How to Plan a Family Trip to Hawaii
Organize a stress-free, multi-generational getaway with our guide.
Hawaii is a near-perfect honeymoon or anniversary destination, of course, but the Aloha State can also be fun with the kids. Logistically, it’s a breeze, allowing you to delve into a unique culture and landscape without having to juggle everyone’s passports, go through customs, or deal with currency exchanges. Kids also provide a constant excuse to get out there and try something you never would have if it was just you and your significant other.
Any of the four major islands (Oahu, Maui, Kauai, and the Island of Hawaii) have countless resort options ready to welcome your brood with an all-inclusive type of experience, but it’s also easy to create an itinerary yourself, tailored exactly for your family. Here, you’ll find a starting point to give you ideas on where to stay, dine, and find adventures that are just a bit off the beaten path.
Hawaiian Airlines offers the most flights from the mainland and between each island, but they also partner with JetBlue, American, and United in point sharing. Other airlines, such as Alaska, American, Delta, United, Virgin America, Allegiant, and WestJet also offer relatively frequent nonstop flights from most major cities across the western U.S.
If you’re feeling overwhelmed by booking the whole family for the entire trip, you can break up the process. It’s sometimes easier to secure the flight from the mainland first. Then, you can take your time to book the flights between the islands. Inter-island flight prices fluctuate less and the flights are a snap to book.
The first thing to figure out is the number of islands you want to visit. Unless you live on the West Coast, it’s worth going to at least two, given the longer travel time.
To avoid baggage fees, pack as light as possible, especially if you’re taking multiple flights throughout your vacation. If you do want to check baggage, Southwest Airlines recently began flights to the islands and allows two checked bags free.
While Hawaii’s tropical climate may have you thinking shorts and flip-flops, what you need depends on where exactly you're going. If you’re visiting higher elevations, such as Haleakala National Park on Maui, you'll want to be prepared for cold temperatures.
To really see Hawaii, renting a car is a must. There really isn’t another easy way to get around, whichever island you’re on, so be prepared for some time behind the wheel as you travel from the hotel to various beaches and sites.
Since flights to Honolulu are frequent and less expensive, you’ll likely end up in the state’s capital city, at least for a few days. It’s worth staying awhile for the uniquely laid-back urban experience you can have here that just isn’t possible on the neighbor islands.
Where to Stay
Steps from the bustle of Waikiki beach and its towering resorts, you’ll find The Surfjack Hotel and Swim Club. While its cool, midcentury modern-inspired design may lead you to think it’s strictly for young hipsters, it’s actually a great choice for families, too. Their two- and three-bedroom suites give you much needed space at a reasonable price, and it’s an easy walk to Waikiki’s shops and the beach. Plus, the onsite restaurant, Mahina and Sun’s, offers creative, delicious farm-to-table food, with plenty of options the kids will love (including a great burger). Just across the street is Lemona Shave Ice, where syrups and toppings are made with fresh fruit.
Where to Eat
Start the day right with hot, fried-to-order malasadas from Leonard’s Bakery. Think hole-less doughnuts with a more flavorful, almost chewy dough. When lunchtime rolls around, check out Ono Hawaiian Foods. This no-frills hole-in-the wall serves a meal for two that’s enough to feed a family of four. It includes traditional dishes like kalua pig, lomi lomi salmon, and haupia (a Hawaiian dessert made with coconut milk). The best of the bunch is the steamed taro-leaf-wrapped pork lau lau, where the greens soak up the porky richness while encasing their meaty juices.
What to Do
Diamond Head and Pearl Harbor are iconic sites for a reason. They’re educational experiences, sure, but not only in an academic sense. The USS Arizona Memorial is (temporarily closed until fall 2019) is unspeakably moving in a way that kids of all ages will feel, even if they don’t yet fully understand its significance. Diamond Head — right in a volcanic crater — is just plain cool. If the whole family is in shape, you can hike the many stairs to the top, where you’ll find some of the best views on the island.
“Lush” is the only word that can begin to describe this island of green mountains, valleys and cute little farm stands. There’s a funky and super chill vibe here, where wild but harmless chickens roam the roads and the vegetation all around you feels incredibly alive. That may be partly because it’s buzzing, literally, with mosquitos, so be sure coat yourself with bug spray.
Where to Stay
The Lodge at Kukui’ula, on the south shore, combines all the comforts of a luxury home rental with the amenities of a high-end hotel, but without the preciousness that makes you hiss, “Don’t touch!” at the kids. In fact, there are plenty of things kids should touch here, like the jars of complimentary candy and a freezer full of ice cream bars in the game room. The no-cash, no-tipping model makes for unusually warm and easy interactions with the staff, all of whom are locals who readily share their favorite haunts and who treat you more like a friend in their home than a guest in their service. With only fifty rental units, the whole place remains blissfully uncrowded. The expansive grounds, fun to get around on bikes, include a communal farm, so cooking with just-picked produce is especially enjoyable. The same vegetables, fruits, and herbs (along with local fish and meat) are prepared exceptionally well in the onsite restaurant. If you have tweens or teens, you’ll appreciate the ability to let them freely roam the property and swim in the collection of cascading saltwater pools while you enjoy a round of golf or a spa treatment. In the evening, everyone reconvenes for dinner and s’mores.
Where to Eat
Check out the daily farmers’ markets, known as “sunshine markets,” all over the island. The tropical produce tastes better and costs less than at supermarkets, and some showcase prepared foods, too. It’s a great place to introduce little ones to exotic fruits. Kids can also enjoy that fruit in dessert form at JoJo’s Shave Ice, where they’re used in the homemade syrups (definitely opt for the macadamia nut ice cream addition, which goes under the shave ice). Or go for all ice cream at Lappert’s Hawaii Ice Cream and Coffee. Their Luau Delight sorbet tastes so creamy from coconut milk that it’s as luscious as the dairy-rich choices.
What to Do
Kauai is known for the phenomenal scenery along its many hiking trails, especially those that hug the Napali Coast. Unless you have older kids who are more experienced hikers, wait until your second honeymoon or until your kids are grown to try that particular route. Instead, drive to the scenic lookouts of Waimea Canyon and check out the Canyon Trail to Waipo’o Falls. Just keep the little ones—and selfie-taking older ones—away from the edges of the canyon.
The gentle waves and warm water of Hanalei Bay are perfect for first-time surfers. Titus Kinimaka’s Hawaiian School of Surfing offers great lessons for families.
Related: Kauai Travel Guide
Pick a side—any side—and then get ready to drive. Most hotels sit along the southern coast in Wailea or the west coast in Ka’anapali and Lahaina. The rest of the island’s wonders span in all directions, so be prepared to be behind the wheel or to pass on the sites and stay put on the beach.
Where to Stay
The Four Seasons Resort Maui at Wailea seems to spoil the kids almost more than the adults. After the lei welcome (and an offer of lemonade), they get treated to gifts: beach toys for toddlers, stuffed animals for kids, and caps for teenagers. Sure, the grown-ups have delicious chocolate welcome cookies, but the little ones have oatmeal raisin cookies, juice, pretzels and locally made soda. When it’s bath time, they’ll find their names spelled out in sponge letters next to the huge soaking tub. Those touches—along with every other Four Seasons luxury — make the stay feel extra special. And even the regular guest rooms have sofa beds and plenty of space for the whole family.
Where to Eat
It’s easy to mistake Sam Sato’s for an office, in its low-slung beige building far from the glitzy tourist stops. Once inside, it’s clear that it’s a restaurant — and a great one at that. Their signature dry mein — a touch thicker than ramen with a killer al dente chewiness — is tangled with slivers of barbecued roast pork, scallions, and bean sprouts. Lightly but perfectly seasoned, it doesn’t even need the accompanying broth for dipping. The other noodle dishes—wonton and chow fun—are also delicious and all are totally kid-friendly.
Pita Paradise serves tasty, well-prepared Greek food that includes fish caught daily by the owner. The kids’ grilled cheese pita is a standout, and the baklava ice cream cake is a stack of sweet genius.
What to Do
If you’re coming from the East Coast or an even earlier time zone and make Maui your first stop, you’ll naturally wake up early enough to catch the mind-blowing sunrise at the top of Haleakala National Park. You'll want to make a reservation (yes, it's that popular), and bundle up as temperatures can drop below freezing. If you’re up for it, stick around for a hike or two through the rocky landscape. It’ll make you feel like you’re on the surface of the moon.
The famous road to Hana is gorgeous, but the hairpin turns may be better enjoyed without the kids. Instead, take them snorkeling or canoeing alongside the friendly sea turtles off Wailea Beach. For older kids who want adventure, try parasailing, off Maui’s west coast.