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The Flamingo Resort (4601 34th Street S., St. Petersburg) is Tampa Bay’s largest gay resort, and since it opened five years ago, it has welcomed tens of thousands of customers, many of whom have become regulars, simply because they can’t get enough of the camaraderie and the fun experiences they have there. flamingo_4 copy

The staff at Flamingo welcomes you for the resort’s fifth anniversary weekend parties, which will be held from August 22-24. The guest of honor and headlining entertainer this weekend is Penny Tration from RuPaul’s Drag Race season five. She holds the distinction of being one of only two queens in the show’s history to be cast by winning a “fans’ choice” online vote. She will be performing with the Flamingo Royal Players on Friday, August 22 at 11 p.m.

flamingo_2 copyThe entire weekend will be filled with parties, shows, special guests, surprise giveaways and contests, including a Flamingo Employee Turnabout on Thursday, August 21 at 9 p.m.; the proceeds from this specific event will benefit AIDS Walk Tampa Bay. There will also be a Drag Olympic Games, which will immediately follow the T-Dance at 6 p.m. on Sunday, August 24. Most everything will be priced in the theme of “5” (for example, room prices will start at $55.55 per night). Forget about cover, though; there is no charge to get in for any event on the anniversary weekend.

I recently had the chance to speak with Flamingo Resort’s owner, Jack Dougherty; Brian Smith, marketing and events coordinator; and David Baker, the resort director, about the anniversary weekend and also some big changes coming to the resort itself.


I hear there are some changes coming to the Flamingo. What all do you have in store for us?

Brian: We are installing sand volleyball courts right now and those should be ready for people to use by the weekend of the anniversary party. We’re doing some light renovations to our main bar, and we’re starting to build a little bridge that will run across the center of the pool so we can hold drag shows and other events right there over the pool. Then we’re also doing room renovations, and those will start in the next thirty days.flamingo_1 copy

What changes are you making to the rooms?

Brian: Phase one of the room renovations involves ripping up all the carpets and replacing them either with tile or with stained concrete. Either way, the carpets will be out of the rooms. We’ll also be adding flat-screen TVs and making the furniture, bedding, and bathrooms more modern.

I also hear that there’s going to be more entertainment options for people to enjoy as well. Tell us about that.

Brian: We’re doing a lot more theater-type shows. Our Blue Room has morphed into a theater and production area where we charge admission for people to see shows.

Coming up for Labor Day Weekend, we’re going to be hosting a burlesque and cabaret show in our Blue Room, and the cast in that show is going to consist of both men and women. There’s going to be three separate showings of this burlesque/cabaret production, one on Saturday night, one on Sunday afternoon and one on Sunday night that weekend.

What secrets can you reveal to us about what’s in store for the upcoming anniversary weekend?

Jack: I will say that Saturday is going to be a full day, filled with of lots of different surprises. The Skyway Marina District is going to be sponsoring a classic car show in our parking lot from 10 a.m. to 2 p.m. and there will also be food trucks for people to enjoy.

We’re bringing back people from our past for the anniversary. We’re going to be bringing back DJ Eric Overstreet, who used to DJ here for years. He’s going to be DJing the pool parties. We’re also going to be bringing back a lot of old show cast members. Luisa Salome and Bobby York will be coming out of retirement just for the anniversary weekend; they will be performing on Saturday night.

We’re going to be having a fireworks show on Saturday night and hopefully on Sunday too if the neighbors don’t complain. [laughs] flamingo_3 copy

What are you most excited about for the future?

David: I think the most exciting thing, for me anyway, is to finally be able to follow through with renovation — to update the rooms. When we opened, it was a ton of work, much more than I think people realize that we had to do in such a short amount of time. We always wanted to go back and redo the rooms, so it will be nice to create nice, clean spaces that are more contemporary. I think once we finish that, it will energize people and make them want to return because things are looking nicer and prettier. I think people will be really excited about our upcoming facelift.

For more information about the Flamingo Resort, visit Book your trip to the Flamingo via their website or by calling their reservation hotline at (727) 321-5000.