10 Unique Key West Events For an Unforgettable Trip All Year Round

Photo by Larry Blackburn

Drynuary, cutting carbs, saving money. Not every New Year’s resolution needs to be so joyless. In the spirit of self-care, you owe it to yourself to get away.

And there’s no hotter destination for gay travelers in 2020 than Key West.

Long a popular destination for LGBTQ tourists thanks to its welcoming atmosphere and vibrant LGBTQ community, Key West is a slice of gay paradise. The weather is perfect, the setting is gorgeous and the liberated spirit makes it a locale like no other.

Truthfully, there are no bad times to visit Key West, because the island has something unique to offer all year round. Take a look at just some of the highlights of the Key West social calendar below, and let us know which one has you booking your ticket today.


Old Island Days Art Festival

Art aficionados need not take a vacation from culture to enjoy Key West’s tropical delights. This juried outdoor fine art festival fills Whitehead Street with paintings, sculpture and photography just as beautiful as the surroundings. This year’s festival, Feb. 22 – Feb. 23, will be the festival’s 55th year.

Catch Some Theater

If your travel plans coincide with this musical adaptation of the cult-fave film Priscilla, Queen of the Desert (March 5 – March 28), make a night of it at the Waterfront Playhouse. But don’t despair if you miss it, because there is tons of high-caliber performance in Key West, like The Complete Works of Shakespeare (37 plays in 97 minutes!) at the Garden Bar at Bourbon April 21 – April 25 or the singing eye candy of The Choir of Man at the Tennessee Williams Theater March 21.

The Choir of Man

Key West Songwriters’ Festival

From May 6-10, Key West is filled with music as the 24th Annual Key West Songwriters’ Festival descends on the island. Curated by BMI, the event packs local venues with artists of all stripes for an intimate evening of song. Most shows are free, but check out the schedule for full details.

Key West Pride

Any time is a gay ol’ time in Key West, but there’s no gayer time than Pride. From June 3 – June 7, get ready to dial up the rainbow energy to an 11 for extra special drag shows, pool parties and, of course, the crowning of Mr, Miss and Ms. Key West Pride. As a spot famous for its relaxed, “Come as you are” attitude and “One Human Family” spirit, there are few places better to party during Pride season.

Celebrating Key West Pride. Photo by Larry Blackburn

Key Lime Festival

Open up and get ready to stuff your piehole with the freshest, most delicious Key Lime pie, cocktails and other culinary creations at this citrus celebration July 2 – July 6. Don’t miss the Key Lime Pie Hop, which is like a bar crawl with more sugar (but less hangovers).

Key West Tropical Heat

Naughty fun is never hard to find in Key West, whether you’re frequenting one of the men-only, clothing-optional guesthouses or cruising the bars on Duval. However, there’s no hotter time in Key West than Tropical Heat, Aug. 12 – Aug. 16. Strip down and turn up at all-male events, parties and adult entertainment. Put down Scruff, and spend these dog days of summer ‘woofing’ at hotties in real life.

Making friends at Tropical Heat. Photo by Larry Blackburn

Key West BrewFest

Grab a pal and a pint for this lovingly crafted Labor Day celebration of all things ale. Sample nearly 200 beers and ales at events throughout the island, including an oceanside tasting festival, special beer-focused menus, tap takeovers and more, Sept. 3 – Sept. 7.

Fantasy Fest

For a city famous for its embrace of clothing-optional spaces, one of the biggest events of the year is this festival of costumed parties. (Sure, sometimes “costume” is little more than some body glitter.) From Oct. 16 – Oct. 25, revelers of all sorts will flood the street in their finest fantasy wear.

Big Dipper performs at Key West Bear Weekend. Photo by Larry Blackburn

Key West Bear Weekend

Nothing to fear here; these bears are of the friendly variety. As long as you don’t mind a little fur, you can embrace a bigger definition of beautiful Oct. 28 – Nov. 1.

New Year’s Eve Shoe Drop

Andy and Anderson have nothing on legendary queen Sushi, whose midnight descent in a red, high-heeled shoe rivals the Times Square drop in terms of most iconic New Year starter. Grab a spot outside Bourbon Street Pub on Duval to kick off 2021 in glamorous style.

Published at Fri, 24 Jan 2020 17:59:30 +0000