The Perfect Family Vacation. How to ensure that every generation is happy!
Jul 30, 2020
02:41 AM


As a travel advisor, it is my job to design journeys for my clients that will leave beautiful and lasting memories. The complexity of trip planning becomes exponential when you add more people and the diversity multi-generational considerations of ages and interests as well as family dynamics. As a wife, mother and grandmother who has taken and planned many extended family vacations, I am also able to provide my clients with first hand tips and tricks on how to make their multi-generational experience positive and as carefree as possible. All of these I have learned through my own family travel mistakes and successes.


One of the key factors to a successful multi-generational trip is to remember that although you are travelling en masse for a family holiday, each member of the family has their own expectations and needs. Although we cannot please everyone, all the time, if we craft a holiday experience by listening to all the hopes, dreams and concerns, everyone will walk away happy and looking forward to the next trip.

With modern medicine and healthy living, we are living longer and slowing down the aging process. Age does not dictate our lifestyle or preferences and to group everyone of similar generations into the same box is one of the biggest mistakes made when planning a multi-gen vacation. Rather than focusing on the different generations in your group focus on the personalities, likes, dislikes, needs and wants. The key challenges come with various ages and abilities, whether it be physical or dependencies on others that need to be considered.


My best advice is to choose locations that will offer something to suit multiple interests and physical levels. Just because you are travelling en masse, do not expect to spend every moment of your vacation joined at the hip. Find a way to allow family members to branch off into groups or go solo to pursue their own interests, which might just boil down to alone time.

All-inclusive resorts and cruises are perfect for this type of holiday as they have multiple activities and amenities to suit all ages. Teenagers are more inclined to party late into the night and sleep in late. The rest of the family, either by choice or the very young or old, because of their dependency on others, will be up at the crack of dawn and ready to start their day with the rise of the sun. When we understand the habits, wants and needs of those in our family, we can accommodate them and focus on the moments we are together. Choose at least one main activity each couple of days to do together whether it be hiking, boating, visiting cultural venues etc. and then let everyone go on and do their own thing. The key factor for any multi-gen family to have at least one meal together each day. This will be a time where natural discussions will take place reflecting on the day and sharing experiences whether it is recapping the day or anticipating the next one. Sharing the day’s events with each other will come naturally and everyone from young to old can and will participate with ease. These are the times when we bond with our family members and even the most sullen of teenagers will open up. Family moments are meant to be remembered and cherished.


It is very important to choose a resort or cruise ship that will accommodate any special needs that your family members may have. In the case of young children, make sure there are appropriate children’s activities and child-minding services. This will give parents a chance to have some “Adults Only” or “Couples” time which is essential. Are there enough activities to keep the teenagers happy? Making sure everyone has relevant options is the key to a successful multi-generational trip.

Some of the best activities that everyone in the family can do together are those that are experiential. Choosing easy to moderate activities will ensure that everyone can participate regardless of age or mobility whether it be hiking in the Andes, taking a Catamaran trip, visiting local towns, or playing in the ocean or pool. Stay away from planning any activities that will make it hard or force one family member to sit out, like snorkeling, where young children and infants must stay on the boat and subsequently will need an additional family member to stay behind to watch them. Don’t plan anything that is too long in the heat of the day or physically exhausting as this will lead to tired, grumpy and a very unhappy family.


The biggest shift in multi-generational travel is to have unique and experiential moments. Most of my clients are looking to take their family on trips that offer more than just sitting on a beach. They want activities, adventure, great food and for many, including an educational aspect to the trip. There is a shifting trend in legacy-giving, where parents and grandparents want to spend their money on their family NOW while they can, to enjoy these experiences with them. This “soft giving” method rather than leaving everything in a will allows them to use their money to share these special memories with their family.

Some of my most successful multi-generational trips that I have planned include Peru with visits to the Sacred Valley and Machu Picchu, sailing around the Galapagos Islands, taking a helicopter and picnicking in Grand Canyon, heritage trips to Israel, expeditions to the Arctic and the list goes on. There are so many places to see in the world and experience that will further enrich our personal and collective lives when we share them with those we love.


From my own personal experience, travelling with my children and grandchildren has given me memories that keep my heart full. Years later we still find ourselves sitting around a holiday table reminiscing about our trips, laughing at specific events or discussing places we saw or people we met. These are stories that we share as a family and will continue to share for generations to come. Memories of family members who are no longer with us are richer when we can reflect and remember those special moments shared on our trips together. It may take some creative planning, require a bit more compromise and a lot more patience, and in the end multi-generational experiences are priceless.

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