Key West events calendar

Upcoming Key West Events, Tourist Attractions, and Festivals

See the Best of Key West, Florida!

The moment we find out about exciting events in Key West, we post them here! With our vast knowledge of the Conch Republic and our keen eye for happenings around town, our Key West events calendar is sure to have something fun for everyone you’re traveling with.

All year long, our island guests can enjoy a variety of Key West events and festivals that will leave you with memories for a lifetime. The most anticipated event in Key West is our annual Fantasy Fest. Fantasy Fest occurs every year during the last week of October, and can be described as a more laid-back Mardi Gras celebration! Visitors can also take advantage of Key West’s idyllic location in the Florida Keys. From our Key West Sailfish Tournament in April to the Yamaha Dolphin Masters Invitational in May, our island is a fisherman’s paradise for its crystal blue waters.

For more active guests, Key West hosts several athletic events, including the Key West Half Marathon in January, the Swim Around Key West in June, and the Hemingway 5K Sunset Run and Paddleboard Race in July. So whether you’re looking for a lively party or an exhilarating athletic challenge, our Key West events calendar has the perfect event for you!

Let us help you plan fun days and unforgettable nights during your next trip to Key West! Browse through our exciting Key West events, tourist attractions, and festivals, and then book your stay at The Inn at Key West!


Upcoming Special Events in Key West:

September 5, 2014 -
September 7, 2014

Robert James Sales S.L.A.M. Celebrity Tournament

September 5-7, 2014

In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted “flats grand slam.” The event raises funds for the fight against cystic fibrosis. Visit, call 305-664-2002 or email

October 17, 2014
12:00 AM - 12:00 AM

Fantasy Fest

Celebrate Fantasy Fest 2014 in Key West, FL!

Don't miss this year's theme "Animéted Dreams & Adventures" during this week-long party!

October 17-26, 2014

Fantasy Fest 2014 in Key West is going to be very lively this year! The 2014 theme for this week-long dress-up party is "Animéted Dreams and Adventures" - lasting from October 17th to 26th. Recharge your creative juices during the craziness that is Fantasy Fest, and enjoy some partying, playing, and just having a great time!

Fantasy Fest occurs near Halloween, which is now one of the busiest times of the year in Key West, FL. Thousands of people visit the island every October, bringing great attitudes and great costumes! Stay tuned for 2014 event news and updates.

Fantasy Fest Goers: Stay at the Inn at Key West

Looking for affordable, but fun accommodations for Fantasy Fest 2014 in Key West? The Inn at Key West is your hotel, just minutes from all the action on Duval Street. And when you’re not celebrating at Fantasy Fest, hotel guests can relax alongside the largest freshwater pool in Key West and enjoy Tommy-bahama guest rooms.

Book your Fantasy Fest holiday with The Inn at Key West today!

November 2, 2014
12:00 AM - 12:00 AM

Key West Super Boat Races

34th Annual Key West World Championship of Super Boat Races 

November 2-9, 2014

Super Boat International (SBI) will hold the 34th Annual Key West World Championship in Key West from November 2nd – 9th, 2014. Members of SBI, Conch Republic Offshore Powerboat Racing Association (CROPRA), and city representatives confirmed that next year’s event will stay in Key West, FL!
About the Super Boat Races

High-speed offshore powerboats will race in Key West Harbor and surrounding waters, continuing Key West's longstanding tradition for 34 years. Known internationally as the Indianapolis 500 of powerboat racing, a portion of the 6.5-mile course runs through Key West Harbor. This smooth water allows racers to achieve speeds of over 140 mph, providing fans and viewers breathtaking displays of skill and power!

Stay tuned for the 2014 schedule of events! 

December 31, 2014
All Day - 12:00 AM

New Year's Eve Shoe Drop Celebration

Key West

New Year's Eve 2015 in Key West, Florida

Enjoy Fireworks, a Famous Shoe Drop, and Plenty of Parties to Ring in the New Year in True Key West Style!

Key West embraces a tropical climate all the year round, making it the perfect destination for holidays, especially New Year's Eve! Experience our spectacular firework display, as well as the iconic "Shoe Drop" events that mark the countdown to NYE 2015.

Our island brings a rather unique interpretation to New York's ball drop on NYE. In true Key West fashion, our island features the "Shoe Drop" - a 6-foot tall red high heel, carrying a drag queen that descends from the roof of the Bourbon Street Pub. Female impersonator, Sushi, headlines the annual "shoe drop" celebration, wearing a dazzling gown while perched in this super-sized high-heel.

Another "drop" occurs at the famous Sloppy Joe's Bar on Duval Street, where their symbol of choice is a conch shell. The arrival of 2015 is celebrated with the drop of this huge manmade shell to the flat roof of Sloppy Joe's Bar. Thousands of spectators gather on Duval Street for this annual party, that starts at 10 pm with dancing in the street. At midnight, the conch shell descends and cheers erupt from the crowd!

In true Key West fashion, New Year's Eve also offers a wide range of parties, from the beaches to restaurants, where crowds will be out in the thousands! Enjoy sparkling fireworks too, which are launched from the end of the White Street Pier over Key West Harbor.

Join us for New Year's Eve in Key West!

Don't miss New Year's Eve in Key West, Florida! Book your stay at the Inn at Key West today! We are just minutes from all the action on Duval Street, and we offer the largest freshwater pool in Key West, FL!

January 18, 2015
12:00 AM - 12:00 AM

Key West Half Marathon Run

16th Annual Key West Half Marathon & 5K Run

Sunday, January 18, 2015

Recognized by Runners World magazine as one of the 10 great half-marathons of the winter season, this competitive race has attracted more than 1,000 annual participants and follows a 13.1-mile course through Old Town Key West past historic landmarks and the island's scenic waterfront. Marathon runners flock to Key West each year, which takes runners on a course to see the wildly colorful sights and sounds of this island at the end of the Florida Keys.

About the Key West Half Marathon Course

Fast, flat, and scenic throughout, the course takes participants mostly around the edge of Key West, and includes a bridge crossing over Key West's Cow Key Channel to Stock Island and back, for a run around the Key West Golf Course and Country Club. There's also a stretch of the race that unfolds through CB Harvey Rest Beach Park near the White Pier, where you can get spectacular views of the sunset later in the day.

This 13.1-mile course for the race starts and finishes at Dante's Restaurant on Caroline Street, on Key West's western end. From there, the course winds its way along several twists and turns through the city streets, turning on Duval Street, Eaton Street, and Whitehead Street before hitting longer straightaways along Atlantic Boulevard and South Roosevelt Boulevard, which is also part of Florida Highway A1A.

Through out the race, runners enjoy views of the ocean waters for virtually the entire course, and pass by local landmarks like the Key West lighthouse, famed author Ernest Hemingway's house, downtown Key West's "old town" area, and the southernmost point in the United States. The biggest elevation change (and the most challenging point in this flat, beginner-friendly race) is the bridge crossing over to Stock Island, over the Overseas Highway. Runners cross the bridge twice - once going over and once coming back - and then head along Key West's northern edge for the second half of the race heading back toward the finish line.

Even though the race takes place in January, it still typically offers relatively warm weather, so runners from cold climates are encouraged to stay well hydrated throughout the race, as aid stations will be available every couple of miles with water and Powerade.


Contact Barbara Wright for more info at 305.240.0727.