Jamie Weitl

Born and raised in rural Illinois, Jamie Weitl began her career as a high school teacher before transitioning to teaching college courses online after welcoming her trio of little ones. As an assistant professor of political science for a major online university, she pursued her Ph.D. in 2014. That same year, she also discovered her true passion—travel—when she started selling vacations as a side business.

In January 2020, Jamie earned her Ph.D., stepped away from teaching, and launched her own independent travel agency—just weeks before the world shut down. Despite the challenges, Pineapple Escapes, LLC. officially opened on February 12, 2020, and has grown into a thriving agency with a dedicated team of travel advisors.

Jamie is the proud mom of three teenagers—Bo (17) and twins Clara and Anna (15). She and her husband of over 20 years, Mike, share their home with their trio, three cats (Ike, Kiki, and Pudge), and their beloved French Bulldog, Chip.
Eclectic and adventurous, Jamie has a love for desserts, reading, her Peloton (#rides4dolewhip), and of course—traveling! She and her family love exploring the world, with favorite destinations including Hawaii and Aulani, Walt Disney World, Universal Orlando, cruises, all-inclusive resorts, and international hotspots like Cape Town, Paris, Rome, and Garmisch-Partenkirchen.

Though she never imagined her career would take this path, Jamie is grateful every day for the experiences and flexibility travel has provided. She is passionate about helping others create lasting vacation memories and believes that travel truly makes life sweeter!

Looking back on my journey, it’s no surprise that I fell into vacation planning.