Key West Festivals and Events

The Key West Triathlon has become one of the most famous triathlons in the physical fitness world, and is only growing larger in popularity every year. The last five years of this triathlon has changed a lot in order to sustain the amount of entries comfortably, and be able to raise money over the whole weekend.

Every November, Key West is host to many events and festivals, and ART! Key West is one of the newer ones added to the things to do in Key West. The Art! Key west is a three day festival held throughout the whole island that showcases the talents and creative work of the artist community of Key West.

Every year Key West and Sloppy Joe’s team up together in search of the best “Papa” Ernest Hemingway look-a-like in the world. Key West’s love and admiration for the Pulitzer Prize winning author, Hemingway has only grown stronger throughout the years, decades after Hemingway used the island as a home and retreat.

With calm, and glassy waters surrounding the island, Key West is one the most perfect places to play on a super speed boat. Every year in November, super speed boats zip in and out and around the island in a matter of minutes. These boats are high adrenaline and high energy, even for those just watching from ashore.

Every year, like-minded individuals who share the love of Jimmy Buffett’s music gather in Key West for this event, and of course, a Key West vacation. These Jimmy Buffett lovers are called Parrot Heads, and they wear the name proudly (as they should!). These devoted fans come together once a year to promote the dedication to community, and raise awareness for social and environmental concerns.

The Annual Key West Film Festival is a phenomenal event to get involved in if visiting Key West in November. This film festival is a celebration of the arts in the Key West community with the medium of film. These films display the creativity that lies within the Key West locals, and shows the talents of many other filmmakers from around the world.

Womenfest in Key West is the celebration of women giving thousand of wonderful women, lesbians, and friends the chance to come celebrate and let loose in the name of being a woman. Every year, the Key West Business Guild plays host to several Gay Key West events, and are proud to promote the island to LGBTA travelers. To show Key West’s appreciation, there’s been many gay-friendly events made in the last decade in support of everyone in the world.

Key West Brewfest started in 2010, and exploded with popularity amongst craft beer lovers in the United States. Word got around that Key West had developed a great taste for deliciously, brewed beer, and supporters keep growing in numbers.

Anyone who enjoys riding a motorcycle, playing poker, and benefiting charities all at the same time should really join in the Key West Annual Phil Peterson Poker Run. For over 40 years, this motorcycle event started with just 46 riders, and is now the biggest riding event for motorist party in South Florida today.