Key West Events Calendar

Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.
Dream Catcher Charters offers visitors to Key West for Special Events Fishing Charters. Save Money and Have A Better Time Booking Direct.

There is never a shortage of activity on Key West. A new year is here and the events keep on coming. Culinary delights start off the year here in the Keys; with events like the Seafood Festival and the Food and Wine Festival foodies are in heaven!  There are also many marathons and other physical events like flag football and SUP for those athletic types. And let’s not forget about the art scene; concerts, art openings, seminars and plays are abundant throughout the year, starting off with the Annual Literary Seminar in January. So no matter when you visit our island Paradise, you will find as much action and entertainment or relaxation as you are looking for.

2024

January

January 1, 2024

January 2, 2024

  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 5:30pm – 7:30pm: The Artist Workshop at The Studios of Key West
  • 6:30pm – 8:30pm: Bingo at American Legion Post 28
  • 8pm – 10pm: A Tuna Christmas at the Red Barn Theater

January 3, 2024

January 4, 2024

January 5, 2024

January 6, 2024

January 7, 2024

January 8, 2024

  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 6pm – 8:30pm: Painting Boot Camp with Jack MacDonald at The Studios of Key West

January 9, 2024

  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 5:30pm – 7:30pm: Shell Decoupage Class at Sacred Space
  • 5:30pm – 7:30pm: The Artist Way Workshop at The Studios of Key West
  • 6pm – 8:30pm: Sashimi & Kantha Style Mending with Indigo Textiles at The Studios of Key West
  • 6:30 – 8:30pm: Bingo at American Legion Post 28
  • 7pm – 9pm: David Wilcox in Concert at the Helmerich Theater at The Studios of Key West
  • 7pm – 9pm: Paint and Sip featuring Lance Berry at 24 North Hotel
  • 8pm – 10pm: A Tuna Christmas at the Red Barn Theater

January 10, 2024

  • 1pm – 3pm: Speaker Series “Discovering Photography to Connect with Art in Nature” at the Key West Botanical Garden
  • 5pm – 6pm: Distinguished Speaker Series “Oh Florida! How America’s Weirdest State Influences the Rest of the Country” at The Tropic Cinema
  • 5:30pm – 8:30pm: David Hihill Self Help Tour at the Key West Theater
  • 6pm – 8:30pm: Sashimi & Kantha Style Mending with Indigo Textiles at The Studios of Key West
  • 6pm – 85pm: David Wilcox in Concert at Hugh’s View at The Studios of Key West
  • 7pm – 9pm: 5 Lesbians Eating Quiche at the Armory
  • 8pm – 10pm: A Tuna Christmas at the Red Barn Theater

January 11, 2024

January 12, 2024

January 13, 2024

January 14, 2024

January 15, 2024

  • The Southernmost Regatta
  • 9:30am – 3:30pm: Painting the Rooftops of Key West at The Studios of Key West
  • 10am – 11:30am: Getting Started on your Novel at The Studios of Key West
  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 6pm – 8:30pm: Painting Boot Camp at The Studios of Key West
  • 7pm – 9pm: M3M Movies – A Starry Sky Above the Roman Ghetto at Congregation Bnai Zion

January 16, 2024

January 17, 2024

January 18, 2024

January 19, 2024

January 20, 2024

  • RokIsland Fest
  • 9am – NOON: Native Plant Sale at the Key West Tropical Forest and Botanical Gardens
  • 10am – 1pm: Understanding and Writing Haiku at The Studios of Key West
  • 10am – 6pm: One Year on Southard, Sip, Shop and Celebrate at Sacred Space
  • 7pm – 9pm: 5 Lesbians Eating Quiche at the Armory
  • 7pm – 9pm: The Reverend Payton’s Big Damn Band at Key West Theater
  • 8pm: “This One’s for the Girls” at the Red Barn Theater

January 21, 2024

January 22, 2024

  • Kelly McGillis Classic
  • 9am – 4pm: Watercolor Workshop at The Studios of Key West
  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 6pm – 8:30pm: Painting Boot Camp with Jack MacDonald at The Studios of Key West

January 23, 2024

January 24, 2024

January 25, 2024

January 26, 2024

January 27, 2024

January 28, 2024

January 29, 2024

  • Kelly McGillis Classic
  • 9:30am – 3:30pm: Painting Key West Conch Houses at The Studios of Key West
  • 1pm – 4pm: How to Write and Sell a Memoir at The Studios of Key West
  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 8pm: Ann Frank, Words from the Shadows at the Tennessee Williams Theater

January 30, 2024

  • 9:30am – 3:30pm: Painting Key West Conch Houses at The Studios of Key West
  • 4pm: Key Western Fest
  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 6:30pm – 8:30pm: Bingo at American Legion Post 28
  • 8pm – 10pm: POTUS at the Red Barn Theater
  • 8pm – 10pm: Singing in the Rain at The Waterfront Playhouse

January 31, 2024

February

February 1, 2024

February 2, 2024

February 3, 2024

February 4, 2024

February 5, 2024

  • 5pm – 6pm: Happy Hour with the Historian at Comedy Club Key West
  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 6:30pm – 7:30pm: Bobby Nesbitt and Carmen Rodriguez at the Truman White House

February 6, 2024

  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 6:30pm – 8:30pm: Bingo at American Legion Post 28
  • 6pm – 8pm: Dar Williams Old Town Folk at The Studios of Key West
  • 8pm – 10pm: POTUS at the Red Barn Theater
  • 8pm – 10pm: Singing in the Rain at The Waterfront Playhouse

February 7, 2024

February 8, 2024

February 9, 2024

February 10, 2024

February 11, 2024

  • 10am – 2pm: Key West Artisan Market
  • NOON – 2pm: Comedy Scene Acting at The Studios of Key West
  • 1pm – 3pm: MONROE COUNTY Sheriff’s Office Animal Farm Open House
  • 7pm – 9pm: A Tribute to Johnny Cash at the Key West Theater

February 12, 2024

  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 7pm – 9pm: The Ultimate Eagles Experience at the Key West Theater
  • 7pm – 9pm: Willie Nelson at the Coffee Butler Amphitheater

February 13, 2024

  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 6:30pm – 8:30pm: Bingo at American Legion Post 28
  • 7pm: Rodney Crowell in Concert at The Studios of Key West
  • 8pm – 10pm: POTUS at the Red Barn Theater
  • 8pm – 10pm: Singing in the Rain at The Waterfront Playhouse

February 14, 2024

February 15, 2024

February 16, 2024

February 17, 2024

February 18, 2024

February 19, 2024

  • Presidential Families Weekend – A series of special events takes place over Presidents’ Day Weekend at the Harry S. Truman Little White House.
  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 7pm – 9pm: M3M Movies – Farewell Mr Haffman at Congregation Bnai Zion
  • 7:30pm – 9:30pm: Enjoyable Astronomy at The Studios of Key West

February 20, 2024

  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 6:30pm – 8:30pm: Bingo at American Legion Post 28
  • 7:30pm – 9:30pm: Enjoyable Astronomy at The Studios of Key West
  • 8pm – 10pm: POTUS at the Red Barn Theater

February 21, 2024

February 22, 2024

  • 2pm – 7pm: Truman Waterfront Farmer’s Market
  • Scott Kirby with David James at the Key West Theater
  • 6:30pm: Key West Characters – True Stories at Fringe Theater’s Williams Hall

February 23, 2024

  • 6:30pm: Key West Characters – True Stories at Fringe Theater’s Williams Hall
  • 7pm – 9pm: Epic Eagles at the Coffee Butler Amphitheater
  • 7pm – 9pm: Telling My Story Dance Key West at The Studios of Key West
  • 7pm – 9pm: Wendell Mobley and Lee Thomas Miller at the Key West Theater
  • 8pm – 10pm: POTUS at the Red Barn Theater

February 24, 2024

January 25, 2024

February 26, 2024

  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 7pm – 9pm: Kathy Gilmour and Friends at the Key West Theater
  • 8pm: Bobby in the Lobby at the Tennessee Williams Theater

February 27, 2024

  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 6:30pm – 8:30pm: Bingo at American Legion Post 28

February 28, 2024

February 29, 2024

  • 2pm – 7pm: Truman Waterfront Farmer’s Market
  • 8pm – 10pm: Lady Macbeth Sings the Blues at The Studios of Key West

March 2024

March 1, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 10am – 2pm: Orchid Fair at West Martello Tower
  • 4pm – 6pm: First Friday Wine Tasting at The Green Pineapple
  • 7:30pm: South Florida Symphony at the Tennessee Williams Theater
  • 8pm – 10pm: Lady MacBeth Sings the Blues at The Studios of Key West

March 2, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 10am – 2pm: Orchid Fair at West Martello Tower
  • 10am – 4pm: Gardenfest at the Key West Tropical Forest and Botanical Garden
  • 6pm – 9pm: Denim to Diamonds Key West Woman’s Club Gala
  • 7pm – 10pm: ZZ Top at Coffee Butler Amphitheater

March 3, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 10am – 2pm: Key West Artisan Market
  • 10am – 2pm: Orchid Fair at West Martello Tower
  • NOON – 2pm: Comedy Scene Acting at The Studios of Key West
  • 4pm – 6pm: Impromptu Classical Concert at St. Paul’s Episcopal Church

March 4, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.

March 5, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 5pm – 7pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.
  • 8pm: Little Women Broadway Tour at the Tennessee Williams Theater

March 6, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.

March 7, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.

March 8, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.

March 9, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 10am: Annual Conch Shell Blowing Contest
  • 7pm – 10pm: One Music Family at The Studios of Key West

March 10, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 10am – 2pm: Key West Artisan Market at Sonny McCoy Indigenous Park (1801 White Street)
  • 7pm: Foreigner at Coffee Butler Amphitheater

March 11, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • March Merkin Invitational Permit Tournament
  • 8pm: JilIian Todd A Celebration of the Music of Joni Mitchell at the Tennessee Williams Theater

March 12, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • March Merkin Invitational Permit Tournament
  • 8pm: Dave Mason at the Key West Theater

March 13, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 7pm: The Last 5 Years at the Fringe Theater’s Armory
  • 8pm: Murder on the Orient Express at The Waterfront Playhouse
  • 8pm: Wishbone Ash will perform at the Key West Theater

March 14, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.

March 15, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • Florida Keys SPCA Spring Social at the Harry Truman Little White House. A lavish buffet by Catered Affairs is to be accompanied by free beer and wine and a cash liquor bar, live music and the presentation of the inaugural Champion of Animals Award to honoree Sue Turner. General admission $60; VIP tickets$125, which include early access to the silent auction and a champagne reception.
  • 1pm – 4pm: 64th Annual Old Island Restoration Foundation Home Tour
  • 7pm: Temptation and The Four Tops perform at the Coffee Butler Amphitheater

March 16, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • Irish Kevin’s 5K / 10K Shamrock Shuffle
  • 11am – 3pm: Artist Studio Tour at The Studios of Key West
  • 1pm – 4pm: 64th Annual Old Island Restoration Foundation Home Tour
  • 7pm: The Marshall Tucker Band performs at the Coffee Butler Amphitheater

March 17, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 10am – 2pm: Key West Artisan Market at Sonny McCoy Indigenous Park, 1801 White Street
  • 7pm: Far from the Shamrock Shores at Key West Theater
  • 8pm: Tennessee Williams’ “Ten Blocks on the Camino Real” at the Waterfront Playhouse

March 18, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.

March 19, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.

March 20, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 8pm: Neil Berg’s 50 Years of Rock N’ Roll Part IV at the Tennessee Williams Theatre.

March 21, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.

March 22, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 7:30pm: Old Dominion at Coffee Butler Amphitheater

March 23, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 7:30pm: Old Dominion at Coffee Butler Amphitheater

March 24, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • 7:30pm: Old Dominion at Coffee Butler Amphitheater

March 25, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.
  • Taste of Key West – This free admission, open-air event features an assortment of beverages and palate-pleasing plates. Restaurants and food vendors from across the Lower Keys and Key West donate their culinary talents to create delectable small plates. Food ranges from seafood, tropical and Caribbean flavors, to European dishes, vegetarian offerings, and desserts.
  • 6pm – 8pm: Glow Hours at Hugh’s View – At Studios of Key West, this is an ideal spot to catch the sunset and a drink on Monday and Tuesday evenings through March 5. The bar is open and admission is free. Capacity is limited, so come early. 533 Eaton Street.

March 26, 2024

  • Tennessee Williams Festival – In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual ‘Tennessee Williams Key West Festival,’ a month-long series of arts and cultural events that takes place each March across multiple venues. Click Here for Details.

March 28, 2024

  • 6pm: Tennessee Williams Festival – , one of the leading American playwrights of the 20th century and a resident of Key West for more than thirty years, often portrayed strong male characters in his works. During the evening’s reading of two one-act plays, at the Little Room Jazz Club, these men will be explored in greater detail. Works that will be examined are “The Parade, or Approaching the End of a Summer,” and “The Big Game.” Doors open 5:30 p.m.; performance at 6 p.m. 821 Duval St.

March 29, 2024

  • 4 – 6pm: Sunset Green Event Lawn Grown Up Easter Egg Hunt – Easter in Key West just got a whole lot more exciting! This all-adult, Grown-Up Easter Egg Hunt includes live music, delicious food and refreshing drinks. There will be lots of prizes to be had, and if you find the golden egg, you win a 1-night stay at 24 North Hotel! 4 to 6 p.m. 3820 N. Roosevelt Blvd.
  • 7:30pm: South Florida Symphony at the Tennessee Williams Theatre

March 30, 2024

  • 9 – 11am: Easter Egg Roll at the Harry Truman Little Whitehouse – In addition to the traditional Easter Egg Roll on the lawn, guests will enjoy arts and craft activities, live music, refreshments, photos with the Easter Bunny, and each child will leave with a commemorative wooden Easter egg. The event is free for all ages. 9 to 11 a.m. on the Little White House grounds. 111 Front Street.
  • 3 – 6pm: Charity Rubber Ducky Hunt at the Marker – Gather around the pool at The Marker, 200 William St. from 3 to 6 p.m. for a Rubber Ducky Hunt. Purchase duckies for $5 each to win prizes and giveaways. Proceeds will be donated to the Key West Police Love Fund.

March 31, 2024

  • Wrecker’s Cup Race – The third race of the 39th annual Wrecker’s Cup Race Series to Sand Key kicks off Sunday at 1 p.m. The all-in-fun race series recalls the tradition of the wreckers from Key West in the 1800s. All sailing vessels, local sailors and visiting yachtsmen are welcome to join the regatta. Spectators can view from Schooner Wharf and the Historic Seaport. After the race, first, second and third place will be awarded in each division, with trophies, a bottle of Pusser’s rum, Schooner Wharf Bar tabs and wrecker T-shirts as prizes. The final race of the series is to be held April 28. Find Schooner Wharf Bar at 202 William St.
  • 10am – 2pm: Key West Artisan Market at Sonny McCoy Indigenous Park, 1801 White Street
  • 5 – 7pm: Live Music at the Gardens Hotel
  • 8pm: Trunk Material at the Waterfront Playhouse

April 2024

April 2, 2024

  • Dinosaur World, Live! – Dare to experience the dangers and delights of Dinosaur World, Live! in this “roarsome” interactive show for all the family. Discover a pre-historic world of astonishing (and remarkably life-like) dinosaurs. Meet a host of impressive creatures, including every child’s favourite flesh-eating giant, the Tyrannosaurus Rex, a Triceratops, Giraffatitan, Microraptor and Segnosaurus! A special meet and greet after the show offers all our brave explorers the chance to make a new dinosaur friend. Don’t miss this entertaining and mind-expanding jurassic adventure, live on stage. Showt at 7 p.m. Tickets $18 to $68. 5901 College Rd.

April 4, 2024

  • First Thursday Open House at the Studios of Key West – During the First Thursday Open House event, the Studios keep the lights on late and throw the doors open to celebrate the newest work in its galleries. Stop in to say hello, relax with a glass of wine on the rooftop terrace, tour the third floor artist studios and see the just-installed exhibitions in the various galleries. 6 to 8 p.m. at 533 Eaton St.

April 5, 2024

  • The Papers, A Musical – A staged reading of a musical adaptation of Henry James’ novella, “The Aspern Papers.” The story, originally set in 1888 Venice, has shifted to contemporary Key West. The piece asks how we contend with the art and accomplishments of flawed people. How do we appreciate the achievements of heroes who may also be villains? Friday, Saturday and Sunday performances at 8 p.m. in Helmerich Theater. 533 Eaton St.
  • Habitat For Humanity Tropical Gala – Visitors are invited to join residents for the annual celebration in support of Habitat for Humanity at the Harry S. Truman Little White House, 111 Front St. The Tropical Gala event features a delicious dinner, top shelf libations, games, auctions and more. 6 to 10 p.m.
  • David Feder Limitless Guitar – David Feder has carved out a niche of his own, playing a signature blend of Flamenco-infused Folk music. His laid-back style easily disguises his virtuosity on the nylon string Flamenco Guitar. Three decades of island-living in the Florida Keys has influenced Feder’s breezy, approachable, and sophisticated music. Doors open at 7 p.m.; show at 8 p.m. Tickets available online or at the box office. 512 Eaton St.

April 6, 2024

  • Wesley House Black Tie Event – The Black Tie Benefit in Key West raises funds for Wesley House Family Services. This evening of Tropical Elegance takes place at Beachside Resort & Residences, 3841 N Roosevelt Blvd. Cocktails at 6 p.m. followed by dinner and dancing.

April 9, 2024

  • The Lifespan of a Fast – With a deadline looming, a talented writer, a desperate magazine editor and a young aggressive fact checker go head-to-head in this oh-so-funny and gripping dispute over factual truth vs. the beauty of literary dishonesty. Showtime 7 p.m. 319 Duval St.

April 10, 2024

  • Tab Benoit – Delta swamp blues master Tab Benoit brings songs of the bayou along with Ghalia Volt and an all-star Louisiana roots band to Key West Theater. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.

April 11, 2024

  • Key West Sailfish Tournament – The inaugural Key West Sailfish Tournament is expected to bring world-class teams for a two-day shootout-style event, battling it out for the top of the leaderboard and prize money. Tournament activities will be held at Dante’s Key West Pool Bar & Restaurant, 955 Caroline St.

April 12, 2024

  • Michael Franti & Spearhead – Globally-recognized musician Michael Franti and his band Spearhead, along with Bombargo, perform in a high-energy show filled with inspiring music. Doors open 5:30 p.m.; show at 7 p.m. 21 E. Quay Rd.

April 16, 2024

  • Connections Project – For years, the Florida Keys Council of the Arts has gathered mini-canvases from area artists to create one large Keys art mural/mosaic its annual Connections Project. This year, the council created five separate murals and, at each opening reception in each region of the Keys, is including live music to create a multi-faceted celebration of the artistic spirit that makes the Keys so special. The free Key West reception on April 16 culminates the Connections Project. It takes place from 5 to 7 p.m. at Williams Hall, 729 Fleming St. Attendees may purchase their choice of individual canvases from the mosaic for $100 each.

April 17, 2024

  • Death and the Maiden – A white-knuckle thriller and riveting tug-of-war. Who do you believe – your deeply troubled spouse, or your new persuasive friend? Winner of the 1992 Olivier Award for Best New Play. Tickets $45-$60. 7 p.m. at the Armory, 600 White St.

April 18, 2024

  • State of the National Marine Sanctuary – Sarah Fangman, Superintendent of the Florida Keys National Marine Sanctuary, discusses managing the sanctuary under stress and how marine researchers and the community have responded in novel ways to try to protect threatened resources. 7 p.m., tickets $5 at the door. 5901 College Rd.

April 19, 2024

  • 42nd Annual Conch Republic Days – Fans and friends of the Florida Keys’ Conch Republic can celebrate the irreverent “nation’s” 42nd birthday with activities including a tall ship pirate adventure, traditional shrimp boil, sunset boat parade, tour of the USCGC Ingham floating maritime museum, reenactment of the Great Sea Battle of the Conch Republic, performances of “Conch Republic — The Musical,” the World’s Longest Parade, Drag Races on Duval Street and more. The annual Conch Republic Independence Celebration commemorates the Keys’ symbolic 1982 secession from the United States and reinvention as the eccentric republic.
  • Conchy Beach Clean Up – Join other citizens of the Conch Republic for the annual Conchy Beach Cleanup, a fun way to meet other celebrants and to help kick off the annual celebration of Independence in the Florida Keys. Show up and tools will be provided for you. Meet at the Key West Bocce Court parking lot, 1801 White St. The cleanup begins at 8 and runs until 9 a.m. Organized by Plogging the Keys and Help Keep the Conch Republic Beautiful.

April 20, 2024

  • Earth Day 5K Run/Walk – The Key West Southernmost Runners’ 26th annual Earth Day 5k Run/Walk takes place Saturday at Truman Waterfront Park at the end of Southard St. The start and finish line is near the U.S .Coast Guard Cutter Ingham Maritime Museum. Proceeds from the race benefit the Conch Republic Marine Army, a local non-profit grassroots organization dedicated to cleaning and restoring the shallow mangrove habitats of the Florida Keys. Registration is $25 per person (free for children under 5 with a parent). Participants can register online or in person at the race location from 5 to 7 p.m. April 19, and at 7 a.m. April 20 before the 8 a.m. race start.
  • OceanFest – Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment during a fun day of crafts, games, music, food, local brews (for ages 21+) and shopping as Mote Marine showcases the Keys’ treasured marine environment while raising money for coral reef research, restoration and conservation. Attendees can explore conservation and environmental exhibits, meet Mote scientists and learn how you can help.

April 21, 2024

  • Earth Day Clean Up at US1 – Join other volunteers for an Earth Day Cleanup event Sunday morning from 8 to 9 a.m. of the area around US 1, the Triangle, the Cow Key Channel Bridge and surrounding streets. Meet alongside Tavern N Town and US 1 to pick up your vest, gloves, bucket and picker. One hour makes a huge difference, so start your day by taking part! After the cleanup, Tavern N Town will provide breakfast and coffee to all volunteers.

April 22, 2024

  • Earth Day Jam with That Hippy Band – Groove to the music of the 60s and 70s focused on environmental protection with That Hippy Band. Doors open at 6 p.m.; show at 7 p.m. Tickets available online or at the theater box office at 512 Eaton St.

April 23, 2024

  • Abbie Gardner in Concert – Abbie Gardner is a fiery dobro player with an infectious smile. Whether performing solo or with Americana group Red Molly, her acclaimed tales of love and loss, both gritty and sweet, are propelled by her impeccable slide guitar playing. Her live show is truly unique—as an award-winning songwriter, captivating vocalist, and a world-class lap style dobro player, she has an unmistakable sound all her own. Wednesday night’s show starts at 8 p.m. on the roof at Hugh’s View; Thursday night’s show is 7 p.m. in Helmerich Theater. 533 Eaton St.

April 24, 2024

  • Lost in Yonkers – Neil Simon’s story, set in 1942 Brooklyn, of two brothers, Jay and Arty, who must learn to live with their stern Grandma, their Aunt Bella, and their Uncle Louie, a henchman for some gangsters. Showtimes at 8 p.m. with a Saturday 2 p.m. matinee on May 4. Tickets $40 to $85. 407 Wall Street at Mallory Square.

April 25, 2024

  • Les Ballets Trockadero de Monte Carlo – The world-renowned, all-male Les Ballets Trockadero de Monte Carlo visits Key West to present a brilliant combination of skillful ballet movements and hilarious parodies of classic ballets such as Swan Lake. Founded in New York in 1974, the company, affectionately known as the Trocks, began by performing late-night in Broadway lofts to small audiences who appreciated the ensemble’s iconoclastic humour. In the 50 years since, the company has grown to appeal to an ever-growing audience who flock to theatres around the world each season to see these “prima ballerinas” perform. Tickets $35 to $135. Show at 8 p.m. 5901 College Rd.

April 26, 2024

  • The Wallflowers – Jakob Dylan and his band, the Wallflowers perform at Key West Theater. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.

April 28, 2024

  • Art in the Garden – Emphasizing harmony with nature, the return of Art in the Garden showcases local art and sculptures with artistic expressions. Artworks are earth-friendly in the selection of materials and themes and include recycled, repurposed, and natural material. Meander over garden boardwalks and down pathways through dappled shade, colorful blossoms and winged creatures to spot many beautiful works of art. View daily through July 31. 5210 College Rd.
  • Wrecker’s Cup Race – The final race of the 39th annual Wrecker’s Cup Race Series to Sand Key kicks off Sunday at 1 p.m. The all-in-fun race series recalls the tradition of the wreckers from Key West in the 1800s. All sailing vessels, local sailors and visiting yachtsmen are welcome to join the regatta. Spectators can view from Schooner Wharf and the Historic Seaport. After the race, first, second and third place will be awarded in each division, with trophies, a bottle of Pusser’s rum, Schooner Wharf Bar tabs and wrecker T-shirts as prizes. Find Schooner Wharf Bar at 202 William St.
  • The Price is Right Live! – The Price Is Right Live is the hit interactive stage show that gives eligible individuals the chance to hear their names called and “Come On Down” to win. Prizes may include appliances, vacations and possibly a new car! Play classic games just like on television’s longest running and most popular gameshow…from Plinko to Cliffhangers to The Big Wheel and even the fabulous Showcase. Playing to near sold-out audiences for more than 20 years, the Price Is Right Live has entertained millions of guests and given away more than 15 million dollars in cash and prizes. Tickets start at $60. Showtime 8 p.m. 21 Quay Rd.

May 2024

May 1-5, 2024

  • 28th Annual Songwriters Festival – The Key West Songwriters Festival is the largest festival of its kind in the world. It revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Performances take place at numerous theaters, bars and event spaces around Key West. The opening night headliner on Duval Street May 1 is Dylan Marlowe; Cole Swindell Performas May 2 in a ticketed concert at Coffee Butler Amphitheater, and many more shows to be announced. 

May 2, 2024

  • First Thursday Open House – During the First Thursday Open House event, the Studios keep the lights on late and throw the doors open to celebrate the newest work in its galleries. Stop in to say hello, relax with a glass of wine on the rooftop terrace, tour the third floor artist studios and see the just-installed exhibitions in the various galleries. 6 to 8 p.m. at 533 Eaton St.
  • Cole Swindell in Concert – Key West Songwriters Festival presents Cole Swindell in concert May 2. Doors open 5:30 p.m.; Showtime 7 p.m. Ticket start at $59. 21 Quay Rd.

May 3, 2024

  • Gallery Talk with Artist Anthony Mancuso – Mancuso’s work focuses on how domestic spaces fit into Florida’s light and landscape, distorting and rendering them with unnatural color to convey the psychological experience of the Sunshine State. The talk takes place int he Sanger Gallery, where Mancuso’s “Florida Room” exhibit is on display. The talk is free but RSVPs are requested.
  • Happy Birthday Capt. Steven Lamp!

May 4, 2024

  • Cow Key Bridge Run – Dress up in your best bovine costume and trek across the infinitely short Cow Key Channel Bridge. Get in the MOO-d from 9 to 11 a.m. before the “race” at the Bloody MOO-ey party at the Rum Row bar at The Gates Hotel. The entire herd will move over to stage at the starting area in front of the bridge between 11 a.m. and 12 p.m. At 12 noon, the race starts with cows away! Everyone is invited back to Rum Row and the Sunset Green Lawn for an after-race party and awards ceremony. Sign-up includes a race bib. Commemorative T-shirts will be available for purchase at the pre-race party. All proceeds benefit the MCSO Animal Farm and the Highgate Foundation.

May 5, 2024

  • Cinco de Mayo Margarita Battle – Gather by the pool at The Marker, 200 William St., at 3 p.m. for the 2nd annual island-wide margarita battle. Bartenders from The Starboard Restaurant & Bar at The Marker, Southernmost Beach Cafe, The Gates Hotel and 24 North Hotel shake up their tastiest margaritas, and you get to be the judge. Live music by Les Greene and The Swayzees.

May 12, 2024

  • One Night of Queen – For over 20 years Gary Mullen and The Works have been performing their world-renowned “One Night of Queen” live concert. Gary Mullen & The Works will have you dancing in the aisles during their show, while the band pays tribute to the stage theatrics, showmanship, and music of Rock & Roll Hall of Fame inductees: Queen. Tickets $45 to $135. Show at 8 p.m. 5901 College Rd.

May 18, 2024

  • Reelin’ For the Cause Kids Fishing Tournament – The tournament raises awareness about congenital heart defects and provides funds to support families with infants born with these disorders. Check in at 9:30 a.m. at Henry B. Knight (White Street) Pier at 9:30 a.m. $15 per child. Rod, reel and bait provided. Lines in at 10 a.m.; awards ceremony at 11:45 a.m. Awards for biggest fish in each age group: 3 to 5; 6 to 8; and 9 to 13. Sharks will be their own category with one award for the largest shark across all age groups. There is also a silent auction at the pier during the tournament.

May 26, 2024

  • Minimal Regatta – Watch sailors make a splash in homemade vessels made from plywood and duct tape in the craziest regatta you’ll ever see on the waters of Key West Bight. Watch from the Historic Seaport walkways near Schooner Wharf. 12 noon at 202 William St.

June 2024

June 1, 2024

  • Pride Follies – The Key West Business Guild opens this year’s PRIDE month with Pride Follies, showing at the Key West Theater, 512 Eaton St. Pride Follies began 17 years ago to give Key West performers who usually perform in bars and restaurants the chance to appear on the professional stage. 2017 Fantasy Fest Queen Destiny Montgomery again directs this year’s production filled with comedy, singing, and dancing. Doors open at 6 p.m.; show at 7 p.m.

June 5 – 9, 2024

  • Key West Pride – Celebrate PRIDE on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or to get lost in the magic of the southernmost city, rediscover Key West and discover how the island has created one of the most integrated and unique communities in the world. Show us your pride, we will show you our Key West Pride!

June 7, 2024

  • Billy Currington in Concert – Well-known for his smooth and distinct voice and songs including “Don’t Hurt Like it Used To” and “People Are Crazy,” Billy Currington comes to the amphitheater with opener Mike Stack. Doors open at 6 p.m.; show at 7:30 p.m. 21 E. Quay Rd.

June 8, 2024

  • Swim Around Key West – Embark on an adventurous competitive swim – a 12.5 loop around the island. The pristine waters around Key West give swimmers great views of both the land and underwater life. Compete in different categories including solo swimmer, solo swimmers with fins, solo swimmers using a mermaid tail or a monofin, or gather your friends and compete in the relay category of 2-person, 3-person, 4-person, 5-person or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim or an 800-yard swim. Swims begin and end at Higgs Beach, 1000 Atlantic Boulevard.

June 15, 2024

  • Truman’s Tropical Fruit Festival – Can you tell the difference between a haden and a kent mango? At the Tropical Fruit Festival, you’ll have the chance to taste all types of mangoes and other tropical fruits, sip tasty cocktails, watch cooking demos, purchase tropical trees, shop with local vendors and more. 9 a.m. to noon. 111 Front St.

June 27-30, 2024

  • 7th Annual Mango Festival – Experience all things mango through culinary treats, education and demonstrations during this celebration of the Keys’ sweet indigenous fruit and its heritage. Stroll around the Mango Mania vendor village at Bayview Park–1320 Truman Ave., enjoy mouthwatering mango-themed specialties during special dining events, attend lectures and more. The festival is presented by the Key West Police Athletic League and supports its local youth programs.

July 2024

July 3-7, 2024

  • Key West Key Lime Festival – Key West’s annual Key Lime Festival celebrates the world’s most sensational citrus with a bountiful array of festivities across the island where Key lime pie was conceived. Over five days, lovers of the lime can indulge in a full menu of activities including a Key lime pie drop competition from the top of the Key West Lighthouse; a Key lime cocktail sip and stroll, Key lime brunches and dinners, and of course, the world famous Key lime pie eating championship at 1:30 p.m. on July 4th at Southernmost Beach Cafe at 1405 Duval St.

July 13, 2024

  • One Night Stand – Since 2007, “One Night Stand, the 24 Hour Theater Project” has prompted creative thinkers to develop new theater from start to finish in only 24 hours. With the clock ticking, dozens of people work together at a wickedly fast pace to write, memorize, rehearse, create backdrops and sets, and comb the island for costumes and props. The result? Four brand new pieces of theater presented in front of a live audience. Performances at 7 and 9 p.m. in the Helmerich Theater. 533 Eaton St.

July 17-21, 2024

  • Hemingway Days – Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West Wednesday through Sunday, July 17-21 for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Events include the legendary Hemingway Look-Alike Contest, the wacky Running of the Bulls on Sat. July 20, presentations, prose and poetry readings, a commemoration of the 125th anniversary of Hemingway’s July 21 birth, a museum exhibit, a 3-day marlin tournament, a 5k run and paddleboard race, a street fair and more.

July 17-20, 2024

  • Key West Marlin Tournament – Coinciding with the 44th annual Hemingway Days celebration, anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes in the marlin division. The event awards $25,000 to the first-place team with the most points for blue marlin, white marlin and spearfish. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day for additional points. Entry is limited to the first 75 boats. Tournament events are based out of the Perry Hotel & Marina, 7005 Shrimp Road.

July 18-20, 2024

  • Hemingway Look Alike Contest – Dozens of stocky, bearded men resembling Ernest Hemingway are to return to Key West for the annual Hemingway® Look-Alike Contest. Staged at Sloppy Joe’s Bar where it began some 40 years ago, the contest’s preliminary rounds are slated for 6:30 p.m. July 18 and 19. The winner is to be chosen July 20, in a final round starting at 6:30 p.m., from a field of about 24 Hemingway hopefuls.

July 20, 2024

  • Hemingway 5K Sunset Run and Paddleboard Race – The Hemingway 5k Sunset Run & Paddleboard Race is to challenge competitors Saturday, July 20. Registration opens at 3 pm. at Southernmost Beach Cafe, 1405 Duval Street. The paddleboard race starts at 5:30 p.m. from Higgs Beach, 1000 Atlantic Blvd; and the 5k Run/Walk starts at 7:30 p.m. at Southernmost Point. The awards party is from 8 to 10 p.m. at Southernmost Beach Cafe with food and beverage tastings, raffles and entertainment. The athletic challenges are part of Hemingway Days, a six-day commemoration of the life and work of the author who lived and wrote in Key West for most of the 1930s.

August 2024

August 29 – September 2, 2024

  • Key West Brewfest – Fans of beers and ales can sample about 150 of them while also discovering the flavors of the continental United States’ southernmost island. Activities ‘on tap’ include brew-focused dinners, pool parties and brunches, and the lavish BrewFest Signature Tasting Festival held Saturday, Aug. 31 on Key West’s South Beach at 1319 Duval St. VIP tickets ($100 per person) and general admission tickets ($45 per person) for the popular tasting festival are to be available online.

September 2024

September 1, 2024

  • It’s 5:00 in Key West: A Celebration of Jimmy Buffett – Join the citizens of Key West and fans from around the world to celebrate the life and music of Jimmy Buffett. Within hours of the news of his passing in September 2023, a celebratory Second Line Procession was organized and held on Duval Street. In 2024, the parade will proceed down Duval, ending at Coffee Butler Amphitheater with a concert.

October 2024

October 18-27, 2024

  • Key West Fantasy Fest – “It’s a 90s Neon Cosmic Carnivale” is the official theme for Fantasy Fest 2024–Key West’s annual multi-day costuming extravaganza in paradise. From October 18-27, revelers can explore an array of exciting events, including the world-famous Bud Light Fantasy Fest parade, the all-hands-on-deck Captain Morgan Masquerade March (aka “Locals Parade”), the exuberant Goombay Festival in the streets, Royal Coronation of the 2023 Fantasy Fest King, Queen, plus concerts, theater productions, a “Heroes and Villains” 5K run/walk, the enchanting Key West Pet Masquerade, the 41st annual Headdress Ball pageant, and more.

November 2024

November 3-10, 2024

  • Race World Offshore World Championship – Leading American and international powerboat teams compete in high-speed races in the powerboat range World Championship. On race days, spectators can get an unmatched view from areas at the Truman Waterfront Race Village and adjacent “Outer Mole” pier. Other popular viewing areas include restaurants and bars at harborfront hotels, as well as Key West’s Mallory Square. Both general admission and VIP viewing options are available.

November 20-24, 2024

  • Key West Film Festival – Named one of the top 25 coolest film fests in the world by Moviemaker magazine, the 13th annual Key West Film Festival is set for Nov. 20-24. The program and schedule will be released closer to the festival date.

December 2024

December 1-31, 2024

  • Key West Holiday Festival – A merry range of celebrations during Key West’s busy holiday season traditionally includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, and New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”

December 4-15, 2024

  • Nutcracker Key West – Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens, roosters, sea fans, anemones, and yes, even a conch shell. Exact dates are to be determined.

December 31, 2024

  • New Year’s Eve Celebrations! – Pirate Wench Drop at the Schooner Wharf, Shoe Drop Celebration, Conch Shell Drop at Sloppy Joe’s

More About Key West

For more information about the fun side of Key West, things to do and see in our island city, go to our Key West Web Site. And, remember to check out our restaurant reviews as you surely must eat while down here! 

Island Genn – Key West Concierge