After 15-years of planning over 7 family trips I’ve done some things right and had some key learnings on how to improve multi-generational trips.  The following are my top dos and don’ts to ensure that every generation on the trip has a great time.  

• Do: Factor in the ages of your Grands as you plan the travel logistics 

During our trip to Acadia National Park we flew into Portland, Maine which required a connecting flight.  After hours of confinement in aircraft I knew it would be cruel to ask our Grands to get into a car for the approximately 3-hour drive to Acadia on the same day.  So, we booked rooms in a hotel, with a pool, for the night.  

Lesson #1: Whenever possible, try to pick destinations with non-stop flights or a total flying time of less than 3-hours or a total driving time of less than 3-hours. 

After breakfast and the 3-hour drive to Acadia, we piled out of the car, tired, hungry, and a little grumpy about the fact that we were still traveling.  Fortunately, the compound of cottages we had rented along Frenchman’s Bay was a stunning reward for the effort of travel.  And while Acadia is 2,227 miles from Austin, Texas and worth visiting, I realized that we needed to select locations that had close proximity to a major airport and preferably with nonstop flights, especially while our Grands were young. 

Lesson #2: If you’re heading to a once-in-a-lifetime destination, break up the travel or postpone the trip until the Grands are a little older. 

• Do: Find a great house where everyone can be comfortable and share meals

On each of our trips, with the exception of Thanksgiving in New York City, we have rented homes through VRBO that were large enough to provide a room and bathroom for each couple and a bed for each Grand.  Sometimes those beds have consisted of pallets on the floor for the younger Grands or a large room with bunk beds. 

Lesson #3: Everyone needs their own bed and adults need their own rooms.  

A second critical factor in selecting a rental home is its location to the major attractions. The more central its location, the less time you will be spending in the car with restless children.  My rule of thumb is that the house needs to be within 15-20 minutes of most activities.  We’ve had worthy exceptions but whenever possible we try to avoid long car rides.  The centralized location makes everyone’s life easier.  

Lesson #4: No one wants to spend their vacation in a car. 

The third key feature for a great rental is a pool.  Pools are a great source of entertainment and an excellent energy drainer for young children.  We’ve also rented houses with ping pong and pool tables.  Some families who play games will enjoy game nights. 

Lesson #5: Embrace the energy of your Grands and give them outlets to use it

The fourth key feature is a great kitchen.  We’re fortunate in that each of our children are great cooks.  During our family trips, breakfast and lunch are on your own and the evening meal responsibility is rotated across the individual family units.  Each family plans their menu, purchases their ingredients, cooks, and cleans up on their assigned evening.  I wish that we were keeping a catalogue of the menus and recipes because there have been many memorable and delicious meals lovingly prepared and served.  If your family does not enjoy cooking consider hiring a local chef to prepare and serve the meals. 

Lesson #6: Ensure dinnertime is seated and shared – some of the best memories have come from time around the table at night

• Do: Plan the trip activities around the Grands ages, interests, and activity levels 

Our Grands and their parents are athletic and active.  They prefer outdoor adventures and experiences.  As a result we have centered all of our trips, with the exception of New York City, in nature.  We’ve visited Acadia National Park, Glacier National Park, and the Grand Canyon.  We’ve also enjoyed two trips to Lake Keowee in South Carolina.  Each trip has allowed the Grands to explore nature, hike, raft, horseback ride, paddle board, kayak, water ski, wake surf, etc. 

Lesson #7: Honestly evaluate and align your trip to what your family will enjoy, not your own interests

• Do: Embrace that it can’t be perfect and that it won’t last forever

Family trips are easy while the Grands are young but as they enter adolescence it can become more challenging to ensure that everyone can participate.  It may also be difficult if you have Grands with divorced parents and the custody schedule doesn’t favorably align with the trip dates.  While you want every family member to be able to participate sometimes it just doesn’t/won’t work out. For our Grand who has divorced parents we create a travel fund for her so that on those rare times when she is unable to join us on the trip. This fund will provide her with money for future travel. While it doesn’t make up for being left behind it does keep the playing field somewhat level. 

As our Grands begin college we are not optimistic that they will be able to join us on the family trips. But we will continue to locate great houses in beautiful settings and provide the funding for travel for those who can join us. 

Lesson #8: Accept that not every family member will be able to attend every trip

• Don’t: Over schedule or structure the trip 

Family trips are intended to create time to relax, rest, and share time together.  Our lives are over scheduled and rushed and we learned early on that the family trips needed to be largely unscheduled.  We typically plan one “all family” outing that we host and pay for,  leaving the remainder of the trip open for each family to make its own plans for side trips or to simply hang out around the pool.  As our Grands have become teenagers they have consistently commented that “having no schedule” is the part they like the best about our trips.    

Lesson #9: Give your family time to do nothing

Every single family is as unique as a snowflake. Embrace that uniqueness and plan with it in mind. If you do, you will have limitless possibilities for unforgettable memories that you will be talking about with your children and Grands for years to come.