Key West Spring & Summer 2025 Festivals and Events Guide

If you’re planning a Key West vacation, there’s no better time than spring and summer—when the island comes alive with music festivals, legendary celebrations, and one-of-a-kind experiences.

From hearing the stories behind the songs at the Key West Songwriters Festival and celebrating Hemingway’s legendary legacy to indulging in festivals dedicated to rum, and all things citrus at the Key Lime Festival, this island is the ultimate place to celebrate. The spirited Conch Republic Independence Celebration and a variety of family-friendly events add even more ways to enjoy it all.

And before summer fades, we gather for one last unforgettable weekend—honoring our beloved Jimmy Buffett with Just a Few Friends.

Explore all the must-attend Key West spring and summer events of 2025 and plan your trip with this insider's guide! 

The best way to experience it all?

Make The Marker Key West Harbor Resort or Southernmost Beach Resort your home base. Prefer harbor views and a lively seaport vibe? The Marker puts you in the heart of the action. Looking for a resort atmosphere with beach access, ocean views, or the charm of a guest house experience? Southernmost Beach Resort delivers just that. No matter where you stay, you’ll be steps from all the action. These sister properties offer the perfect accommodations for every traveler. Plus, you won’t want to miss our pool parties, beach parties, and competitions—all happening at our Key West resorts!

With so many festivals happening, planning ahead is key! Check out our Ultimate Festival Tips for Key West to make the most of your experience—where to go, what to bring, and how to soak up every moment like a local.

April

Circus of the Sea – A High-Flying Pirate Show

April 13th | 4:00 PM – 5:30 PM
Southernmost Beach Resort

Acrobats, pirates, and daring stunts—this isn’t your average beach day. Circus of the Sea brings a pirate-themed aerial and trampoline show to Key West, featuring gravity-defying tricks, hilarious skits, and interactive entertainment. 

Bonus: Your ticket includes access to the pre-show pool party!

Tickets: $30
Get Tickets Here

4th Annual Charity Rubber Ducky Hunt  Benefit

April 19th | 2:00 PM
The Marker Key West Harbor Resort

Event Information

The Marker's springtime 4th Annual Charity Rubber Ducky Hunt event is back! For $5 per duck, you’ll get a chance to pull a lucky rubber duck from the pool and win prizes, giveaways, and more.

But the real prize? Knowing 100% of proceeds benefit the Key West Police Love Fund. There will be music, mermaids, and poolside drink specials.

Conch Republic Independence Celebration – Battles, Bed Races & Parades

April 18–27
Website

What happens when an island secedes from the United States? You get the Conch Republic. Established in 1982 as a humorous protest, this 10-day festival transforms Key West into a playground of pirate battles, quirky parades—including bed races—and the legendary Great Sea Battle, where schooners armed with water cannons take on the U.S. Coast Guard in a battle of good-natured rebellion.

Easter Egg Hunt & Beach Party – Are you eggcited!

April 20th | 11:30 AM
Southernmost Beach Resort 

Event Information

Get egg-cited for an Easter celebration packed with fun! Kids can enjoy a high-energy egg hunt, Slime Time activities, and Legos, while the grown-ups sip on craft Bloody Marys and mimosas. The hunt starts at noon sharp—don’t be late! 

29th Annual Key West Songwriters Festival

April 30 – May 4
Website

This is the largest festival of its kind in the world, bringing over 150 of the best songwriters to Key West for five days of intimate performances, unforgettable collaborations, and behind-the-scenes storytelling.

2025 Featured Artists Include:

Nate Smith & Chase Matthew – Country stars kicking off the festival
Chuck Cannon – Songwriter for Toby Keith & John Michael Montgomery
Rebecca Lynn Howard – Two-time Grammy winner with powerhouse vocals
Raul Malo – The Mavericks frontman blending country, rock & Latin influences

The Key West Songwriters Festival isn’t just about the music—it’s an experience. With intimate performances, collaborative sessions, and poolside gigs happening across the island (including at our resorts!), this five-day celebration brings you up close with the talent behind the songs.

Catch singer/songwriter performances at The Marker’s poolside stage and Southernmost Beach Resort’s beach and poolside venues. While the official lineup for our resorts hasn’t been finalized yet, you can stay updated by checking the Key West Songwriters Festival schedule for the latest details.

Southernmost Beach Resort and The Marker Key West Harbor Resort are proud lodging partners of the 2025 Key West Songwriters Festival!

May

Kentucky Derby Party at The Parlour – Mint Juleps & Southern Charm

May 3rd | 5 PM – 7 PM
The Parlour at Avalon

Break out your biggest hat and best bow tie—it’s time for Derby Day, Key West style! Celebrate the most exciting two minutes in sports with mint juleps, themed cocktails, and high-stakes fun. Whether you're betting on the races or just here for the southern-style party, this event is a must.

Did You Know? The Kentucky Derby has been running since 1875, making it the longest-running annual sporting event in the country.

Cinco De Mayo Pool Party & Battle of the Bars
May 4th | 3 PM
The Marker Key West Harbor Resort

This isn’t your typical Cinco de Mayo celebration—it’s a cocktail competition where Key West’s best bartenders battle it out for the Don Julio Championship Belt. Guests are the judges, and you’ll get to taste each creation before voting for your favorite. The best part, it’s happening poolside and we’ll have a DJ, food and drink specials.

 
Memorial Day Weekend

Memorial Day Weekend BBQ

Southernmost Beach Resort

Kick off summer the right way—with BBQ, beach vibes, and ice-cold drinks by the ocean!

Join us for a laid-back beachside BBQ featuring delicious eats, refreshing cocktails, and unbeatable ocean views. It’s the perfect way to soak up the sunshine, relax with friends, and celebrate Memorial Day Weekend in true Key West style.

Stay tuned for details—follow us on Facebook and Instagram so you don’t miss a thing!

The Marker Salute to Service Weekend
May 24–26

Kick off the summer season with a patriotic weekend of music and family-friendly fun celebrations at The Marker Key West Harbor Resort.

●      Live music & entertainment all weekend.

●      A community race honoring first responders

●      Pool party + food & drink specials

●      A portion of proceeds benefits the local VFW

Salute To Service Special Package

In a sincere tribute to our nation’s heroes, The Marker Key West Harbor Resort proudly presents its Salute to Service package—a heartfelt thank-you to active military, Veterans, first responders, teachers, and healthcare workers. This special initiative offers exclusive savings and carefully curated experiences that invite you to relax, recharge, and experience the true spirit of Key West. Learn more about the Service Special Package.

June

Key West Pride – A Celebration of Love & Inclusivity
June 22–29
Website

This year's event theme is "Still Rising," honoring the history of the LGBTQ+ community. Along with Key West Art & Historical Society and the Stonewall National Museum, a special exhibit will showcase "50 Years: The Stonewall Uprising." This year's Pride also features late-night dance parties, historical tours of Gay Key West, daytime and sunset sailing excursions, a private beach party, pool parties, film screenings, drag performances, comedy night, a bar crawl by trolley, and much more. Every moment is a celebration of love, inclusivity, and island magic."

July

Key Lime Festival – A Tart & Tangy Celebration
July 3–7
Website

Key West is home to the Key Lime Pie, so of course, we have a festival dedicated to Key Lime! It’s not just about eating pie (though you’ll have plenty)—it’s a full-blown citrus celebration with Key West’s signature flair. 

●      World-Famous Key Lime Pie Eating Contest

●      Key Lime Pie Drop from the Key West Lighthouse

●      Key Lime Cocktail Stroll

●      Pool Parties and more… 

Did You Know? The first recorded Key lime pie recipe appeared in Key West in the 1930s, and many believe it was created by Aunt Sally, a cook for Florida’s first millionaire, William Curry.

4th of July Fireworks – Where to Watch

Experience the most spectacular fireworks display in paradise from the best viewing spots in Key West:

●      White Street Pier – Up-close views over the water

●      Higgs Beach - Close to the pier and another great option.

●      South Beach – Can’t beat the location and the views from Southernmost Beach Resort.

●      Smathers Beach – A relaxed beachfront spot

Hemingway Days
July 23–27

Each summer, Key West celebrates the legacy of Ernest Hemingway with a festival featuring the Lorian Hemingway Short Story Competition, the Key West Marlin Tournament, the famous Hemingway Look-Alike Contest at Sloppy Joe’s, the Running of the Bulls (Key West-style!), a Caribbean street fair, and more. The festival wraps up with Papa’s Birthday Bash and the Hemingway Rum Stroll across the island’s most iconic bars.

 

August

 

Rum Fest Key West
August 11–17
Website

Celebrate the island’s rum-running history at Rum Fest Key West! Enjoy premium rum tastings, sunset sails, Hemingway-inspired experiences, and nonstop island fun—from beach parties, live music, poolside events (including at our resorts), and incredible culinary experiences. Sip, sail, and celebrate—because nothing says island time like a week dedicated to rum!

LABOR DAY WEEKEND

Just a Few Friends: An Island Celebration Honoring Jimmy Buffett

August 29 – September 1

Website

This Labor Day Weekend, Key West honors the life and music of Jimmy Buffett with Just a Few Friends—a four-day celebration filled with music and live performances, parties by land and sea, and unforgettable island moments.

Festival Highlights: 

●      Live performances by Nadirah Shakoor, Will Kimbrough, Roger Bartlett, and more

●      Second Line Memorial Parade and Party in the Park Sunday, Aug. 31

●      Margarita Strolls, brunches, happy hours, and culinary experiences

●      ​Sunset sails, tiki cruises, pool parties and beach parties

●      Book signings, film screenings, and Buffett-inspired panels

●      Exclusive meetups, contests, and afterparties

●      Raising funds for Reef Relief, Bahama Village Music Program, and the Key West High School Marching band

Did you know: Jimmy Buffett finished writing "Margaritaville" while stuck in traffic on the Seven Mile Bridge—then debuted it live in Key West hours later. Curious about where he performed it? Read the full story here.

As official partner hotels, Southernmost Beach Resort & The Marker Key West Harbor Resort offer exclusive Just a Few Friends packages, VIP perks, and the ultimate island escape.

Make it a Labor Day Weekend to remember. Book your Just a Few Friends package now.



Getting Here: New Non-Stop Flights to Key West

Getting to paradise has never been easier! With new non-stop flights to Key West, your island getaway is closer than ever. Check out our latest blog for all the details on flight options, the new airline flying direct to Key West, and more travel updates: New Non-Stop Flights to Key West & Airport Updates (March 2025).

“Wrinkles will only go where the smiles have been.” – Jimmy Buffett

Let’s make more smiles, soak up the sun, sip something cold, dance barefoot in the sand, watch the sunset, and celebrate all the incredible events happening this spring and summer. We can’t wait to see you! And don’t forget to follow us on Facebook & Instagram. #lovethemarker