Roadmap: Planning a Multigenerational Vacation

Keeping everyone in your family happy, from the littlest kids to the elders, seems impossible but it’s not—with these tips.

Traveling is one of the most transformative and life-changing experiences for travelers of any age. It becomes even more enriching when grandparents, siblings, children, and other extended family are included. And, today, since many families are geographically separated due to the demands of life, sometimes a multigenerational getaway is the only way families can gather in one place. With grandparents living longer, staying more fit and active, and financially able to subsidize meaningful experiences and interactions with their children and grandchildren, this kind of family travel is becoming the go-to option.

According to a 2023 travel and tourism report by Gitnux, multigenerational travel accounts for 15% of all leisure travel with motivations ranging from culture and education to adventure and escape. According to one by the National Tourism Association, 35% of leisure travelers are grandparents who traveled with their grandchildren last year, multigenerational vacations represent about half of all vacations taken by parents and grandparents, and 45% of all leisure travelers brought kids along on their trips.

CondeNast Traveler reports “In 2024, travelers will be putting what’s important to them front and center of their plans, valuing deeper experiences that leave a positive impact, time spent with loved ones, and wellness moments that last well after checkout.”

These statistics highlight that multigenerational travel is on the rise and that multigenerational travel getaways are increasingly seen as a great way to bond and spend quality time with extended family members. But it’s no secret that travel planning can be complicated at the best of times. Throw in grandparents and toddlers and keeping everyone happy becomes a mammoth task. Travel industry experts can provide insights to help take the guesswork out of multi-generational travel planning.

Making New Memories

Ariel Alexander, regional coordinator for Latin America at Word Made Flesh Foundation and frequent multigenerational traveler, recently took a family trip to Costa Rica with her husband, parents (grandparents), and her school-aged children. Ariel shares that, “In deciding to visit Costa Rica, we made sure all the adults participated in the planning conversation to ensure that everyone’s needs were factored in. We also included the children in conversation elements that had to do with identifying their preferred activity choices and excursion preferences.”

In Alexander’s family’s case, two reasons led to them choosing Costa Rica, one was family ties to Costa Rica and a desire to visit important places from the family’s past, and the other was for eco-tourism and plenty of family-friendly options of places to visit and activities to do. Whether traveling in the United States or outside of it, sometimes “why” is as important as the “where” to travel, especially when planning a multi-generational getaway.

Alexander’s recent family trip to Costa Rica is a great example of the adage, “The journey is more important than the destination.” For Alexander’s family, Costa Rica had cultural significance. Her parents were able to share memories and teach the family’s history to her children. Her children were able to learn about the family’s legacy in the country and make their own memories. For multigenerational travelers, choosing destinations that facilitate conversations and strengthen connections is important.

Sonya Belletti, LCSW, says that according to Bowen’s Family System Theory, which sees the family as a unit with its own complex systems, multigenerational interactions are valuable and can foster healthier relationships for everyone. But generational trauma can stifle that growth, creating more stress than harmony.

“It is important to establish boundaries around expectations, desires, and intentions before planning a trip, says Belletti. “Quite often, people forget that all the needs of family members are important and can be met with effective communication.”

“Vacations are a time for relaxation and exploration, so it is important to decide who you want to spend that time with,” says Belleti. “Practical considerations include destinations that can accommodate family members of all ages and physical abilities. Excursions should reflect the abilities of all family members—younger kids and elderly family members may not be at their best with a full day of excursions.”

Regardless of a family’s history, whether there is past trauma or not, through clear and consistent communication, expectation management, and input from everyone, travel planning will not only be effective but strong and healthy intra-familial bonds will be built.

For families looking to get away, travel and family relationship experts offer their pro tips for multigenerational travel planning Dos and Don’ts:

Planning Makes Perfect

Plan and schedule everything in advance—excursions and activities, hotel, travel, recommends travel expert Roni Faida. Faida adds that by planning and scheduling in advance, travel can be more affordable as it allows travelers to take advantage of early bird deals and discounts. It also means you can score and lock in better airline ticket prices but it can also include other travel perks like airport transfers, and assistance with rebooking flights if you face cancellations, among other money-saving benefits.

Communicate a lot in advance while taking into consideration differing expectations, and what activities people want to do, advises Alexander. Family health and wellness resources suggest that the key to successful family travel is to foster effective communication. Communicating openly, creating an environment where all participants can express their preferences and choices, making decisions by consensus, and practicing active listening all contribute to an efficient getaway planning process and an even better vacation.

Insure Your Trip

Consider getting family travel insurance (an annual plan if your family travels a lot during the year), Belletti recommends. Travel insurance is an important aspect that is often overlooked. Travel insurance offers protection against unforeseen events such as flight cancellations, lost luggage, travel delays, or medical emergencies, and could be particularly useful to have when taking a multi-generational trip.

Make Space—And Time

Recent travel reporting indicates that when traveling with larger families it is important to have separate accommodations for grandparents. There are many reasons for this, but among the most important is having privacy and space where grandparents can be comfortable and able to rest and escape as needed. Adjoining rooms or suites can be ideal for multigenerational travel as they give space and privacy but also the convenience of being close to each other.

Make time for me/we time when taking multigenerational travel getaways. Grandparents seeking quality time with grandchildren will relish the opportunity to watch the kids on occasion so parents can enjoy a date night, couples massage, or a stroll along the beach. At the same time, this gives parents peace of mind that their children are with trusted and loving family members. As long as these expectations are managed and agreed upon in advance, everyone can benefit from this multigenerational travel perk.

Little ones and grandparents will also get more tired in an unfamiliar environment with lots of stimulation. Having an agenda is great to keep things organized but be open to shifting as needed. Leave some free time available, do not prebook all your excursions unless they require reservations. According to the Level Hotels and Furnished Suites website,“Leave some room to explore the neighborhood or take advantage of downtime. Sometimes the best memories are made when there is no plan at all.”

It’s Time For An Adventure

Don’t be afraid to go off the beaten path. “One of the most memorable experiences was taking the local commuter train from one city to the next. The kids had a blast with the train, and it was a relaxing and cheap way to explore for all the adults,” says Alexander. Not every trip needs to be curated for kids to be a family-friendly adventure if you prepare properly.

Still, Faida reminds families for the success of multigenerational trip planning that it is critical to, …Manage expectations. An 80-year-old is going to have a different experience than a 3-year-old. The key is finding something they can do together, where each can enjoy it from their perspective,” she says. “And if there is nothing they can do together, taking turns picking activities that cater to each generation may be necessary.”

A 3-year-old and an 80-year-old will not have the same travel experience, so when choosing which activities to pursue, find activities that both can enjoy and ideally do together. For example, make sure your hotel has a pool where they can both cool off and swim around together, find museums that cater to the interests of the adults but offer tactile and hands-on exhibits to keep little people busy and engaged and choose restaurants where the cuisine appeals to the adults but where there are the kid-friendly food options and activities to keep their attention.

When options are scarce, leave room in your itinerary for separate activities, or have a day that is decided by the 80-year-old and a day that is decided (with help) by the 3-year-old, and do it in advance. Allowing for this type of flexibility in the schedule will ensure that all travelers can take ownership and feel like their needs and wants have been met.

Alexander shares a final tip: “With good planning, willing companions, and lots of flexibility, multigenerational getaways are truly among the best opportunities to create lifelong memories.”