2018 Key West Festival Guide

2018 Key West Festival Guide

Key West knows how to throw a party and it’s the hottest destination for festivals, celebrations and events. The festival lineup and our top picks for the 2018 festival season include some of the things we just happen to love: Music, Beer, Fast Boats and a 10 day festival filled with the most creative costuming and themed parties in paradise. Plan ahead and mark your calendar because we know you don’t want to miss out on any of the fun.  Add these Key West festivals to your travel bucket list.

Mile 0 Fest February 7 – 10

The first annual Mile 0 Fest Key West, February 7 – 10, 2018, is a new must see music fest featuring the best in the burgeoning Red Dirt & Americana music scene and it’s happening right here in paradise!   The venues include some of our theaters and bars and the big shows will take stage at Key West’s new state-of-the-art Truman Waterfront Park Amphitheatre.   New Festival and New Amphitheatre – great way to start the new year in Key West!

Headliners include the Turnpike Troubadours, Cody Jinks, Wade Bowen, Pat Green and Shooter Jennings. View the Mile 0 Fest Schedule of Events and Performers.

Satellite Stages and Venues include Smokin’ Tuna Saloon, Irish Kevins, South Beach at Southernmost Beach Resort, Rick’s Key West/Durty Harry’s, and the San Carlos Institute.

Learn more about

Key West Songwriters Festival May 9-13

Plan ahead, make your reservations and head to paradise for the 23rd Annual Key West Songwriters Festival, May 9 – 13, 2018. It’s the biggest, the best and the the largest festival of its kind in the world.  What you can expect to see is 200 + Performers, 50 + Shows in five days and nights all taking place right here in Key West.

Southernmost Beach Resort has been a long time sponsor of this event and we look forward to welcoming the amazing songwriters and performers to the island.

Did you know some of the events take place right here at our resort? There will be pool parties and beach parties along with a Songwriters Beach Brunch and it’s all happening in our backyard.  Book your Songwriters festival getaway at Southernmost and meet the voices and stories behind the song.

Most of the Key West Songwriters Festival events are free and some are ticketed so make sure to stay up to date by visiting the website. The festival lineup and schedule will be coming soon.   Visit the Key West Songwriters Festival to learn more.

Key West Brewfest, Labor Day Weekend

Time to celebrate BEER! We’ve dedicated a whole weekend to do just that during the Key West Brewfest held Labor Day Weekend to benefit the Key West Sunrise Rotary Club and their charitable efforts.

What you can expect to see and taste during the Brewfest weekend: Beer Dinners, Beer Brunches, Happy Hours, Pool Parties, Late-Night Parties, Seminars and the Signature Tasting Festival event on the beach.  If you love Beer then this is the place for you as you will have the opportunity to try tasting close to 200 beers in one weekend!

The 2018 Brewfest event schedule has not been updated yet but we encourage you to bookmark the Brewfest website so you can keep tabs on what’s happening in the future.

Learn more about Key West Brewfest.

Fantasy Fest Key West, October 19 – 28

Oh what fun! That’s the first thing you think of when you think about Fantasy Fest Key West.  This is a 10 day festival taking place each year at the end of October where fun-loving revelers from around the world bring their creativity, costumes and imagination to the Southernmost city!

Why you want to consider attending all 10 days.   Last year there were new events added to the schedule and those include the Zombie Bike Ride, Tu Tu Tuesday Party as and new after March party happening at South Beach in our backyard.  We encourage you to take time to visit the Fantasy Fest website to see last year’s schedule of events so it will give you an idea of all the parties, contests and festival events happening throughout the week.  Visit the Fantasy Fest website to learn more about the 2018 schedule of events.

If you’ve never attended Fantasy Fest make sure to read our Ten Tips and Must Do’s for festival attendees.  One more tip – book now for Fantasy Fest as rooms on the island will be scarce – it’s so popular that Key West hotels sell out.



The 2018 Fantasy Fest Theme is “Oh…THE GAMES WE PLAY” Whether you are a single player, multiplayer, or just a player, this year’s theme is sure to get your cranium creating some costume ideas. Become your favorite game show host, bring to life your childhood board games, or transport yourself into your most loved netherworld. The ideas are endless, so roll the dice on your favorite game to play and meet us in Key West for a game worth playing!

Learn more about Fantasy Fest Key West.

38th Annual Key West World Championship Races Nov 4 – 11

Photo Credit: Super Boat International

Super Boat International returns to Key West in November for the 38th Annual Key West World Championship Races, internationally known as the Indianapolis 500 of the offshore powerboat racing.  If you like fast boats, you won’t want to miss this event.

Super Boat International (SBI) recently released the 2018 race schedule to teams and fans in preparation for the upcoming year. You can learn more about the race schedule here.

The reason we wanted to share the 2018 Key West Festival Guide with you is to make sure you had the dates of the events, festivals and celebrations handy so you could plan and book your trip to Key West ahead of time.

Do you have a favorite Key West festival, event or celebration? #somolife

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