The Events We’re Looking Forward to at Key West Pride 2023

On an island that’s as “live and let live” as Key West, it makes perfect sense that we were one of the first popular LGBTQ+ travel destinations in the country. It’s also no surprise that Pride is a big holiday for us. After all, our official motto is ‘One Human Family’ - and we do know how to throw a party. Where else do you get to carry the rainbow flag from coast to coast? That said, Key West Pride is back June 7 - 11, 2023. Here are some of the Pride events you can’t miss:

Sea-to-Sea Diversity Flag 20th Birthday Events

The iconic Sea-to-Sea Diversity Flag turns 20 years old in 2023, and there are tons of events honoring its birthday. First up, there’s a special Flag Bash at Hard Rock Café on Wed. June 7 at 5:30 p.m. The party kicks off Key West Pride 2023, and entry is only $20 and includes open bar access and an array of appetizers and desserts. For three nights, June 9 - 11 from 8 - 10 p.m., there’s the Sea-to-Sea Diversity Flag Laser Light Show the entire length of Duval Street. Lastly, there will be a free documentary on the creation of the Key West Pride flag that will be shown in the 800 block of Duval Street on June 10 at 8:30 p.m.

Hedwig and the Angry Inch

Wed. June 7, through Sat. June 10, 2023 @ 8 p.m., The Waterfront Theater

The award-winning musical about Hedwig Robinson, a genderqueer, East German singer of a struggling rock and roll band. The musical follows Hedwig and her backing band, the Angry Inch, as they seek retribution from her former pupil and musical collaborator. Phillip Cole White stars as the lead character in John Cameron Mitchell and Stephen Trask’s uber popular musical, which has been an on-and-off Broadway mainstay since the 90s. Get tickets to Hedwig and the Angry Inch here.

For more live theater, see The Gulf at Fringe Theater, June 7 - 8, which won the Lammy Award for LGBTQ+ Drama. Get tickets to The Gulf here.

Fury “Tea on the Sea” Sunset Sail

Thurs. June 8 @ 6 p.m., Opal Key Marina

Fury is hosting a one-night-only “Tea on the Sea” Sunset Sail that puts a new twist on the tea dance. The two-hour sunset sail aboard the state-of-the-art catamaran includes a DJ and dancing, a large sunset viewing area, and appetizers, margaritas, Champagne, and more boozy beverages. Get tickets to the Fury Sunset Sail here.

The Gates Hotel has partnered with Fury to offer a very special Fury Watersports Package. Save up to 25% off your nightly rate with this exclusive special offer, plus choose from two amazing Key West experiences with the best tour company in the Keys.

The Big Gay 5K Key West

Sat. June 10 @ 8 a.m., 725 Duval St.

The over-the-top inaugural run begins and ends at the famous Rainbow Crosswalk on Duval. Best of all, with awards like ‘Most Spirited’, ‘Best Hair’, ‘Hottest Socks’, and ‘Shortest Shorts’, The Big Gay 5K Key West is sure to be a spectacle. The first 100 runners to cross the finish line get something extra special as well.

Key West Pride Parade

Sun. June 11, 2023 @ 5 p.m., Duval Street

This is the big one - and in our opinion one of the most beautiful representations of Pride in the country. Here you’ll see the mile-long rainbow Key West Pride flag stretching from the Gulf of Mexico to the Atlantic Ocean, held up by members of the Key West community. It’s a profound moment to witness in person. Don’t miss the closing ceremony on the corner of Duval and Petronia St. at 8 p.m.

[Check out the Biggest LGBTQ+ Festivals in Key West]

Are you joining us for Key West Pride 2023?

The Gates Key West ensures you do Pride in style. Check our availability here. From the Key West Pride Street Fair to the Street Fair Disco Party on Duval, see a complete list of events at the Key West Pride 2023 Schedule.

The Gates Hotel is a Condé Nast award-winning hotel located in New Town, which offers free shuttle service to Old Town. Exciting onsite amenities - like a food truck, cigar lounge, and a spectacular swimming pool - puts The Gates in its own special category. See our special offers online.