Key West has activities and special events happening throughout the year.  For a comprehensive list, organized by month, view the official Florida Keys & Key West Calendar of Events.

Listed below are some of the major events that occur annually in Key West along with tips for booking your stay.

2015 Key West Florida Events

Key West Sailing EventJanuary

A world-class yacht racing event, Regatta Key West, takes place the third week of January.  Sailors from around the world arrive to compete in major boat classes for top sailing honors. Albury Court Hotel is located just one block from Race Headquarter.  The Inn is a sponsor of the event and provides accommodations for several race officials as well as crew from some of the race teams.


February & March

The months of February and March are peak season in Key West.  Valentines Day, President’s Day, and St. Patrick’s Day are especially busy.  Visitors should plan to book their hotel stay three months ahead in order to get the best room selection.  Advance reservations are a must and minimum stays of two or three days may be required.

Key West Conch Republic Event


Conch Republic Days takes place the last week of April.  Events occur every day throughout the week.  Favorites are the conch shell blowing contest, the bed race down Duval Street, and the re-enacted maritime battle for independence of the Conch Republic.




Memorial Day Weekend is always a big three-day weekend in the Keys.  Visitors should book rooms at least one month in advance for the best selection of rooms.  Advance reservations are a must.


Pridefest takes place during the second week in June.  This local event encourages everyone to adopt Key West’s “One Human Family” state-of-mind.

Key West Fireworks

July 4th weekend is a busy three-day weekend in the Keys.  Reservations should be made at least a month ahead for the best room selections.  Lobster mini-season takes place the last Wednesday and Thursday in July.  This two-day lobster season is meant especially for recreational divers to get the first jump on the season’s catch.  Hotels throughout the area run full with Key West scuba divers for the mini-season.



Like birds flocking south for the winter,  once a year the Ernest Hemingway look-alikes come to Key West to compete in the contest and celebrate some Hemingway fun. The festivities include museum exhibits of rare Hemingway memorabilia, a zany “running of the Bulls” and a three-day Marlin tournament to honor Hemingway’s devotion to the deep-sea sport.

A Note About Hurricane Season

Hurricane season in the Atlantic officially runs from June 1 to November 30.  Locally, we are most watchful from mid- July to early October.  Summertime brings warm water (80+ degrees) and calm winds.  Consequently, it’s also an excellent time for water sports like snorkeling, diving and fishing.  Concern about hurricanes should not curtail your travel plans to Key West.  You will find the best rates of the year in summer, moderate temperatures, and many inviting activities.

In the event a hurricane does develop in the Atlantic and moves toward south Florida, local officials may call for a precautionary evacuation order.  When this scenario occurs Historic Key West Inns will assist to reschedule or cancel reservations, and refund advance deposits.

Key West Poker RunSeptember

Labor Day weekend is a busy three-day weekend in the Keys.  Reservations should be made a month ahead for the best room selections.  Poker Run is an annual rally of motorcyclists that occurs the third weekend in September.   This is an extremely popular event and tends to fill all hotels throughout Key West.  Reservations are recommended six months in advance.  Rates are higher for this weekend.


Key West Fantasy Fest

Fantasy Fest is the biggest event of the year in Key West.  This is a ten day event that starts with Goombay Festival the third weekend in October and runs through the last Saturday of the month with a huge, mardi gras-style parade.  Fantasy Fest is best described as a very adult Halloween party.  Many events are fund-raisers for local charities as the whole town gets involved in this 20 year tradition.  Any lodging in Key West should be planned many months in advance for the best room selections.  Rates are high and minimum stays apply.  The best bargain is to visit mid-festival (Sunday thru Tuesday) to enjoy great events at much lower lodging rates.



If you are seeking a Meeting of the Minds, you must be a Parrothead making the annual pilgrimage to Key West.  This festival of Jimmy Buffet fans takes place the first week of November.  Be prepared for an adjustment of latitude, and lots of live music.  Lighthouse Court features a daily jam session hosted by Kelly McGuire.  This unofficial Parrothead event is free to all guests of Historic Key West Inns.  Reservations for MOTM should be made several months in advance.  Minimum stays apply.


Key West Powerboat Races

Superboat World Championship Racing takes over the harbor the second week in November.  Listen to the roar of these giant powerboats as they speed through Key West harbor at speeds over 100 mph.  Lodging reservations should be made at least three months in advance.  Minimum stays apply.




Early December is the best kept secret for an affordable Key West vacation.  Summer rates apply during the first three weeks of the month, and the weather is sunny, dry, and gorgeous.

Key West Christmas Vacation


Christmas to New Years is a very busy vacation time in Key West.  Many special activities are planned including Christmas concerts, holiday meals, house tours, and theatre productions.  Key West has its own unique New Year’s traditions which include fireworks and several locations with midnight countdowns.  CNN is usually on-site at Bourbon Street Pub to watch Sushi, a local drag queen, descend from a giant red slipper at the stroke of midnight.  The New Years celebrations are within easy reach from all of the Historic Key West Inns.