Diane Silvaroli

I have been planning family travel for many years. With kids and parents so busy these days, I think a family vacation is a wonderful way to carve out precious family time, and it is essential to get it right. By arranging experiences that will draw a family together, I feel I am helping them create memories that help foster lasting bonds. 

Often, grandparents fund trips for their whole family. Once we decide on the basics, I handle every aspect of a trip, right down to making sure everyone’s passports are in order. One grandmother was frustrated that her adult kids were not being responsive; trips fall apart over things like that, but as an outsider and a professional, I can make it happen. 

The most important thing for families, and especially for multi-generational family groups, is to ensure that everyone returns home with special shared experiences that they will hold onto. I plan activities that appeal to children and adults and work with engaging guides all over the world who make their destinations accessible to everyone.  

In Ireland, for example, I often suggest two very Irish activities that appeal to all ages: attending a Riverdance performance and visiting a fairy garden where dollhouse like fairy homes are tucked into the landscape. You also might visit a family sheep farm and learn to shear sheep, and then dine with the family in their home. Plus, many resorts offer falconry, archery, fly-fishing, and other family-friendly activities; when parents suggest one of those activities, it makes them look very cool. 

My regular clients often like me to add in some surprises. In Morocco, I planned a ride on ATVs to meet camels for a ride to a Berber Camp for dinner under the stars for a dad and his three sons—ages 21, 19, and 16. On their itinerary, I only wrote: “dinner in the desert.”  They loved it!  

I think through every trip from the viewpoint of each family member. For a family visiting their daughter who was studying in Spain, I planned an afternoon for the son at a soccer stadium so he would feel the trip was not all about his sister.  

Another family had me plan a “Grand Tour” of Europe for two sisters before the older one started her semester abroad in Venice. After their travels, I arranged for their guide to spend four hours familiarizing the student with her neighborhood. The guide walked her from her student apartment to the grocery store,  her classrooms, and fun restaurants and showed her how to use the laundromat. The girl’s mom was almost in tears telling me how grateful she was that I’d thought to arrange that. 

The U.S. also has a lot to offer families, including some fantastic resorts for multigenerational gatherings such as The Broadmoor in Colorado Springs and The Pointe in Saranac Lake, N.Y.  I recently rented a whole dude range in Montana for a family of 50. 

I love thinking of outside-the-box ways to make a family trip more special.  Please call me if you’d like me to handle your next family vacation.