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:

20th Annual Key West Songwriters’ Festival

May 6, 2015 - May 10, 2015
12:00 AM

May 6 – 10, 2015

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 20th 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 2015 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!

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.

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!