What's Happening This Year in Key West?

March 4, 2024

*Greetings from Key West Florida Mural at The Cuban Coffee Queen. Photo: Cayobo via flickr*

If traveling more is one of your new year's resolutions, make sure Key West is on your travel list. We have great weather all year long, wonderful people and rich history—what's not to love about our little slice of paradise?

We've made planning your tropical vacation to Key West easy by shining a light on the coolest events happening every month. Check it out below.

Generally speaking, the best time to travel to Key West is from March to May. The winter crowds thin out so both airline and hotel prices will be easier on the wallet and the weather is perfect!

On a tighter budget? Consider traveling in the offseason during the months of June to November. But be aware, while the prices may be down, the temperature and chances for rain are up. As long as you pack for changing weather you should be fine.

Key West Calendar of Events 2019

January - March

January 18th - 19th: 59th Annual Key West House & Garden Tour

January 23rd - 29th: 10th Annual Key West Food & Wine Festival

January 29th - February 2nd: 2nd Annual Mile 0 Fest

February 2nd: 12th Annual Rock & Roast Fest

February 23rd - 24th: 54th Annual Old Island Days Art Festival

March 2nd: 57th Annual Conch Shell Blowing Contest

March 7th: 10,000 Maniacs in Concert

March 30th: 2019 Key West Gala

April - June

April 4th: Beach Boys in Concert

April 6th: 38th Annual 7-Mile Bridge Run

April 19th - 28th: 37th Annual Conch Republic Independence Celebration

May 8th - 12th: 24th Annual Key West Song Writers Festival

June 1st: 43rd Annual Swim Around Key West

June 5th - 9th: Key West Pridefest

June 15th: Swim Around Key West

Welcome To Key West — *Photo: Flickr - Cayobo*

July - September

July 4th - 7th: 7th Annual Key Lime Festival

July 16th -21st: Hemingway Days & Sloppy Joe's 39th Annual Papa Look-a-Like Contest

August 8th - 11th: 23rd Annual Key West Lobsterfest

August 21st - September 2nd: 10th Annual Key West Brew Fest

September 4th - 8th: Womenfest Key West 2019

*Photo: 13th Annual Florida Keys Seafood Festival*

October - December

October 15th: Official 2019 Stone Crab Season Opening

October 18th - 27th: 40th Annual Key West Fantasy Fest

November 2nd: 27th Annual ABC 5K Walk/Run

December Events: TBA

These are just the major events happening each month, check back to our blog to see a more detailed list of events.

Do you have any Key West Travel tips? Comment below or join the conversation on Facebook and Instagram. Don’t forget to sign up for our newsletter and follow us on social media!