May is a great time to come to Key West – the weather isn’t too hot yet, the winds are down and the water is clear.

1. Mile Zero Fest

Apr 27, 2021 – May 1, 2021

This annual fest brings the best of Americana and Red Dirt Music to the island paradise for five full days of bands, acoustic jams and songwriter swaps. 

2. Key West Songwriters Festival

May 5, 2021 – May 9, 2021

Since 1997, BMI has been a presenting sponsor of the festival, the largest festival of its kind in the world, and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs

3. Pride Follies

May 22, 2021

Pride Follies returns to headline this year’s PRIDE celebration presented by the Key West Business Guild. Fantasy Fest Queen Destiny Montgomery is to direct this year’s presentation of Key West talent not usually seen on a professional stage, at the Key West Theater, 512 Eaton St. Does open 7 p.m., show starts 8 p.m. Tickets available online for general admission

4. Memorial Day Weekend

May 28, 2021 – May 31, 2021

Take advantage of the extended weekend with a vacation to Key West!

Spend the weekend like a local and get on the water – Rent a boat, Do a sandbar charter, charter a tiki bar boat, or try one of the many watersports Key West is know for!

5. Key West Whiskey Festival 2022

May 26, 2022 – May 30, 2022

Starting in 2022 – This innaugural food, drink and music festival is one of the most eagerly awaited on

Florida Keys’ busy social calendar. Featuring top class whiskey,

Popular highlights will include a range of Tastings, Whiskey walks, Workshops, Brunches and plenty more.

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