OWNERSHIP & TRAVEL Page 25 Jul / Aug, 2026 | TimeSharing Today
Gayle O’ Malley’ s Timeshare Journey—
Four Decades of Family Travel, Memories, and Value
For more than 40 years, Gayle O’ Malley has watched the timeshare industry evolve from fixed-week ownerships into flexible points systems, cruise exchanges, and worldwide travel opportunities. Along the way, she and her late husband, William, built something far more meaningful than a portfolio of vacation ownership interests. They built a lifetime of family experiences that stretched from Disney World and Yellowstone to Hawaii, Europe, and Alaska— creating memories now shared by children and grandchildren alike.
Today, Gayle reflects on those experiences not simply in terms of dollars spent or maintenance fees paid, but in terms of the opportunities her family enjoyed together. From military life and constant relocation to retirement travel and multigenerational vacations, Gayle’ s story illustrates how timeshare ownership became deeply woven into the fabric of her family life.
Growing Up Between Chicago and California
Gayle currently lives in Anaheim, California, but her childhood was anything but stationary. Her father worked in racetrack betting operations, which meant the family spent summers in Chicago near the racetracks before traveling west each winter to California during the Santa Anita racing season.
Those annual drives along the original Route 66 left a lasting impression on Gayle. Historical markers, Native American settlements, and roadside discoveries became part of her childhood education long before she entered a classroom as a teacher herself.
“ We would stop constantly along Route 66,” Gayle recalled.“ My father always wanted us to learn about the places we were traveling through.”
The traveling lifestyle eventually became difficult for Gayle’ s sister, who struggled attending two schools every year. By the time Gayle reached fourth grade, the family had settled permanently in La Habra, California, where they be-
www. timesharingtoday. com to start or renew memberships.