Lobsterfest Trivia
Get ready to test your knowledge at the Key West Lobsterfest, featuring an evening of Pub Style Trivia with a Lobster Twist. For $50 per person, attendees can enjoy the competitive atmosphere along with a fresh lobster roll and a drink included with their entry.
Tropical Heat
TROPICAL HEAT is Key West’s HOTTEST event for all gay, bi, queer, and trans brothers!
The temperature is not the only thing that will rise during Tropical Heat. The theme parties, pool parties, and adult-oriented entertainment promises to be HOT! August on the Island is always HOT, but during Tropical Heat it promises to be STEAMY! Five hot guys and fun days are the best way to experience Key West. Tropical Heat 2026 August 12th - 16th! Don't miss it!
With the V.I.P. band, you will receive entry or discounted entry to all parties & 5-day pass to Island House.
Key West oktoBREWfest
The main tasting event takes place on Saturday, October 3rd from 3-8pm. Expect over 60 beer vendors, more than 225 types of beers, live entertainment, and a guaranteed great time! Plus the Southernmost Beach Café will be open with beer hall food specials and cocktails for those who want to change it up!
VIP tickets: early 3pmadmission to beat the crowd, comes with a commemorative poster, special stainless steel VIP mug, and a Bavarian themed buffet - $125
GA tickets: $50 (5-8pm)
Designated Driver: includes admission, soft drinks and a coupon good for 1 food item - $20
43rd Anniversary of the Headdress Ball 2026
This unforgettable evening of creativity, glamour, and entertainment will once again be hosted by legendary Key West entertainer Randy Roberts, with music by WEOW’s RudeGirl. Guests will experience an extraordinary showcase as twelve to fifteen contestants unveil their stunning Headdress creations, judged from the shoulders up, all competing for the coveted $5,000 grand prize. The evening will also feature performances by some of Key West’s most celebrated local talent, making this a true highlight of Fantasy Fest. Guests can enjoy full bar service, specialty wines, and the convenience of preordered food delivered directly to their tables.
Paint the Town Proud Pub Roll
Join us on the Old Town Trolley Tour for the "Paint the Town Proud Pub Roll", an exciting adventure outside Key West's historic and vibrant Gayborhood. This unique event celebrates the island's LGBTQ+ cultural heritage while you enjoy specially curated Pride-themed drinks at each stop. Be sure to dress in your favorite color of the rainbow to win best dressed! We'll kick off the tour at Bobby's Monkey Bar, where you can enjoy delicious breakfast bites and a welcome drink. A cash bar is also available for mimosas, Bloody Marys, or any other drinks you might want to have before the tour begins!
A Mojito Masterclass
Join us at Tropicado Mojito Bar at La Concha Hotel for an immersive, hands-on mojito experience in the heart of Key West!
Shake, “slap”, and sip your way through the art of crafting the perfect mojito as you explore Papa’s rum, fresh ingredients, and the vibrant spirit of Havana. This interactive class is a must-do for cocktail enthusiasts, curious beginners, and anyone looking to elevate their island experience.
Official Key West Pride Kick-off
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!
Songwriters Soul Brunch: Sunday Songs
Join us to celebrate the end of Songwriters Festival with a Southern-style brunch at Williams Hall's Unity Table before the "Sunday Songs: Music & Mimosas"
Brunch includes exclusive balcony seating for the show.
Comedy Songwriters Show with Keifer Thompson
It's Songwriter's Festival in Key West, and songwriters are famously funny... So join us for a night of musical comedy!
Keifer Thompson is an award-winning country music artist and songwriter and now comedian. He is co-founder of the Grammy nominated multi-platinum country music duo Thompson Square. Keifer will be joined by hit songwriter Bobby Pinson and singer/songwriter Paul Orehovec. He will also be joined by a few surprise comedians and musical guests, (local and visiting), performing brilliantly fun original and parody songs that you've never heard.
Sunshine at the Sandbar with a Sunset
Kick Off Songwriters Week on the Water with Erica "Sunshine" Lee! ☀️🎤
Get ready for the ultimate private concert experience! We’re hitting the waves for 6 hours of sun, music, and good vibes. Catch a live 1-hour performance by Erica "Sunshine" Lee while we cruise.
Saturday Parade Viewing Party
Get ready for the most spectacular event of the year! Vinos on Duval invites you to a special viewing party for the legendary Fantasy Fest Parade.
Located directly on Duval Street, Vinos offers a perfect vantage point to take in all the elaborate floats, wild costumes, and electrifying energy of the parade. Join us on Saturday, October 25th, as Key West transforms into a vibrant playground of "Bedtime Stories & Magical Monsters."