Meet the Most Popular Travel Company You Probably Didn’t Know Existed – Thrillist
Finding love, lust, and everything in between
In Floratos’s 20-year tenure at Olivia, she’s seen a dramatic change in demographic. Whereas in the past they may have skewed older and coupled up, today’s guests range from 21 to 92 years old (the older guests are called OWLs, or Older Wiser Lesbians), arriving as friends, couples, chosen families, mothers supporting daughters, and vice versa. Attendance numbers are also rising for non-binary and trans clientele.
“On [the Generation Q] trip we started to see more transgender guests join and have this sense of feeling so welcome in the community, whether that’s female to male or male to female,” says Floratos. “And there were so many guests that I met and came up to me and introduced themselves as non-binary, or clearly were in the transgender community. And that’s the beautiful thing about Olivia, as the company continues to grow it’s beyond just women as well.”
But the biggest growth in population by far has been solo travelers. “We had nearly 400 solo travelers on the [L Word Generation Q] trip,” says Floratos. There are so many solo travelers booking Olivia trips, in fact, that there’s now dedicated solo programming, should you want to participate. “You can go and have your alone time if that’s what you want,” says Floratos. “But you know that this is where you’re gonna have your meals, this is where you’re gonna sit in the theater for the shows, these are the events that we’re gonna have during the day, so that you can meet other solos.”
And though they don’t actively promote the “single ready to mingle” ethos, as Floratos puts it, an Olivia trip could easily serve as a vacation singles club. Or even a matchmaking service. “We want solos to feel that they have space to meet other solos,” says Floratos. “There have been many guests who have found their love on Olivia.”
For evidence, look no further than Floratos herself. 18 years ago, she was approached by DJ Rockaway, the woman who would eventually become her wife. “I was leading a resort, and my wife was on as a vacationer,” she says. “She came up to me at the end of the week and said ‘I’m a DJ in New York, here’s my business card—if you’re ever looking for a DJ, call me.’”
A year later, they hired Rockaway as regular entertainment for the company. Then things started to happen. “There’s an interesting thing about our Olivia team, our entertainers, our DJs—we’re like a real family,” says Floratos. “There were a few years where we would be on trips together, [but] in other relationships. And then on one trip to Punta Cana, we were both single. We’d always had a fondness for each other as friends, and we realized, ‘My gosh, I think there’s something a little more than just friendship here.’”
They got married in 2015, and in what seems like a dream married life scenario, often work together in paradisiacal locations. Inspired, perhaps, by her own journey, Floratos imagines writing a book about all the relationships she’s seen blossom on the trips. “Where else are you gonna find the love of your life? An Olivia vacation!”