When you think of The Keys, you probably first think of an easy-going Key West getaway with the people you love. You probably think of lounging by the water, eating good seafood and sipping refreshing drinks. What should also pop up on your radar are the great music festivals in the city, and let us confirm it for you: there are many.

Some of the most exciting and unique festivals in the state are held in Key West, including the Key West Songwriters Festival which is the largest of its kind in the entire world. If you missed it last year, don’t worry because it happens every May. It’s done over a 5-day period where guests can not only immerse themselves in cool sounds, but also learn about the people behind the music while doing so. And best of all? The majority of this festival’s events are completely free, so guests don’t have to worry about breaking the bank to attend.

Another big festival is the nearby Key Largo Original Music Festival. It also happens in May of every year, and is open for the whole family. The festival features country, pop, rock and even blues music from artists all over The South, and like the Songwriters Festival, admission is free. And then, there’s Parrots Head in Paradise, which is a major event in Key West with an even bigger backing.

Parrots Head in Paradise is an international club that works to promote educational, charitable and communal activity by way of “Jimmy Buffett and the tropical lifestyle he personifies.” They hold annual events called “Meetings of the Minds” all over the country, and they feature different musicians, pops of culture and overall happy and positive community involvement. This year’s Meetings of the Minds is in Key West from Thursday, October 31st through Saturday, November 2nd.

Festival-goers can expect lots of entertaining and engaging artists like Brent Burns, Barefoot Reggie Starrett, The Saltwater Troubadours, Gene Mitchell and much, much more! Keeping in accordance with the season, there will also be an official Halloween contest where guests can dress as their favorite person while jamming to good music. Then, as the festival comes to its end on the 2nd, you can expect to rightfully rock out with Jimmy and the Parrots all night long.

Grab your dancing shoes, your best friends, and maybe something sweet to drink, and enjoy these festivals while you can!

The Keys are Waiting For You!

Book Your Next Vacation

Explore Hilton Hotels

Previous Article

VIDEO: Explore Key West, From Daytime Adventures to Night Vibes

Next Article

The Dive Capital of the World in the Florida Keys

Related Guides