Key West Pride

6:30 pm – Key West Pride Follies at the Key West Theater

Join us for an outrageous, unforgettable night as the legendary Key West Pride Follies returns, bolder than ever with Dominic Paolillo and new co-host, Claire Caplan! This precursor to Pride tradition is one you won’t want to miss, featuring local talent showcasing a variety of acts, including singers, dancers, and more! Wear your favorite rainbow color and come ready to have a fantastic time! Tickets are now available HERE.

Noon – Key West Business Guild Membership Luncheon: Pride Edition

More info coming soon!

5-8 pm – The GOLD Party @ Island House for Men 

No clothing required, but wear something GOLD! Come celebrate 50 Years of Fabulous at the Best Gay Resort in The World! Gold crowns, tiaras, body paint, sequins, spandex- you name it- just make it GOLD! Tons of free appetizers served by Golden pool boys, free shots, giveaways, and 2-4-1 on all cocktails! $20 Donation benefits our friends @ Womankind. All gay, bi, queer, trans + brothers welcome.

5:30 pm –KEY WEST PRIDE KICK-OFF – The Key West Cooking Show – 291 Front Street (inside The Shops of Mallory Square, up the escalator) Presented by the Key West Business Guild and Gay Key West, this year’s Pride event carries the overarching theme of “Color the Island: A Celebration of Identity Through Color & Creativity.” Join us for a vibrant kick-off to Pride 2026 as we transform the island into a living canvas of self-expression, artistry, and community. Color the Island is more than an event; it’s an immersive celebration of identity, where every hue tells a story, and every voice adds to the theme. The celebration features local DJ Mr. Enjoy, local vendors, delicious food, and unlimited drinks! All included with your entry! Come ready to color the island with pride! This event is 21+ only. Tickets available HERE

Noon – 4 pm –  Rainbow Runway: Poolside Glam-Off  at the Lighthouse Hotel – 902 Whitehead St

Celebrate Pride poolside in full color at our Rainbow Runway: Poolside Glam-Off. DJ Rude Girl will be setting the vibe. Calling all main-character energy only. Arrive ready to showcase your style because at 3pm, we crown the Best Poolside Look, followed by a champagne spray finale you won’t forget. Glitter optional. SPF required. Pride mandatory. 21+ event. Free entry.

6 pm – Key West Pride Annual Tea on the Sea  on Fury Watersports – Opal Key Marina 241 Front St. Hop aboard Fury Water Adventures for one of Key West Pride’s most iconic traditions, a floating Tea Dance that sails straight into the sunset! With DJ Mr. Enjoy spinning  grooves, you’ll dance across the deck as the sky lights up in rainbow hues. Your ticket includes unlimited beer, wine, champagne, margaritas, and tasty appetizers—so come thirsty, come hungry, and come ready to slay at sea. Check-in by 5:45 pm, for a 6 pm departure. Tickets available HERE

9 pm – Key West Local Bartender Competition at Bourbon St. Pub – 724 Duval St

Local bars are competing to be crowned the ultimate bartender champion for Pride 2026, along with earning bragging rights! Which bar will take home the prize this year? All are welcome. 21+ event. Free entry.

11 am – Key West Pride Brunch Sail & Swim aboard the Argo Navis – 0(Zero) Duval St.

Come out sailing in support of Gay Key West and Key West Pride Week! We’re hosting a brunch, sail, & swim at this festive fundraiser ~ a portion of every ticket sold goes back to Gay Key West! Come in your favorite color or representation of the rainbow to celebrate this year’s Pride theme, “Color the Island”, and you just might be crowned the 2026 winner of Argo’s Annual Pride Cossie Contest! Guests enjoy a delicious light brunch, Bottomless Mimosas, Bloody Marys, house made Sangria and Cocktails along with Miller Lite and local craft brews. During our first hour, we sail along the historic Key West shoreline, giving you a great vantage point to take in the sights of the island. Then we anchor the boat and get ready for fun in the sun and playtime in the water! After swim time enjoy a fresh water rinse, an ice cold towel for your face and a piece of pineapple to rinse the salt taste from your mouth. Finish the afternoon with another cool drink and a sweet treat– a perfect end to the day! Tickets are available HERE

12 pm – ALL WELCOME “RU WET” Annual Pool Party at Alexander’s Guesthouse  – 1118 Fleming St.

We’re turning up the heat with Ms. Bouvee on hand serving fierce looks and fabulous fun for Drag Bingo you won’t want to miss. Enjoy poolside drag bingo, live musical performances, comedy, and audience interaction.  Plus drink specials and a live DJ playing the latest hits!

12-5pm – Sausage Fest at Island House for Men – 1129 Fleming St.
The title says it all! Join the boyz of Island House for a naked sausage fest like no other! Gourmet sausages from around the world, served by our friendly pool boyz. Savor signature Stoli frozen drinks, & food specials! All gay, bi, queer, trans + brothers welcome.

8 pm – BERTHA: Grateful Drag hosted by Beatrix Dixie at the Key West Theater – 512 Eaton St

The world’s first Grateful Drag band, BERTHA is an all-star collective of queer and allied East Nashville talent coming together in wigs and full face for a good cause. Fronted by a harmony trio of Berthas and backed by a rocking all-Bertha band. Find out why Rolling Stone Magazine said “Nashville’s Bertha, gives The Dead an irreverent, joyful maker.”, and JamBase said “BERTHA: Grateful Drag is far from a gimmick. These musicians are the real deal and have some of the best harmonies and vocals of any Grateful Dead tribute act.” Doors open 7:00 pm. Tickets Available HERE

11:30 am – Paint the Town Proud Pub Roll starting at Bobby’s Monkey Bar – 900 Simonton St.

Celebration of Identity Through Color and Creativity Street Fair  is a vibrant gathering honoring the beauty of self-expression, community, and love in all its forms. Stroll through a lively open-air festival filled with vendors, live music and dance performances. Enjoy delicious food from diverse vendors, connect with community organizations, and discover safe spaces designed for conversation, inspiration, and celebration. Whether you come to dance, create, learn, or simply soak in the joyful atmosphere, this event welcomes everyone to show up exactly as they are.

Bring your brightest outfits, your loudest cheers, and your truest self because when we celebrate identity through color and creativity, we paint a future rooted in pride, unity, and love. All welcome, family friendly event. VENDOR APPLICATION IS NOW OPEN!

10 am – MCC Church Pride Service – 1215 Petronia St.

10 am – Unity of the Keys Pride Service – 1011 Virginia St.

11:30 am – Key West Pride Drunken Drag Brunch at Mangoes Key West – 700 Duval St.

Mangoes Drag Brunch has been proudly voted Top 10 Drag Brunch Shows in the USA by the Miami Herald. This high-energy, crowd-favorite event will be featured in their air-conditioned Ricky Ricardo Private Event Space, complete with a private bar and private bathrooms; the perfect setting to enjoy an unforgettable brunch experience in comfort and style. Mangoes offers a special à la carte brunch menu, featuring delicious brunch favorites available for purchase. After the show, stick around for a meet-and-greet and the opportunity to take photos with our local stunning drag queens. Ticket Options: VIP Tickets – VIP tickets include access to the fabulous drag show, the best seats in the house, and exclusive VIP swag take-home gifts. General Admission Tickets – General Admission tickets include access to the fabulous drag show with regular admission seating.

Important Information: This event is 21+ only due to current Florida state laws. No one under the age of 21 will be admitted. No refunds. Please double-check your purchase before clicking the buy button. All tickets are non-refundable, no exceptions.

Noon – HOT NAKED SUNDAY at the Island House for Men 1129 Fleming St.

After church, and before tea dance, comes Island House! A Gay Key West tradition for over 20 years! All gay, bi, queer, trans + brothers welcome.

7 pm – Color the Island Pride Parade

Join us as we celebrate the closing of Key West Pride 2026 with our annual Parade! The parade route will begin at the Quay at Truman Waterfront, continue down Whitehead Street to Front Street, turn right onto Duval Street, and finish at United Street. After the parade, we’ll make our way to La Te Da for the “last dance.” The parade line-up will begin at 5 pm. Participants interested in joining the parade MUST complete the application available on the website above. 

Museums: Key West Butterfly Conservatory, Little White House, Key West Aquarium, Mel Fisher Maritime Museum, Key West Firehouse Museum, Key West Light House, Key West Ship Wreck Museum,  Audubon House, Oldest House and Garden Museum, USCGC Ingham Museum, Tennessee Williams Museum, Hellings Curry Museum/ Home of the Key West Woman’s Club, Ernest Hemingway Home & Museum

Land Activities: Key West Food Tours,  iWitness True Crime Tours, Fort Zachary State Park, West Martello Tower, KW Tropical Forest and Botanical Garden, Key West Cemetery, Key West Adventures, Papa’s Pilar Rum Distillery, Ghost Hunt, Old Town Trolley Tours, Conch Tour Train, Haunted Key West, Ghosts and Mysteries, Ghosts and Gravestones, D’vine Wine Gallery, Key West Fine Wine, Key West Wildlife Center, Tart Tales.

Water Activities: Argo Navis, Blu Q, Classic Harbor Lines, Cruisin’ Tikis, Danger Charters, Fish N Chicks, Fury, Island Vibe Charters, Island Vibe Charters, Java Cat, Jolly Rover II, Key West Eco Tours, Key West Sailing Center, Key West Snorkeling, Hindu Charters, Land Boat Charters, Namaste All Day Key West , Schooner America, Sunset Sail Key West, Sunset Watersports, SV Argo Navis, Yankee Freedom III