LGBTQ

LGBTQ-Friendly & Family

As a gay man myself, I understand the special and unique challenges that LGBTQ+ individuals face when traveling – as I deal with them myself. Whether it’s picking a safe destination for you and your family, looking for someplace with the activities and entertainment you’re seeking, or how travel insurance will affect you should an emergency happen, I’m here to navigate those complexities with you.

I provide personalized services, taking the time to understand each client’s individual needs and preferences. Whether it’s a romantic getaway, an adventurous exploration, or a relaxing vacation, I curate itineraries that provide safety, inclusivity, and cultural richness. To do this, I stay updated on the latest travel advisories, legal considerations, and local attitudes to ensure a smooth and worry-free journey. I have strong relationships with a network of trusted partners who share my commitment to diversity and inclusion.

From recommending vibrant LGBTQ+ nightlife and cultural events to suggesting destinations with supportive communities, I strive to exceed expectations. My goal is to empower LGBTQ+ travelers to explore the world with confidence and pride, creating memories that last a lifetime. And, remember, my services are completely free to you when you book.

Trusted Partner in the LGBTQ Community

My partner Nate and I have been together since 2009. When we moved to the Chicago area in 2013, we wanted to find an inclusive community to meet other LGBTQ friends. We founded a local bowling league, Out! Bowling in 2014, where our community could come together to find connection and form bonds. In the 11+ years since that founding, over 600 members of our community have come together through bowling and other connections producing friendships, relationships, marriages, and more!

In 2024, I was honored to be presented with the 1st Annual Director’s Award from NaperPride, a local community service organization for the LGBTQ Community in Naperville, Illinois and its surrounding areas. The award was given “in gratitude and grateful recognition of your outstanding service, dedication, and leadership in support of the LGBTQ+ community.” I was honored to be surrounded by Out! Bowling members and other members of our community when receiving the award, and most honored to have my life partner by my side as I accepted it.

I also have been part of NaperPride’s Annual PrideFest for 3 years running, where I get to meet a ton of people who may be looking to take a trip anywhere. You definitely can’t miss my setup and if you’re local to Naperville or the surrounding area, I can’t wait to see you at this year’s fest. To learn more about NaperPride, I encourage you to checkout their website here and to connect with them on Facebook here.

And, if you’re a member of the LGBTQ+ Community and are looking for a trusted travel advisor who can navigate the complexities of travel, please let me help you. You can email me at caseywooley@mainstreetandmoretravel.com or call me at 734-718-6024.