5 Destinations Our 90-Year-Old Grandma Rates a 10/10
Family-friendly vacations from the wee little ones to the great-wise ones.
Multi-generational travel is booming—and for good reason. Recent reports show that more grandparents than ever are joining family vacations, and kids remember these shared adventures far more than any toy or gift. It’s the togetherness they hold onto.
And yes… the planning, prepping, and packing can feel a bit like the opening scene of Home Alone—chaotic, loud, and slightly unhinged. But once you’re there? That chaos melts into connection, memories, and joy.
Finding a destination that works for everyone—the baby who needs naps, the teens who need space, the parents who need sanity, and the grandparents who need accessible accommodations—can feel daunting. But I promise you: adaptable spaces, inclusive activities, and accessible products do exist… and they can make your next family adventure a whole lot easier.
We’ve brought our 90+ year-old grandmother, lovingly known as Mee Maw, on every big family trip. Today, she’s sharing her top 10/10 destinations—and why each one earned her stamp of approval (plus tips and resources!).
⸻
1. Maui, Hawaii – Paia
A tucked-away home in the heart of local Maui—spacious, peaceful, and made for multi-generational families. Mom and Dad stayed in their own guest house while grandparents enjoyed the main house with the kids. Mee Maw had her own suite on the main level with a zero-step entrance, perfect after a long day of exploring.
Travel Tip: Break up long flights with walk-and-stretch breaks for babies and grandparents.
Read more about our Maui experience and tips here → LINK
Mee Maw’s Review:
“A dream come true. Being so close to the clouds. I thought I would never experience Hawaii. Best part? Being with family. P.S… it was extra special because some people discouraged me from going, saying I was too old to fly that far.”
⸻
2. Anna Maria Island, Florida – East Side
A private beachfront home with an elevator—life-changing for Mee Maw and for our uncle who lives with Multiple Sclerosis. The elevator also saved the day for grocery runs, strollers, and luggage.
Read more about this trip here → LINK
Mee Maw’s Review:
“Appreciating the beauty of the ocean and surroundings. Best part—being with family and being inspired by Chris’ (my brother-in-law) determination.”
⸻
3. Michigan City, Indiana – Beachwalk Community
A charming golf-cart community designed for families. The accessible beach wheelchair allowed Mee Maw to join us for the 4th of July fireworks right on the sand. Playgrounds, water activities, ice-cream shops, wide paths, and golf carts made it easy for every generation to explore at their own pace.
Tip: Many homes offer main-floor bedrooms, step-free entrances, and ramps.
Read more about our Northern beach town experience here → LINK
Mee Maw’s Review:
“I learned new and interesting facts. Best part—being with the entire Cross family. The unique ride through the sand to see the sunset and fireworks made me appreciate freedom in a new way.”
⸻
4. Park City, Utah
Mountains can feel intimidating for travelers with mobility challenges—but accessible options do exist. Our stay offered zero-step entry, wide open spaces perfect for rolling and walking, and panoramic views right from the living room. Exploring the outdoors by car—and stepping out in select locations—made the mountains feel magical for every generation.
Pro Tip: We stayed at Stein Eriksen Residences – Deer Valley right before peak ski season. Lower rates, experienced the snow, a little holiday decor and no crowds! At 7 months pregnant with a 24 month old…they made our stay a breeze offering a crib with our stay. It was an effortless and sweet memorable trip with our Mee Maw before baby #2 arrived.
Mee Maw’s Review:
“It seemed like a foreign country. The beauty of the mountains! Best part—being with family.”
⸻
5. Branson, Missouri – Table Rock Lake
Often underestimated, Branson surprised us with one of the most joyful Thanksgiving trips we’ve ever taken. Accessible homes with zero-step entrances, first-floor bedrooms, and main-level gathering spaces made it easy for the whole family to stay together comfortably.
Read about our Thanksgiving in Branson here → LINK
Learn more about our favorite rental company + promo code → LINK
Mee Maw’s Review:
“I enjoyed reminiscing and seeing it all anew. Best part—being with family.”
⸻
The Joy of Multi-Generational Travel
This list is just the beginning. Traveling with multiple generations—babies to great-grands—is completely possible with the right planning, the right tools, and the right mindset.
The chaos? Worth it.
The packing stress? Temporary.
The memories? Everlasting.
Our hope is that these destinations and reviews inspire you to dream a little bigger, explore a little farther, and experience the joy in the chaos—together.
⸻
Ready to Plan Your Next Family Adventure?
✨ Subscribe to The Joyful Blueprint for travel tips, accessible design resources, and multi-generational travel guides sent right to your inbox.
Stay connected with us on Instagram @thetiffanydill for real-time adventures, behind-the-scenes family travel, and joyful home design inspiration.
