Matthew started SideQuests Travel because he was tired of trips that felt like checklists instead of connection. He wanted a space where you could show up—whoever you are—and instantly feel like you belong. What started as a group trip experiment turned into a full-blown mission to fight loneliness (and maybe ugly-cry on more than one flight home). It’s travel built for community, especially for LGBTQ+ folks—because the best journeys aren’t just about where you go, they’re about who you find along the way.

Michael is the reason SideQuests actually functions. He handles all the behind-the-scenes chaos to ensure trips feel like magic. He’s the calm in the airport storm and the guy who quietly makes sure every traveler feels taken care of. (Also, definitely the one reminding everyone to hydrate.)

Peter brings years of experience in travel, community, and advocacy — from presidential campaigns to queer group tours. As a lifelong LGBTQ+ advocate, he’s passionate about creating spaces that feel inclusive, intentional, and full of connection. He’ll be leading new SideQuests adventures starting in 2026, including Sicily, the San Juan Islands, and a Mediterranean cruise.

Ryan is a full-time digital nomad and experienced group travel host who has led multi-day trips since 2022. As the founder of Capsule Adventures, a sober travel company, he brings a calm, organized, and deeply thoughtful approach to creating trips that feel smooth, safe, and genuinely meaningful. Passionate about LGBTQ+ community-building, Ryan creates spaces where queer travelers can fully relax, be themselves, and move through the world together. Having traveled to nearly 40 countries, he believes the best travel moments happen in the in-between, the late nights, shared laughter, and unexpected connections. He’s deeply invested in making sure everyone feels taken care of… and of course, he isn’t shy of a little light roasting, and to break out some humor along the way.