All the main events and entertainment to expect at Big Gay Key West!

Don’t miss Big Gay Key West, the chub/chaser event of 2023 in the LGBT island paradise of Key West, Florida! Big Gay Key West will make a splash from September 13 – 18, 2023! 

Big Gay Key West features exclusive access to 4 beautiful luxurious all-male clothing optional resorts: Island House, New Orleans House, Alexander’s Guesthouse, Equator Resort.  Enjoy reciprocal access to all of the guesthouses (short walking distance from each other). Nightly happy hours, Rotating pool parties at multiple resorts/bars, featuring complimentary cocktails, hors d’oeuvers, 24/7 access to Healthclub amenities at Island House, and many surprises!

And since Valentine’s Day season is upon us, why not register you and your special honey Bear to attend Big Gay Key West this year as a Valentine’s Day gift? Big Gay Key West has held off on increasing registration prices until after February 15th!

Check out this list of the featured entertainment and events Big Gay Key West have to offer this year!

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. Enjoy Complimentary cocktails and hors d’ouvers.

Location: Island House Key West, 1129 Fleming Street, Key West, FL 33040

Date & Time: Friday, September 15, 2023: 4:00pm

Bourbon St. Pub Welcome Party

This will be a big one! Enjoy complimentary cocktails and snacks!!

Meet all the chubs and chasers at the legendary Bourbon St. Pub complex.  Try any of the 3 indoor bars with ample seating, or head outside to the the pool, hot tub, lounge on the “beach”, or pull up to the garden bar. 

The famous Men of Bourbon will be dancing for your entertainment, featuring dancers of all sizes. Our unique Chub/Chaser contest follows immediately at 10pm.

Location: Bourbon St. Pub Complex, 724 Duval Street, Key West, FL 33040

Date & Time: Thursday, September 14, 2023: 8:30pm

Poolside Bingo with Miss Bouvèé

Join this hilarious 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 1:00pm, bingo starts at 1:30pm. Come on out for a cocktail, laughs, make some song requests, and enjoy some BINGO!

Miss Bouvèé

For information on our hostess, visit

Location: Alexander’s Guesthouse, 1118 Fleming St., Key  West, FL 33040

Date & Time: Saturday, September 16, 2023: 1:00pm

Jersey Mike’s Welcome Lunch

After getting your registration bag, enjoy a complimentary Jersey Mike’s sandwich lunch, poolside at the Garden Bar at Bourbon St. Pub. 
Lunch is followed immediately by the Nantaimori Party. 

Complimentary Sandwiches provided.

Location: Garden Bar @ Bourbon St. Pub, 724 Duval St., Key  West, FL 33040
Date & Time: Wednesday, September 13, 2023: 12:30pm

Photo Shoot & Pool Party @ Equator Resort

Calling all models (and viewers)!  We’re organizing a professional artistic nude (no genitals in photo) photo shoot of men of all sizes from our community to be featured in a “coffee table” style book that will be published after the event and shared with the community. 
Participate in the photo shoot (registration will be available soon), or sip complimentary cocktails while enjoying the show from your favorite spot in one of the Equator pools or hot tubs. 

Photo by Larry Blackburn

All “Key West Conch” package holders will receive a complimentary copy of the book. Professional Photos/Portraits by Key West local photographer Larry Blackburn.

2 Hours of Complimentary cocktails featuring Crystal Head Vodka for all event attendees. 

Location: Equator Resort, 822 Fleming St., Key  West, FL 33040
Date & Time: Wednesday, September 13, 2023: 4:00pm

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 and marina. Thank you to our VIP’s for supporting our event and our community.

Complimentary hot appetizers and cocktails.

Location: A&B Marina, 700 Front Street, Key West, FL 33040
Date & Time: Saturday, September 16, 2023: 4:00pm

Cabana Boy Nantaimori Party

A first (we think) for our events, Our Nantaimori Party features fruits and snacks displayed and served on a naked man. Enjoy the show and join the action by having a snack!

Location: Garden Bar @ Bourbon St. Pub, 724 Duval St., Key  West, FL 33040
Date & Time: Wednesday, September 13, 2023: 1:00pm

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.

The Menu:

  • Caribbean Pulled Pork
  • Black Beans and Rice
  • Deep-Fried Sweet Plantains
  • Grilled Chicken Marinated in Pineapple and Soy Sauce
  • Fried Fish with Lemon and Tartar Sauce
  • Pasta Salad
  • Mixed Veggies
  • Mashed Potatoes
  • Cuban Bread and Butter

Open Well Bar:

  • Unlimited Well Mixed Drinks
  • Draft Beer
  • Margaritas
  • Wine
  • Champagne
  • Rum Runners
  • Soft Drinks

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!

Open Bar and free clothes check provided.

Stores include:

  • Graffiti Key West: 721 Duval Street
  • In Touch: 706-A Duval Street
  • LeatherMaster Key West: 418 Appelrouth Lane

Date & Time: Saturday, September 16, 2023: 10:00am

Farewell Breakfast

Say your goodbye’s while enjoying a delicious hot and cold breakfast. Enjoy a sit down plated breakfast cooked to order and pair it with unlimited mimosas.

Unlimited mimosas included!

Location: TBD
Date & Time: Monday, September 18, 2023: 8:00am

Please Note: The Farewell Breakfast is included with the “Cabana Boy” and “Key West Conch” packages only.  If you have the “Beachcomber” package, you can purchase the Farewell Breakfast Buffet add-on for $40.

Chub & Chaser Contest

Our Key West style Chub & Chaser competition features a stripper pole, clothing optional, and more sexy props to show-off our community’s hottest men.  Taking place immediately after the Welcome Party at Bourbon St. Pub, 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
Date & Time: Thursday, September 14, 2023: 10:00pm

Crystal Head Dance Party

Dance the night away at Key West’s newest dance club: Club 504. Entertainment will be announced closer to the event.

Complimentary cocktails for the first 2 hours of the party!

Location: Club 504, 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

As you can see, this year’s Big Gay Key West will definitely be a BIG one! If you haven’t registered yet, what are you waiting for? Register today, and find out everything you need to know about packages and events! 

For more info and scheduled events, visit

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