Upcoming Events in Key West
Everything happening soon in Key West. See what's on this weekend.
Thanksgiving Day
The Pub marks Thanksgiving with a special menu of holiday-inspired drinks and a festive atmosphere for guests to give thanks together. While details are pending, patrons can expect a relaxed, family‑friendly environment to enjoy the holiday on Duval Street.
Bone Island Bare It All Winter 2026
Bone Island Bare It All invites gay naturists and open‑minded guests to a weekend of clothing‑optional fun at the Pub’s pool and garden spaces. The event runs from December 3‑6, offering a blend of music, social mixers, and a relaxed island vibe for those who love to go au naturel.
Welcome Back
After a season-long hiatus, Waterfront Playhouse throws open its doors for a celebratory "Welcome Back" night on December 14, inviting the Key West community to rediscover the theater’s intimate charm. Guests can expect a lively opening program that showcases the venue’s eclectic mix of local talent and a glimpse of upcoming productions. The event captures the island’s festive spirit while highlighting the theater’s role as a cultural gathering place.
13 Days of Christmas
Starting December 17, the Pub launches a festive series of daily holiday events, each offering unique activities, drink specials, and seasonal décor. The 13‑day celebration runs through December 30, giving guests plenty of opportunities to soak up Christmas cheer in Key West’s most lively nightlife spot.
Ugly Sweater Party with Holly Dae
Holly Dae hosts an ugly‑sweater soirée where guests compete for the most hilariously hideous holiday attire while enjoying themed cocktails and a festive playlist. The Pub’s poolside bar adds a tropical twist to the classic winter tradition, making it a must‑attend for holiday revelers.
Under the Mistletoe – Onesie Party
Guests are invited to don cozy onesies for a relaxed holiday gathering featuring a mistletoe‑themed photo booth, seasonal drinks, and a laid‑back DJ set. The Pub’s indoor garden bar provides a warm, festive setting for friends to mingle and celebrate the season in comfort.
Christmas Light Trolley Tour from Bourbon Street Pub
The Pub offers a guided trolley tour of Key West’s most dazzling holiday light displays, complete with a festive cocktail served on board. For $25, participants can enjoy a scenic ride through the city’s decorated neighborhoods while sipping a seasonal drink and snapping photos of the twinkling streets.
Red Underwear Party for Men
A men‑only night where participants wear red underwear, enjoy a $15 cover, and dance to a high‑energy DJ set in the Pub’s pool area. The event blends playful dress‑code fun with the venue’s signature adult‑only atmosphere, creating a memorable night for the local gay community.
Holly Dae Christmas Special
Holly Dae hosts a festive holiday special featuring Christmas‑themed games, a sing‑along, and special drink promotions. The evening runs from early evening into the night, giving guests a chance to celebrate the season with a beloved local personality.
Merry Merry Christmas – Live Music Singalong
A holiday‑themed sing‑along invites guests to belt out classic Christmas tunes while a live band provides upbeat accompaniment. The Pub’s festive décor and seasonal cocktail menu create a warm, communal atmosphere perfect for families and friends gathering for a musical celebration.
Miracle on Duval Street – Let It Snow!
On Christmas Eve, the Pub creates a winter wonderland with artificial snow, holiday drink specials, and live music that keeps the festive spirit alive into the night. Guests can enjoy a magical, snow‑filled experience right in the heart of Key West’s bustling Duval Street.
Christmas Day – BYOC (cookies!)
The Pub invites guests to bring their favorite cookies for a BYOC (Bring Your Own Cookies) celebration, paired with holiday drink specials and a cozy, festive atmosphere. It’s a sweet way to spend Christmas Day with friends, family, and fellow island locals.
Great Gatsby NYE 2026
Click here for Tickets ~ Great Gatsby NYE 2026 ~ Click here for Tickets