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:

April 25, 2014 -
April 27, 2014
All Day - 12:00 AM

The Conch Republic Independence Celebration

April 18-27, 2014

You've got to attend the Conch Republic Independence Celebration with more than a week of events, including The Raising of the Colors at Fort Taylor, The Great Conch Republic Drag Race, a Music Festival, Pet Stroll, Parade and much, much more! For a full schedule of events please visit

April 26, 2014 -
April 27, 2014
12:00 AM - 12:00 AM

Key West Sailfish Championship

April 23-27, 2014

The 2nd Annual Key West Sailfish Championship Tournament features divisions for professional and non-pro anglers with first place through third place payouts, including a first-place pro division prize of up to $50,000. Prize amounts are based on a paid minimum field of boats. This Key West fishing tournament is limited to 50 boats per division.
Sailfish Tournament Dates:

  • April 23rd, 2014 - Captains Meeting, 6 pm

  • April 24th, 2014 - Fishing 8 am - 4 pm, Dock Party, 5:30 pm

  • April 25th, 2014 - Fishing 8 am - 4 pm, Dock Party, 5:30 pm

  • April 26th, 2014 - Lay Day

  • April 27th, 2014 - Fishing 8 am - 3 pm, Awards Party, 6 pm

Sailfish Tournament Entry Fee: Pro Division

  • $3,500 Entry Fee

  • $3,250 Early Entry

Sailfish Tournament Prizes: Pro Division

  • 1st place Prize $50,000

  • 2nd place Prize $15,000

  • 3rd Place Prize $10,000

*Based on 25 paid entries.
Sailfish Tournament Entry Fee: Non Pro Division

  • $1,800 Entry Fee

  • $1,500 Early Entry

Sailfish Tournament Prizes: Non Pro Division

  • 1st place Prize $15,000

  • 2nd place Prize $7,000

  • 3rd Place Prize $5,000

*Based on 20 paid entries.
Visit or call 305-340-2737.

May 1, 2014 -
May 4, 2014
12:00 AM - 12:00 AM

Key West Paddleboard Classic

May 1-4, 2014

During this ocean paddleboard race, participants enjoy a challenging 12-mile course over crystal blue waters, circling Key West through scenic mangroves, passing by the Historic Seaport district and more. The race around Key West is open to paddlers on standup paddleboards, prone boards, outrigger canoes, dory boats, surf skis and kayaks. Other weekend beach and paddling activities are planned.

May 7, 2014 -
May 11, 2014
12:00 AM - 12:00 AM

19th Annual Key West Songwriters’ Festival

May 7 – 11, 2014

This May, join the talent, music, and fun at the largest festival of its kind in the WORLD. Yes, we said world! Over 5 days and nights, guests can enjoy 30 shows and 150 performers during the 19th Annual Key West SongWriters Festival!

See more than 20 free shows, staged at a variety of Key West’s most popular drinking holes and hot spots, where live music flourishes among the crowds. These diverse line-ups feature more than 100 top songwriters, who offer one-of-a-kind moments to our island paradise.

Festival Guests: Find Comfort at The Inn!

The Inn at Key West is your perfect hotel for the 2014 SongWriters Festival! When you’re not enjoying the live music, find comfort in our Tommy Bahama-inspired guest rooms, enjoy complimentary Internet, and relax beside the island’s largest freshwater pool! Plus, The Inn is just a short taxi drive away from famous Duval Street, where you can enjoy all the nightlife, and then retreat back to our soothing Key West hotel.

The SongWriters Festival looks forward to seeing you this year!

May 31, 2014
12:00 AM - 12:00 AM

13th Annual Yamaha Dolphin Masters Invitational

May 31st, 2014

Famous for its beautiful clear water, Key West is famous as a fishermen's paradise.

In this fishing challenge headquartered at Key West's Historic Seaport, more than $13,000 awaits the angler scoring the highest total combined weight of three dolphin catches. Many additional prizes await other top anglers, and there is no limit on the number of participating boats. If you are an angler, love watching a great competition or just want to have some fun you should see the Dolphin Masters Invitational!

For more information, please call John Stuempfig at 305-304-7674 or email

What: Dolphin Masters Invitational

When: May 31, 2014

Where: Conch Republic Seafood Company

June 11, 2014 -
June 15, 2014
12:00 AM - 12:00 AM

Key West Pride

June 11-15, 2014

Key West shows its Pride every day, and this is your chance to be a part of the celebration! This five day celebration includes a film festival, dance parties, drag shows, bike tours, clothing-optional pool parties, water excursions, a street fair, Pride Pageants, and a 'Pride in Our Community' Parade down Duval Street.

June 28, 2014
12:00 AM - 12:00 AM

38th Annual Swim Around Key West

Saturday, June 28, 2014

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.


Presented by: The Key West Athletic Association

Date: Saturday, June 28, 2014

Time: First Wave Start: 8:30 AM, Second Wave Start: 9:00 AM

Location, Start/Finish: West end of Smathers Beach (Atlantic side)

Solo Swimmers: They cap the solo entry at 90 swimmers.

Relay Teams: They have separate applications for each category - two and three-person relays. Each teammate must fill out his/her application separately, completely and sign the waiver. The cap for the relay teams are: 10 two-person teams and 25 three-person relays.


July 15, 2014 -
July 20, 2014
12:00 AM - 12:00 AM

Hemingway Days

July 15-20, 2014

The 34th annual celebration of the legendary author's work and lifestyle features literary readings, a theatrical premiere, short story competition, fishing tournament, Sloppy Joe's Look-Alike Contest (July 17-19) and a pre-birthday "party" commemorating Ernest's July 21st birthday. Street Fair on July 19th. Contact: (305) 296-2388 (Look-Alike); 294-0320 (literary)

July 17, 2014 -
July 19, 2014
12:00 AM - 12:00 AM

34th Annual Sloppy Joe's "Papa" Hemingway Look-Alike Contest

July 17-19, 2014

This annual contest takes place at Sloppy Joe's Bar, 201 Duval St., where Ernest Hemingway often enjoyed cocktails with cohorts. The event attracts look-alike contestants from around the United States and international locales to vie for the title of "Papa," and is a highlight of the annual Hemingway Days celebration of the legendary author's literary prowess and colorful lifestyle.

July 19, 2014
12:00 AM - 12:00 AM

Hemingway 5K Sunset Run & Paddleboard Race

July 19, 2014

Runners and paddleboard enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle during the Hemingway 5k Sunset Run and Paddleboard Race on Saturday, July 19, 2014. These physical challenges are part of the annual Hemingway Days Festival that commemorates the life and work of the author who lived in Key West throughout the 1930s. This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West's most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point, and the famous Green Parrot Bar!

The Lazy Dog Paddleboard Race is to kick off at 6 pm at the island city’s Southernmost Beach, 1405 Duval St. on the Atlantic Ocean. Competitors are tasked with paddling a 3-mile ocean course before finishing back at the beach.

The 5k run is to begin at 7:30 pm at the Southernmost Point in the continental United States, overlooking the ocean at Whitehead and South streets. The fast, flat 3.1-mile course takes runners through picturesque Old Town Key West past landmarks including the Ernest Hemingway Home & Museum. There is a walking division as well.

Afterwards, a post-race awards party is scheduled at the Southernmost Hotel, 1319 Duval St. Paddleboard awards are to be presented to the first through tenth place male and female finishers. In the 5k, awards await the top three male and female overall finishers, top three male and female masters, and top three male and female finishers in age categories ranging from 9 and under to 75 and over. In addition, special medals will be awarded to those competing in both the paddleboard and 5k challenges.

A registration booth is to be open 3-7 p.m. race day at the Southernmost Hotel. Race packets can be picked up there. Interested participants can register online at Registration forms can be downloaded from or picked up at local hotels and fitness centers.

The registration fee is $37 per adult for either race ($45 on race day), and $25 per entrant under age 15. The fee includes a collectible race tech shirt, food, libations, and giveaways.


Paddleboard Race 6:00 pm
Sunset Run 7:30 pm

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.