and a few pop-up sets that aren’t on any schedule. Music runs roughly 11am to 11pm daily\, with late-night shows after the amphitheater sets. \n2027 marks the festival’s 10th anniversary\, and organizers are calling it their biggest year yet. New for the anniversary: The Reach Key West joins as a daily venue\, the amphitheater gets upgraded premium viewing and guest amenities\, and more guesthouse buyouts turn additional properties into festival lodging. \n2027 Lineup\nHeadliners include Cross Canadian Ragweed\, Ryan Bingham\, Old Crow Medicine Show\, Wyatt Flores\, and Kaitlin Butts. \nAlso on the bill: Wade Bowen\, 49 Winchester\, William Clark Green\, Stoney LaRue\, American Aquarium\, Tanner Usrey\, Cody Canada and the Departed\, Silverada\, Corb Lund\, Jason Scott & The High Heat\, Taylor Hunnicutt\, Kevin Fowler\, Roger Creager\, Micky & the Motorcars\, The Creekers\, The Jack Wharff Band\, Nicholas Jamerson\, Pony Bradshaw\, The Droptines\, Bri Bagwell\, Courtney Patton\, Adam Hood\, Jamie Lin Wilson\, and Shelby Stone\, among more than fifty artists. \nPasses & Packages\nFull experience packages bundle lodging with festival access and include perks you can’t buy separately — a Tuesday kickoff happy hour\, a private “Songwriter Spotlight” theater show\, and the “Sessions at Sea” live music sail. \n\nPlatinum Premier Package — from $3\,326 per person (based on two) · Sold out\nGold Premier Package — from $2\,683 per person\nPirate Package — from $2\,033 per person\nBeach Bum Package — from $1\,856 per person\nWeekender Package — from $1\,233 per person (three nights\, Thursday–Sunday)\n\nFestival-only passes are also available: \n\nPlatinum VIP Pass — $1\,646 · Sold out\nGold VIP Pass — $1\,175\nBeach Bum Pass — $587\n\nA $50 per-order discount is available through GOVX for military\, first responders\, and law enforcement. Single-day passes are expected to be released closer to the festival. \nGood to Know\nParking near the amphitheater is essentially nonexistent — walk\, bike\, or take a taxi or rideshare. All events run rain or shine. The festival app carries the full daily schedule\, typically posted about 30 days out\, along with set times and pop-up announcements. Mile 0 Fest gives back\, too. In 2026 fans raised more than $55\,000 for the Red Dirt Relief Fund\, Key West Wildlife Center\, and Key West Civic Association\, with signed guitars auctioned nightly. \nSchedule and lineup subject to change. Information courtesy of Mile 0 Fest — see mile0fest.com for packages\, passes\, and complete details. \n\n\nBOOK YOUR VACATION RENTAL FOR THE Mile 0 Fest \n\n\nDon’t wait to book your Key West vacation rental if you’re planning on attending the Mile 0 Fest. Choose from our selection of luxury homes\, vacation rentals with a pool\, pet friendly rentals\, condos or townhomes. \nBrowse Vacation Rentals>>>
URL:https://www.historichideaways.com/event/annual-mile-0-fest-key-west/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Concerts,Festivals,Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270127
DTEND;VALUE=DATE:20270201
DTSTAMP:20260831T184548Z
CREATED:20230105T192722Z
LAST-MODIFIED:20260831T184548Z
UID:642-1801008000-1801439999@www.historichideaways.com
SUMMARY:Key West Food and Wine Festival
DESCRIPTION:2027 Key West Food and Wine Festival\nJanuary 27–31\, 2027 \n5 continents ~ 5 wines ~ 5 stories ~ 5 dishes ~ 5 chefs \nWelcome to Key West Food & Wine Festival 2027\nA curated journey through the culinary heritage of five continents\, featuring world-renowned chefs\, their signature dishes\, and the legendary wines that define their regions. \nThis journey spans five continents with iconic wines\, each telling a story of terroir\, history\, and culture: \n\nAfrica: a smoky Pinotage\nEurope: a structured Bordeaux\nSouth America: a robust Malbec from Mendoza\nOceania: a vibrant Marlborough Sauvignon Blanc\nNorth America: a cool-climate Pinot Noir from Oregon\n\nThe Key West Food and Wine Festival is recognized as one of the best food and wine festivals in the country by the Travel Channel. If you’re a foodie\, Key West is the place to be in January. With many unique events\, held at spectacular island locations\, this is an opportunity to enjoy a wide variety of wines and cuisine\, with waterfront tastings\, wine/food pairings\, and local events around Key West. \nAt a Glance\nWednesday\, January 27 — Welcome to the Festival\nVIP Welcome Party · 5–7pm · Realty One Group Destination\, 1075 Duval St \nThursday\, January 28 — Around the World\nThe Wine Game\, a tasting challenge · 11am–1pm · Key West Cooking Show\, 291 Front St\nWelcome to Oceania: Island Flavors Dinner with Chef Dave Fuhrman · 6–9pm · Audubon House & Tropical Garden\, 205 Whitehead St \nFriday\, January 29 — Europe & North America\nHidden Gems & Golden Sips · 1:30–4pm · Trolley departs Gardens Hotel\, 526 Angela St\nFive Continents Grand Tasting · 6–8pm · Key West Aquarium\, 1 Whitehead St\nAn Exclusive Celebration of American Spirit · 7–10pm · Truman Little White House\, 111 Front St \nSaturday\, January 30 — Key West\, North America & South Africa\nCooking with Love: The Saturday Kitchen Party · 8:45–10am · 1215 Petronia St\n“A Dream Come True” · 12–2pm · Venue TBA\nWelcome to South Africa: Lost Kitchen Supper Club · 6–9pm · Trolley pick-up 5:45pm \nSunday\, January 31 — Europe\nPranzo on the Amalfi Coast · 12–2pm · Conchiglia Key West\, 816 Duval St \nSchedule subject to change. Information courtesy of the Key West Food & Wine Festival — see their website for tickets\, updates\, and complete details.
URL:https://www.historichideaways.com/event/key-west-food-and-wine-festival/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Festivals
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BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270128T080000
DTEND;TZID=America/New_York:20270206T170000
DTSTAMP:20260905T202701Z
CREATED:20260905T202701Z
LAST-MODIFIED:20260905T202701Z
UID:3355-1801123200-1801933200@www.historichideaways.com
SUMMARY:Unnecessary Farce
DESCRIPTION:January 28 – February 6\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Waterfront’s mainstage returns to Paul Slade Smith\, whose The Angel Next Door played there previously\, with Unnecessary Farce. Two cops have set up a sting in a cheap motel\, hoping to catch the mayor taking a bribe. There are two adjoining rooms\, a video camera pointed at the wrong one\, an accountant\, three crooks\, a Scottish hit man\, and eight doors. \nSmith’s play premiered in 2006 and has since become one of the most frequently produced comedies in American regional theater\, largely on the strength of its construction — the plot is engineered so that every escalation follows logically from the last\, however absurd things get. \nReviewers have called it the funniest thing they’d seen in years\, and credited Smith with making the in-one-door\, out-the-other machinery feel new again. It runs about two hours. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/unnecessary-farce/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270201
DTEND;VALUE=DATE:20270202
DTSTAMP:20260905T193433Z
CREATED:20260905T193433Z
LAST-MODIFIED:20260905T193433Z
UID:3315-1801440000-1801526399@www.historichideaways.com
SUMMARY:The Pirates of Penzance
DESCRIPTION:Monday\, February 1\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nThe New York Gilbert & Sullivan Players bring their production of  to Key West this February. NYGASP has been the country’s leading Gilbert & Sullivan repertory company for more than fifty years\, and Pirates is the piece they’re best known for — a full staging with orchestra\, chorus\, and the kind of comic timing that only comes from performing the same material for decades without getting tired of it. \nThe plot runs on one of Gilbert’s better absurdities. Frederic has been apprenticed to a band of soft-hearted pirates and intends to leave their service on his twenty-first birthday to devote himself to stamping out piracy. The catch is that he was born on February 29th\, which means his twenty-first birthday won’t arrive until 1940. Duty being duty\, he goes back to the pirates. What follows involves a false claim of orphanhood\, a squad of thoroughly reluctant policemen\, and a resolution that hinges on everyone turning out to be a nobleman. Along the way you get “I Am the Very Model of a Modern Major-General\,” still the most famous patter song ever written and still\, done well\, genuinely funny. \nThe New York Times has praised the company’s staging as opulent and inventive\, singling out the chorus of pirates\, daughters\, and policemen and the strength of the orchestra. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/the-pirates-of-penzance/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270209
DTEND;VALUE=DATE:20270210
DTSTAMP:20260905T193730Z
CREATED:20260905T193730Z
LAST-MODIFIED:20260905T193730Z
UID:3318-1802131200-1802217599@www.historichideaways.com
SUMMARY:Afrique en Cirque
DESCRIPTION:Tuesday\, February 9\, 2027\nDoors 5:30pm\, Show 6:30pm · Tennessee Williams Theatre \nAfrique en Cirque comes to Key West as part of the Tennessee Williams Theatre’s new Family Fun Series\, a slate of shows programmed for audiences of all ages. It’s the signature production of Cirque Kalabanté\, the company founded by Guinean acrobat Yamoussa Bangoura\, and it draws directly on the daily life\, movement\, and music he grew up with in Guinea. \nThe show pairs high-level acrobatics with live music rather than a recorded score. Performers build human pyramids\, tumble\, and work the Cyr wheel while a band plays Afro-jazz built around percussion and the kora\, the twenty-one-string West African harp that gives the music its distinctive rippling sound. There’s no elaborate set to hide behind — the appeal is bodies\, rhythm\, and a company of young performers doing genuinely difficult things a few feet from the audience. \nIt’s a good fit for families\, and the earlier curtain reflects that: doors at 5:30 and a 6:30 start rather than the theatre’s usual 7:30. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/afrique-en-cirque/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270211
DTEND;VALUE=DATE:20270212
DTSTAMP:20260905T205649Z
CREATED:20260905T205649Z
LAST-MODIFIED:20260905T205649Z
UID:3374-1802304000-1802390399@www.historichideaways.com
SUMMARY:Who's Bad
DESCRIPTION:Thursday\, February 11\, 2027\nKey West Theater\, 512 Eaton Street \nWho’s Bad brings its Michael Jackson tribute to the Key West Theater. The group has been at this since 2003 and has logged more than 2\,500 performances — theaters\, clubs\, festivals\, and House of Blues rooms across the U.S.\, plus tours through the U.K.\, China\, Thailand\, Mexico\, Canada\, Germany\, and the Gulf states\, including a run at London’s O2 Arena. \nThe band’s stated approach is re-creation rather than impersonation: a live cast of musicians and dancers\, drawn from backgrounds including Broadway and Super Bowl halftime shows\, working through the grooves\, vocal inflections\, and choreography rather than miming them. Taalib York fronts the group. \nWho’s Bad has shared stages with Aretha Franklin\, the Four Tops\, Boyz II Men\, the Backstreet Boys\, and Pitbull. Michael Jackson’s longtime manager Frank DiLeo said after seeing the show that Michael would have been proud. \nSchedule subject to change. Information courtesy of Key West Theater — visit thekeywesttheater.com for tickets and complete details.
URL:https://www.historichideaways.com/event/whos-bad/
LOCATION:Key West Theater\, 512 Eaton Street\, Key West\, FL\, 33040
CATEGORIES:Concerts
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END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270211T080000
DTEND;TZID=America/New_York:20270213T170000
DTSTAMP:20260905T203003Z
CREATED:20260905T203003Z
LAST-MODIFIED:20260905T203003Z
UID:3358-1802332800-1802538000@www.historichideaways.com
SUMMARY:Call Me Elizabeth
DESCRIPTION:February 11 – 13\, 2027 \nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Spotlight Series continues with the Florida premiere of Call Me Elizabeth\, written and performed by Kayla Boye. It’s set on a single morning in May 1961 at the Beverly Hills Hotel\, drawn from Elizabeth Taylor’s real conversations with the writer Max Lerner about a biography he planned to write. Lerner is never seen — the audience occupies his chair. \n \nTaylor has just won the Academy Award for Butterfield 8\, a film she thought little of\, and is still recovering from the bout of pneumonia that nearly killed her. Over the course of the morning she works through her early life\, her marriages\, her films\, and the gap between the woman she is and the one the fan magazines have invented. The compassion that would later make her one of the first major public figures to take up the fight against AIDS is visible throughout. \nBoye is a Chicago-based actor whose credits include Chicago Shakespeare Theater\, Drury Lane\, and Porchlight Music Theatre; Call Me Elizabeth was her first play. It premiered virtually through the Edinburgh Festival Fringe during the pandemic before its live world premiere at the 2022 Hollywood Fringe Festival\, and has toured since. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/call-me-elizabeth/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270213
DTEND;VALUE=DATE:20270215
DTSTAMP:20260706T185504Z
CREATED:20230105T153819Z
LAST-MODIFIED:20260706T185504Z
UID:595-1802476800-1802649599@www.historichideaways.com
SUMMARY:Florida Keys Seafood Festival
DESCRIPTION:Florida Keys Seafood Festival\nFEBRUARY 13-14\, 2027\n\n\nTwo Days of Seafood\, Music & Family Fun!\n\n\nJoin us for the 20th Annual Florida Keys Seafood Festival at Truman Waterfront Park in Key West. For just $10 admission\, enjoy two full days of fresh\, local seafood\, live music\, activities\, and the vibrant island atmosphere that make this festival a Florida Keys favorite. This family-friendly event not only highlights the freshest local catch but also showcases the dedication of our commercial fishermen and women.\n\n\n\n\n\n\n\nOn the Menu…\n\n\n\n\nFried Fish baskets or platters with slaw and black beans & rice\, Fried Shrimp basket\, Grilled Spiny Lobster Platters\, Stone Crab Claws with key lime mustard sauce\, peel and eat Key West Pink Shrimp with cocktail sauce\, Smoked Fish Dip with crackers\, Creamy Lobster Bisque\, Bahamian style Conch Chowder\, Conch Ceviche\, & Conch Fritters. Hot dogs and hamburgers also will be for sale. Beverages include beer\, wine\, rumaritas\, rum runners\, water\, soda and coffees. Desserts include Key Lime Pie and other homemade treats. \nActivities \n\n\n\n\n\nRaffle to win $250 in seafood shipped to your home!\nGreat shopping and art\nFantastic entertainment all day\n\nChildren’s Eco Discovery Zone with activities \n\nAdult beverages\, beer\, wine\, frozen rumaritas with First Legal Rum\nEvent t-shirts\, mugs and authentic lobster trap buoys for sale\n\nThe Florida Keys Seafood Festival directly supports the mission of the Florida Keys Commercial Fishermen’s Association (FKCFA)\, an organization dedicated to protecting\, promoting\, and sustaining the Keys’ commercial fishing community.\n\n\nCREDIT: http://www.floridakeysseafoodfestival.com/ \nInformation / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)
URL:https://www.historichideaways.com/event/florida-keys-seafood-festival/
LOCATION:Truman Waterfront Park\, Key West\, FL\, United States
CATEGORIES:Festivals,Outdoor Activities
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2023/01/keywestshrimp.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270227
DTEND;VALUE=DATE:20270228
DTSTAMP:20260905T194427Z
CREATED:20260905T194427Z
LAST-MODIFIED:20260905T194427Z
UID:3321-1803686400-1803772799@www.historichideaways.com
SUMMARY:Ailey II
DESCRIPTION:Saturday\, February 27\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nAiley II is the junior company of Alvin Ailey American Dance Theater\, and calling it a training ensemble undersells it considerably. Founded in 1974 as the Alvin Ailey Repertory Ensemble\, it exists to pair the strongest early-career dancers in the country with choreographers who are themselves still building their reputations. The result is a company with the technical polish of a major troupe and none of the caution — these are dancers with everything to prove\, performing work that hasn’t yet settled into repertory. \n \nPhoto by Nir Arieli and Danica Paulos\, courtesy of Ailey II\nSylvia Waters\, chosen by Alvin Ailey himself as founding artistic director\, led the company through its first thirty-eight seasons and built it into one of the most popular touring ensembles in American dance. Francesca Harper directs it today. Recent programs have included Rena Butler’s In Session and Judith Jamison’s Divining\, mixing new commissions with pieces drawn from the Ailey legacy. \nThe company tours widely but doesn’t often come this far down the Keys. Dance Magazine has called Ailey II second to none\, and The New York Times has described an evening with the company as its own distinct experience\, separate from the parent troupe. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/ailey-ii/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270302T080000
DTEND;TZID=America/New_York:20270320T170000
DTSTAMP:20260905T201141Z
CREATED:20260905T201141Z
LAST-MODIFIED:20260905T201141Z
UID:3339-1803974400-1805562000@www.historichideaways.com
SUMMARY:Liberation
DESCRIPTION:March 2 – 20\, 2027 · Tuesdays–Saturdays at 7:30pm\nRed Barn Theatre\, 319 Duval Street (rear) \nThe Red Barn stages Bess Wohl’s Liberation\, winner of the 2026 Pulitzer Prize for Drama and Best Play at the 2026 Tony Awards. Developed by Roundabout Theatre Company\, it premiered off-Broadway in February 2025 and transferred to Broadway that October\, running through February 2026. \nIt’s a memory play set in two times at once. In 1970\, in the basement of an Ohio rec center\, a woman named Lizzie gathers a small group of women to talk. Fifty years later her daughter looks back\, trying to understand who her mother was before she became her mother. The daughter narrates directly to the audience\, moving the play between past and present. \nThe Pulitzer board cited the play for exploring how the women’s movement grew out of conversation. Wohl’s other work includes Grand Horizons\, Small Mouth Sounds\, and Camp Siegfried. \nThe Red Barn production is directed by Joy Hawkins and features Morgan Fraga Pierson\, Lauren Thompson\, Cassidy Timms\, Fritzie Estimond\, Jessica Miano Kruel\, Ivy Munnerlyn\, Shannon Edwards\, and Jack McDonald. \nSchedule subject to change. Information courtesy of Red Barn Theatre — visit redbarntheatre.com for tickets and complete details.
URL:https://www.historichideaways.com/event/liberation/
LOCATION:Red Barn Theatre\, 319 Duval Street - Rear\, Key West\, Florida\, 33040
CATEGORIES:Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270304T080000
DTEND;TZID=America/New_York:20270320T170000
DTSTAMP:20260905T203412Z
CREATED:20260905T203412Z
LAST-MODIFIED:20260905T203412Z
UID:3361-1804147200-1805562000@www.historichideaways.com
SUMMARY:Come From Away
DESCRIPTION:March 4 – 20\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Waterfront’s mainstage series presents Come From Away\, the musical by Irene Sankoff and David Hein about what happened in Gander\, Newfoundland\, on September 11\, 2001. When American airspace closed that morning\, 38 planes were diverted to Gander’s airport\, and a town of about 9\,000 people took in nearly 7\,000 strangers for the better part of a week. \n \nThe show is built from interviews the writers conducted with Gander residents and the passengers who ended up there. A cast of twelve plays both the townspeople and the travelers\, switching between them onstage\, and the score draws on Newfoundland folk music — fiddle\, accordion\, bodhrán\, Irish flute. It runs about 100 minutes with no intermission. \nCome From Away opened on Broadway in 2017 and ran for five years\, earning seven Tony nominations and a win for Christopher Ashley’s direction. It is about a terrible day\, but it is not really about the attacks; it’s about what a small place did in the days that followed. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/come-from-away/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270313
DTEND;VALUE=DATE:20270314
DTSTAMP:20260905T210046Z
CREATED:20260905T210046Z
LAST-MODIFIED:20260905T210046Z
UID:3380-1804896000-1804982399@www.historichideaways.com
SUMMARY:Elton Dan & The Rocket Band
DESCRIPTION:Saturday\, March 13\, 2027\nKey West Theater\, 512 Eaton Street \nElton Dan & The Rocket Band bring their Elton John tribute to the Key West Theater. The band formed in 2015 and has since played more than 700 shows across 38 states\, including a crowd of 18\,000 at Kool Deadwood Nights in South Dakota in 2024 and a sold-out night at the Wynn Palace in Macau. \nThe set draws from the run of albums Elton John released across the 1970s and 80s. Expect “Rocket Man\,” “Crocodile Rock\,” “Philadelphia Freedom\,” “The Bitch Is Back\,” and “I’m Still Standing\,” with deep cuts and band favorites like “Levon\,” “Tiny Dancer\,” “Madman Across the Water\,” and “Pinball Wizard” turning up as well\, plus the occasional duet. \nDan’s piano playing carries the show\, along with the costumes. The band’s pitch is a room full of people who came to sing along\, and they play to that. \nSchedule subject to change. Information courtesy of Key West Theater — visit thekeywesttheater.com for tickets and complete details.
URL:https://www.historichideaways.com/event/elton-dan-the-rocket-band/
LOCATION:Key West Theater\, 512 Eaton Street\, Key West\, FL\, 33040
CATEGORIES:Concerts
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270316
DTEND;VALUE=DATE:20270317
DTSTAMP:20260905T195643Z
CREATED:20260905T195022Z
LAST-MODIFIED:20260905T195643Z
UID:3324-1805155200-1805241599@www.historichideaways.com
SUMMARY:Celtic Angels Ireland
DESCRIPTION:Tuesday\, March 16\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nCeltic Angels Ireland arrives in Key West on the eve of St. Patrick’s Day with a full-scale production built around traditional and contemporary Irish music. The show is assembled by a creative team based in Ireland and cast with award-winning and World Champion singers\, dancers\, and musicians\, and it moves through more than thirty tunes over the course of the evening. \nThe vocal ensemble at the center of it — the Celtic Angels themselves — handle the close harmony work that gives the show its name. Around them\, the Celtic Knights Dancers bring the percussive step dancing the tradition is known for\, and the Trinity Ensemble plays everything live. No backing tracks\, which matters more in this repertoire than in most; the fiddle and whistle lines are half the point. \nThe program swings between registers the way Irish music tends to — laments and emigration songs on one side\, reels and set pieces on the other\, often within a few minutes of each other. It’s a good family show and an easy one to bring people to who don’t think they have an opinion about Irish music. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/3324/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
ATTACH;FMTTYPE=image/webp:https://www.historichideaways.com/wp-content/uploads/2026/09/CAILogoFinal.webp
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270319
DTEND;VALUE=DATE:20270320
DTSTAMP:20260905T205842Z
CREATED:20260905T205842Z
LAST-MODIFIED:20260905T205842Z
UID:3377-1805414400-1805500799@www.historichideaways.com
SUMMARY:The Linda Ronstadt Experience
DESCRIPTION:Friday\, March 19\, 2027\nKey West Theater\, 512 Eaton Street \nThe Linda Ronstadt Experience brings its tribute concert to the Key West Theater\, fronted by American Idol alum Tristan McIntosh and backed by a full band. The show focuses on Ronstadt at the peak of her career\, when she was the biggest-selling female recording artist in the country. \nThe set covers the chart singles — “You’re No Good\,” “When Will I Be Loved\,” “That’ll Be the Day\,” “Blue Bayou” — along with songs Ronstadt made famous by Jackson Browne\, Elvis Costello\, Tom Petty\, Neil Young\, Warren Zevon\, and the Rolling Stones. Ronstadt’s gift as an interpreter was picking material from writers who hadn’t broken through yet and turning their songs into hits\, and the show leans into that range. \nSchedule subject to change. Information courtesy of Key West Theater — visit thekeywesttheater.com for tickets and complete details.
URL:https://www.historichideaways.com/event/the-linda-ronstadt-experience/
LOCATION:Key West Theater\, 512 Eaton Street\, Key West\, FL\, 33040
CATEGORIES:Concerts
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2026/09/uploadedimage-jpg_6a8355c8044c2.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270329
DTEND;VALUE=DATE:20270330
DTSTAMP:20260905T195529Z
CREATED:20260905T195529Z
LAST-MODIFIED:20260905T195529Z
UID:3328-1806278400-1806364799@www.historichideaways.com
SUMMARY:Legally Blonde the Musical
DESCRIPTION:Monday\, March 29\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nThe Broadway national tour of Legally Blonde the Musical stops in Key West this spring. Adapted from the 2001 film\, the stage version arrived on Broadway in 2007 with music and lyrics by Laurence O’Keefe and Nell Benjamin and a book by Heather Hach\, and it went on to win a fistful of Olivier Awards in London. It has been a staple of touring theater ever since\, largely because it does what it sets out to do without apologizing for any of it. \nElle Woods gets dumped by a boyfriend headed to Harvard Law who has decided he needs someone more serious. Elle follows him there\, talks her way in\, and spends the rest of the show discovering that she is considerably sharper than anyone — including herself — had assumed. The pace is relentless\, the choreography is athletic\, and the score runs from bubblegum to something closer to genuine feeling in “So Much Better” and the title song. Bruiser the chihuahua appears\, as required by law. \nIt holds up better than its reputation suggests. Underneath the pink there’s a real story about being underestimated and deciding not to accept it\, and the show is smart enough to let the joke land without ever making Elle the punchline. Good pick for a mixed group\, and a reliable crowd-pleaser for anyone bringing teenagers. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/legally-blonde-the-musical/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/webp:https://www.historichideaways.com/wp-content/uploads/2026/09/Screenshot2026-05-24174011.webp
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270405
DTEND;VALUE=DATE:20270406
DTSTAMP:20260831T193107Z
CREATED:20230105T194612Z
LAST-MODIFIED:20260831T193107Z
UID:666-1806883200-1806969599@www.historichideaways.com
SUMMARY:Taste of Key West
DESCRIPTION:Taste of Key West\nMonday\, April 5\, 2027 · 6:00–9:00 PM · Truman Waterfront Park\nKey West’s Premier Food & Wine Festival\nKey West’s biggest food and wine night takes over the Truman Waterfront for one evening each spring. Sample your way through dishes from dozens of the island’s best restaurants\, work through curated wines\, craft beers\, and spirits\, and watch the sun go down over the harbor. The event benefits Keys Health and Housing\, which marks 41 years of health\, housing\, and community programs across the Florida Keys in 2027. \nWhat to Expect\nCulinary Excellence — Nearly forty local restaurants participate\, from Duval institutions and waterfront kitchens to food trucks and neighborhood favorites. Past years have included Blue Heaven-era classics alongside newer spots — Bagatelle\, Café Solé\, Garbo’s Grill\, Green Parrot\, Hot Tin Roof\, Latitudes\, Nine One Five\, Square Grouper\, and many more. \nPremium Beverages — Curated wines\, craft beers\, and spirits\, with sommeliers on hand to walk you through the pours. \nWaterfront Views — Three hours of sunset over Key West Harbor from the Truman Waterfront lawn\, with live music throughout. \nTickets\nGeneral Admission — Free entry\, pay as you go\nEvent access is free. Tasting tickets are $1 each (most tastings run 4–6 tickets)\, with a wine or pint glass at $5 and a plate at $5. \nTwo for Taste Pass — $75\nSixty tasting tickets and two commemorative glasses. Built for couples or a pair of friends. \nVIP Pass — $150\nExclusive VIP tent access\, unlimited food and wine tastings\, butler-passed hors d’oeuvres\, a VIP sommelier experience\, a commemorative glass\, and flexible seating in the VIP area. \nPrices as listed by the organizers; confirm current pricing at purchase. \nSchedule subject to change. Information courtesy of Taste of Key West and Keys Health and Housing — see tasteofkeywest.org for tickets and complete details. \nBOOK YOUR VACATION RENTAL FOR TASTE OF KEY WEST \nDon’t wait to book your Key West vacation rental if you’re planning on attending Taste of Key West. Choose from our selection of luxury homes\, vacation rentals with a pool\, pet-friendly rentals\, condos or townhomes. \nBrowse Vacation Rentals>>>
URL:https://www.historichideaways.com/event/taste-of-key-west/
LOCATION:Truman Waterfront Park\, Key West\, FL\, United States
CATEGORIES:Festivals,Outdoor Activities
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2023/01/Taste-of-Key-West-2025.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270408T080000
DTEND;TZID=America/New_York:20270417T170000
DTSTAMP:20260905T204125Z
CREATED:20260905T204125Z
LAST-MODIFIED:20260905T204125Z
UID:3364-1807171200-1807981200@www.historichideaways.com
SUMMARY:Dial M for Murder
DESCRIPTION:April 8 – 17\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Waterfront’s mainstage season concludes with Dial M for Murder\, Frederick Knott’s 1952 thriller in Jeffrey Hatcher’s 2022 adaptation. A husband decides his wealthy wife is worth more to him dead\, and sets out to arrange the perfect murder. What follows is a cat-and-mouse game between him\, his wife\, her lover\, and a police inspector who keeps noticing the small things that don’t add up. \nHatcher’s version\, commissioned by the Old Globe in San Diego\, keeps the 1950s London setting and Knott’s clockwork plotting while reshaping the central triangle and adding a few turns of its own. \nThe Waterfront positions it alongside Wait Until Dark and Accomplice\, both audience favorites at the theatre — tightly built thrillers where the tension comes from watching people think. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/dial-m-for-murder/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2026/09/OTSPoster_1800x2700_DialM_26-27-scaled-1.jpeg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270411
DTEND;VALUE=DATE:20270412
DTSTAMP:20260905T210307Z
CREATED:20260905T210307Z
LAST-MODIFIED:20260905T210307Z
UID:3383-1807401600-1807487999@www.historichideaways.com
SUMMARY:10\,000 Maniacs
DESCRIPTION:Sunday\, April 11\, 2027\nKey West Theater\, 512 Eaton Street \n10\,000 Maniacs play the Key West Theater. The band formed in Jamestown\, New York in 1981 and has sold more than 10 million records\, moving from the indie circuit to a central place in the alternative rock of the late 80s and early 90s. \nThe 1987 album In My Tribe was the breakthrough — it stayed on the charts for 77 weeks and produced “Like the Weather” and “What’s the Matter Here?” The platinum albums Blind Man’s Zoo and Our Time in Eden followed\, with “Trouble Me\,” “These Are Days\,” and “Candy Everybody Wants.” Their MTV Unplugged set\, which included their version of “Because the Night\,” sold over four million copies. \nMary Ramsey leads the band today on vocals and viola\, alongside founding members Jerome Augustyniak on drums\, John Lombardo on guitar\, Dennis Drew on keyboards\, and Steven Gustafson on bass\, with Ben Medina on guitar. The band marked its 45th anniversary in 2026 with the Candy Everybody Wants box set covering their Elektra years\, and their first album of new material in over a decade. \nSchedule subject to change. Information courtesy of Key West Theater — visit thekeywesttheater.com for tickets and complete details.
URL:https://www.historichideaways.com/event/10000-maniacs/
LOCATION:Key West Theater\, 512 Eaton Street\, Key West\, FL\, 33040
CATEGORIES:Concerts
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2026/09/uploadedimage-jpg_697236926e603.jpg
END:VEVENT
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
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2023/01/shutterstock_1682920561_0.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270701
DTEND;VALUE=DATE:20270706
DTSTAMP:20260831T191928Z
CREATED:20230105T195325Z
LAST-MODIFIED:20260831T191928Z
UID:680-1814400000-1814831999@www.historichideaways.com
SUMMARY:Key Lime Festival
DESCRIPTION: Key Lime Festival\n\n\n\n\n\nJuly 1–5\, 2027 · Key West\nAmerica’s Favorite Citrus Celebration\nIn the Florida Keys we celebrate the things that make our islands unique: citrus\, eccentrics\, people\, and pie. The Key Lime Festival is five days of exactly that — pie tastings\, cocktail strolls\, wild competitions\, and a whole island leaning into its signature flavor. Come down to the birthplace of Key Lime Pie for a little taste and you’ll see what we mean. \nSince the festival wraps around the Fourth of July\, the week also brings the Rotary 5K\, poolside holiday parties\, and fireworks over the water. \nWhat to Expect\nThe 2027 schedule hasn’t been released yet. These are the recurring events that anchor the festival each year. \nKick Off Party & Key Lime Spirit Pageant — Opening night on Duval with live music\, cocktails on the veranda\, and a welcome keynote from festival co-founder and Key Lime pie historian David L. Sloan. Contestants compete in themed challenges to be crowned Key Lime Festival Emperor and Empress. \nKey Lime Pie Hop — A guided walking tour through the town where Key Lime pie was born\, stopping to sample versions from classic to creative. Multiple tour times through the day. \nKey Lime Bike Tours — A morning ride past island landmarks and hidden gems\, with a swim stop\, a slice of pie\, and a champagne toast at the finish. \nWheeling & Dealing Hot Wheels Race — Low-rider racing\, beer chugging\, and hula hooping in an alley off Duval. Considerably harder than it looks. \nPub Style Trivia with a Key Lime Twist — Five rounds\, a cocktail\, and the title of Wisest on the Island. Seating is limited. \nSloppy Joe’s Ultimate Key Lime Pie Smash Party — Donate and vote to watch local personalities and Sloppy Joe’s staff take a pie to the face\, all benefiting the Sloppy Joe’s Foundation. \n5-Alarm Pie Challenge — Free samples of the hottest Key Lime pie on the island at the historic Firehouse Museum\, built with cayenne graham cracker crumbs\, habanero cream\, and a jalapeño topper. \nKey Lime Sip & Stroll — Bar-hop between participating spots as they compete for your vote on the best Key Lime cocktail in Key West. \nPool Parties — Several resorts host Key Lime themed pool parties through the week\, with DJs\, food and drink specials\, and no shortage of lime-green swimwear. \nKey-Lime-O-Rama at the Truman Waterfront Farmers Market — The weekly waterfront market goes citrus\, with Key Lime creations alongside the usual produce\, orchids\, crafts\, and sunsets. Free. \nKey Lime Vendor Village — Handcrafted goods\, tropical art\, and local treats. \nWorld Famous Key Lime Pie Eating Championship — Contestants take on a full nine-inch pie with their hands behind their backs. Limited spots to compete\, free to watch. \nKey Lime Kid Zone — Slime making\, crafts\, games\, music\, and conch shell blowing lessons. \nKey Lime Pie Drop — Competitors try to outsmart gravity by dropping a pie from the top of the Key West Lighthouse without damaging it. Free to watch\, free to enter\, cash prize for whoever pulls it off. \nJF Haden’s Battle of the Bartenders — Six bartenders pulled out of their home bars and put poolside to compete head-to-head\, with live music through the afternoon. \nRotary Club 4th of July 5K and Fireworks — The annual run/walk benefits the Edward B. Knight Scholarship Fund\, followed later by a patriotic grill-out and fireworks after dark. \nKey Lime Menus All Week — Restaurants\, bars\, distilleries\, and spas across the island run Key Lime menus\, tastings\, and specials throughout the festival. \nFrozen Pie Pick-Up & Ship — Take Key West home with you. Kermit’s Key Lime Pie Shoppe and Key West Key Lime Pie Co. both ship; call ahead to reserve. \nSchedule subject to change. Information courtesy of the Key Lime Festival — see keylimefestival.com for the full schedule\, tickets\, and complete details.
URL:https://www.historichideaways.com/event/key-lime-festival/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Festivals
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270721
DTEND;VALUE=DATE:20270725
DTSTAMP:20260831T190631Z
CREATED:20230105T195821Z
LAST-MODIFIED:20260831T190631Z
UID:690-1816128000-1816473599@www.historichideaways.com
SUMMARY:Key West Marlin Tournament
DESCRIPTION:46th Annual Key West Marlin Tournament\nJuly 21–24\, 2027 · Key West \nCelebrating 46 years of world-class sportfishing\, the Key West Marlin Tournament returns to Key West July 21–24\, 2027. \nThe tournament coincides with Hemingway Days\, drawing anglers eager to test “The Wall” — the deep blue water off Key West — while the island hosts a week of Hemingway-themed festivities. Crews compete across three fishing days in the Marlin Division for blue marlin\, white marlin\, and spearfish\, with an optional Fun Fish Division for dolphin\, wahoo\, and tuna. Off the water\, the schedule includes the captains meeting\, nightly on-location dinners\, and the awards banquet. \nEntries are limited to the first 75 boats. \nFor reference\, the 2026 tournament paid out $260\,000 in total cash prizes\, including a $50\,000 Marlin Division purse. Prize structure and entry fees for 2027 have not yet been announced. \nThe full 2027 schedule of events\, entry fees\, and prize details will be posted by the organizers as they’re finalized. \nSchedule subject to change. Information courtesy of the Key West Marlin Tournament — see keywestmarlin.com for registration\, the full schedule\, and complete details.
URL:https://www.historichideaways.com/event/key-west-marlin-tournament/
LOCATION:FL
CATEGORIES:Outdoor Activities
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DTSTART;VALUE=DATE:20270811
DTEND;VALUE=DATE:20270816
DTSTAMP:20260831T190129Z
CREATED:20230105T211816Z
LAST-MODIFIED:20260831T190129Z
UID:703-1817942400-1818374399@www.historichideaways.com
SUMMARY:Key West Tropical Heat
DESCRIPTION:2027 Dates: 8/11 – 8/15\n\nTropical Heat is the HOTTEST annual 5-day party for gay men ages 21 and up in Key West and the Florida Keys! The all-male themed parties\, pool parties\, clothing optional events\, and adult-oriented entertainment promise to be HOT! August on our tropical island is always HOT\, but during Tropical Heat it promises to be even more so! What better way to experience our tropical paradise than joining us for 5 days with hot guys!? In addition to all our scheduled events\, you can also enjoy our many other activities on land and sea!\n  \n__________________________________________________________________________________________ \n\n\n\nTropical Heat 2026 Schedule of Events\n\n\n\n\n\n\n\n\n\n\n\n\n\n\nWednesday\, August 12th\n\n\n\n5 PM– Cowboy Ken’s PINK Pool Party  AND Kick-off @ Island House  – 1129 Fleming St.\nThink pink at the southernmost mojo-dojo-casa-house! Pink cowboy hats\, pink hankies\, pink speedos\, OR LESS! Just make it PINK! Free appetizers and ½ price cocktails. VIP band holders can also pick up their bands at this events. Bands can also be picked up at the Gay Key West Visitor Center at 808 Duval St. through Tropical Heat between the hours of 9 am and 5 pm. For more info call (305) 294-4603. \n\n\n\n\n\n\n\n\nThursday\, August 13th\n\n\n\n10:30 AM – All Male Day Trip 🏳️‍🌈Ages 18+ • 4 Hours • BYOB *Snorkel\, Sandbar or Kayak on Blu Q \nTrip includes: \n\nAll Male + Clothing Optional\nSnacks & Water Included\, BYOB\nSnorkel & Kayak Gear Included\nCaptains-Choice: activities tailored to the day’s weather conditions. We all want to have an amazing Key West day on the water!\nFree Cancellation up to 6 days (144 hours) prior to scheduled departure time.\nBring a towel\, and feel free to bring your own drinks! Our amazing crew will make sure your drinks stay cold in our coolers. They’re great at keeping track of who brought what and will keep you refreshed all day.\n**Sandbar and Snorkel is our typical day on the water\, but on certain weather and tide days\, it can be tough to go to a sandbar\, so we offer the option to kayak instead.\n\nTickets are available HERE \n\n9:30 PM – Nightly Karaoke at Bobby’s Monkey Bar – 900 Simonton St \nUnpretentious dive bar at 900 Simonton St in Key West (a block off Duval)\, known island-wide as one of the best karaoke spots in town. Karaoke runs nightly from 9:30 until late\, with the place typically just getting going around 10pm and rocking by 11. \n\n10:00 PM – Dancers on The Bar at Bourbon St Pub – 724 Duval St \nThe Bourbon St. Pub has been known all around the world for its Hot Men. And you can catch them each and every night on top of the bar for your viewing pleasure\, starting at 10 PM. \n\n\n\n\n\n\n\n\nFriday\, August 14th\n\n\n\n10:30 AM – Tropical Heat Snorkel Trip @ Blu Q Key West – 120 Margaret St. \nIf you haven’t set sail on Blu Q yet\, you’re missing out on the best gay experience in Key West! Blu Q guests keep coming back for more and it’s no surprise why. Their four-hour Tropical Heat trip is the perfect way to experience the turquoise waters of Key West while basking in the Florida sun. You can snorkel\, kayak\, swim\, or just relax on the boat – it’s totally up to you! Our crew is always ready to make your trip unforgettable\, with their warm smiles\, expert guidance\, and a hard work ethic. So what are you waiting for? Hop on board the Blu Q and let’s make some memories! This one sells out quickly. Tickets available HERE \n\n1 PM – 5 PM  Splash Pool Party @ Bourbon St. Pub – 724 Duval St. \nJoin World Famous Puddin’ Tane for some fabulous pool games and get a chance to meet the Adult Stars of Saturday Night’s Big ‘O’ Party while you beat the heat with ice cold drink specials from Key West Pride’s award-winning bartenders! Entrance and free clothes check included with your weekend pass bracelets! $20 or FREE \n\n9PM – 4AM Heat Stroke: Leather Gear and Underwear Party @ Saloon One – 504 Petronia St  \nWhether you’re rocking your favorite leather\, stripped down to your best underwear\, or somewhere in between\, this is your space to let loose\, connect\, and own the night. Expect pulsing beats\, a bold crowd\, and an unapologetically sexy atmosphere. Dress to impress\, or undress to express. \n\n\n\n\n\n\n\n\nSaturday\, August 15th\n\n\n\n10:30 AM–Enjoy a 4-hour Male All Day Trip with Blu Q Key West. \nIf you haven’t set sail on Blu Q yet\, you’re missing out on the best gay experience in Key West! Blu Q guests keep coming back for more and it’s no surprise why. Their four-hour Tropical Heat trip is the perfect way to experience the turquoise waters of Key West while basking in the Florida sun. You can snorkel\, kayak\, swim\, or just relax on the boat – it’s totally up to you! Our crew is always ready to make your trip unforgettable\, with their warm smiles\, expert guidance\, and a hard work ethic. So what are you waiting for? Hop on board the Blu Q and let’s make some memories! This one sells out quickly. Tickets are available HERE \n\n12 PM –Five-Alarm Pool Party@ Island House – 1129 Fleming St \nAll fireman report to the pool deck for this high-energy firefighter themed pool party! Slide down the pole and get ready to get blasted by our pool boy CO2 cannon! Expect hot men & cold cocktails to make the perfect sizzling summer memory with friends! \n\n10 PM – The Big “O” Exhibition @ Bourbon St. Pub – 724 Duval St. \nA Voyeurs Dream Come True! The biggest blow out of the weekend! Foam party. Play areas. Pool & Jacuzzi. Hot Exotic Dancers and Adult Industry Performers. \nLive Exhibition Shows. Free entry with your VIP bands\, or $20 for non pass holders at the door. Free clothes check! \n\n\n\n\n\n\n\n\nSunday\, August 16th\n\n\n\n\n12 PM –Hot Naked Pool Party@ Island House – 1129 Fleming St \nAfter church\, and before T-Dance\, comes Island House! For over two decades\, this party brings visitors and locals together in true Gay Key West spirit! Hot-Naked-FUN! \n\n\n\n\n\n\n\n\nDaily Activities\n\n\n\nMuseums: Ernest Hemingway\, Key West Butterfly Conservatory\, Little White House\, Key West Aquarium\, Mel Fisher Maritime Museum\, Key West Firehouse Museum\, Key West Light House\, Key West Ship Wreck Museum\, Audubon House\, Oldest House and Garden Museum\, USCGC Ingham Museum\, Tennessee Williams Exhibit. \nLand Activities: Key West Food Tours\, Up the Keys Eco Tour\, Fort Zachary State Park\, West Martello Tower\, A & M Scooter Rental\, Key West Tropical Forest and Botanical Garden\, Key West Cemetery\, Key West Adventures\, Papa’s Pilar Rum Distillery\, Ghost Hunt\, Old Town Trolley Tours\, Conch Tour Train\, Haunted Key West\, Ghosts and Mysteries\, Ghosts and Gravestones\, D’vine Wine Gallery\, Perky’s Key West Excursions. \nWater Activities: Argo Navis\, Blu Q\, Classic Harbor Lines\, Cruisin’ Tikis\, Danger Charters\, Fish N Chicks\, Fury\, Island Vibe Charters\, Island Vibe Charters\, Java Cat\, Jolly Rover II\, Key West Eco Tours\, Key West Sailing Center\, Key West Snorkeling. Land Boat Charters\, Off the Charts\, Schooner America\, Sunset Sail Key West\, Sunset Watersports\, SV Argo Navis\, Yankee Freedom.
URL:https://www.historichideaways.com/event/key-west-tropical-heat/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Festivals,Outdoor Activities
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270811
DTEND;VALUE=DATE:20270816
DTSTAMP:20260831T190312Z
CREATED:20230105T212024Z
LAST-MODIFIED:20260831T190312Z
UID:706-1817942400-1818374399@www.historichideaways.com
SUMMARY:Key West Lobsterfest
DESCRIPTION:Mark your calendars! We are already looking ahead and can’t wait to do it all over again. Please join us for the 29th Annual Key West Lobsterfest\, taking place August 11–15\, 2027.\n______________________________________________________________________\nGet Ready to Crack! Key West Lobsterfest 2026 Dates are Set!\n\nThe wait is officially over! Get your butter warmers ready because we are thrilled to announce the dates for the biggest and tastiest summer celebration on the island: Key West Lobsterfest 2026 is happening from Wednesday\, August 5th through Sunday\, August 9th! \nJoin us for five unforgettable days as we celebrate the opening of the Florida Spiny Lobster season with an island-wide party. From the savory kickoff Lobster Boil to the massive Duval Street Fair with live music and endless crustaceans prepared every way imaginable\, this is the ultimate crustacean celebration. \n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n \nHistory of Key West Lobsterfest\n\n\n\nBorn from a Brawl (Over Lobster\, No Less!)\n\n Believe it or not\, Key West Lobsterfest started with a friendly (or maybe not-so-friendly) dispute. Two friends couldn’t agree on who made the best Lobster Chilau\, a Key West staple. What else to do but settle it with a cook-off? The inaugural throwdown went down in the courtyard of Rick’s & Durty Harry’s Entertainment Complex\, with secret family recipes and judges galore. The event was such a hit (though we’ll keep the winner a secret)\, they knew they had to take it bigger. The next year\, Lobsterfest moved to the bustling Duval Street\, welcoming more participants\, spectators\, and sponsors than ever before. Fast forward to today\, and this epic food fight has transformed into a 4-day extravaganza that takes over the entire island! \n\nKEY WEST LOBSTERFEST 2026 28th Annual\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.)\nWEDNESDAY\, AUGUST 5 \n6:00 PM – 9:00 PM Key West Lobsterfest Kick-Off Party Rick’s & Durty Harry’s Entertainment Complex 202 Duval Street\, Historic Old Town \nHome of the inaugural Lobsterfest — this is where it all began with a contest for the best lobster dish on the island. Join us to kick off the 28th Annual Key West Lobsterfest. We need to empty the freezers to make room for freshly caught lobster! \nEnjoy amazing lobster pizza and drink specials featuring our Official Sponsors Sun Cruiser Iced Tea and Cuervo 1800 Tequila. \n\nTHURSDAY\, AUGUST 6 \n6:00 PM – 9:00 PM Lobster Boil at The Porter Mansion Courtyard – 429 Caroline Street\, Historic Old Town \nJoin us for our annual seafood lobster boil in a beautiful Key West setting with a full bar\, music\, and delicious food. \n\nFresh lobsters\nJumbo Key West shrimp\nRed skin potatoes\nFresh corn on the cob\nFresh baked jalapeño corn bread & melted butter\n\nEach ticket is good for one guest’s admission and meal. \n\nFRIDAY\, AUGUST 7 \n3:00 PM – 6:00 PM Pool Party at The Marker Resort – Key West Harbor Resort – 200 William Street \nFree Admission – Relax and soak up the fun. \n8:00 PM – Midnight Lobsterfest Duval Pub Crawl Check-in: The Marker Resort Pool Bar\, 200 William Street \nJoin us for the 28th Annual Lobsterfest Pub Crawl! The fun starts immediately after sunset and goes until midnight. \nWhat’s included: \n\nOfficial Lobsterfest T-shirt\nSouvenir lanyard\nAmazing drink specials on Sun Cruiser Iced Tea and Cuervo 1800 Tequila at participating bars\n\nTickets: $25 in advance / $30 at the door. A portion of proceeds benefit the Key West High School Scholarship Fund. Pick up your T-shirt\, lanyard\, and crawl instructions at the Marker Resort Pool Bar on August 7th from 3:00 PM – 7:30 PM. All items must be picked up in person. \n\nSATURDAY\, AUGUST 8 \nNoon – 11:00 PM – Street Fair & Concert 100–500 Blocks of Duval Street – Free Admission \nArts & crafts\, merchandise\, and more lining Duval Street all day. \nLocal bars and restaurants will be serving fresh Florida Lobster — everything from appetizers to full meals. No entrance fee; food and drinks sold individually. \nLocal bars will also be set up on Duval Street featuring ice-cold Corona\, Blue Chair Bay Rum cocktails\, and more. \nLive Music Lineup: \n1:00 PM Just George – Duval St. & Greene St. \n3:00 PM Fried Newt – Main Stage \n5:30 PM Jordan Oaks – Main Stage \n8:00 PM The Durtbags – Main Stage — then continuing late night at Durty Harry’s
URL:https://www.historichideaways.com/event/key-west-lobsterfest/
LOCATION:FL
CATEGORIES:Festivals,Outdoor Activities
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