Key West Events Calendar

From annual festivals to holiday celebrations, the fun never stops in Key West. We're looking forward to these upcoming Key West events. For details on any event or planning a holiday vacation, contact our local team! We're happy to provide nearby vacation rental recommendations and the inside scoop on all things Key West. 

key west pride follies


Nov 7 2020 - 7:00pm
November 7, 2020 The Key West Business Guild, the nation’s oldest LGBTQ marketing organization celebrating its 42nd anniversary, proudly presents “Pride Follies” at the Key West Theater, 512 Eaton St. Follies, highlighting the island’s legendary celebration of diversity, stars lively local entertainment featuring the best...Read more
key west film festival

Key West Film Festival

Nov 18 2020 - 12:00am to Nov 22 2020 - 12:00am
Key West Film Festival will happen - outdoors The Key West Film Festival (KWFF) revealed its plans today for the 9th annual festival, set for Nov. 18-22, 2020. Building off the mantra of “Passion Meets Paradise,” the festival will be embracing its tropical paradise setting...Read more
key west at christmas

Lighting of the Bight- Key West Harbor Walk of Lights

Nov 25 2020 - 6:00pm
Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2020 Key West “Harbor Walk of Lights” with more lights and creative displays than last year, all continuing the “Maritime History of Key West” theme! The...Read more
key west christmas tree

Lighting of the Holiday Tree

Nov 30 2020 - 6:00pm
The Lighting of the Holiday Tree is November 30, 2020 in Bayview Park, 1320 Truman Ave Key West FL 33040 at 6:00 PM.Read more
key west bikes

Key West Lighted Bike Ride

Dec 2 2020 - 7:00pm
The Key West Lighted Bike Ride is scheduled for Wednesday, December 2nd at Bayview Park. Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers. Wesley House Family Services coordinates this bike ride - registration begins October 1st at more
key west

World s Longest Parade

Dec 3 2020 - 5:30pm
It all begins with a Pre-Party Muster at the Southernmost Point Guest House (bring a snack to share and your drink of choice). We line up at 7:30; Parade rolls down Duval Street with our "Counter Intelligence Bar" at 8 PM and we're Keeping it...Read more
key west christmas

Christmas Parade

Dec 5 2020 - 7:00pm
Key West will be showing its holiday spirit with the annual hometown parade with marching bands, groups and floats. Route proceeds down Truman Ave to Duval, where it takes a right and continues on to Eaton Street. Some streets will be closed for this event...Read more
Conch Republic Flag

Annual Conch Republic Independence Celebration

Nov 27 2020 - 8:00am to Dec 6 2020 - 6:00pm
With activities such as a lighthearted sea battle featuring tall ships, the Conch Republic's 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys. The event normally takes place in the early spring but in 2020 will take place in early...Read more

Lighting of the Menorah

Dec 10 2020 - 5:30pm
The community is invited to join us at Bayview Park for the traditional lighting of the menorah. Rabbi Shimon Dudai from Congregation B’Nai Zion and Rabbi Jacob Zucker from Chabad of the Florida Keys will say the blessings.Read more