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Note: All travel is subject to frequently-changing governmental restrictions—please check federal, state, and local advisories before scheduling trips. All information is current to the best of our knowledge as of date of publication.

Feeling festive? If you’re here, you’re queer, and you want to enjoy some holiday cheer, there are plenty of things to do in December. Think Speedo-clad runners, drag extravaganzas, NYE bashes, and more. Before heading out, check to make sure events are still happening and know that some may require participants to be fully vaccinated.

RELATED: Visit our LGBTQIA travel hub for welcoming hotels, the ultimate queer events calendar, inspiration, and more!

A Drag Queen Christmas: Multiple cities

It’s a crossdressing Christmas for all of us as hosts Trinity the Tuck and Monét X Change drag (pun intended!) an entourage of notable queens like William, Sasha Velour, Shea Couleé, Jaida Essence Hall, and others across the country for this multi-city holiday extravaganza with stops in major cities like Phoenix, Dallas, Austin, LA, Orlando, Portland, and elsewhere. In fact, this show officially kicks its heels up beginning November 10 in Detroit so sashay on over to their official website and snatch a couple tickets in a city near you.

Excited for the holi-gays? Book an LGBTQ-welcoming hotel here!

Key West NYE High Heel Shoe Drop

Photo: Andy Newman/ Florida Keys News Bureau

It’s a NYE tradition befitting of the kooky Conch Republic. At the stroke of midnight in front of neighborhood LGBTQ bar the Bourbon Street Pub, local drag queen Sushi cradles herself inside a giant red high heel and is then dropped from 20 feet high. Expect to see all of Key West in attendance, from families with small children to bachelorettes to festively clad queer folks.

Let the sun shine in. Book your Key West hotel here!

Masterbeat NYE: Los Angeles

Photo: Courtesy of Masterbeat

The City of Angels cools off considerably in December, but expect plenty of sweat and heat at this massive La La Land NYE party, which claims to be the largest in the world. This year’s theme is Under the Big Top (yes, we’re chuckling, too) and this 3-ring circus includes 8 ringmasters to help usher in the new year. This one begins December 30 and continues nonstop until 2022. You’ve been warned.

Fa la la land? Book your Los Angeles hotel here!

Puerto Vallarta NYE 2022

Why spend just one night celebrating New Year’s Eve when instead you could do seven? Yes, Puerto Vallarta NYE 2022 (Dec 28–Jan 4) is a spinoff of the famous White Party, and offers seven sun-drenched days in coastal Mexico’s undisputed queer paradise, coupled with seven nights of wild parties hosted by some of the most renowned DJs in the scene. As for PV weather in December… It’s darn near perfect.

Looking for the Mex best thing? Book your Puerto Vallarta hotel here!

The Return of the Jinkx Monsoon and Dela Holiday Show, Live!: Multiple cities

Photo: Jiji Lee

You better watch out, you better not cry… well you might cry tears of laughter as drag stars Jinkx Monsoon and Dela (aka BenDelaCreme) sweep across the nation with the return of their song and dance and sass-filled holiday extravaganza. This show kicks off stateside November 30 in Portland, Maine and includes stops in most major cities along the way. But both these queens hail from the Pacific Northwest, so it’s the five-night Seattle residency (Dec 21–24, 26) at the Neptune we so badly want to see.

Travel doesn’t have to be a drag. Book an LGBTQ-welcoming hotel here!

San Juan Winter Pridefest

Puerto Rico, we love you. When winter has us feeling blue, you are the guaranteed antidote. Winter Pridefest (Dec 9–13) offers a glitter-filled shot of Vitamin D, including beautiful beaches, dozens of live performances, circuit parties, and more in the Caribbean’s LGBTQ capital.

Juan more? Book your San Juan hotel here!


Santa Speedo Run: Multiple cities

Photo: Rodney Brown (Flickr, Creative Commons)

It started with five guys running around the streets of Boston in December 2000 in nothing but skimpy swimsuits and Santa hats, and has since turned into an annual tradition that has raised millions and—not surprisingly—has been co-opted by the LGBTQ community. These days the costumes have gotten increasingly outlandish (leather fetish Rudolph, anyone?), and since 2000, the run has spread to other cities nationwide, including Atlanta, Chicago, Denver, and San Francisco. In 2020, the Boston run happened in small groups to accommodate the pandemic, so we imagine this year’s Beantown run (and also other cities) will be a go!

If you think a Speedo is neat-o, book an LGBTQ-welcoming hotel here!

Tagged: Boston, California, Caribbean, Florida, Key West, LGBTQIA, Los Angeles, Mexico, Puerto Rico

Note: Orbitz compensates authors for their writings appearing on this site.

Jason Heidemann

Jason Heidemann

Jason is a Lead Content Specialist for Expedia Group, and manages content initiatives across numerous Expedia-owned brands. His work has been featured in the Chicago Tribune, Time Out, the Huffington Post, Chicago Magazine, Passport and many others.

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