Note: All travel is subject to changeable government restrictions frequently – please check federal, state and local advice before scheduling a trip. All information is present as the best of our knowledge as of date of publication.
Feeling festive? If you’re here, you’re curious, and you want to enjoy some holiday fun, there are plenty of things to do in December. Think speedo-clad runners, drag extravaganza, NYE bash and more. Before heading out, check to make sure events are still happening and be aware that some participants may need to be fully vaccinated.
Related: Visit our LGBTQIA Travel Center to welcome hotels, the ultimate bizarre event calendar, inspiration and much more!
A Drag Queen Christmas: Multiple Cities
As the host of Trinity the Tuck and Monet X Change Drag (pun intended!) It is a crossdressing Christmas for all of us, William, Sasha Vellore, Shea Cooley, Zaida Essence Hall and a group of notable queens across the country like Phoenix, Dallas, Austin, LA, Orlando, Portland, and elsewhere, including city stops. In fact, the show officially kicks off in Detroit on November 10, so Cucumber went to their official website and snatched a few tickets to a town near you.
Excited for Holi-Guess? Book a LGBTQ-Welcome Hotel Here!
Key West NYE High Heel Shoe Drop

Photo: Andy Newman / Florida Kiss News Bureau
This is a NYE tradition suitable for the Cookie Conch Republic. During a midnight stroke in front of the nearby LGBTQ Bar Bourbon Street Pub, local drag queen Sushi wrapped herself in a huge red high heel and was then lowered from a height of 20 feet. Expect to see all of Key West in the presence of weird people dressed in festive costumes, from little kids’ families to bachelors.
Let the sunlight come. Book your Key West Hotel here!
Masterbit New: Los Angeles

Photo: Courtesy of Masterbit
Angels City gets quite cold in December, but lots of sweat and heat can be expected at this huge La La Land NY party, which claims to be the largest in the world. This year’s theme is Under the Big Top (yes, we’re laughing too) and this 3-ring circus includes 8 ringmasters to help in the new year. It started on December 30 and will continue till 2022. You have been warned.
Fa la la land? Book your Los Angeles hotel here!
Puerto Vallarta NYE
Why spend just one night celebrating New Year’s Eve when you can do seven instead? Yes, Puerto Vallarta NYE 2022 (December 28-January 4) is a spinoff of the famous White Party, and offers seven sunny days at the undisputed Quier Paradise in coastal Mexico, with which seven nights wild party is organized. DJ in the scene. For PV weather in December … it’s close enough.
Max looking for the best thing? Book your Puerto Vallarta Hotel here!
The Return of the Jinkox Monsoon and Della Holiday Show, Live !: Multiple Cities

Photo: Gigi Lee
Take good care, you won’t cry… well you can cry tears of laughter as drag stars Jinkox Monsoon and Della (aka Bendelacrum) spread across the country with their songs and dances and sass-filled holiday outings. The show kicks off on Nov. 30 in Portland, Maine, and includes stops in most major cities along the way. But both of these queens come from the Pacific Northwest, so this is the five-night Seattle Residency in Neptune (December 21-24, 26) which we want to see very badly.
Travel doesn’t have to be a draw. Book a LGBTQ-Welcome Hotel Here!
San Juan Winter Pridefest
Puerto Rico, we love you. When we feel blue in winter, you are the sure antidote. Winter Pridefest (December 9-13) Caribbean LGBTQ offers a dazzling shot of vitamin D in the capital, with beautiful beaches, dozens of live performances, circuit parties and more.
Juan more? Book your San Juan Hotel here!
Santa Speedo Run: Multiple Cities

Photo: Rodney Brown (Flickr, Creative Commons)
It began in December 2000 with five people running through the streets of Boston, with nothing but skimpy swimsuits and Santa hats, and since then it has become an annual tradition that has grown to millions and – not surprisingly – co-opted by the LGBTQ community. Nowadays clothing has become increasingly foreign (leather fetish Rudolph, anyone?), And since 2000 the race has spread to other cities across the country, including Atlanta, Chicago, Denver, and San Francisco. In 2020, the Boston race was in small teams to accommodate the epidemic, so we imagine there will be this year’s Bintown race (and other cities too)!
If you think a Spido is clean and tidy, book an LGBTQ-welcome hotel here!
Tagged: Boston, California, Caribbean, Florida, Key West, LGBTQIA, Los Angeles, Mexico, Puerto Rico
Note: Orbitz compensates authors for appearing on this site.