January

Local Residents Ride Free

Ring in the new year by showing your loved ones around your city! Monroe County residents can take advantage of some of our tours and attractions for FREE when accompanied by a full fare adult paid guest with Hometown Pass!

Go to Hometown Pass for more information.

Tennessee Williams Theatre: Stars of the New York City Ballet

Behold principal dancers from the New York City Ballet gracing Key West’s stage at the Tennessee Williams Theatre. Experience a mesmerizing showcase featuring ballets that span from timeless classics to the most cutting-edge contemporary works of today.

The Studios of Key West: David Wilcox in Concert

Enjoy a memorable evening listening to one David Wilcox’s smooth baritone voice and virtuoso guitar playing as he plays his repertoire of over 30 years worth of folk music!

Key West Literary Seminar: Florida - The State We're In

Every January, literature enthusiasts and writers gather for a vibrant and focused four-day celebration of words and stories. The event, “Florida: The State We’re In,” features a diverse lineup of novelists, poets, historians, humorists, and cultural critics. Join a literary exploration of Florida, where our renowned authors share their insights. Many events take place at the Coffee Butler Amphitheater.

14th OIRF House Tours

Presented by Old Island Restoration Foundation, the house tours feature five architectural and design gems.

26th Annual Key West Half Marathon and 5K

The Key West Half Marathon and 5K offer an amazing race experience through the stunning backdrop of Key West. Run through famous landmarks across the island while on the 13.1-mile trek.

RokIsland Fest

Join in on the ultimate rock experience this January at Key West’s RokIsland Fest! Get ready for over 20 of the most legendary rock bands to take the stage in the Southernmost City in the US. You won’t soon forget this celebration of rock music!

Red Barn Theatre: This One's for the Girls - The Women of Country Music

Christine Mild returns, focusing on the captivating tales and music of the women in country music. Join her for her newest show!

Key West Art & Historical Society: Happy Hour With the Historian

This January, learn more about Key West’s various maritime enterprises such as sponging, shrimping, and wrecking industries. Join Dr. Cori Convertito as she discusses how our waterfront has changed over time as well as its future!

South Florida Symphony: Brahms, Bach, Montgomery & Price

Witness the stage of Tennessee Williams Theatre come alive with the music of virtuoso composers. This January, the South Florida Symphony takes the stage for their 26th season as they play compositions from modern composers like Price and Montgomery, as well as classic composers, Bach and Brahms.

Key West Food & Wine Festival

The festival boasts a lineup of more than 20 distinct events, showcasing waterfront wine tastings and delectable food pairings. In 2024, the theme is, “Ole Espana,” which honors the rich wine and culture of Spain, paying homage to its influence on Key West.

Mile 0 Fest

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!

Waterfront Playhouse: Singin’ in the Rain

Waterfront Playhouse is putting on one of the most quintessential movies to take the silver screen, Singin’ in the Rain. This play features all of the lovable and memorable songs of the iconic film including “You are My Lucky Star” and “Fit as a Fiddle.” It will rain in the Waterfront Playhouse this January!

Truman Music Series

Enjoy the music of Bobby Nesbit and Carmen Rodriguez as they present their new show, “Thanks For the Memories — A Celebration of the USO”.