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:

October 29, 2014 -
November 2, 2014

"Meeting of the Minds" Parrot Head Convention


October 29, 2014  - November 2, 2014

It’s that time of year when Parrot Heads start migrating south to Key West, gathering with members of the Parrot Head Nation from all over the world. The 23rd Annual ‘Meeting of the Minds’ Parrot Head Convention is scheduled for October 29th – November 2nd, which will be a 4-day party of Havana Daydreamin!

This “Meeting of the Minds” is an annual event that assists in community and environmental concerns, as well as providing a variety of social activities for its members. PHIP’S motto is “Party with a Purpose” and the Parrot Head Nation will converge in Key West to do just that! Scheduled events include beachside concerts, auctions and raffles for charity, a street festival, and a sunset cruise.

Held each year on the weekend following Fantasy Fest, “Meeting of the Minds” is the gathering place for thousands of Havana Daydreamers to sing, dance, drink, and listen to their favorite artists. To attend this Parrot Head party, you must be a member in good standing of a sanctioned Parrot Head Club. There are over 200 chapters in the US, Australia, Canada, and Europe.

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 5, 2014 -
December 7, 2014
All Day - 01:00 AM

Fort Taylor Pyrate Invasion

Fort Zachary Taylor Historic State Park

Experience three days of piracy as Fort Zachary Taylor Historic State Park transforms into a British stronghold defending her shores against an invasion of pirates. Step back in time to encounter piracy from 1675 through 1825 with pirate encampments, living history demonstrations, live battles, activities for the kids, and more, from 10 am. to 5 p.m. daily. Visit website for details and activities schedule.
Contact:  305-797-1659

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.

January 25, 2015
04:00 PM - 07:00 PM

The 21st Annual Master Chefs Classic

Sunday, January 25, 2015 from 4 pm - 7 pm

The 21st Annual Master Chefs Classic®, held at the Westin Key West Resort & Marina Pier, 245 Front St, is a culinary competition and tasting that benefits the Monroe Association for ReMARCable Citizens (MARC provides life services for developmentally and intellectually disabled adults in the Florida Keys). This 21st anniversary of one of Key West's most spectacular food events and promises to be amazing!

This is a premier food event of the Key West season. Restaurants compete in appetizer, entrée, and dessert categories providing an amazing array of incredible food for the lucky 450 people attending. Awards are given in each category by judges and people’s choice ballots.

Held on the beautiful Key West Westin Resort and Marina pier overlooking the Key West Harbor, this stunning venue is highlighted by a large tent covering the Master Chefs Classic event in comfort and style for the lucky attendees. Please join us!

*This event sells out early and it is a FUNDRAISER for MARC Inc. It is NOT INCLUDED in the Key West Food and Wine Festival's VIP pass. Tickets are NOT refundable. Please read your options carefully before you purchase your tickets at the website.


Master Chefs Classic Event Information:

Who: Benefits the Monroe Association for ReMARCable Citizens (MARC).

What: A Culinary Competition and Tasting featuring some of the finest Chefs and Restaurants in the Lower Keys.

When: Sunday, January 25, 2015 from 4 pm to 7 pm.

Where: The Westin Key West Resort & Marina, 245 Front St, Key West, FL. 33040.

Why: This event raises funds for the Monroe Association for ReMARCable Citizens (MARC, Inc.) program. MARC provides life services for Adult Developmentally Disabled residents of the Florida Keys.

Contact: Gordon Ross – 305-294-9526 ext. 25

February 28, 2015

World Sword Swallowers Day

Ripley's Believe It or Not! 108 Duval Street Key West, FL 33040

Sword Swallower's Day at Ripley’s Believe It or Not! 

Dangerous, exciting and alluring, Sword Swallowers Day showcases the art of sword swallowing. Do we even need to tell you not try this at home?

Ripley’s Believe It or Not! Key West Odditorium celebrates World Sword Swallower’s Day with free sword swallowing demonstrations - held on the last Saturday of February in conjunction with National Swallowing Disorders Month. Sword swallowers will be making appearances, signing autographs, performing their individual signature acts, or unveiling new stunts, some of which have never been witnessed before in public! More than 20 sword swallowers will risk their lives when they “drop swords” at Ripley’s Believe It or Not! In all, more than 125 feet of solid steel will go down the hatch – hopefully without a scratch!

Ripley's Believe It Or Not
Duval Street
Key West, FL 33040

Founded in 2001 to preserve the art of sword swallowing, SSAI is comprised of sword swallowers from around the world and maintains a website with general information on sword swallowing for the general public at

February 28, 2015
11:00 AM - 08:00 PM

ConchFest - A Celebration of Conch Heritage

Bayview Park Key West, FL 33040

February 28, 2015

The Rotary Club of Key West is extremely pleased to announce the Fifth Annual “ConchFest - A Celebration Of Conch Heritage”. There will be vendors selling arts and crafts of every imaginable kind, and other treasures. There will be a Queen Conch cook-off, lots of great food for sale including conch fritters, conch salad, pork, and other more traditional fare. There will be children’s activities, a co-ed softball tournament, live music, and much more.

Last year’s event drew thousands of locals and guests alike to Bayview Park. Rotary Club volunteers will be selling alcoholic beverages, food and soft drinks. Admission to the event is free with food and beverages for sale at very reasonable prices. ConchFest raises money for college scholarships for local children. The tournaments will have a small entry fee and benefit this scholarship program.

When: Saturday, February 28, 2015

Where: Bayview Park in Historic Old Town Key West

Time: 11:00 am - 10:00 pm





March 7, 2015
12:00 PM - 02:00 PM

53rd Annual Conch Shell Blowing Contest

The 53rd Conch Shell Blowing Contest 
March 7, 2015

An Old Island Days tradition, this unique contest features novel sounds produced by contestants in several age categories as they attempt to make "music" on fluted conch shells. While most contestants only manage blasts or squawks, each year a few produce complex melodies that impress judges and audiences alike. Winners are chosen for the quality, duration, loudness and novelty of the sounds they make, with trophies awarded in multiple age categories. The festivities typically include performances by talented "pucker pros."

This Key West contest is located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10:30 a.m. and contest begins at noon.

More about the History of the Conch Shell Blowing Contest

The contest was conceived 53 years ago by the Old Island Restoration Foundation, founded in 1960 to advocate preservation of Key West's culture and historic buildings. Conch shells have been used as signaling devices in the Florida Keys for more than 200 years. Native-born islanders are called Conchs and the Keys are nicknamed the Conch Republic. In the 1800s, when the local economy was largely based on salvaging cargoes from ships wrecked on the nearby reef, sailors attracted attention by blowing piercing blasts on the shell. However, the Keys' connection with conch goes far beyond instrumental and communications applications. The slightly tough meat of the hardy mollusk is the prime ingredient in conch chowder and conch fritters, two of the island chain's signature dishes. Keys natives proudly proclaim their own tough, hardy nature by calling themselves "conchs" and their home the Conch Republic.

March 14, 2015

Annual St. Patrick's Day Bar Stroll

Saturday, March 14, 2015

A Key West St. Patrick's Day tradition since 1979! Stay up-to-date on this years participating bars, how to get your official t-shirt, and more at

From Rick Dostal, Founder and Event Organizer:

I started the St. Patrick’s Day Bar None Suds Run in 1979 with the help of Curly McGinn. Curly owned the Sandcastle Bar (now Michael’s restaurant on Margaret St.). At his request the run ended at his bar and every year that it did, Curly, myself and the Strollers drank the place dry!

Key West artist and muralist Steve Heuel drew the shirt for me using the bar as his easel (see 1st annual t-shirt). For various and sundry reasons certain people were barred from one bar or the other so I got permission from the bar owners that a guy could "get a pass" for the run, hence the name.

It was an absolutely crazy race and everyone who actually ran in it blasted into a bar, chugged a beer, and then "purged" on the fly to the next joint. After a few years of guys and girls running and puking through an increasingly congested Old Town the event had to change to today's format, a "stroll".

The last time it was a race it was won by Key West's own Buco (Pantellis) who is the reigning champion. He still bugs me every year to bring back the run! Maybe next year, B!

The first year we started at the Full Moon Saloon, the legendary and definitive bar from the golden age of Key West. Gone now but it stood roughly where the Southernmost Hotel is (Tiki Bar!).

Stop two was the Holt brothers' Simonton St. Station, now the Monkey Bar at Simonton and Olivia streets. Then the Blue Boar, which is now just a distant memory; the Lowell C, now Mango's. Then we were off to The Bull and Whistle, Maynard's (now Ricks Bar), Sloppy Joe's, Billy's Bar (now Red Fish Blue Fish), the Chart Room at the Pier House (later we used the Cistern Bar, a very cool little underground bar on their property right beside Duval St. built in - what else!?! - a cistern!), Dills Pickle (now a parking lot on the corner of Greene and Simonton streets). Then off to the Half Shell Raw Bar, and finally finishing up at the Sandcastle!

I remember Dave Dill served Becks Dark but he added green dye, and put a little gerkin in the glass. It was not really what a runner wanted just then.

The only bar that was in the first year and has been in every year since is The Bull and Whistle. Rick's came in as soon as they opened (2nd Annual) and have been a stop ever since. The Schooner Wharf Bar has also been in since they opened (as Cafe Diamant!), and is a fine place to unwind at the end of all that strollin'.

We all thank the great bars and their staff that welcome the strollers each year and we welcome some new bars, some brand new to the "Stroll".

April 4, 2015
11:00 AM - 06:00 PM

Mote Marine Presents: 6th Annual Florida Keys Ocean Festival and Waterfront Craft Show

Eco-Discovery Center 32 East Quay Road Key West, FL 33040

6th Annual Florida Keys Ocean Festival 
Saturday, April 4, 2015

Annual Florida Keys Ocean Festival and Waterfront Craft Show is held every year in March to benefit Mote Marine Laboratory's Coral Reef Restoration Programs. Enjoy many activities for children, including a fishing seminar for kids, live entertainment all day, more than 70 arts, crafts, food vendors, and exhibitors, as well as a silent auction.

Presented by Florida-based Mote Marine Laboratory, the event is set for 11 am to 6 pm at the Florida Keys Eco-Discovery Center, located on Key West’s Truman Waterfront past the end of Southard Street. Admission and parking are free.


  • Free Sky Rides on Keys Energy Bucket Trucks

  • Nautical Themed Face Painting

  • Rock Climbing, Bounce House, Bungee Game, Water Wheels

  • Touch Tanks and Live Animals on display

  • Kids Treasure Hunt

  • Passport to the Ocean Game

Contact  305-393-6022 for more information.


June 6, 2015

39th Annual Swim Around Key West

Saturday, June 6, 2015

This 12.5-mile endurance swim competition begun in 1977 by Anna Fugina. Anna had suffered injuries from a car accident and she chose to begin swimming as therapy to assist in her recovery. As her health improved, so did her swimming ability and love for swimming.

Anna wondered if it was possible to swim the circumference of the Island of Key West. Though she inquired, she could find no evidence that anyone had even attempted the challenge, much less completed the swim. She concluded that someone had to be the first, so on July 4th she entered the water at Mallory Square at Key West Harbor. She completed the swim in 12:59:00. Later, she found that if she studied the tidal current, the swim would be an easier task. Anna swam again in 1978 and improved her time considerably, finishing at 8:00 hours.

This historic, round-the-island event is the longest-running sporting event in the Florida Keys. Since the swim is in June, the water temperatures will likely be between 84 and 86 degrees. Every entered swimmer will receive a technical T-shirt listing the overall first place swimmers and their finish times from 1977 to 2013.