Big Gay Key West Gears Up for Sunny Bear Fun and Extra-Special Photo Shoot


Key West is famous for its colorful LGBTQ+ community, welcoming travelers for special events and for year-round fun in the tropical sun. Visitors from around the U.S. and the world come to South Florida's quirky, welcoming destination to enjoy great food, recreation, and a sense of easygoing kinship. Queer travelers are especially drawn to this island led by out lesbian mayor Teri Johnston–Florida's first-ever lesbian mayor–where a rainbow flag flies all year at City Hall and "One Human Family" has long been the official motto.

Among many fabulous Florida-Keys events, few make a splash like Big Gay Key West, one of the top social gatherings of the year for gay bears, chubs, chasers, and their admirers. Happening September 13-18, 2023, Big Gay Key West makes the country's southernmost city the most fun, safe destination for big, beautiful gay guys to connect and relax over six festive late-summer days.

This year's event will kick off on day one with an extra-special photo shoot of beautiful chubby male bodies, as well as other types of bodies, which will be part of a hardcover photo book.

Big Gay Key West features exclusive access to four lovely, luxurious all-male clothing-optional resorts: Island House, New Orleans House, Alexander's Guesthouse, and Equator Resort. All four guesthouses are located walking distance apart, and they'll share reciprocal access throughout the six Big Gay days. For 2023, the Marriott Beachside Key West Hotel has joined to accommodate even more event guests.

Across the participating host hotels, enjoy nightly happy hours, rotating pool parties, 24/7 access to Island House's health club, and plenty of surprises. The event is proudly sponsored by and Crystal Head Vodka, along with five hotel partners: The Key West Business Guild, the Monroe County Tourist Development Council, and other vital supporters.

Big Gay Key West features packages of activities, excursions, parties, and perks available at three pricing tiers, which include souvenirs, complimentary cocktails and hors d'oeuvres, as well as access to resorts, nightclubs, and exclusive venues.

Level up to second-tier "Cabana Boy" status to add in a sunset dinner cruise, event T-shirt, and farewell breakfast. Or with the top-tier "Key West Conch" package, guests will get added VIP benefits, one-of-a-kind event swag, and supporter listing in the event program.

Hotel lodging and transportation to/from Key West are not included with any of the event packages, so be sure to book your hotel and airfare separate from your event-registration package.

This year's Big Gay Key West features a very special photo shoot for the community to be part of a unique hardcover photo book. On September 13th at Equator Resort, organizers will hold a nude photoshoot focusing on the artistic beauty of the big gay man's body, body hair, and curves (excluding privates), while capturing the strength and manliness of each subject. This project aims to showcase beautiful relationships between men of all sizes, with artfully erotic and romantic flair. All registered guests are invited to the photo shoot, hosted by Equator with complimentary cocktails and bites.

Big Gay participants can apply to pose for the photo shoot by emailing [email protected] with your full name, phone number, and headshot. Photo models will pose as unpaid volunteers, though they will receive a complimentary copy of this original coffee table–style book upon publication. Participants who purchase the Key West Conch package also will receive a complimentary copy of the book.

Here are some top highlights ahead for Big Gay Key West 2023.

Here are some top highlights ahead for Big Gay Key West 2023.

Big Gay Key West Kickoff at the New Orleans House
New Orleans House Garden Bar, 724 Duval St.
Wednesday, September 13, 12 noon

Event attendees pick up their registration bag of goodies, then enjoy a complimentary Jersey Mikes welcome lunch poolside at the New Orleans House Garden Bar. Expect to behold beautiful men displayed as serving trays, known as Nantaimori, for refreshing bites.

Photo Shoot & Pool Party
Equator Resort, 822 Fleming St.
Wednesday, September 13, 4 pm

Apply in advance to participate as a model, or just enjoy the view while we conduct a professional artistic nude photo shoot of men of all sizes from our community. The photos will be featured in a "coffee table" style hardcover book that will be published after the event and shared with the community. Complimentary Crystal Head cocktails included.

Bourbon Street Pub Welcome Party
Bourbon Street Pub, 724 Duval St.
Thursday, September 14, 8:30 pm

The Men of Bourbon dancers of all sizes will entertain, followed by the chub/chaser contest at 10pm. Complimentary Crystal Head cocktails and snacks included.

Big Gay Key West Welcome Party provided by the Island House Resort
Island House Key West, 1129 Fleming St.
Friday, September 15, 4 pm

The famous Island House Resort will provide gourmet hors d'ourvers and Crystal Head cocktails. The friendly naked boys of the Island House Resort will serve tasty shots poolside.

Poolside Bingo with Miss Bouvèé
Alexander's Guesthouse, 1118 Fleming St.
Saturday, September 16, 1 pm

Join poolside bingo featuring the hilarious Ms. Bouvèé. Complimentary Crystal Head cocktails and snacks included.

Key West Conch VIP Reception
A&B Marina, 700 Front St.
Saturday, September 16, 4 pm

Prior to the Sunset Dinner cruise, Key West Conch–package attendees will mingle dockside by the A&B Marina while enjoying live music, hot appetizers, and complimentary cocktails.

Key West Sunset Dinner Cruise
Key West Harbor
Saturday, September 16, 5:30–7:30 pm

Enjoy the largest privately chartered sunset cruise for chubs, chasers and bears in Key West, with an amazing tropical food buffet and open well bar.

The Club 504 Crystal Head Dance Party
Club 504, 504 Angela St.
Saturday, September 16, 9 pm

Dance the night away at Key West's newest dance club, Club 504. Complimentary two-hour Crystal Head cocktails during the party.

Farewell Breakfast
Saint Hotel Key West, Autograph Collection, 417 Eaton St.
Monday, September 18, 8 am

Bid adieu to your fellow Big Gay Key West friends while enjoying a sit-down plated breakfast cooked to order, paired with unlimited mimosas (included).

Be sure to register for Big Gay Key West before packages sell out, and book your hotel and airfare soon for the September 13-19 event.

by Kelsy Chauvin

Kelsy Chauvin is a writer, photographer and marketing consultant based in Brooklyn, New York. She specializes in travel, feature journalism, art, theater, architecture, construction and LGBTQ interests. Follow her on Instagram and Twitter at @kelsycc.

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