Multigenerational Travel Tips That No One Talks About
What No One Tells You About Multigenerational Travel (But I Will!)
Ah, multigenerational travel. The idea sounds dreamy—sunset dinners on the beach, cousins splashing in the pool, grandparents beaming at the grandkids’ joy. And while those magic moments do happen (and they’re amazing), there’s also a behind-the-scenes truth to these big family getaways: they take planning, patience, and a little insider know-how.
As a travel advisor who specializes in family, group, and accessible travel, I’ve seen the full range of multigenerational travel—both the Pinterest-perfect memories and the “Why did I agree to this?” moments. So let’s talk about what no one tells you… but I absolutely will.
1. Everyone Has Different Vacation Styles (and That’s Okay)
Grandparents may want relaxation and slower-paced days. Parents might be juggling kids and craving convenience. Teens might want independence, and young kids just want pool time and snacks.
Pro tip: Pick accommodations (like cruise ships or resorts) that offer options for all ages. A resort with a spa and a kids' club? Yes, please. Cruises are great for this too—you can be together, but still do your own thing.
2. Not Everyone Likes to Wake Up at 7 a.m. on Vacation
One person’s dream is early morning yoga; another’s is sleeping until brunch. Multigenerational travel only works when everyone has the space to be themselves without guilt or judgment.
Pro tip: Build in flexibility. Don’t overschedule every moment. Create pockets of “together time” and “do-your-own-thing time.” That way, everyone has room to breathe.
3. Mealtimes Can Get Complicated
Food allergies, picky eaters, meal preferences, and dietary needs? Multiply that by 3 generations and you might find yourself needing a spreadsheet.
Pro tip: Choose all-inclusive resorts or cruises that offer buffet and à la carte options. Many will accommodate special diets or sensory food preferences with advance notice—something I always help clients arrange.
4. You’ll Need to Be Thoughtful About Mobility
Grandparents might not want to hike up hills. Parents might have strollers. Someone may use a wheelchair or just need frequent rest breaks. Mobility matters more than you’d expect.
Pro tip: Look for destinations that offer transportation, elevators, ground-floor rooms, and accessible excursions. I work with properties that consider mixed mobility needs without compromising fun.
5. Privacy Is Everything
It’s tempting to squeeze everyone into a big house or adjacent rooms, but let’s be real: downtime away from the group can save relationships.
Pro tip: Book villas with separate sleeping areas, connecting rooms with doors that close (bless them), or cruise cabins on the same hallway but not next to each other. A little separation goes a long way.
6. Someone Has to Be the Point Person (and It Shouldn’t Be You)
Group texts get chaotic. So do shared calendars. When it comes to booking and organizing, you need someone who can handle the logistics—without also trying to herd the family cats.
Pro tip: That’s where I come in. I take care of everything from coordinating flights to booking accessible ground transportation and confirming allergy-friendly meal options. Your job? Show up and enjoy.
7. The Best Memories Come from the Most Unexpected Places
Sure, you’ll remember the sunset dinner, but you might treasure the rainy-day card game or spontaneous group karaoke night even more.
Pro tip: Leave room for spontaneity. Don’t plan every second. Let the magic find you.
Ready to Plan Your Next Multigenerational Adventure?
Multigenerational trips can be deeply meaningful, filled with moments your family will talk about for years to come. With the right planning—and a travel advisor who gets it—you can skip the stress and go straight to the good stuff.
Reach out today and let’s start planning a trip that brings your family together, beautifully.
