Around the Resort
Local Events
Calendar of Events

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. 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 17 - 20, 2015
2015 Phil Peterson Poker Run

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!

October 23 – November 1, 2015
Fantasy Fest
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. 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.

November 4 - 8, 2015
"Meeting of the Minds" 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.

November 8 - 15, 2015
Key West Super Boat Races
12:00 AM
35th Annual Key West World Championship of Super Boat Races

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. 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!