10 Questions With Jonathan Bennett and Jaymes Vaughan of OUTbound

Jonathan Bennett (above right) and Jaymes Vaughan are the owners of the LGBTQ+ travel company OUTbound, but you probably know the gay fiancees from TV. Althoguh Bennett may be best known for his breakout role as Aaron Samuels on Mean Girls, he also hosted Cake Wars and Cupcake Wars on Food Network and stared as the first gay lead in a Hallmark Channel holiday movie (last year’s The Christmas House). He was named to Out magazine’s OUT100 list in 2020. 

Vaughan is a television host and the former host of Chippendales in Las Vegas who competed on The Amazing Race 21 with fellow Chippendale James Davis. The duo very nearly won – coming in second to The Fabulous Beekman Boys stars and partners Josh Kilmer-Purcell and Brent Ridge (the last gay couple to win until 2020’s Will Jardell and James Wallington). Vaughan now hosts Celebrity Page, and American Music Awards' Red Carpet Live.

Bennett and Vaughan's company, OUTbound creates bucket list travel adventures all over the globe, often partnering with local LGBTQ+ tour operators, to offer cruises and vacations that connect travelers with LGBTQ+ communities around the world  

In this exclusive interview the couple talk to Out Traveler about their relationship, their careers, their company, and the OUTbound cruise to the Greek Isles they're leading in November.

What first got you each into travel?

Jonathan: On our very first date we bonded over the fact that we had both lost our Dad’s to cancer at the same time.

Jaymes: Don’t worry it sounds sad, but it gets happy.

Jonathan: And my Dad’s tagline was “It’s All About Adventure.” He always said that about everything.

Jaymes: So on our first date we decided that we wanted adventure to be a theme of us if we ended up being something. 

Jonathan: And it turns out we worked out, we’re now engaged.  And that tagline has been what’s driven us to explore so much of the world as a couple.

Jaymes you competed in Amazing Race and very nearly won. What was that experience like?

Jaymes: Aw thank you for phrasing it that way! “Nearly won,” I like that. I always say I feel like I won though. Yes, I got second so I didn’t get the money, but I got the most incredible experience. As someone who always wanted to compete on the show, to then make it all the way to the end, it was unreal. There’s really no substitute for an experience like that where you not only get to race around the world, but you also get so warmly welcomed by and allowed to learn from so many different cultures.

A favorite part of travel for me is food! Jonathan you’ve hosted Cake Wars, are you a baker or chef yourself? Do you like culinary tours?

Jonathan: You had me at culinary tours, yes! If there’s good food, I’m there. There’s nothing like getting to taste food in the place where it originated. I’d like to think I’m both a chef and baker, but I’m definitely more of a chef. My cookbook The Burn Cookbook, an authorized parody cookbook for Mean Girls fans showcases that for sure. Not a lot of baking, but a lot of fun recipes that taste really good. 

A big part of tourism is built on performances and entertainment. As performers (Jaymes in a huge Vegas show and Jonathan in a huge Hallmark holiday movie), what is it like when you get to be the tourist rather than the entertainers?

Jaymes: As a performer I’ve pretty much spent the majority of my adult life living and performing in tourist destinations. Which if you’re not careful will make you take stuff for granted. I think I did that the first 25 years of my life, which is why I try so hard to make up for it now; by doing things like racing around the world or launching an LGBTQ+ travel company with my fiancée. 

Jonathan: The entertainer part is so much fun too, though! A lot of the time when I get to go to amazing destinations it’s to film a movie or a TV show and 95 percent of your day is spent working. So when you do get that chance to be a tourist it’s even more special. It’s a chance to turn off and just enjoy.

What led you to start OUTbound, in particular, what made you want to lead travel adventures and take other LGBTQ+ travelers with you?

Jonathan: It’s all about creating spaces where we are not only safe to be ourselves, but also celebrated. I think we’ve all had those times where we didn’t get to fully enjoy a moment or experience because we weren’t fully sure if we were safe in that space. 

Jaymes: We shouldn’t have to wonder “is it safe to kiss my partner at dinner or are we going to get dirty looks if we hold hands here?” But we want to see the world and be able to do that too! That’s why we created OUTbound. So our entire LGBTQ+ community can check off their bucket lists going to amazing places, and also get to fully be themselves at the same time.

Jonathan: And we are doing it with smaller groups on more intimate ships because it gives us a chance to not only fully be ourselves, but also bond with each other and form a community to see the world with. It’s very exciting!

What makes tours with other LGBTQ+ people different than those with straight or mixed groups?

Jaymes: Can I say LGBTQ+ people are the best? I mean maybe I’m biased, but we totally are. 

Jonathan: Because when it’s our space, our safe space to be ourselves fully, there’s something so special and fun about that. 

Jaymes: We don’t get many opportunities to be the majority, but with OUTbound, we are.

What makes an OUTbound Travel Adventure special?

Jonathan: At OUTbound everyone is welcome. We wanted to create a way to see the world that is for every member of our LGBTQ+ community. We’re so fortunate that our circle of people in our everyday life is represented by every letter of the LGBTQ+ community and there’s something so special about that. 

If you were going to take a friend someplace special, where would it be?

Jaymes: That’s what’s so cool about OUTbound. It’s the answer to that question! That’s exactly how we plan all our cruises, trips, adventures, etc.

Jonathan: Yeah, we say “where would we absolutely want to take our friends and family?”  And that’s what we choose for trips. I’ve always thought everyone should get the chance to see the Greek Isles, and that’s where we are going this November with OUTbound.

Jaymes: And for me the really “adventurey” stuff is what I always want to take everyone on. So our Mekong River Cruise to Cambodia and Vietnam next year as well as our Adriatic Sea Cruise (hello it’s where they filmed Game of Thrones) were no-brainers for me.

What are you most looking forward to about travel in 2021?

Jaymes: Finally getting out of the house! We finally were able to get vaccinated and just that feeling alone feels like the world is starting to heal. We are all about travelling responsibly so we are waiting until the CDC and local governments say it’s safe not only for us to travel, but also for the people we are visiting to receive us. But it feels like that time is coming sooner and sooner. So we have the trips planned and ready! 

Jonathan: And we are definitely not alone. I don’t think we anticipated just how many people are ready to get out there and travel again. And then we launched OUTbound and the response has been overwhelming. Which is also really touching because it feels good to have that support from our own community.

Tell us about a #TravelFail and how you overcame it.

Jonathan: I like my suitcases to match, so they are all the same. I packed my bag to go film a movie in the Dominican Republic, where obviously it’s warm so it was a lot of shorts and things. And when I got there I opened my bag and clearly I had brought the wrong suitcase because when I got to the hotel and opened it up, it was not my clothes I needed for the next 6 weeks, instead it was my ski stuff I keep stored in the same kind of bag. Oops!

Jaymes: Did you see Episode 4 of The Amazing Race my season? I literally fell directly on my face running to the pit stop. Three feet from checking in. I can’t think of a bigger fail than that! And thankfully someone turned it into a gif, so it’s the fail that just keeps giving and giving.