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 actually be fun with the kids, too. 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 if it was just you and your significant other.
Any of the four major islands (Oahu, Maui, Kauai, and the Big Island) 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 off 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—that’s because inter-island flight prices fluctuate less and the flights are a snap to book.
- Related: Honolulu International Airport guide
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. Hawaii’s tropical climate means that heavy clothes aren’t necessary unless you’re visiting high elevations, such as Haleakala National Park on Maui.
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.
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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. And it’s worth staying awhile for the uniquely laid-back urban experience you can have here that just isn’t possible on the outer islands.
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, 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 & 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.
Related: Best family beach hotels
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 (reserve tickets online in advance) 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—being 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.