Home > California > Debbie Kessler > Multigenerational & Family Travel

Debbie Kessler

San Francisco, California Travel Agent

Multigenerational & Family Travel

Increasingly, people are traveling with their extended family, from grandparents down to the grandchildren and perhaps, great-grandchildren. Often, the family office or grandparents foot the bill for everyone.

In one case, my client was a grandmother who chartered a 747 airplane and took the family on a trip to Africa. I arranged private safaris, bought out lodges in different locales for the family, and hired the best and most family-friendly private guides. The family did a lot of group activities, but I also planned for sub-groups to follow their individual interests as well. My client spent upwards of $250,000, and it was a trip everyone will cherish. 

On the other hand, it doesn’t take a fortune to create amazing family memories. What is necessary is to recognize that each age group and each person has different needs and priorities. I always emphasize that family bonding doesn’t mean spending every second of every day together.

I often start by pretending it is 7 a.m. on the first day. I ask myself and my clients what that is like for each family member. Who will go for a walk on the beach? Who will be sleeping in? What will the kids be clamoring to do? 

That gives me a clue as to what type of vacation will work. A villa can be great when a group of people shares common interests and habits, but if some of the group sleeps in, how do you keep the early-risers and kids quiet. And if you put the babies to bed at 7 p.m., will the laughter and talking keep them up?  

Often, especially when three or four generations are traveling together, I need to create more privacy. A resort or cruise with childcare or kids programs could provide parents with some important adult time. All-inclusive trips are helpful when various families are paying their own way because there is no bill-splitting or questions about who will pay for what.

Sometimes grandparents crave quiet and privacy. For that, side-by-side sister all-inclusive resorts where one is adults-only and the other is family-friendly, or a ship with an adult-only section offer a great solution. Everyone can meet up for dinner and select shared activities without being pushed together when aren’t ready to be.

Cruising also can be wonderful for some families. I took a master course and am familiar with all the lines. I find that older generations may not enjoy the mega ships with the climbing walls and go-cart tracks that get kids excited about a trip. Crystal Cruises or Celebrity Cruises can be a good solution; they are a bit more elegant and, while they don’t have the mega-slides and zip lines, they do have good kids programs. Other families, especially when the kids are a bit older, are happy with some of the smaller upscale lines like Silversea. In all cases, private shore excursions provide opportunities to get everyone together for fun family time, and they are usually less expensive than booking each person individually. 

My goal is to arrange multigenerational trips that create wonderful shared memories without engendering Thanksgiving Day-level stress. To do that, I make sure I understand each traveler’s interests and the different family dynamics and find the sweet spot to plan a getaway that family members will happily reminisce about for years to come.

Share my profile: