How to arrange and make the most of multi-generational holidays

Travel fills my soul and my grandchildren fill my heart. Combine them and it’s magic. Holidays together are precious—a chance to create family memories that will last a lifetime. But multi-generational travel isn’t a one size fits all. Choices are infinite, including camping, hotels, resorts, cabins, luxury cottages and cruises. 

There are many different elements to consider when planning a getaway with a group. This article will provide the steps and tools to organise and manage a multi-generational trip. When you start the process, you need to decide on the big items first: destination, timing and budget.

Several friends I spoke to said that for their families the destination always comes first and the dates and budget later. The destination determines the mode of travel. Is it a road trip or are flights involved? What season do you want to travel in?

Our recent road trip with three generations to Finger Lakes in upstate New York was for five days. We travelled separately and met at the house rental. Having our own cars gave us all flexibility in time of arrival and departure and choices while there.

Location is important for activity planning. Is everyone renting a car or will you book a van so everyone stays together? What everyone wants to do while there has an effect on where you go. The location sometimes depends whether it’s a general holiday of exploring together or is there a focus on hiking, winter skiing, snorkelling, golfing, or is everyone wanting a simple “fly and flop” resort holiday?   

Work out the date after the destination and the rest will follow. Have a family meeting or develop a group email, WhatsApp or Zoom call. Coordinate the date everyone is available and the length of time for the holiday. Pick out the top three possibilities and hope that one date works for everyone.

Once the start date is set, the destination will dictate the length of the trip, whether it’s a long weekend or an entire week. If it’s the family’s first trip, a long weekend for a trial run is a good idea to iron out any issues.

Unless it’s not of great concern, the budget may need to be discussed at the same time as the destination and the schedule. Most important is the conversation around who pays what. Is a team budget involved or are the grandparents bankrolling everything? Some grandparents cover all the costs, others cover the resort or house rental and leave flight costs to the younger families.

Open and honest communication is key. One family I spoke to shares all costs with their adult children. If you are the grandparent, be upfront about what you can cover and keep in mind that paying the accommodation is one thing, but who pays for the food and any activities? Several families I spoke to said the conversation on how much each branch could contribute was in itself a bonding exercise.  

Do you want to rent a self-catering chateau, cottage or stay at a resort where everything is taken care of? One friend recently organised a resort holiday for their family of 13 and had a blast meeting up for meals, beach time, snorkelling and activities within the resort. If it’s a rental, the required number of beds and baths quickly reduces the available properties.

For many families, and mine is no exception, a holiday rental on the water is a common goal. With a lakefront location comes so many activities including swimming, canoeing, kayaking, beach time and hiking. There are no worries about cleaning or bringing bedding as everything is supplied. Starting out with breakfast at your rental sets you up for a day’s activities and gives you options for dining out or in.

Several families as well as mine said that consensus is most often rentals. With three generations, the recent waterfront rental on Lake Owasco in Finger Lakes was ideal as one family was on the top level and the grandparents were on another, giving everyone their own space.

Talk about expectations, especially if you are staying in a rental. Not any one person should have to shoulder meal prep, cooking and clean up, but a division of labour, including the children, is a good idea. 

In the summer when our entire family of nine went away to a cottage rental, our plan was that the grandparents provided the first night’s meal and the next generation cleaned up. Then we alternated with each family providing a meal and the rest doing clean up.

Share basic menu ideas ahead of time so it isn’t barbecued burgers every night. Breakfast fell to Nana who volunteered each morning to cook, and it was wonderful to gather around the table with the small ones still in jammies with tousled hair. However, an all-inclusive resort would work very well with everyone in separate rooms meeting up for meals to discuss the plans for the day.

Have a planning meeting to discuss what everyone is interested in doing. You don’t have to be in each other’s pockets, day in and day out, but doing group activities is the raison d’etre. Activities often depend on the age of the children involved. Everyone needs downtime no matter how old or young they are, whether its naps or screen time. Do you want to tour museums, water parks, have a beach holiday, golf, tour historic properties or a little bit of everything?

Outings in the Finger Lakes region were a mixture of cultural hits, swimming, board games and charades. A highlight was the Strong Museum of Play, the world’s largest museum devoted to the creativity and educational angles of play. Interspersing history with fun is a great way for children to learn about an area. We spent a few relaxing hours on the Canandaigua Lady, a replica double decker paddlewheel steamboat touring the Lake while the captain shared the history of the area which was fun for every layer of the family.

Making everyone happy is impossible but covering several bases is possible and splitting up in different directions is realistic when you’re there.

Flexibility and compromise are key as well as letting go of expectations, no matter what the ages of the children are. There are tantrums, tiredness, off days and sicknesses.

This year part of the family joined us a day late and left three days early as one of the granddaughters was sick. You have to roll with it and everyone has to do what works best for their branch of the family tree.

Patience and understanding go a long way with a group. As the grandchildren grow, plans change and evolve as interests and availability changes.

There is at least one person in each family who likes to organise. A Type A personality needs to take the group by the reins and keep things on track, coordinate with the rental owner or manager of the resort and collect deposits and send out timely reminders to the group. If you are reading this article, it’s probably you.

To keep it fair and have everyone involved, give each person/team player a role to play according to their strengths, such as research on what to see in the area, taking photos, or organising a specific activity. Closer to the leaving date, details to discuss include meals (prep or farm out), who is bringing what, daily outings, how to meet at the property and timing.

While you are away with the family:  check in at the beginning of the day to make sure everyone is still keen on that day’s plans. Going in different directions is okay too and arrange to meet up at the end for a meal or drinks and appetisers works to share stories about the adventures you each had. 

On our trip to Finger Lakes, our small granddaughter insisted on a game of charades every day in the late afternoon on the porch, with happy hour drinks and snacks, which she referred to as our daily “porch party.”

We did our first week away last year with nine of us—myself, Grandad, my adult son and his family and my daughter and her family. We had a lot of fun and created a lot of unforgettable memories. Were there moments of outbursts, crying, tiredness, tantrums? Absolutely, but we dealt with them as they arose.  

The laughter and special times outweighed those moments. (Tip: Do not let the grandkids pick the topics for charades. You will find yourself mimicking being constipated!) At the end of that first cottage week, I asked if anyone wanted to do it again and the answer was a resounding, "Yes”. We rented the same cottage this summer, and it is now booked for next year as well. 

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