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Events in Key West

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Key West for 2023

  • November 11 - Dec 03, 2023 Key West
  • Key West Art & Historical Society: Headdress Ball - 40 Years of Creativity
  • Website
  • Combining captivating entertainment and creative competition, the Key West Headdress Ball has been the premier LGBTQ+ event of the Fantasy Fest celebration for the last 40 years. The ball typically features up to 25 contestants showcasing their unique headdresses, some that tower high above their designers. This special exhibition showcases the works of art worn in the 2023 competition. On display daily from 10 a.m. to 5 p.m. at the Custom House Museum, 281 Front St.

  • November 23 - Dec 31, 2023 Key West
  • Harbor Walk of Lights
  • Website
  • The “Harbor Walk of Lights” stretches along the seawall past Greene, William and Margaret Streets to the Key West Ferry Terminal. A nautical theme honors the maritime history of the Key West waterfront. The harbor walk area in the Historic Seaport glimmers with holiday displays throughout the season, all themed to celebrate the island city’s maritime heritage. Elements include tens of thousands of lights, dozens of lighted palm trees, a lobster trap holiday tree, a nautically decorated pine and a tree adorned with fishing buoys that resemble giant ornaments.

  • November 29 - Dec 16, 2023 Key West
  • Waterfront Playhouse: Little Shop of Horrors
  • Website
  • The deviously delicious Broadway and Hollywood sci-fi smash musical Little Shop of Horrors comes to Waterfront Playhouse for a three-week run. Tickets range from $40 to $75. Showtimes at 8 p.m. along with an additional 2 p.m. matinee on Dec. 9. 407 Wall Street at Mallory Square.

  • November 30 - Dec 03, 2023 Key West
  • Coast is Clear Festival
  • Website
  • As another Atlantic hurricane season closes, the Coast is Clear Festival kicks off the high season in Key West with a weekend of music and cultural events throughout Old Town. Highlights include a series of nighttime ticketed events, plus multiple free shows daily at the Green Parrot, and a public sandlot baseball tournament Saturday at Bayview Park. Tickets are available for single events or there is a full weekend pass available at www.coastisclearfest.com.

  • December 02 Key West
  • Key West Hometown Holiday Parade
  • Website
  • Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Truman Avenue and White Street beside Bayview Park and proceeds down Duval Street. Seeing Santa is a highlight for kids.

  • December 03 Key West
  • Mote's Ocean Fest: A Community Celebration
  • Website
  • Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment at Mote Marine Laboratory's annual Ocean Fest from 10 a.m. to 4 p.m. Enjoy an outdoor community celebration of the oceans at Truman Waterfront Park. Enter at 100 Southard Street for a day of family activities, raffles, live music, shopping and environmental exhibits. Mote scientists will be there to answer questions about coral reef research and restoration. Family activities include children's fishing clinics, live animals, bounce houses and a rock wall. Adult attendees will get a free beer ticket with the donation of a new-unused toy in Mote's Toys for Tots bin.

  • December 03 Key West
  • Key West Artisan Market: Red Ribbon Edition
  • Website
  • Key West Artisan Market supports World Aids Day December 3, from 10 a.m. to 2 p.m. Pick up a free ribbon to wear from the volunteers of the Friends of the Aids Memorial. Shop for fine arts and crafts, jewelry, apparel, produce, delicious foods and drinks and more. In the park near Higgs Beach, 1801 White St.

  • December 03 Key West
  • Conch Republic Seafood Company: Santa Meet and Greet
  • Website
  • Come out to meet Santa and get your holiday photos with the jolly old elf. Donations support the Key West Police Department Love Fund, which provides aid to any department member in crisis. 5 to 8 p.m. at 631 Greene Street.

  • December 03 Key West
  • Montessori United 5k Run/Walk
  • Website
  • Runners and walkers are invited to participate in the Montessori United 5k and Kids Fun Run beginning and ending at Truman Waterfront Park. The 5k run, walk and stroller divisions are $35 and begin at 8 a.m. The Kids 1-Mile and Kids Half-Mile registration fees are $20 and races start at 9 a.m. Spectators can register for VIP tickets to enjoy a light breakfast and mimosa while cheering on race participants. The run benefits Montessori education in Key West.


  • December 03 Key West
  • Key West Woman's Club: Santa, Sweets and Holiday Tree Lighting
  • Website
  • Celebrate the season with the Key West Woman’s Club and Key West Mayor Teri Johnston at the historic Hellings Curry Museum at 319 Duval St. Enjoy appetizers, desserts, Amsterdam eggnog, and holiday music performed by the Bahama Village Children’s Choir and the Key West Community Orchestra. Donations of unwrapped, new clothing items for students K-12 appreciated.

  • December 07 Key West
  • Florida Keys SPCA - POSH Fundraiser
  • Website
  • The 10th annual POSH (Paws Often Steal Hearts) fundraiser benefitting Florida Keys SPCA takes place from 6 to 9:30 p.m. at Audubon House and Gardens, 205 Whitehead St. The gala affair encourages guests to dress up and don their favorite fascinators. Silent auctions, raffle prizes, a tapas-style dinner and live music are all part of the fun. Follow the Second Line Procession at the end of the night to continue the party.

  • December 08 Key West
  • Holiday Historic Inn Tours: Night #1
  • Website
  • In this first of two holiday historic inn tours, explore four beautifully decorated locations and their unique architecture and history from 6 to 8 p.m. Sample sweet and savory holiday treats and libations. Locations are: the Key West Butterfly and Nature Conservatory, Wicker Guesthouse, The Mermaid and the Alligator, and the Marquesa Hotel. The tours are self-guided. $40 tickets available online, but must be picked up after 5:30 p.m. on Dec. 8th at the first location, the Butterfly and Nature Conservatory, 1316 Duval Street. The second inn tour takes place Dec. 15.

  • December 08 - 23, 2023 Key West
  • Old Town Trolley's Holiday Sights & Festive Nights Tours
  • Website
  • The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West's best-decorated neighborhoods, buildings and homes on fun-filled 60-minute excursions. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m.

  • December 08 - 23, 2023 Key West
  • Conch Tour Train's Holiday Sights & Festive Nights Tours
  • Website
  • Lively Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 7:30, 8 and 8:30 p.m. on evenings from Dec. 8 to 12 and 15 to 23. Included are holiday lights glasses as keepsake items. The one-hour tour takes riders past the island's most elaborately decorated houses, buildings and neighborhoods, with holiday caroling.

  • December 08 Key West
  • Key West Art & Historical Society: Annual Holiday Concert & Bazaar
  • Website
  • This popular annual celebration features some of the Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House. The bazaar offers shoppers a treasure trove of unique gift items and there will be plenty of food and festive libations Free and open to the public, the event takes place on the front porch and the street in front of the Customs House Museum at 281 Front Street.

  • December 09 Key West
  • Key West Pet Pictures With the Grinch
  • Website
  • Bring your critters for pet pictures with the Grinch Saturday, Dec. 9 at the Hard Rock Cafe, 313 Duval St. from noon to 3 p.m. $20 per photo session. Proceeds benefit River's Wish, a non-profit senior dog sanctuary.

  • December 09 Key West
  • 32nd Annual Schooner Wharf/Abosult Vodka Lighted Boat Parade
  • Website
  • Deck the hulls, it's time for the annual Schooner Wharf Lighted Boat Parade along Key West Bight and Historic Seaport. The glittering parade of illuminated watercraft begins at 8 p.m. There are multiple viewing spots from bars and restaurants and from spots all along the Harbor Walk. Family fun begins at 6 p.m. with the Bahama Village Music Program's House of Pans steel band playing calypso Christmas carols at Schooner Wharf Bar, 202 William Street.

  • December 09 Key West
  • Carl Hiaasen in Conversation With Judy Blume
  • Website
  • Best-selling "Florida Fiction" author Carl Hiaasen appears Saturday, Dec. 9 at 3 p.m. in conversation with Judy Blume at the Helmerich Theater at the Studios of Key West, hosted by Books & Books. They'll discuss his new middle-grade novel for young readers, WRECKER, about the teenage descendent of a Key West shipwreck salvager and his exploits with shady characters after he finds them wrecked in their speedboat. The event is sold out but there is a waiting list. Access the online ticket link to sign up. The event takes place at 533 Eaton Street.

  • December 09 Key West
  • 10th Annual Parade of Paws & Holiday Bazaar
  • Website
  • Celebrate dogs at this annual dog parade and holiday bazaar with local vendors. Santa will be there for photos with the pups along with the Smooch-a-Pooch booth, raffles and tons of fun. Higgs Beach Dog Park, corner of Atlantic and White St. from 10 a.m. to 2 p.m.

  • December 10 Key West
  • Sheriff's Animal Farm: Christmas on the Farm
  • Website
  • Don't miss the special Christmas on the Farm open house at the Sheriff's Animal Farm from 1 to 3 pm. Visit the animals and enjoy holiday crafts, music, gifts, and Santa! The farm is located at 5525 College Rd. at the Sheriff's Office Headquarters complex. The event is free to attend, but the family-friendly farm welcomes donations. In addition to cash, suggested donations include fresh produce for the animals or items from the MCSO Animal Farm Amazon wishlist.

  • December 10 Key West
  • Key West Lighting of the Menorah
  • Website
  • The City of Key West's annual Lighting of the Menorah ceremony takes place at Bayview Park Sunday, Dec.10 starting at 5 p.m. 1320 Truman Avenue.

  • December 10 Key West
  • Key West Artisan Market: Merry Marketplace on the Beach
  • Website
  • Shop for holiday treasures from local artisans while enjoying live music, tasty treats, fun drinks, activities for the kids – including a ‘snowman’ building contest and even a visit from old St. Nick. 10 a.m. to 3 p.m., Southernmost Beach Resort, 1317 Duval St.

  • December 10 Key West
  • Eaton Street Christmas Stroll
  • Website
  • Eaton Street becomes a southernmost North Pole Sunday afternoon and evening. Wander the blocks between Whitehead and Simonton, starting with a concert at Key West United Methodist at 3:30 p.m. Then stop in at multiple venues for shopping or special presentations, including Key West Theater, Woman's Club of Key West, Salt Gallery, the Bahama Village Music Program at Williams Hall, an open house at The Studios of Key West, classic cartoons at Tropic Cinema, and a final Keys Choral Arts Christmas concert at St. Paul's Episcopal at 7 p.m. The event is free but tickets are required. Sign up at Tropic Cinema's website.

  • December 12 - 16, 2023 Key West
  • Fringe Theater: The Best Christmas Pageant Ever
  • Website
  • Mischief and mayhem ensue at the annual Christmas pageant when the town's young hoodlums enact a coup and unexpectedly teach the town the true meaning of Christmas. An endearing family show with performances Dec. 12 through 17 at 7 p.m., and Dec. 16 at 2 p.m. Tickets $35 adults; $20 for ages 15 and under. Shows at the Historic Armory, 600 White St.

  • December 12 Key West
  • 24 North Hotel: Paint & Sip Night with Artist Lance Berry
  • Website
  • Get ready to laugh and have a blast with the whole family or a couple of pals at Paint and Sip night with Key West artist, character and life-of-the-party, Lance Berry. Your $40 ticket includes your first drink, plus all the art supplies and instruction you'll need to create your own masterpiece. The class takes place the second Tuesday of the month at Republica Bar & Lounge at 24 North Hotel, 3820 N. Roosevelt Blvd.

  • December 12 Key West
  • The Studios of Key West: Ann Hampton Callaway
  • Website
  • Ann Hampton Callaway is one of America’s most gifted artists in pop and jazz. A leading champion of the great American Songbook, she’s made her mark as a singer, pianist, composer, lyricist, arranger, actress, educator, TV host and producer. 7 p.m. in the Helmerich Theater. Tickets $55. 533 Eaton St.

  • December 14 Key West
  • Key West Art & Historical Society: Happy Hour With the Historian
  • Website
  • Join historian Dr. Cori Convertito for a talk about how Florida's east coast became known as the "American Riviera" as Henry Flagler constructed numerous luxury hotels during the Gilded Age. This talk explores the assorted hotels’ histories to provide insight into what life was like for the leisure class in the 19th and 20th centuries. $15 ticket includes one glass of wine, beer or a soft drink. 5 to 6 p.m. at Comedy Key West, 218 Whitehead Street.

  • December 14 - 17, 2023 Key West
  • Gay Holiday Getaway
  • Website
  • Cuban-inspired hotel Havana Cabana is about to serve up a festive fiesta in partnership with the iconic Provincetown, Massachusetts, premier LGBTQ+ hotel and entertainment complex Crown & Anchor. From December 14th-17th, Havana Cabana is bringing Key West a falala-fabulous experience with their Gay Holiday Getaway that you won’t want to miss! Sip on punchy poolside cocktails and engage in sensational sunset performances that'll have you caroling all the way home. From classic holiday sing-alongs hosted by Tina Burner to Vibrator Races at Mary Ellen’s Bar (yes, you read that right), this is a yuletide experience that's anything but ho-hum. Whether you’ve been naughty or nice, all travelers can warm up their winter with this memorable holiday getaway. Accommodations start from just $169 per night and reservations can be booked online.

  • December 15 Key West
  • Holiday Historic Inn Tours: Night #2
  • Website
  • In this second of two holiday historic inn tours, explore four beautifully decorated locations from 6 to 8 p.m. while enjoying sweet and savory holiday treats and libation samplings. Locations are: Papa’s Pilar Distillery, Island City House, The Conch House Heritage Inn, and the Lighthouse Hotel. The tours are self-guided. $40 tickets available online, but must be picked up in person at the first location - Hemingway's Library at Papa's Pilar Distillery, 201 Simonton Street.

  • December 15 - 30, 2023 Key West
  • Key West Waterfront Winter Wonderland
  • Website
  • The Coffee Butler Amphitheater at Truman Waterfront Park transitions into the Key West Waterfront Winter Wonderland for an all ages, family friendly holiday experience Dec. 15 through 30 including stunning light displays, an ice skating rink, games, rides, attractions, music and more. The amphitheater’s vendor village is to offer a variety of food options and local artisans perfect for holiday shopping. Don't miss out on special holiday experiences including photo opportunities with Santa, crafts and more. Admission $10 per person, with children 5 and under free. For an additional $20 per person, you can enjoy a one-hour ice skating session. $10 all-you-can-ride wristbands are available for rides including carousels, swings and slides. Tickets go on sale mid-November.

  • December 16 Key West
  • 'A Positive Step' 5k Rudolph Red Nose Run
  • Website
  • Don your festive holiday jammies and join in the 15th 'A Positive Step' 5k Rudolph Red Nose Run, starting and ending at the Southernmost Beach Café, 1405 Duval Street. Race day check-in starts at 7 a.m. with start time at 8 a.m. Prizes are awarded for most festive and most unusual PJ's. After the race, enjoy refreshments and a fabulous silent auction to benefit A Positive Step of Monroe County, a non-profit serving at-risk kids and their families.

  • December 16 Key West
  • Tennessee Williams Theatre: Fiesta de Navidad Tropical
  • Website
  • Featuring grooves such as salsa, bachata, and cha cha cha, this high energy live performance event presented by the Key West-based Pasión Project studio features World Salsa Champion dancers Carine & Rafael and Mambo royalty Eddie Torres, Jr. with his partner Princess. With live music by Caribe and friends, get ready to move, shake and celebrate all night long, and even dance onstage with the band. Tickets $30-$75. 8 p.m. at 5901 College Rd.

  • December 17 Key West
  • Holiday Classic Car Show
  • Website
  • See classic cars from a variety of eras at the official show of the Florida Keys Southernmost Car Club, and choose a People’s Choice winner with your votes. Located at the Conch Republic Seafood Company parking lot at the corner of Greene and Elizabeth Streets. Attendees are asked to bring an unwrapped toy for the Monroe County Domestic Abuse Shelter. 11 a.m. to 3 p.m.

  • December 17 Key West
  • Key West Artisan Market: Shop Local Edition
  • Website
  • Shop for fine arts and crafts, jewelry, apparel and more items that would make great gifts, along with fresh produce, delicious foods and drinks at this open-air bazaar from 10 a.m. until 2 p.m. Santa Claus will be onsite starting at noon for free pictures with anyone who wants one! Located in the park at Higgs Beach, 1801 White St.

  • December 19 - Jan 13, 2024 Key West
  • Red Barn Theatre: A Tuna Christmas
  • Website
  • In the third-smallest town in Texas, radio station OKKK news personalities report on Yuletide activities.The hilarity never lets up in this comedic romp for all seasons featuring many colorful Tuna denizens played by two very funny actors, Brandon Beach and David Black. Showtime 8 p.m. Tickets $49 to $60.

  • December 20 Key West
  • Key West Theater: Peter Mayer Stars & Promises Christmas Tour
  • Website
  • Peter Mayer, singer, songwriter and guitarist brings the 24th anniversary of his widely acclaimed “Stars and Promises” Christmas tour to Key West. Mayer has released 25 of his own albums, toured internationally with his own band, and has been lead guitarist for Jimmy Buffett’s Coral Reefer band for three decades. Don't miss this "Christmas show like now other." Doors open at 6:30; show at 7:30 p.m. Tickets $35 to $55.

  • December 21 Key West
  • The Studios of Key West: MicroPARTY with Electric Blue Yonder
  • Website
  • Electric Blue Yonder examines the mysteries of the universe and reports their findings through song. The MicroPARTY is a unique live performance of the band's upcoming music that also includes a special sneak peak at unreleased animated music videos, and some info about their next big adventure. MicroPARTY is music and fun for everyone – the young and the young at heart. Performance at 6 p.m. in the Helmerich Theater. Tickets $35. 533 Eaton St.

  • December 24 Key West
  • Jazz in the Gardens
  • Website
  • Find festive outdoor jazz in The Gardens Hotel's famous outdoor garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly. 5 to 7:30 p.m. 526 Angela St.

  • December 29 - 30, 2023 Key West
  • Key West Home Tours: Holiday Style
  • Website
  • The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating from 1960. This 64th series features self-guided tours of several Key West homes and gardens, each festively dressed for the holidays. Home Tour tickets provide entry to 5 homes at your self-guided pace, between 1-4 p.m. during the Friday-Saturday tour. Address are to be provided when tickets are purchased.

  • December 31 Key West
  • New Years Eve Red Shoe Drop
  • Website
  • The iconic Key West New Year's Eve "Red Shoe Drop" at Bourbon St. Pub features a new queen riding in the shoe, after the 25-year reign of queen Sushi came to an end after New Year's Eve 2022. Christopher Peterson, famous for his EYECONS female impersonation show, will ride the shoe on New Year's Eve 2023 leading into the 2024 New Year. The public can watch for free from the street in front of the club at 724 Duval St. A limited number of VIP balcony tickets go on sale Dec. 1.

  • December 31 Key West
  • Great Gatsby New Year's Eve with "Plane Drop"
  • Website
  • Dress to impress in your best Gatsby era outfits at First Flight, Enjoy an open bar, champagne toasts, chef-manned stations and live band. At the stroke of midnight, a replica of an old Pan Am airplane with a real-life "stewardess" will take flight in the garden for a "plane drop" to ring in 2024. Tickets $250. 301 Whitehead St.

  • December 31 Key West
  • Schooner Wharf Bar: New Year's Eve Pirate Wench Drop
  • Schooner Wharf Bar invites you to join the party to witness the annual tradition of the Lowering of Pirate Wench Evalena, who will once again descend from the towering mast of Schooner America 2.0 to welcome in 2024. The fun starts in the afternoon with live music continuing into the New Year.

  • December 31 Key West
  • Sloppy Joe's Bar: Dropping of the Conch Shell
  • Website
  • This year at Sloppy Joe's, the conch shell will drop at the approach of midnight for the 30th time at the corner of Duval and Greene Street to ring in the New Year! Watch it live in the street or watch from inside the bar on the Sloppy-Tron. No reservations for New Year's Eve inside the bar, tables are on a first-come basis.

  • December 31 Key West
  • Key West Artisan Market: New Year's Eve Edition
  • Website
  • Start your New Year's Eve celebration at the market located near Higgs Beach at 1801 White St. from 10 a.m. to 2 p.m. with great food, libations, entertainment, arts and crafts, jewelry and much more.

  • January 04 - 06, 2024 Key West
  • Waterfront Playhouse: Joe Posa as Joan Rivers
  • Website
  • Having performed alongside Joan Rivers on two separate occasions, Joe Posa was lovingly called by Ms. Rivers, her “favorite Joan Rivers Impersonator.” See his amazing performance at Waterfront Playhouse for three nights only. Showtime 8 p.m. 407 Wall St.


  • January 06 Key West
  • Pole Vault in Paradise Competition
  • Website
  • Pole Vault in Paradise brings together pole vaulters of all ages to compete alongside some of the best pole vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club, the event is to be staged at Key West High School's track at The Backyard sports complex, 2100 Flagler Ave. The main event is Saturday. The first flight of pole vaulters starts at 9 a.m.

  • January 09 - 10, 2024 Key West
  • The Studios of Key West: David Wilcox in Concert
  • Website
  • Folk singer-songwriter David Wilcox’s lyrical insight is matched by a smooth baritone voice and virtuoso guitar playing, giving him a range and tenderness rare in folk music. More than twenty albums into a career spanning over 30 years of touring extensively around the U.S and world, he continues to deliver joy, inspiration and invention to his legions of fans. Tuesday night at 7 p.m. in Helmerich Theater; Wednesday night at 6 p.m. on the roof at Hugh's View. Ticket prices vary. 533 Eaton St.

  • January 11 - 14, 2024 Key West
  • Key West Literary Seminar: Florida - The State We're In
  • Website
  • Readers and writers gather every January for this festive four-day literary celebration. For “Florida: The State We’re In,” you'll find a cast of novelists, poets, historians, humorists, and cultural critics who know the Sunshine State better than anybody. During this literary exploration of Florida, we may not solve all the problems of this crazy place, but we’ll sure have a good time talking about it. Featured authors include Dave Barry, Carl Hiaasen, Craig Pittman, Diane Roberts, Campbell McGrath and others. Most seminar events take place at Coffee Butler Amphitheater at Truman Waterfront Park, 21 Quay Road.

  • January 14 Key West
  • 26th Annual Key West Half Marathon, 5k, Rum Stroll & Beach N' Beer Mile
  • Barbara Wright 305-240-0727 Email Website
  • Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, the 2024 race follows a 13.1-mile course that includes the Southernmost Point, Duval Street, Smathers Beach and more. The race typically attracts American and international runners to compete in Key West's balmy January climate.

  • January 15 - 19, 2024 Key West
  • The Southernmost Regatta
  • Website
  • Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing / Cruising Keelboats. Spectators can watch the races from various waterfront venues, mingle with sailors and view sailboats at the Galleon Resort's marina, 617 Front Street, after each day’s races.

  • January 16 - 20, 2024 Key West
  • RokIsland Fest
  • Website
  • More than 20 of the best and most iconic rock bands and performers bring their massive hits to the Southernmost City in the U.S. for five days of unforgettable songs, sun & sand at RokIsland Fest. The lineup includes Bret Michaels, Styx, Stone Temple Pilots, Night Ranger, Don Felder and many more. Multi-day passes with and without rooms and VIP experiences are available, with most performances at Truman Waterfront Park, 21 Quay Rd.

  • January 17 - 20, 2024 Key West
  • Red Barn Theatre: This One's for the Girls - The Women of Country Music
  • Website
  • Christine Mild returns with a new show featuring the best of women who sing country . . . their stories and their incredible music. She sold out her Patsy Cline show last season so don't miss this one! Starring Christine Mild with Musical Direction by Jim Rice, Gary Rivenson on bass and Gary McDonald on drums. Tickets $75. Showtime 8 p.m. 319 Duval Street.

  • January 18 Key West
  • Key West Art & Historical Society: Happy Hour With the Historian
  • Website
  • Join historian Dr. Cori Convertito for a talk that explores the diversity of work historically done along the Key West waterfront, including shipbuilding, wrecking, sponging, turtling and shrimping. Important questions will be addressed about how the waterfront has changed over time, the reasons for these changes, and implications for the future. $15 ticket includes one glass of wine, beer or a soft drink. 5 to 6 p.m. at Comedy Key West, 218 Whitehead St.

  • January 20 Key West
  • South Florida Symphony: Brahms, Bach, Montgomery & Price
  • Website
  • South Florida Symphony Orchestra kicks off its 26th Key West Season with the works of two trailblazing composers: Florence Price, the first African American female to have a work premiered by a major U.S. orchestra, and Jessie Montgomery, one of today’s most compelling composers. The stage comes alive as virtuoso pianist Awadagin Pratt presents Montgomery's latest piano concerto alongside another Symphony premiere, Bach’s Keyboard Concerto No. 4. All of this is anchored by Brahms' lyrically beautiful Symphony No. 1. Tickets start at $25. Tennessee Williams Theatre, 5901 College Rd. Curtain time is 7:30 p.m.

  • January 23 - 27, 2024 Key West
  • Mile 0 Fest
  • Website
  • With a carefully curated line-up of well-known and up-and-coming artists, Mile 0 Fest offers an unforgettable music experience. The event’s “Mile 0” moniker refers to Key West’s location at “mile 0” of U.S. 1. Tickets are selling fast, with Platinum and Premiere Packages sold out. Pirate and Beach Bum packages are still available. Single day passes may become available, but are not guaranteed. Performances take place at Coffee Butler Amphitheater, 21 Quay Rd. and at other locations around Key West. Talent includes Morgan Wade, Tanner Usery, the Randy Rogers Band and many more.

  • January 23 - 28, 2024 Key West
  • Key West Food & Wine Festival
  • Website
  • The festival include over 20 unique events including waterfront wine tastings, winemaker/chef collaborations, local events that present an authentic taste of Key West, and an amazing grand tasting event. The theme for 2024 is Ole Espana, celebrating the wine and culture of Spain and its impact on Key West. Key West, or Cayo Hueso (Island of Bones) was discovered by Ponce de Leon, named Las Martines and claimed by Spain in 1513. In 1815 Don Juan de Estrada granted Key West to Juan Pablo Salas for meritorious service to the crown.

  • January 26 Key West
  • Tennessee Williams Theatre: Puppy Pals, Live!
  • Website
  • Join the stars of the show, America’s Got Talent Quarterfinalist “The Puppy Pals” along with our all-star cast for an afternoon of fun! There will be a special meet and greet after the show with your favorite Puppy Pals for photos and ‘paw’shakes. Tickets $25 to $95. 5901 College Rd.