Magical Memories: Planning the Perfect Multigenerational Vacation
There’s something truly magical about traveling with your whole family. Grandparents, parents, and kids all discovering the world—together. But let’s be honest: planning a multigenerational vacation isn’t always easy. How do you find a destination that keeps everyone happy?
If you’re planning a trip to celebrate a milestone birthday, retirement, graduation, or simply to reconnect, I’ve pulled together some favorite travel styles and destinations that are perfect for all ages—and all personalities.
Ocean Cruises: Classic and Crowd-Pleasing
Why It Works:
Ocean cruises remain one of the top picks for multigenerational trips—and for good reason. With kids’ clubs, adult-only pools, enrichment classes, live entertainment, and endless dining options, there’s something for everyone. And with everything taken care of onboard, it’s a stress-free way to travel.
Where to Go:
- Disney Cruise Line: Best for younger kids and families who want the magic of Disney at sea.
- Royal Caribbean: Offers more variety and adventure for tweens, teens, and active grandparents.
- Looking for something unique? Explore Alaska, the Mediterranean, or the Norwegian Fjords for a more adventurous twist on the classic cruise.
Beach Vacations: Sun, Sand & Simplicity
Why It Works:
There’s nothing quite like a beach day with the whole family. But for the adults, especially grandparents, traditional beach house rentals can feel like more work than rest. That’s why I recommend resorts that offer villa-style accommodations—with housekeeping, dining, and kids’ activities included.
Where to Go:
Hilton Head, SC is a standout. With gorgeous beaches, world-class golf and spas, and plenty of kid-friendly amenities, there’s something for every generation. Plus, nearby Savannah adds culture, cuisine, and charm just a short drive away.
River Cruises: Europe, Simplified
Why It Works:
River cruising offers a smooth, immersive way to experience Europe—without constant packing and unpacking. Disney’s partnership with AMA Waterways has made river cruising family-friendly, with cabins for families of four, onboard youth programming, and curated excursions.
Where to Go:
- Seine River (France): A perfect first-timer’s itinerary, with stops in Paris, Normandy, Giverny, and Rouen.
- Danube & Rhine Rivers: Great for families with older kids interested in castles, history, and culture.
- Rhone River: A food lover’s dream through Southern France.
Heritage Travel: Trace Your Family’s Roots
Why It Works:
Heritage travel is incredibly meaningful—walking the streets your ancestors once did, visiting hometowns, sharing stories with the next generation. It’s emotional, enriching, and unforgettable.
Where to Go:
It depends on your family’s heritage! I’m currently planning a trip to Greece with my father and daughter—a dream he’s had for over 20 years. Other popular heritage destinations include Italy, Ireland, and Portugal. For families with younger children, Ireland is especially easy and engaging.
Villa Rentals: Slow Down, Savor, and Reconnect
Why It Works:
For families spread across different cities or states, a villa rental offers the perfect chance to slow down and reconnect without too many structured activities. It’s ideal for families who just want to enjoy good food, good wine, and good company.
Where to Go:
I’m partial to the Tuscan countryside or Provence, France—especially on a working farm where you can pick up fresh bread in the village or enjoy tastings at a nearby vineyard. It’s a chance to live like locals and experience another culture in a deep, authentic way.
Let’s Plan Something Extraordinary
Multigenerational travel brings your family together in the most special way—but it also comes with its own set of logistics. Multiple flights, different interests, ages, and energy levels can make it tough to plan. That’s where I come in.
As a travel advisor who specializes in multigenerational vacations, I help families like yours plan memorable trips—without the stress or extra cost.
Ready to start planning?
Schedule a time to tell me about your family →
And in the meantime, check out my quick guide to How to Plan a Multigenerational Vacation (Without Losing Your Mind) so you can skip the stress and focus on the fun.
