How To Plan a Multigenerational Trip Everyone in the Family Will Enjoy

By Jamie Edwards

“I’d love to play pickleball!” my mom says excitedly. “Golf, too!” my brother-in-law adds. “A quiet place to read my book would be nice,” my sister continues. “Will there be a pool?” the four grandkids ask in unison.

Guess who’s in charge of the family’s summer vacation this year? You got it.

Multigenerational travel is filled with memories everyone will treasure, but getting it planned is no small feat. In fact, planning a trip that spans multiple generations can suck the fun out of the holiday if you let it. Each generation has needs to be met. Grandma and Grandpa need a room on the main floor. Your 6-month-old nephew needs a crib and a highchair. And your teenage niece needs a bike to escape her tormenting brother.

What do you need? How about a strategy? Keep reading, you’ve come to the right place.

The Benefits of Multigenerational Travel

Multigenerational travel is a trend that has taken off at lightning speed. The desire for families to spend vacation time together has increased dramatically since the pandemic. Whether that be at a beach house, a resort, or on a boat, the message is clear—families want to make the most of their time together while they can. There’s no time like today to start planning.

Traveling with our parents and kids has many benefits. First and foremost, it allows grandparents to spend quality time with their grandchildren. Grandparents will relish sharing family history and telling them funny stories about their parents’ childhoods. Fostering connections between generations is even more critical as families today tend to live farther away from each other than previously.

Being together at a chosen destination rather than at home relieves many pressures. As is often the case on vacation, no one has to cook, clean, do laundry, or make the bed. Taking these chores off the table creates space to enjoy each other differently. This could mean playing a game of ping pong with the teens, kayaking with the in-laws, or reading aloud to a toddler at naptime.

A tangential benefit for parents is that with grandparents cooing over the kids, they can take advantage of time to themselves—a long walk on the beach or a game of tennis, for instance. Knowing the kids are in capable and loving hands is the ultimate perk of having grandparents on hand.

5 Ideas for Multigenerational Trips

Today, resorts and properties have found brilliant ways to cater to larger groups. The desire for extended family vacations has changed how hotels meet guests’ needs. Some hotels have kids’ kits, including indoor and outdoor group activities. Other hotels offer private bike tours or guided hikes for all ages. Personalized service is critical when traveling with a large group spanning ages 8 to 88.

Families can travel together in many ways, yet still have time to themselves. Are you the travel planner in your family? Five crowd-pleasing ideas follow.

  1. African Safari: Botswana, South Africa, and Tanzania are all fantastic safari options for multigenerational travel. Safaris are great for kids who are patient enough to sit still for a few hours in a jeep observing animals. Although the age will differ for each family, the wonder and excitement of seeing animals in the wild is truly ageless. Most safari outfitters are well-versed in keeping guests of all ages happy and content while exploring the bush. An African safari is a truly unique experience for intrepid families.
  2. Private Gulet: Chartering a private boat in countries like Croatia, Turkey, and Greece offers days of endless sun and water-based activities. A captain and crew are on hand to ensure all needs are met, from dietary restrictions and culinary preferences to booking restaurants and excursions. Traveling by private charter is a lovely and decadent way to travel as a family.
  3. Beach House: One of the most relaxing ways to spend a family holiday is with our feet firmly planted in soft white sand. Beach areas like the Outer Banks in North Carolina, the Jersey Shore, and the Hamptons are fabulous East Coast options designed to please. La Jolla, Santa Barbara, and Laguna Beach are Pacific Coast counterparts. Choose a house and location that appeals to the sun worshippers in your crew and enjoy the leisurely-paced beach life for a while.
  4. Caribbean Island Resort: Island resorts in the Caribbean are pure paradise and a natural fit for large family groups. They are usually small enough that everyone can be together but large enough that you aren’t on top of one another. Many island resorts, like Antigua’s Jumby Bay or Petit St. Vincent, have no motorized vehicles, creating an intimate and finite setting to wander and explore. Collect shells, ride waves, snorkel, or just sit under a thatched umbrella with a daiquiri, there’s nothing quite like whiling away the hours on a private island.
  5. European Villa: European cities are suffering from overtourism. What better way to beat the crowds than renting a country villa? Choose a villa on the outskirts of Siena in Italy, or just outside Cannes in France, and escape the throngs of tourists at your private oasis. Whether your family is inclined to head to Greece, Portugal, or Croatia, villas have extraordinary amenities and beautiful grounds and rooms to please everyone.

Travel Planning Tips for Multi-Gen Vacations

A little upfront planning will make tackling a multigenerational trip much more smooth. Here are five essential tips and strategies to help simplify the process.

  1. Plan in advance: Multigenerational trips require even more advance planning, as there are more flights to coordinate and schedules to align. Pre-planning dinner reservations and group activities is a must. A good rule of thumb is to start organizing at least 6-12 months in advance to get your preferred property and take advantage of the best airfares.
  2. Decide money issues upfront: Are the trip costs equally divided among family members, or are the grandparents treating? Knowing who is footing which bills is critical when planning a trip of this nature. No one wants to feel resentful or taken advantage of. Discussing the monetary issues in advance will troubleshoot any possible money-related tensions.
  3. Set rules and expectations: Is everyone ok with less screen time for the kids? Will bedtimes be pushed? Are the days a free-for-all with the only requirement being to meet up for dinner? Agreeing upon the answers to these kinds of questions will alleviate any stress between family members.
  4. Identify the trip’s goals: Are you away to chill out, go sightseeing, or participate in full-day excursions? While everyone can have different vacation goals, knowing what they are in advance will reduce confusion and manage expectations. The fact that you’ve all decided to take this trip in the first place means family togetherness is a priority. Keep that top of mind as you think about your goals.
  5. Don’t over plan: Regardless of energy level or age, incorporating downtime (even one hour a day) is essential when traveling in a large group. A midday nap, reading on the porch, or a leisurely walk is bound to recharge batteries and make the other hours of the day more rewarding.

Most importantly, use a travel advisor to help put the many pieces of this complicated puzzle together. The team at CIRE is well-equipped to handle the specifics and needs of your multigenerational group. Beyond helping you find the right property in the right destination, they can coordinate flights, reserve restaurants, and take care of excursions.

Who’s in Charge?

After researching several options with my CIRE travel advisor, we decided to rent a village home in South Carolina’s Lowcountry. Palmetto Bluff’s Village Home 33 has a porch swing where my sister can read the latest Kristin Hannah novel. The resort has pickleball courts for my mom, a golf course for my brother-in-law, and a heated pool where the grandkids can shout ‘Marco’ and ‘Polo’ to their heart’s content. Or, until their dad yells ‘Mercy!’ Bikes are on hand in case anyone needs a quick getaway. Everyone’s needs are happily met.

What about me? Everyone in my family is relaxed and happy. What more could I possibly want?


Jamie Edwards is an avid traveler, travel writer, and photographer. She launched I am Lost and Found, her adventure/luxury travel website after 25 years of living and traveling around the globe. Jamie’s goal is simple, to inspire travel.

CIRE Travel is a full-service travel agency headquartered in New York, NY.  Our expert corporate travel planners, honeymoon travel agents, and luxury travel planners support clients across the country and around the world.

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