It isn’t actually Orlando Pride until the middle of October, but they start off World Pride Month with three different multi-day events over the first few days of June. I was lucky enough to check out One Magical Weekend, Gay Days, and Girls in Wonderland over three days of fun in the sun this year. There is a lot to check out at each of them, with a wide variety of events and people to choose from.
Each organization has a host hotel where the majority of their events take place, but I stayed at the Margaritaville Resort in nearby Kissimmee. Orlando is quite a spread-out city so with planning to attend events from all three organizations I had to spend time on the road regardless to get to all of them. This resort only opened in 2019 so it’s quite new and it’s huge, covering a whopping 300 acres that includes a shopping center and water park.
For the events, One Magical Weekend has three days of non-stop partying with the Sheraton Lake Buena Vista Resort being the home of the "Therapy" pool party each afternoon and the "Cadabra" after-party each night. During the evening, in between those parties, are the main events – "Riptide" at Disney’s Typhoon Lagoon, "Varsity Red" at the House of Blues, and "Wig Party" at the host hotel.
GayDays provides a variety of dance parties over multiple days as well, in addition to some other events like XXX Bingo, the Miss GayDays Crowning, Mr GayDays Leather, and the Puppy Mosh – which all take place at host hotel Avanti Palms. A special day at Disney World and SeaWorld are also included as options for being out and about with other GayDays attendees.
Both One Magical Weekend and GayDays are aimed at and primarily attended by men so of course the women need somewhere to party too and that’s where Girls In Wonderland comes in. Over the three days there are a variety of parties and events, live music and comedy, and everything from happy hour lounges to rocking after-parties – many taking place at their host hotel, the Grand Orlando Resort.
After two years of not being able to have any of these events there was definitely a sense of excitement and gratitude for being able to gather again like this, by both the organizers and attendees. I went to an afternoon pool party at Girls In Wonderland, joining a lesbian couple who invited me along, and it was packed with all kinds of women having a great time. I went to both an afternoon and an evening pool party at GayDays and saw a wide variety of men, so they seemed to have something for everyone. And for One Magical Weekend I went to an afternoon pool party and two of the main evening events, where I noticed plenty of eye candy along with some famous drag entertainers.
Orlando certainly provides a unique and varied combination of exciting events to kick of Pride month. The city has been named America’s top LGBTQ-friendly destination by ParkSleepFly.com and has continued to be loud and proud despite hardships experienced by the community. While in the city I also visited the Pulse Interim Memorial where photos, posters, and other memorabilia can be found on the site of the former nightclub. The permanent National Pulse Memorial will eventually be located there, along with a museum and education center about half a kilometer away. A Survivor’s Walk will also trace the three-block journey that many victims and first responders took the night of the tragedy to get to a medical center, during Pride month 6 years ago.
With its famous amusement parks, LGBTQ-friendly atmosphere, and variety of events to choose from for whoever you are and whatever/whoever you’re into, Orlando kicks off World Pride month with a bang, while also putting a focus on how far the community has come and some of the adversities faced along the way.
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Contributor Josh Rimer |
Locale Orlando |
Topic Travel |

Josh Rimer is a travel writer and content creator who may be best known for his video segments on YouTube and OUTtv, but he was also Mr. Gay Canada 2019. Follow him on Instagram at @JoshRimer.