Events & Activities
Welcome Party @ Island House
Kick off your trip to Key West with a party at the world famous Island House Resort. Hang out poolside and enjoy complimentary hors d'ourvers, cocktails, and shots from the naked cabana boys of Island House.
Complimentary cocktails and hors d'ouvers provided.
Location: Island House Key West
1129 Fleming Street, Key West, FL 33040
Date & Time: Thursday, September 14, 2023: 6:00pm to 9:00pm
A&B Marina VIP Reception
Mingle with our event VIP's at the beautiful Key West Harbor. Enjoy live music, hot appetizers, and cocktails as you take in the sights and sounds of the Key West harbor.
Complimentary hot appetizers and cocktails.
Thank you to our VIP's for supporting our event and our community.
Location: A&B Marina
700 Front Street, Key West, FL 33040
Date & Time: Friday, August 31, 2018: 11:00am to 1:00pm
Beachball Pool Party
Join the boys at Bourbon St. Pub's men-only clothing optional Garden Bar. Try the pool, hot tub, lounge on the "beach", or pull up to the bar. Complimentary cocktails and weiners provided.
Location: Bourbon St. Pub Garden Bar, 724 Duval Street, Key West, FL 33040
Date & Time: Saturday, September 16, 2023: 12:00pm to 2:00pm
Poolside Bingo with Bouvèé
Join this New Orleans queen as she serenades you, laughs with you, drinks with you, and calls BINGO for you... all POOLSIDE!
Complimentary cocktails and snacks beginning at 4:30pm, bingo starts at 5:00pm.
Come on out for a cocktail, laughs, make some song requests, and enjoy some BINGO!
For information on our hostess, visit www.missbouvee.com
Location: Alexander's Guesthouse, 1118 Fleming St., Key West, FL 33040
Date & Time: Sunday, September 17, 2023: 5:00pm to 7:00pm
Sunset Dinner Cruise
All aboard for Key West’s legendary sunset dinner cruise celebration! Enjoy unbeatable views of the sunset along with an amazing tropical food buffet and open well bar. Grab a tropical beverage and groove into the sunset as our local steel drum performer fills the air with tropical vibes.
Location: Key West Harbor
Date & Time: Saturday, September 16, 2023: 5:30pm to 7:30pm
Please Note: The Sunset Dinner Cruise is included with the "2nd" and "3rd" packages only.
If you have the "1st" package, you can purchase the Sunset Dinner Cruise add-on for $80.
Clothing-Optional Shopping Experience
Another only in Key West Experience!
During our exclusive shopping event, 3 unique Key West stores will be open only to event attendees and will be allowing clothing-optional shopping so that you can get that perfect fitting.
Remember to put something on while walking between stores!
Graffiti Key West: 721 Duval Street
In Touch: 706-A Duval Street
LeatherMaster Key West: 418 Appelrouth Lane
Date & Time: Wednesday, September 13, 2023: 6:00pm to 9:00pm
Say your goodbye's while enjoying a delicious hot and cold breakfast. Choose from a selection of eggs, bacon, fresh fruit, pastries, coffee, tea and juice.
Date & Time: Monday, September 18, 2023: 8:00am to 10:30am
Please Note: The Farewell Breakfast Buffet is included with the "2nd" and "3rd" packages only. If you have the "1st" package, you can purchase the Farewell Breakfast Buffet add-on for $25.
Chub & Chaser Contest
We're presenting a sexy Chub & Chaser competition for our community's hottest men. Contestants vying for the Mr. Chub and Mr. Chaser titles will be judged by a hot panel of previous contest winners.
All attendees will be eligible to enter the contest.
Location: Bourbon St. Pub Garden Stage
Date & Time: Sunday, September 17, 2023: 9:00pm
Conch Train Tour
See the Best of Key West on the train tour that's been entertaining visitors to the Island City of Key West, Florida since 1958. The Conch Train is one of Florida's most popular attractions, and for good reason. Their expert 'engineers' and friendly staff have delighted over 15 million guests with legends such as Ernest Hemingway and lores of this charming tropical paradise. Your tour of Key West will give you a conch's eye view of all the wonderful Key West attractions.
Location: 303 Front Street, key West, FL 33040
Date & Time: Wednesday, September 13, 2023: 3:30pm
Crystal Head Dance Party
Dance the night away at Key West's newest dance club: Sidebar.
Entertainment will be announced closer to the event.
Complimentary cocktails for the first 2 hours of the party!
Location: Sidebar Key West, 504 Angela St., Key West, FL 33040
Date & Time: Saturday, September 16, 2023: 9:00pm
Note: This party is included in all packages.
Card & Board Games
Socialize over your favorite card and board games, while enjoying the Key West vibe, music, drinks, and men-only environment of Garden Bar.
Location: Bourbon St. Pub's Garden Bar, 724 Duval St., Key West, FL 33040
Dates & Times: Please see the schedule for daily hours.
Come As You Are @ Saloon 1
Come As You Are is the official Key West motto.
Anything goes at Saloon 1, featuring an outdoor patio, sling, and other special areas. Their famous Cock Shock contest will take place at Midnight, featuring special contest categories and prizes that focus on body proud and sex proud.
Location: Saloon 1, 504 Petronia St., Key West, FL 33040
Date & Time: Friday, September 15, 2023 from 11:00 PM
Check-in when you arrive!
The registration desk will be available for all guests to check-in for the event, collect their welcome packet, and get their personalized event badge. The badge will be required to access and participate in any of the event activities, excursions, and to gain reciprocal access to all the venues. All event guests are required to check-in with the registration staff upon arrival.
Aside from the check-in process, the staff at the registration desk will also be there to assist you throughout the event with excursions, upgrades, schedules, Key West info, or any other questions.
Wednesday: Bourbon St. Pub Garden Bar
Thursday-Sunday: Island House Key West
Dates & Times: Please see the schedule for daily hours.