How to Enjoy Vacation in Maui: From Babies to Grandparents

Family, Travel
July 24, 2025
2:19 pm

(Originally posted in June 2023, updated 2025)

Dreaming of Hawaii With the Whole Family? You’re Not Alone.

Are you planning a family trip to Hawaii but worried about accommodating everyone—from squirmy toddlers to wise and wonderful grandparents?

Been there. Done that. Still tired—but it was SO worth it.

Don’t let travel hurdles stop you from experiencing the joy, culture, beauty, and accessibility of the Hawaiian islands with your whole crew. Do NOT let anyone tell you grandma or your kids should stay home. Multi-generational travel to Maui is possible!

With intentional planning, my family made it happen—and I’m here to help you do the same. In this guide, I’ll walk you through how we made our trip to Maui accessible, relaxing (mostly 😅), and truly unforgettable.

Where We Stayed: An Accessible Oceanfront Rental in Paia

We stayed in a home I now lovingly call “the hidden gem”—a place where you can walk into town for coffee, hear waves crash while you sleep, and roll a stroller or a walker right through the front door.

📍 Location: Paia, Maui
🏡 Rental: Oceanfront, walkable to downtown Paia
🔗 VRBO Listing: #3161601

Why Paia?

Paia is a laid-back, cultural beach town far from the typical tourist bustle. Don’t let the drive past a small cemetery fool you—this home is a gem, especially for families who value space and accessibility.

Pricing

The North Shore (Paia) is often more affordable than resort-heavy areas like Wailea or Kaanapali. That means more space for less cost—a win when you’re traveling with a large group.

Stress-Saving Travel Tips (From a Mom + OT Who’s Been There)

✈️ Long flights + littles = plan ahead.
We were strategic about our flights—from choosing nap-friendly hours to packing ALL the snacks, sensory toys, and comfort items. (Pro tip: Save new activities for the plane!)

🧳 Minimize luggage by renting larger items locally.
⏳ Stay at least 7 nights to allow wiggle room for jet lag, rest days, and rainy-day reroutes.
📞 Call ahead to ask detailed accessibility questions for your family’s needs.

Equipment Rental Recommendations:

Maui Vacation Equipment Rentals – baby + beach gear
Gammie HomeCare – medical and mobility equipment (they even allow island-hopping!)

Fun fact: When Alaska Airlines misplaced our Mee Maw’s rollator, Gammie HomeCare saved the day—and the airline reimbursed us for a new one!

Top Accessible and Family-Friendly Things To Do in Maui

🌅 Haleakalā National Park
Sunrise is magical (but requires a reservation). We chose sunset instead—less stress, same wow factor. Pack snacks, layers, and patience.

🐟 Maui Ocean Center
Perfect for kids and wheelchair accessible. My husband took the boys while I had a family day on another island—everyone was happy!

🍽️ Mama’s Fish House
Book 4–6 months in advance. MeeMaw called it “the best food in my 92 years!” (That’s not paid influencer hype—that’s MeeMaw truth.)

🌺 Feast at Mokapu (Andaz Resort)
A stunning luau with amazing food. Reserve early. Bonus: They offer VIP golf cart transport for guests with mobility needs—our baby and MeeMaw both got the royal treatment.

Simple Upgrades to Make Any Vacation Home More Inclusive

(Take-home tips from your OT friend!)

✅ LED stair lights or contrast tape (essential with kids or nighttime trips)
✅ Rubber threshold ramps for wagons, rollators, or strollers
✅ Removable shower head on a slide bar (hello postpartum mamas, seniors, and even housekeepers)
✅ Teak bench or portable shower chair
✅ Grab bars in key spots (modern options are actually cute!)
✅ Vertical grab bar at the garage step

Even if a home isn’t fully designed for accessibility, small updates like these make a huge difference for people of all ages and abilities.

Location Perks of Paia

🚘 15 minutes from the airport
🏖️ 25–30 minutes to South Maui beaches (Wailea, Kihei)
⛱️ 45–60 minutes to West Maui (Kaanapali, Lahaina)
🌄 ~90 minutes to Haleakalā for sunrise/sunset
🗺️ Already ON the scenic Road to Hana

Paia has a relaxed, artsy vibe that feels like real Hawaii, not just the resort version.

Final Thoughts From Our Family to Yours

This trip wasn’t just a vacation—it was a multi-generational memory-maker. Sure, there were some chaotic moments (like a visit to the ER with our toddler), but also joy, rest, and connection.

Accessibility should never be the reason someone stays home—and in Maui, it doesn’t have to be.

If you’re considering Hawaii with your whole crew—do it. With the right prep (and the right rental!), you can include everyone from sippy cups to walkers and create memories that stick.

✅ Want More Family Travel Tips Like This?

👉 Sign up for my newsletter, The Joyful Blueprint—where I share monthly tips for accessible family travel, simplified living, and joyful chaos.
📸 Follow me on Instagram @thetiffanydill for behind-the-scenes travel tips and design inspo from our family to yours.

Read more on survival tips and strategies for traveling with multiple generations from babies to seniors 👉 The Ultimate Guide to Multigenerational Travel: From Infants to Seniors.

Disclaimer: Some links may be affiliate links, which means I may earn a small commission—at no extra cost to you—if you make a purchase. I only recommend what I truly trust and use for my own family.

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Meet the Blogger

Hi, I’m Tiffany Dill!

As a mom with profound hearing loss, I know firsthand the beauty and chaos of navigating life with young kids, extended family, and all the little surprises along the way. At Blue Day 2, I’m all about creating spaces and experiences that bring joy to families of all ages and abilities. From home designs that work seamlessly for everyone to sharing my favorite picks from my LTK and Amazon shops, I’m here to make life and travel simpler, more accessible, and filled with joy. Stick around for plenty of inspiration, a little less stress, and a whole lot more fun as we embrace life’s perfectly imperfect adventures together!

Let's Get Personal!

Click on the tabs below to learn more fun facts about me. Do we have anything in common?

Tiffany, you've been married to Andrew for over 16 years now. Any special anniversary traditions?

Oh, absolutely! Every year since we got married in September 2008, we’ve worn the exact same clothes we left our wedding reception in. Yup, I'm talking my gold cocktail dress, wedding jewelry shining, and Andrew rocking his wedding suit. We’re not about to let that tradition slide. It’s been 16 years of pure anniversary magic. I guess you could say we’re "stuck" in our wedding day outfits, but in the best way possible!

Completing an Ironman and earning a doctorate in occupational therapy in the same year sounds intense. How did you pull that off?

Intense is one way to put it! But honestly, raising two energetic boys might just be the hardest thing I’ve ever done. The Ironman and doctorate were definitely tough, but mom life? That’s the ultimate endurance race. It’s the one that keeps me—and even Andrew—on our A-game, every single day. I wouldn’t trade it for the world, though. There’s nothing like their opposite personalities and they surprise you with so much joy even in the chaos, and that's where my energy goes—no finish line required.

You’ve set a pretty ambitious goal with playing ‘Sweet By and By’ on the piano. What’s the story there?

Ah, yes! I miss playing the piano. I started playing piano since second grade and even made it to an advanced level through college. But now, my life goal is to master Sweet By and By (again) before I leave earth. It’s definitely a stretch, but that’s the fun part, right? First, though, I need to add a piano in a room I’ve been dreaming of since we built our home. Playing piano was always my outlet. Until then, running is my stress reliever.

Hidden talent alert: You can read lips. How’d you discover that one?

Oh, this one goes way back! When I was four years old, I managed to fool five different audiologists during my hearing tests. It wasn’t until a doctor noticed that I wasn’t repeating what she said when she turned around (back in those days they didn’t cover their lips nor did they have tinted windows in the sound booth)! I had spinal meningitis at 13 months, which nearly took my life and left me in a coma for a week. As a result, I had to start over on a few developmental milestones and missed a lot of early speech and language development. Thanks to years of speech therapy and a knack for lip-reading, I still manage to fool people with my profound hearing loss. It comes in handy when someone wants to know what the ref said on the field or TV, or if I’m in a crowded room and want to eavesdrop—just kidding. Sort of.

On the flip side, what are some things you’re not a fan of?

Confined spaces. Cilantro. Olives. Blue cheese. I could live without all of those. And don’t even get me started on being stuck inside for hours at a time. I'm much more suited to wide-open spaces, the great outdoors, and pretty much anything that involves fresh air.

We all know you’re a planner, but what do you hold closest to your heart?

Sentiments. They’re irreplaceable. There’s something about the things that carry emotional weight—whether it’s a moment or an object—that just can’t be duplicated. I’ve learned to really appreciate the simple, meaningful stuff in life. In fact, our Christmas tree is adorned with over 20 years of ornaments symbolizing memories from a loss of loved ones to trips and even sour times. It’s like finding joy in the simple little things whether they are happy or sad or even bad memories.

You’re a busy mom and entrepreneur, but how do you manage to squeeze in family time?

Time? What’s that? Ha! Honestly, there’s just not enough of it. And the thing is, we can’t get it back. So I prioritize memory-making with my family. That’s my top priority. Whether it’s hiking, running, biking, traveling, or exploring the great outdoors with my boys, I live for those moments. In fact, I devote one day off work a week to be with my little guys and my husband and I carve out a weekly date night.