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Local Events

Mark Your Calendar

From fishing strolls and harbor walks to bustling parties and live music, The Perry Hotel offers eclectic opportunities for mingling, celebrating, and simply enjoying life. Get out there and explore the many events happening right here.

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If you prefer milder temperatures and wilder celebrations, then fall is a wonderful time to visit our island city. Don’t miss October’s Fantasy Fest, Key West’s most exciting street party.

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  • Labor Day Weekend | 8/31 - 9/2/2019

Whether you long to explore beautiful beaches or prefer hanging out at Key West’s top bars, there’s a near endless variety of things to do here during Labor Day Weekend.

During this female-centric festival, women from across the globe gather to mingle and celebrate with exciting Key West activities.


Hundreds of runners and walkers come together to cross the finish line each year at this waterfront race.

Always free and family friendly, this lively street party features arts and crafts, food, and music in Key West’s historic Bahama Village neighborhood.

This 10-day street festival is an adult paradise, showcasing parades, parties, and plenty of more exciting, one-of-a-kind activities.  


If you love Jimmy Buffett, this Key West Parrot Head event is for you! Meet like-minded individuals as you dance, sing along, and celebrate.

Featured on NASCAR’s "Countdown to Green," "The Today Show," and Forbes magazine, the premier offshore powerboat races are returning to Key West.

This nonprofit celebration of all things film invites filmmakers, film educators, and film lovers alike to attend classes, enjoy movies, and experience Key West.

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With warm weather all year round, Key West still has plenty of sunshine and fun to offer in its winter months. Check out our holiday festivities and more interesting events.

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A Key West tradition, our annual holiday parade takes place down Duval Street through Old Town and ends with a visit from Santa and Mrs. Claus.

Locals and tourists alike get together to celebrate the unique history and eclectic charm of Stock Island every year at this lively festival. Get off the beaten path and taste a selection of curated plates and beverages at our Taste of Stock Island event right here at The Perry! Then, finish your evening at the Stock Island Lighted Boat Parade with a procession of lighted vessels in all sizes.


Experience Stock Island's unique art scene and creative culture at the Stock Island Art Walk at their annual Spring Art Walk, where you can tour all of the art studios from 11am - 4pm on January 11th, February 8th, and March 14th.

This scenic half marathon invites participants to race through the streets of historic Old Town and Key West’s waterfront areas.

This popular food and wine festival is comprised of a diverse selection of events that showcase the very best of Key West. Make your way over to The Perry for the "Meet the Fleet" Shrimp Boil where there’s enough Key West Pink Shrimp — and an array of wines to pair — for everyone to enjoy.

The Mile 0 Fest has turned from the "must see" 2018 freshman festival to the "can't miss festival of the year".


Experience Stock Island's unique art scene and creative culture at the Stock Island Art Walk at their annual Spring Art Walk, where you can tour all of the art studios from 11am - 4pm on January 11th, February 8th, and March 14th.

      • Valentine's Day | 2/14/2020

From sunset sails to intimate dinner dates, there’s an eclectic assortment of romantic activities for you and your partner to enjoy in Key West.

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Ah, springtime! This time of renewal brings even more than a chance for a break. All season long, Key West offers a diverse and entertaining assortment of events.

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Experience Stock Island's unique art scene and creative culture at the Stock Island Art Walk at their annual Spring Art Walk, where you can tour all of the art studios from 11am - 4pm.

  • St. Patrick's Day | 3/17/2020

What better place to spend St. Patrick’s Day than the city of good-hearted debauchery? Head to Key West for St. Patrick’s Bar Stroll and even more good times.


All ages are welcome to this event in which attendees can explore conservation and environmental exhibits, meet live animals, all while raising money for coral reef research and restoration.

Don't miss this annual event that celebrates the variety of cuisines that Key West has to offer. Extra bonus: The Perry's very own Matt's Stock Island Kitchen and Bar will have a booth where you can sample some of our favorite selections!

Celebrate our eccentric community and the independence of the entire Florida Keys with ten days of races, parties, and fun at this annual event.


The Key West Songwriters Festival, the largest festival of its kind, is celebrating its 25th year. The festival takes place over five days and nights where attendees get to witness the stories and performances from the artists first-hand. The Perry is one of the official venues for the event!

  • Memorial Day Weekend | 5/25/2020

From ghost tours to boat excursions, Key West offers an ideal environment for entertaining every member of the family during Memorial Day Weekend.

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There’s nothing quite like Key West in the summertime, especially when it comes to our eclectic variety of summer events, from mermaid meet-ups to paddleboard races.

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Every year, swimmers get together to compete in this incredible 12.5 mile, open-water journey around the pristine waters of Key West.

There's no better place to celebrate PRIDE than colorful Key West, where we're all about One Human Family and having a good time.


From pie eating contests to fireworks to the iconic and exciting Key Lime Pie Drop, this one-of-a-kind festival has something for everyone.

Perfect for the whole family, this truly fintastic three-day event is all about ocean awareness, fun in the sun, and mermaids!

Celebrate the work of Ernest Hemingway at this offbeat annual gathering, featuring a look-alike contest, literary readings, a one-of-a-kind running of the bulls, and more.

Run, walk, and paddleboard the same streets and waters that Ernest Hemingway once called home at this excited 5k race.


Kick off Lobster Season with the biggest party of the summer, and enjoy plenty of fresh lobster, cold beer, and live music!

Don't miss Key West’s hottest event for men! Four days of all-male theme parties, pool parties, and adult-oriented entertainment is the best way to experience Key West.

The end of August marks the start of our Labor Day Weekend BrewFest, featuring an array of events, including beer brunches, beer dinners, and every beer in between.

Conch Republic

No matter the season, there's always an assortment of exciting festivities going on in the Conch Republic. Check out our current Key West events and start planning your getaway today.

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