Our Founder
2024 Conde Nast Traveler- European “Top Travel Specialist”
2022 Travel + Leisure “Rising Star” Award
Out & About was created when its founder, James Lilla, walked away from his Fortune 100 Advertising Sales career to satisfy his wanderlust to travel the world solo for a year. What started as a year turned into two, and what started as a passion turned into a lifestyle. After inspiring many of his friends and acquaintance's through his journey, James started “Out & About Holidays” to offer his friends exciting travel experiences and long lasting memories. Out & About specializes in Beach & Sun, Food & Wine and LGBTQ Gay Travel. The majority of our clients are successful professionals who have the budget but not the time to plan their leisure travel.
In 2020 Out & About Holidays became an independent affiliate of Chicago’s Q Cruise + Travel. Q is an award-winning boutique travel agency on Chicago’s Magnificent Mile that specializes in luxury cruises, tailored land vacations, expeditions and safaris. Q is a member of Virtuoso, the leading global network of agencies dedicated to luxury and experiential travel.
About James
Born: Alaska
Raised: Iowa
Home: Chicago
Favorite Vacation: Chartering a Yacht in Greece with six of my best friends. We all live scattered throughout the US but we meet every Summer for an epic International trip. We chartered a yacht with a captain and maitre’d and they took us all around Mykonos. We stopped for a swim off a remote bay on Rhinia Island and then took a smaller dinghy boat to the beach with no other people in sight for a glass of Rose in the sand. We’ve done it two years in a row and I can’t wait to go back!
Favorite American Vacation Spot: Palm Springs. The architecture, the “Old Hollywood” History, the amazing restaurants and the pools with palm tree and mountain views. I love taking the 10 minute aerial tramway up to the San Jacinto Mountains. You go from 100 degrees to seeing snow in 10 minutes, the views are absolutely breathtaking.
