Home > New York > Gloria Greenstein > Family, Grandparent, and Multigenerational Travel

Gloria Greenstein

New York, New York Travel Agent

Family, Grandparent, and Multigenerational Travel

Gloria Greenstein's family in Prevence

Family travel comes in many forms, and all can be wonderful with the right planning. My husband and I started taking our grandchildren on trips when they were not quite camp age. It gave their parents a nice break and helped us form strong bonds with our grandkids.

As all grandparents know, the secret to this is getting parents, your children, to entrust their little ones to you. My advice is to build everyone’s confidence by starting small; perhaps a short visit to Williamsburg or Disneyland.

Family reunion trips are especially valuable for families that are spread across the country. Even if you get together for holidays every year, it’s rare that cousins spend enough time together to develop close relationships. Building a strong sense a family takes conscious effort. That’s why many grandparents host an annual trip. 

Villa vacations are a great choice. My family has been taking an annual trip to Half Moon, Jamaica for more than a dozen years. Unlike a hotel, where you need to make plans to meet in the lobby for activities or to have meals together, in a multi-bedroom villa, home or condo, you can simply relax together. With a cook, maid, and butler, there are no chores, and a swimming pool or living room creates a natural gathering place. Since you are not going to restaurants for every meal, no one stresses about being late; your table is always waiting, and your family reunion can be stress-free. On our trip, we usually do one or two family activities each trip, for example, a snorkeling cruise, or a day at a nearby water park. 

It is especially fun to take the whole the family to an exotic locale. One client, who traditionally hosts their three grown children, spouses and six grandchildren for an annual Caribbean getaway, recently took a bucket-list trip to Africa. Highlights included safaris at Sanctuary Chief’s Camp in Botswana, touring Victoria Falls by helicopter, and staying at a private villa with a chef, maid, and vehicles and guides at their disposal for game drives at the Royal Malewane, a luxury safari lodge in South Africa's Kruger National Park. It was a super experience for everyone! 

Cities such as Paris can also be great family destinations. I know which hotels will guarantee connecting rooms and which top restaurants have a kid-friendly menu and ambiance. Plus, for large groups, I pre-arrange the main meals so tables can be set up in advance.

Cruises are also great for family vacations. The larger ships offer activities that many kids find thrilling and some families like that everyone doesn’t have to do the same thing at the same time. On the other hand, we’ve enjoyed taking our grandchildren on super-upscale lines where passengers usually find it a treat to see children, and we can arrange in-port excursions that kids will love.

My advice to all families is not to wait. Kids change every year, and at some ages, they won’t want to come unless it’s a tradition. Wherever you go, plan ways for everyone to enjoy happy, stress-free and congenial time together. That’s what I’m good at creating!

Share my profile: