Grandparents Foot the Bill for Family Vacations Twice a Year

Francine Bookbinder, 61, has revived a decades-long tradition of multi-generational trips with her children and grandchildren.

Apr. 3, 2026 at 1:11pm

Got story updates? Submit your updates here. ›

A highly stylized, abstract illustration featuring sweeping gradients of tropical colors and bold, geometric shapes suggestive of a luxury resort or cruise ship, conveying the sense of adventure and celebration of a family vacation.A vibrant, geometric illustration captures the grandeur and excitement of a multi-generational family vacation.Bayonne Today

Francine Bookbinder, a retired teacher's aide from New York City, has been taking her family on vacation twice a year for the past three decades. She and her husband, Robert, cover the costs of the trips, which can total around $30,000 annually, to create lasting memories with their two daughters, son-in-law, and two grandchildren.

Why it matters

Bookbinder's story highlights the value of multi-generational travel and the importance of family traditions, especially as grandparents take on a more active role in their grandchildren's lives. It also showcases how financial planning and a commitment to quality time together can enable families to enjoy regular vacations, even as costs continue to rise.

The details

Bookbinder and her husband began the tradition of family vacations in the 1990s, when their own children were young. At the time, her mother and grandmother covered the costs of Caribbean cruises, allowing the family to create cherished memories. Now retired, Bookbinder and Robert have revived the tradition, taking their two daughters, son-in-law, and two grandchildren on all-inclusive trips to destinations like the Dominican Republic, Aruba, and Bermuda. They've learned to save money by booking interior staterooms on cruises and working closely with a travel agent to find the best deals.

  • Bookbinder and her family began the tradition of multi-generational vacations in the 1990s.
  • In recent years, Bookbinder and her husband have taken their family on two vacations per year, typically escaping the winter in New York.
  • In June 2026, the family is planning a weeklong cruise from Bayonne, New Jersey to Port Canaveral, the Bahamas, and the cruise line's private island.

The players

Francine Bookbinder

A 61-year-old retired teacher's aide from New York City who has been taking her family on vacation twice a year for the past three decades.

Robert Bookbinder

Francine's husband, who is also retired and helps cover the costs of the family's regular vacations.

Alison

Francine and Robert's 36-year-old daughter.

Abigail

Francine and Robert's 34-year-old daughter.

Bill

Alison's husband.

Got photos? Submit your photos here. ›

What they’re saying

“Rooms are just for sleeping in,”

— Alison

What’s next

Bookbinder and her family are planning a weeklong cruise from Bayonne, New Jersey to Port Canaveral, the Bahamas, and the cruise line's private island in June 2026.

The takeaway

Bookbinder's story highlights the enduring value of multi-generational travel and the importance of family traditions, even as the costs of vacations continue to rise. By prioritizing quality time together and leveraging financial planning, the Bookbinder family has been able to maintain their regular vacation routine, creating lasting memories for all three generations.