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:

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!