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.
2023
April 2023
April 1 – 30, 2023
- Bahama Village: Relics of a Fading Community Exhibition – Through education, religious institutions, businesses, food, music, and voluntary associations, Key West’s Black community created ways to serve and strengthen their village and the island. Bahama Village, in the westernmost portion of the city, was a neighborhood comprised of Black Bahamians and Black Cubans, Chinese, and other groups of color. In this exhibition that will run from Friday, January 13th through Sunday, May 21st, their history and stories will be woven together through various events that shaped the Black and Indigenous cultures of Key West. The Custom House operates Monday to Sunday from 10:00 a.m. to 5:00 p.m. (last admission is at 4:30 p.m.) This exhibition is in the Bryan Gallery.
April 15 – 16, 2023
- NAS Key West Southernmost Air Spectacular – NAS Key West is hosting the U.S. Navy Blue Angels on April 15 & 16, 2023 onboard Boca Chica Field, Naval Air Station Key West for the NAS Key West Southernmost Air Spectacular. Spectacular flying, static displays, a Kid’s Zone, souvenirs, and concessions – there is no better way to spend a day with family and friends! General admission and parking are FREE. Gates open at 10 a.m., air show starts at 11 a.m., and the Blue Angels fly at 2:30 p.m. For preferred paid seating options, please click here.
April 21 – 30, 2023
- 41st Anniversary of the Founding of the Conch Republic Celebration – Mark your calendars for the 41st Anniversary of the Conch Republic Independence Celebration set for April 21-30, 2023. Daily: 10 a.m. to 8 p.m. – Conch Republic Welcome Center & “Official” Merchandise Booth at Thompson Plaza, Key West Historic Seaport, Greene & Elizabeth Streets. 8 a.m. to 9 a.m. – Conch Republic Conchy Beach Cleanup at Higgs Beach.
April 22, 2023
- 25th Annual Earth Day 5K Run/Walk – The Key West Southernmost Runners are to team up with the Conch Republic Marine Army for the 25th annual Earth Day 5K Run/Walk on Saturday, April 22nd at Key West’s Truman Waterfront Park at the end of Southard Street. Registration is $25 per person (free for children under 5 with a parent). The start and finish line is near the U.S. Coast Guard Cutter Ingham Maritime Museum. Proceeds from the race are to benefit the Conch Republic Marine Army, a local nonprofit grassroots organization dedicated to cleaning and restoring the shallow mangrove habitats of the Florida Keys.
- Rotary Club of Key West’s 4th Annual Cornhole Tournament – Join the Rotary Club of Key West for their 4th annual Cornhole Tournament! The event will be held at the DoubleTree Resort by Hilton Grand Key on Saturday, April 22, 2023 starting at 12:00 p.m.
- Annual Papio Kinetic Sculpture and Art Bike Parade – The annual Papio Kinetic Sculpture and Art Bike Parade – a family-friendly, art-inspired, human-powered mobile sculpture and art-bike parade that celebrates creativity and innovation using recycled materials – is set to roll down the length of Duval Street on Saturday, April 22, which also happens to be Earth Day. Mobile sculptures and art bikes will launch at noon from the Key West Museum of Art & History, traveling the full length of Duval Street to the Southernmost Pocket Park where a block party and awards ceremony celebration will take place from 1:00 to 3:00 p.m. Registration is $25 for kinetic sculpture floats and $15 for art bikes.
May 2023
May 1 – 21, 2023
- Bahama Village: Relics of a Fading Community Exhibition – Through education, religious institutions, businesses, food, music, and voluntary associations, Key West’s Black community created ways to serve and strengthen their village and the island. Bahama Village, in the westernmost portion of the city, was a neighborhood comprised of Black Bahamians and Black Cubans, Chinese, and other groups of color. In this exhibition that will run from Friday, January 13th through Sunday, May 21st, their history and stories will be woven together through various events that shaped the Black and Indigenous cultures of Key West. The Custom House operates Monday to Sunday from 10:00 a.m. to 5:00 p.m. (last admission is at 4:30 p.m.) This exhibition is in the Bryan Gallery.
May 3 – 7, 2023
- 27th Annual Key West Songwriters Festival – The Key West Songwriters Festival is the largest festival of its kind in the world. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices, and stories behind the songs! Most festival shows are free, but information on ticketed shows is available at the website link below. 150+ performers, 50+ shows, 5 days and nights!
June 2023
June 14 – 18, 2023
- I Love Stock Island Festival – This five-day festival is to feature one-of-a-kind Stock Island-inspired activities and authentic immersive experience in local community, culture, and art. It’s a great way to celebrate Father’s Day weekend with friends and family in the laidback atmosphere of Stock Island, just across the Cow Key Channel Bridge from Key West. For more information and a schedule of events as it’s finalized, visit https://ilovestockisland.org/events/festival/.
June 7 – 11, 2023
- Key West Pride – Celebrate PRIDE on a tropical island 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 get lost in the magic of our tropical island, rediscover Key West and discover how one island’s One Human Family philosophy 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!
July 2023
June 30 – July 4, 2023
- Annual Key Lime Festival – From June 30-July 4, 2023, Key West, Florida’s annual Key Lime Festival is set to celebrate the world’s most sensational citrus with a bountiful array of festivities across the very island where key lime pie was conceived.
July 18 – 23, 2023
- Hemingway Days 2023 – Fans of Ernest Hemingway’s literary greatness and vigorous life, including scores of bearded Hemingway look-alikes, are to converge on Key West Tuesday through Sunday, July 18-23, for Hemingway Days 2023. The annual celebration salutes the Nobel Prize–winning author’s writing achievements, sporting pursuits and enjoyment of the island’s easygoing lifestyle. The festival’s undisputed highlight is the Hemingway® Look-Alike Contest at Sloppy Joe’s Bar, 201 Duval St., a frequent hangout for the writer during his 1930s residence in Key West. Scores of stocky, bearded entrants are to parade across Sloppy Joe’s stage before a judging panel of previous winners during preliminary and final rounds.
July 26 – 27, 2023
- Lobster Mini Season – July 26-27, 2023 (last consecutive Wednesday and Thursday in July each year) Daily Bag Limit: 6 per person for Monroe County and Biscayne National Park; Possession limit on the water: equal to the daily bag limit; Possession limit off the water: equal to the daily bag limit on the first day and double the daily bag limit on the second day; *Possession limits are enforced on and off the water.* Minimum Size Limit: Carapace must be larger than 3″ measured in the water. Possession and use of a measuring device required at all times. Find out how to measure a spiny lobster.
August 2023
September 2023
October 2023
October 12 – 14, 2023
- Legends of Music Row Music Festival – Legends of Music Row is coming to Coffee Butler Amphitheater in Key West, October 12-14, 2023! Line up coming soon. Legends of Music Row is a festival like no other, featuring world class country music superstars and singer/songwriters, along with music’s future hit-makers, in a three-day musical extravaganza in the tropical paradise of Key West.
October 20 – 29, 2023
- Fantasy Fest 2023 – SAVE THE DATE FOR FANTASY FEST 2023! THIS YEAR’S THEME IS UNIFORMS & UNICORNS: 200 YEARS OF SAILING INTO FANTASY!
November 2023
December 2023
December 16, 2023
- 15th Annual 5K Rudolph Red Nose Run – Don your festive holiday jammies and join in the 15th A Positive Step 5K Rudolph Red Nose Run, taking place Saturday morning, December 16, starting and ending at the Southernmost Beach Café, 1405 Duval Street, Key West. Race day check-in starts at 7:00 a.m. with 8:00 a.m. start time. After the race, enjoy refreshments, prizes, and a fabulous silent auction.
December 31, 2023
- 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