How to Plan a Family Trip to Hawaii

Hawaii is always a near-perfect honeymoon or anniversary destination, but the Aloha State can also be fun to experience with 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. Besides, bringing your kids along gives you a constant excuse to get out there and try things you probably wouldn't with only you and your significant other.

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 just for your family. Use this guide as your starting point when working out where to stay, dine, and find adventures that are off the beaten path but still kid-friendly.

Getting There

Hawaiian Airlines is a reliable carrier providing lots of options for flying to and between the Hawaiian Islands, and it often partners 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. to Hawaii.

If you’re feeling overwhelmed by booking the entire trip on one reservation — perhaps because you want to maintain some flexibility around when you're traveling between the Hawaiian Islands — 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 within the archipelago. Inter-island flight prices fluctuate less, and the flights are a snap to book.

Getting Ready

The first thing to figure out is the number of islands you want to visit. Unless you live on the West Coast and can travel to Hawaii fairly easily, it’s worth going to at least two, given the long flight.

To avoid baggage fees, try to limit packing to a carry-on, especially if you’re taking multiple flights throughout your vacation. If you do want to check baggage, consider flying with Southwest Airlines, which permits each passenger to bring two checked bags for free. Otherwise, try limiting the number of checked bags by sharing suitcases between family members.

While Hawaii’s tropical climate may have you thinking about shorts and flip-flops, what you'll need depends on where exactly you're going. If you’re visiting higher elevations, such as Haleakala National Park on Maui, you should be prepared for cooler temperatures.

Renting a car is the easiest way to really see Hawaii, so you might also prepare for some time behind the wheel as you travel from the hotel to various beaches and sites.

Oahu

Because flights to Honolulu are frequent and less expensive than flying to smaller cities in Hawaii, you’ll likely start your trip on Oahu. It’s worth staying in the state capital awhile for the uniquely laid-back urban experience you can have there that just isn’t possible on the neighbor islands (or in most other U.S. cities, for that matter).

Where to Stay

Steps from the bustle of Waikiki beach and its towering resorts, you’ll find the Surfjack Hotel & Swim Club. While its cool, mid-century modern-inspired design may lead you to think it’s strictly for young hipsters, it’s actually a great choice for families, too. Its 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 on-site restaurant, Mahina and Sun’s, offers creative, delicious farm-to-table food, with plenty of options the kids will love (including a great burger).

Where to Eat

Start the day right with hot, fried-to-order malasadas from Leonard’s Bakery. Think doughnut holes with a more flavorful, almost chewy dough. If you're in the mood for a traditional lunch, head north of downtown Honolulu to Nico's Pier 38 for some of the best pork lau lau (pork wrapped in taro leaves), lomi-lomi salmon (a type of raw-fish salad), and poi (a starchy paste made from taro) in the area. You'll find fresh seafood in Waikiki, too, but true foodies tend to travel out of the touristy area for a taste of real Hawaiian fare.

What to Do

There are so many cool things to do on Oahu, though 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 at Pearl Harbor 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 — a volcanic tuff cone — is just plain cool. You can hike 560 vertical feet to a lookout point at the top of the crater, where you'll find some of the best views on the island. The climb is steep and requires scaling more than 100 stairs, so keep that in mind if you have young kids.

Kauai

“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 to douse yourself in bug spray.

Where to Stay

The Lodge at Kukui’ula, on the south shore, combines the comforts of a luxury home rental with the amenities of a high-end hotel; it comes 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, most of them locals who readily share their favorite haunts and treat you more like a friend in their home than a guest in their service.

The expansive grounds, fun to explore 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 on-site 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. They're great places to introduce little ones to different fruits.

Kids can also taste some of those Hawaiian fruits 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. Its coconut milk-based Luau Delight sorbet is as creamy and 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, you might want to wait to try that particular 20-mile 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.

Additionally, 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.

Maui

Pick a side — any side — and then get ready to drive. Most hotels sit along Maui's 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 get 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 standard 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. Its signature dry mein — a touch thicker than ramen with an 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 totally kid-friendly.

Another Maui institution, Pita Paradise serves tasty 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 further, you can take advantage of the jet lag and get 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 beware that the hairpin turns may turn carsick-prone kids' stomachs. Alternatively, you could 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.