When I planned our trip to Hawaii, I imagined days packed with ziplining, hiking, snorkeling, and scenic drives. After all, what grown adult wouldn’t want to make the most of every moment in paradise, right? Well… my two sons had a slightly different idea.
We spent five nights on Kauai and three on Oahu, and while we definitely got our share of unforgettable adventures (and I’ll get to those!), I was surprised by just how much down time they wanted—and needed. It turns out, vacationing with adult kids is a whole different experience than when they were little. It’s a mix of big laughs, new memories, and quiet time that I didn’t know we all needed.
In this post, I’m comparing our time on two very different Hawaiian islands—Kauai and Oahu—through the lens of family travel with adult kids. If you’ve ever thought about taking a multigenerational trip or reconnecting with your grown children through travel, I hope our experience gives you some inspiration, ideas, and maybe even a few laughs.
Kauai: Scenic Roads, Sleepy Starts, and Sweet Pineapple
We kicked off our Hawaiian adventure on Kauai—“The Garden Isle”—and it immediately lived up to its name. Lush, peaceful, and way more laid-back than Oahu, Kauai was the perfect place to start unwinding… even if that unwinding came with more sleeping-in than I ever expected.
Our first full day started strong(ish). I’d rented a Jeep and downloaded the Shaka Guide app, which turned out to be one of my favorite tools of the whole trip. The app uses GPS to guide you through scenic routes while sharing fun facts, history, and tips. It gave us the freedom of exploring on our own, but with a local in our ear the entire time.
Coffee First, Always
We made our way to Kauai Coffee Company for a quick self-guided walk through the coffee farm, which smelled incredible. They offer free samples, and we grabbed one of my all time favorite treats, an affogato (ice cream topped with espresso.
Waimea Canyon – The “Grand Canyon of the Pacific”
From there, we headed up through Waimea town toward Waimea Canyon State Park. The drive is gorgeous, but the earlier you go, the better—lesson learned. We got a late start (thanks to my 20- and 22-year-old snoozing like it was still midnight), and by the time we made it to the lookout, rain and fog had rolled in. There’s a small entrance fee—$10 per car and $5 per person—but the views are absolutely worth it on a clear day. Still, even in the mist, it was stunning.
One of my favorite (and also most what-was-I-thinking?) stops was grabbing coconuts from a roadside stand. My sons took one sip of the coconut water and quickly passed them off to me—two massive coconuts that lived in our fridge for the rest of the trip until they met their fate in the trash on our final day.
But That Pineapple
Now the sugarloaf pineapple? Life changing. I'm not being dramatic. It was hands-down the best pineapple any of us had ever tasted. You’ll thank me later. It doesn't have the acidity other pineapples tend to have and it was so juicy. If you see one while you're in Kauai—get it.
Learning to Slow Down
The following days had a rhythm: late starts, short outings, and a surprising amount of downtime back at the condo. I had booked a budget-friendly condo knowing we’d be out and about most of the day. But spoiler alert: we weren’t. If I could go back, I’d splurge a little more on something with better views, more space, or resort-style amenities because it turns out, your adult kids may want to spend a lot more time lounging than you plan for.
We still got in some great mini-adventures:
Visiting Spouting Horn Park and a quick stop at Poipu Beach, though crowds and long lines had us skipping the iconic Puka Dog and grabbing musubi from a nearby food truck instead. This was one of the best priced and favorite bites we got during our entire trip.
Coffee at Java Kai just before a classic Kauai downpour sent us back to the room once again.
My youngest took a study day in the room while my oldest and I booked a cabana day at The Royal Sonesta Resort & Spa. It was peaceful, relaxing, and honestly one of the best moments of one-on-one time on the whole trip. I highly recommend this resort, especially if traveling with kids!
Chasing Sunsets in Princeville
On our last full day, we finally rallied in the late afternoon for a drive up to Princeville and Haena Beach. The waves were wild and the sunset was everything I’d hoped for. It’s not a great spot for swimming due to strong currents, but it was the perfect place to just sit, watch, and be. Across from Haena Beach is a cave that is sometimes filled with water. Legend has it, that the people of Hawaii would hide treasure in the cave as to not be stolen by passing ships. We were able to explore the cave since it was empty of water (and tourists) being later in the day.
Looking back, Kauai gave us more rest than rush, and I didn’t hate it. I had to adjust my expectations and slow down my pace—but maybe that was the point all along.
Oahu: Island Adventures, Muddy Trails, and a Little More “Friends”
After a quick 19-minute Southwest flight from Kauai, we landed on Oahu ready for the next chapter of our Hawaiian adventure. We grabbed an Uber to our home base for the next few days: the Outrigger Waikiki Beachcomber Resort.
The location couldn’t have been better—central Waikiki, steps from the beach, surrounded by high-end shopping, the lively International Marketplace, and even the brand-new Cirque du Soleil show, Auana. The hotel itself had everything we needed: a small pool, hot tub, coffee shop, and Maui Brewing Company restaurant right on site.
We booked a partial ocean view room, but honestly, it’s not something I’d upgrade to again. We could only spot a sliver of the ocean if we leaned out over the balcony. That said, the resort overall fit our needs really well—clean, convenient, and a perfect base for exploring.
One unique perk was the on-demand rental cars through the Hui app. You simply upload your ID, a selfie, and payment info, and rent a car parked right at the hotel. We grabbed a Toyota RAV4 for about 8 hours (around $147) without paying the $55 overnight parking fee the hotel charges.
Island Drive: Grand Circle Tour with Shaka Guide
Around 11 AM (again, sleepy boys meant a late start), we picked up the car and set out on an island-wide road trip using the Shaka Guide’s Grand Circle Island Tour. If you’re visiting Oahu, I definitely recommend getting an earlier start—traffic and crowds were heavier by midday—but it was still an amazing day.
Highlights included:
Scenic East Coast Drive with jaw-dropping coastal views at every turn.
Lunch at Crouching Lion, a hidden gem with delicious food and stunning views.
Polynesian Cultural Center, where we stopped to walk around, shop, and soak in a bit of island culture. Polynesian Cultural Center offers immersive cultural villages, shows, and a luau experience. If you have more time, it’s worth booking a full day here to explore and do the luau.
Dole Plantation, where we indulged in Dole Whip. They also offer train tours, a giant pineapple maze, and a garden tour if you have time to explore.
We ended the day relaxing back at the room watching “Friends” reruns and laughing until we fell asleep. Honestly, not a bad way to close out a day in paradise.
Adventure Day: UTV Tour at Kualoa Ranch
Our next big outing was the Kualoa Ranch UTV Tour, and it was hands-down one of the top highlights of our entire trip.
Kualoa Ranch is famous for its role in movies like Jurassic Park/World, Kong Skull Island, and Hawaii Five-0. It's a privately-owned nature reserve offering movie set tours, horseback, zipline, etc. We booked a UTV tour, and while the first half was spent soaked from a downpour, the muddy trails just made it that much more fun.
The second half of the tour cleared up with blue skies and lush green mountains. My oldest drove, my youngest was his co-pilot, and I held on tight in the backseat as we bounced along cliffside trails. The scenery was unreal, and the laughter from all three of us was something I’ll never forget.
Tours at Kualoa Ranch book up fast. If you want to include this in your trip, reserve your spot early.
A Taste of Waikiki: Dukes and Hula Pie
After our muddy adventure, we grabbed an Uber back into the city and stopped at Duke’s Waikiki—a must-visit restaurant for oceanfront dining and their famous Hula Pie (macadamia nut ice cream pie topped with hot fudge and whipped cream). It was every bit as decadent and delicious as it sounds.
The Perfect Last Day: Hilton Hawaiian Village Resort
With a 10 PM flight on our final day, I wanted a relaxing place to stretch out and enjoy a little more sunshine. I used the ResortPass app to book a day pass at Hilton Hawaiian Village—giving us access to a day room, multiple pools, beach areas, and plenty of loungers to relax. It was the perfect sendoff.
Final Thoughts
This trip was full of incredible adventures, but also full of slower moments I didn’t see coming—like binge-watching sitcoms together or just chilling poolside with no agenda. Traveling with adult kids isn't about packing every second with activities; it's about being together, however that looks.
Whether you’re chasing adventures, finding unexpected rest, or simply wanting a beautiful backdrop for family memories, Hawaii truly has something for everyone.
If you're dreaming of a Hawaiian escape with your family, I'd love to help you plan it. From finding the perfect island match to picking tours that fit your travel style, I’ll help you craft a trip that’s unforgettable—with just the right amount of downtime.
Let’s start planning your family’s Hawaiian adventure.
