Multigenerational Travel: Pipsqueaks, Grandparentals and Everyone in Between

Our Top Tips for Memorable (and fun!) Multi Generational Travel


We are deep believers in connecting with family through travel, so it comes as no surprise to us that taking the kids – and grandma too – along on vacation is one of this year’s top travel trends. By traveling together with younger and older relatives, families can  create closer bonds and lasting memories — and parents can get free baby-sitting and much-needed alone time.

Perhaps it all started with the destination wedding (where multiple generations were brought together to celebrate a special family occasion) or maybe it’s the proliferation in vacation home rentals (hello AirBnB!); but no matter the exact reason, while multigenerational travel is nothing new, it is definitely seeing a spike in popularity. These days,  ”children are calling the shots, grandparents are increasingly funding the cost of the trip, and an overwhelming percentage of Millennials – 91% of those surveyed – say a multigenerational trip is something they try to take every year,”according to Lindsey Ueberroth, President & CEO of Preferred Hotel Group.  

Vice president of sales and marketing for Xanterra Parks & Resorts, Betsy O’Rourke concurs: “The combination of families being increasingly spread out geographically these days, the affordability of travel and a desire among Boomers to check off items on their travel bucket list, has triggered enormous growth in multi-generational travel. It’s a growth trend that’s likely to continue throughout 2018 because multi-generational travel checks off so many boxes. Not only do such trips provide quality time for families to reconnect in today’s fast-paced world, they’re a fun getaway for kids and an opportunity for the entire family to share experiences.”

Here are our top tips for great multi-generational family travel:

1 The more the merrier

Traveling with a bigger group means more entertainment for the kids, and more people who can look after them. And it means more time for everyone to catch up with family. Traditionally “multigenerational vacation” includes 3 generations of family traveling someplace together. And while this makeup still represents the bulk of such trips, the “multigenerational travel group” has now expanded beyond immediate nuclear family to include siblings, cousins, and even non-relative friends.

2 It’s all about the kids…

Parents, and especially grandparents, really just want to hang out with the family and watch the younger kids have fun. Thus the variety and scope of activities for children is often the driving factor when families are planning their vacations. And, depending on the age of children, it’s important to involve the kids in the planning process, letting them decide what they want to see and do.

3 …but it needs to be accommodating for all

Just having options for kids is not enough. When deciding on when and where and what to do, it’s important to keep in mind that the activities — and travel logistics! — need to be (potentially) well-suited for 7 month olds, 7 year olds and 70 year olds (and can therefore work for anyone in between). The itinerary should have a good mix of scenery, leisure, adventure and offer enough activities at different levels for different age groups so as to keep people entertained but not overwhelmed. P.S. Wine country is one of our favorite places that makes everyone happy!

4 Dining together, dining apart

Meals provide the perfect opportunity to bring family members together, and dining while on vacation should be no exception. Here are lots of any-age-friendly ways to explore the local culture through food while traveling. Gathering around the table together is the perfect way to experience a multigenerational holiday!

But also use the opportunity (and trusted family babysitters) to build in some alone time with your spouse — plan a romantic date night and enjoy a special meal.

5 Boomer Grandparents just wanna have fun

More and more boomers are becoming grandparents. And unlike their predecessors, boomers are typically younger, healthier, and want to spend quality, fun time with their grandchildren. Moreover, grandparents are more inclined to pay for multidimensional trips to help make sure everyone can attend – bonus!

6 Exploring cultures and adventures together

These more mobile grandparents are able to experience more active getaways. This means multigenerational travel is not just about relaxation and fun but also education and exploration. Many parents want their children to learn local culture and history on family trips — and it’s nice that you can also bring grandpa to climb the ruins of Chichen Itza or venture to more adventurous destinations like Croatia, Iceland or even Antarctica with grandma.

7 Ideal vacation spots – keep it simple to start

When first venturing into multigenerational travel, it’s best to keep the destinations simple to allow everyone to warm to the idea and grander trips later. The tried and true favorite destinations are the Carribean, Mexico, Hawaii, Orlando, and Europe with England, Italy and France topping the lists. And of course, cruises, guided tours and all-inclusive resorts are no-brainers when it comes to planning. What’s great about these vacations is that they are typically already family-friendly, can meet the diverse interests and travel styles of various ages, and removes the stress of having to coordinate activities. Plus, depending on how large your group is, there could be significant discount/special pricing.

8 Making new traditions

Most people who have taken multigenerational holidays plan to do so again, even making it an annual family tradition / make a trip every year. When quality time is harder and harder to come by, multigenerational travel can provide many benefits for families (built-in babysitting comes to mind). The kids will enjoy extra time bonding with grandparents, cousins, aunts and uncles, while you can enjoy having extra hands to help wrangle said children. The benefit for extended family members is that they get to spend time with you and be part of the experience (rather than just following along on social media).

9 Know your limits

The idea of renting a big house and staying all together under one roof may be delightful for some, or a recipe for family friction for others. If some relatives don’t get along, or you know your spouse can only take so much time with the in-laws, plan accordingly. Whether that is separate cabins by the lake or hotel rooms on different floors — or limiting a trip to a long-weekend — plan accordingly.

“We’ve found the key to multigenerational travel is ensuring each member of the family has an unforgettable vacation experience individually as well as together,” says Kelly Poling, Senior Vice President of Marketing at Karisma Hotels & Resorts. “This means offering everything from exceptional culinary to engaging kids clubs to spa treatments for all ages. Further, [properties] dedicated to multigenerational travel with expansive multi-bedroom suites, swim-ups, 24-hour room service and beach butler service so families have the space and personalized services to relax and create memories that will last a lifetime in a truly carefree environment.”

While it may seem troublesome to organize a vacation with everyone together, once you do it, you’ll find that it’s not as difficult as you might have imagined… and the benefits are hard to pass up!