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:

39th Annual Swim Around Key West

June 6, 2015

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.

 

 

Key West Pride

June 10, 2015 - June 14, 2015

June 10-14, 2015


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.

Mel Fisher Days

July 9, 2015 - July 12, 2015

ONE OF THE LARGEST FESTIVALS IN KEY WEST!

2015 is the 30th Anniversary Celebration of the Discovery of the Mother Lode of the Atocha and Mel Fisher Days will be a BLAST this year!

Each year a celebration is held in honor of the anniversary of Mel Fisher's discovery of the Motherlode of the Atocha. This year we celebrate the 28th anniversary. A series of events are scheduled that will run from July 9-12, 2015. 100% of all net proceeds from these events will be donated to Wesley House Family Services, Inc.

 

About the Mel Fisher Days

Come celebrate the day when Mel Fisher’s crew found nearly $400 million in shipwrecked gold, silver, and emeralds on the ocean floor! Mel Fisher Days is one of the largest festivals in Key West, kicking off at the Schooner Wharf Bar with a costume contest, raffle, and live entertainment.

With the Atocha Costume Contest, contestants make their own treasure-themed costume or wear one that they already own! Festival guests can also enjoy a Diver Meet and Greet and Charity Cook-Off, as well as the 6th Annual Midnight Gambler Texas Hold ‘Em Poker Tournament.

The Duval Street Block Party takes place on Saturday, July 11th from 2 pm – 8 pm along the 200 block of Duval Street and features live music and street fair food. Attendees can expect a huge silent auction, food, drinks, and fun for the whole family.

Hemingway Days

July 21, 2015 - July 26, 2015
12:00 AM

July 21-26, 2015

The 35th 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, and a pre-birthday "party" commemorating Ernest's July 21st birthday.

35th Annual Sloppy Joe's "Papa" Hemingway Look-Alike Contest

July 23, 2015 - July 25, 2015
12:00 AM

July 23-25, 2015

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.

Hemingway 5K Sunset Run & Paddleboard Race

July 25, 2015
12:00 AM

July 25, 2015

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 25, 2015. 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.

 

 

2015 Phil Peterson Poker Run

September 17, 2015 - September 20, 2015

JOIN 10,000 MOTORCYCLE RIDERS ON THIS FAMOUS POKER RIDE TO THE FLORIDA KEYS

September 17-20, 2015

Phil Peterson created a poker run to boost the motorcycle business and Key West tourism during the month of September. An event that started with 46 riders has grown to become South Florida’s biggest motorcycle party!

Known as Phil Peterson’s Poker Run, over 10,000 riders from all over the country enjoy this classic motorcycle ride. Starting in Miami, they rumble their engines all the way to Key West, crossing over the many bridges to our island paradise. During the Phil Peterson Poker Run, the motorcycle riders make 5 stops and draw a card at each stop. At the end of the ride, the person who draws the best hand wins! Plus, if you draw one of the top 10 hands, you get a chance to play one round of Texas Hold ‘Em at Cowboy Bill’s on Duval Street!

In addition to poker game, Key West blocks off 8 blocks of Duval Street for the Phil Peterson Poker Run, where a huge bike show is held in front of Rick’s, Durty Harry’s, and Sloppy Joe’s Bar. Locals, tourists, and bikers enjoy this mini-Mardi Gras with its carnival atmosphere, music, food, and cold beer!

Fantasy Fest

October 23, 2015 - November 1, 2015

Celebrate Fantasy Fest 2015 in Key West, FL!

October 23 – November 1, 2015


Fantasy Fest 2015 in Key West is going to be very lively this year! 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 2015 event news and updates.

 

Fantasy Fest Goers: Stay at the Inn at Key West


Looking for affordable, but fun accommodations for Fantasy Fest 2015 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!

"Meeting of the Minds" Parrot Head Convention

November 4, 2015 - November 8, 2015

JOIN THIS YEAR’S PARROT HEAD CONVENTION 

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 24th Annual ‘Meeting of the Minds’ Parrot Head Convention is scheduled for November 4th - 8th which will be a 4-day party!

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.

Key West Super Boat Races

November 8, 2015 - November 15, 2015
12:00 AM

35th Annual Key West World Championship of Super Boat Races 

November 8-15, 2015

Super Boat International (SBI) will hold the 35th Annual Key West World Championship in Key West from November 8th - 15th, 2015. 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 35 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 2015 schedule of events!