While there, the Pride House Mission team hopes to deliver its message of inclusion directly to the International Olympic Committee.
"To go into that kind of environment and show the IOC that it's so important to ensure this never happens again. It undermines the credibility of the games, the power of the Games to bring people together in peace and sport."
Douglas says she knows it will not be easy being a gay advocate in Russia. President Vladimir Putin recently passed anti-gay laws, and a rash of attacks on the gay community have some calling for a boycott of the Games.
"I think the first day is really going to be about getting a sense of how does this place fee. Is it excitement? Is it trepidation? We will have to get a sense of that when we get there."
Douglas and Stevenson will be trying to meet with Olympic officials. She knows getting access to them could be challenging.
"If we find that we are getting shut out, it does change the story and it turns this homophobic situation into something far, far greater."
Douglas' wife Cindy Filipenko supports her, but did not want to go herself.
"Having gone through the Whistler experience, which was so inclusive, such a fantastic experience, I think going to Sochi would be a sad comparison," says Filipenko.
Douglas says she'll be continually testing the waters.
"I want to wear a Canadian flag slash rainbow pin. Is that going to get me stopped on the street? We will have to decided when we get there if it's too dangerous to do."
Despite her trepidation, she says she's hoping for the best and going in with a positive attitude.