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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 | 9/1 - 9/3/2018

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. Be sure to check out the Fantasy Fest Ringmaster's Pool Party happening right here at The Perry! 


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.

Join and watch as renowned sculptors compete against each other to build elaborate and beautiful sand creations.

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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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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.

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.


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.


  • Valentine's Day | 2/14/2019

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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  • St. Patrick's Day | 3/17/2019

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.

As an official "Conch Sponsor," The Perry Hotel Key West makes the perfect home base for this one-of-a-kind air show.

*The Perry Hotel Key West is a "Conch Sponsor" for the NAS Key West Spectacular Air Show


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


  • Memorial Day Weekend | 5/27/2019

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

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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