Multigenerational Family Travel Tips for Easy Trip Planning


Although multigenerational travel is projected to be a top trend for 2023, we think it’s here to stay. From Baby boomers to Gen Z, we all love to travel. And, with all the technology and innovation at our fingertips, planning a trip with family is easier and more accessible than ever. 

Multigenerational travel gives us the opportunity to spend quality time with family in new environments and create memories that can last a lifetime—this is especially meaningful for families who are spread out over the map.  As we continue to value experiences over material goods, we’re glad to see a shift in priorities.  

5 tips for planning your multi-gen trip  

Coming up with multigenerational family travel ideas is the fun part. Next comes planning. This can be challenging, depending on how large your family is. Unlike planning for solo travel, which can be time consuming on its own, planning the logistics of an entire family trip is something else!  

Hope these tips help make your next family trip one to remember. 

Multigenerational family travel, Italy

1. Decide who’s coming along on the trip  

Who will you be travelling with? Your parents? Your children? Your grandchildren? Your siblings and their families? Planning ahead and being realistic about who can go on the trip, logistically speaking, is the best starting point. 

2. Make sure everyone who’s coming can actually make it

People are busy, so make sure everyone’s schedules match up. The more people in your family, the harder it may seem to find a time that works for everyone. But don’t worry, there are plenty of online tools to help with scheduling, you can try Doodle Poll, When2meet or have an in-person family meeting to decide on a time.  

Ensure that everyone can book the right days off or they can easily reschedule any other obligations. 

3. Have all parties agree on a budget

Every household has its own budget. Create an expected budget and cost breakdown to avoid causing financial stress. Shared accommodation such as vacation home rentals or Airbnbs can often lead to cost savings, especially with a large group. 

4. Include each family member in the planning process

Letting everyone have some say in where to go and what to do can prevent possible disagreements during the trip (or sometimes may even lead to them, so exercise caution!). 

Here are a few ideas to help minimize disagreements: 

  • Avoid making major decisions solely through online channels. This is more inclusive for family members who aren’t familiar with technology.  
  • Play to your family members’ strengths. If you have a relative that is a major foodie, asking them if they would like to plan the restaurants on the trip is a great way to get them involved. 

5. Stick to family-friendly activities

Whenever you travel in a group with a wide age range, it’s best to plan activities that  generally appeal to all the members of that group. You can’t always please everyone, but the more activities people can participate in, the more fun it’ll be! 

Bonus: If your family is  bigger or you’re too busy to take on the trip planning, consider enlisting the help of a travel agent to plan your trip. They’re likely to have more experience booking multiple travellers and might even be able to score group discounts on transportation, accommodation, activities and tours that you might otherwise not have access to. 

women jumping the pool

Get family travel insurance!

When two adults 59 years old or younger are travelling with up to 6 dependent children, a Family & Friends plan is the most economical option, whether you’re purchasing a Single Trip or a Multi Trip Annual Emergency Medical plan. Travellers can travel together or separately, meaning they don’t have to leave on their trip at the same time. 

Here are some details about the Family & Friends plan:  

  • Coverage is available for up to two individuals 59 years and under and up to six dependent children. (The individual(s) don’t have to be the parent(s) or guardian(s) of the dependent children.) 
  • Dependent children can be on a Family & Friends plan without an adult. 
  • All travellers will be covered under one Policy. 

Not sure if a Family and Friends plan is for you? Check out this handy infographic.

Note: Grandparents 60+ years old won’t be able to take advantage of a family & Friends plan, but there are other ways to save on their travel insurance. The healthier they are, the lower their premiums will be, since our Medical  Questionnaire rewards healthy travellers by offering competitive rates. 

Remember that family travel requires open-mindedness, flexibility, and patience before and during your trip! Every multigenerational vacation experience is going to be unique because every family is unique. Each family member adds to the list of needs and wants, which can be both challenging and rewarding. 

Need some multi-gen travel ideas for your family? All-inclusive resort vacations or cruise vacations are great choices. They allow travellers to spend less time planning and more time relaxing. Sometimes though, you might find that a simple, old-fashioned family road trip across Canada is all you’ll need. 



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