The best Hawaiian island to visit can best be determined by the age of your little one. Hawaii is a great destination to visit with children. There are countless things to do, whether you’re looking for a relaxing trip or one with more adventure. If you live in the western or midwest United States, nonstop flights are plentiful, making it a trip that is considerably easier than perceived.
My husband and I have visited all major Hawaiian islands about a dozen times. It is absolutely our favorite vacation destination. We’ve gone on romantic couples trips, with extended family, and have taken our two boys at all ages through the years. We continue to go back because there is no shortage of activities and you can’t beat the ease of mind of traveling to a place you’re familiar with, especially when you’re in the Working Moms Club.
Traveling with Babies: Maui
Maui is my favorite of the Hawaiian islands. It has the perfect balance of sunny beaches on the west side (leeward) and lush greenery and waterfalls in Hana on the east (windward) side. It’s half as busy as Oahu, but still has luxury shopping and 5-star resorts abound.
While many people think of it as a honeymoon destination, Maui is perfect for traveling to with babies! Maui is the best island to enjoy picturesque beaches, mai tai’s by the pool, and your best #ResortLife while your baby splashes and naps by your side.
Listen up you overachieving high expectation mamas (like myself) of the Working Moms Club: your babies cannot do literally anything but lay around and be picture perfect cuties! So honestly, capturing photos of them in one of the most romantic, photogenic islands on earth should be the only goal!
On Maui, there are two primary resort areas to stay: Kaanapali and Wailea. Kaanapali is on the northwest part of the island) and Wailea is the southwest part of the island. I’ve stayed in both, as well as Hana on the windward side. Personally, our favorite is Wailea. You have beautiful views of Lanai and Kaanapali. Wailea is repeatedly Travel + Leisure and Condé Nast Travelers’ top 10 beaches in the world. Important benefit: the Wailea part of the island has significantly less traffic when driving in from the airport in Wailuku.
Our two favorite resorts are the Grand Wailea, a Waldorf Astoria (Hilton) resort and the Hyatt Andaz. The Grand Wailea is more kid-friendly, with a larger resort and pool complex overall. The Andaz is much of the most modern, escapist resorts across all of the Hawaiian islands. It’s more quiet and romantic than the Grand Wailea, but perfect for couples with a young baby that plan on just hanging by the pool or beach. At both resorts, moms and dads lounging in the sun while holding their sleeping (shaded) babies was such frequent, sweet sight.
Traveling with Toddlers & Younger Kids: O’ahu
Oahu is the most popular of the Hawaiian islands for many obvious reasons. Since it is home to the capital, Honolulu, Oahu is the most connected, busiest island. That means it has established freeways, infrastructure, global restaurants, and luxury shopping. And this isn’t all by happenstance – although the most populous, it is still home to some of the most beautiful beaches on the planet.
One of Hawaii’s most popular beach, Waikiki, has the reputation of being a touristy, busy beach, but it is still nowhere on the ‘spectrum of busy’ when compared to a California beach. And while it is a bit busier than the other remote island beaches, it has one of the prettiest, most iconic backdrop of Diamondhead crater that can be viewed for miles.
Oahu is the best Hawaiian Island to travel with toddlers and young kids because of its accessibility. It’s easy to drive to the different parts of the island (yes! a rental car is a must), the airport is a breeze, and the list of Things to Do is endless. Some of my favorite things to when traveling to Oahu with kids include:
Waikiki: The area of Waikiki beach is the most “touristy” of the Hawaiian Islands. The experience is a bit like the Las Vegas Strip or Time Square, because there are a lot of tourist-designed attractions within a stone’s throw of each other. But that’s where the comparison ends. Waikiki is the perfect place to book your hotel and enjoy an easy Hawaiian experience. There is world class shopping and dining, and walking access to one of the world’s most iconic beach is at your fingertips. Plus, the cost of the hotels in this area are the most reasonably priced of anywhere across the Hawaiian Islands. Along the east end of Waikiki is the Honolulu Zoo, one of the best, large, and cost-friendly zoos in America and perfect for toddlers and young kids.
Hanauma Bay: Formed within a volcanic cone, Hanauma Bay is a pristine marine ecosystem that was Voted Best Beach in the United States in 2016. Hanauma Bay is a great place for young kids to learn about conservation, as local volunteers run a booth on-site to help visitors learn about the importance of reef preservation and the types of fish that live there. Hanauma Bay is the best snorkel spot in the Hawaiian islands for older and younger kids alike, with easy-to-rent snorkel gear and easy ocean conditions due to its formation. The bay is protected by vertical crater walls and a peripheral reef which help keep the water calm and tranquil, making it an ideal spot for swimming, snorkeling, and observing marine life.
Kualoa Ranch: Kualoa is a 4,000-acre private nature reserve and working cattle ranch, as well as a popular tourist attraction and filming location on the windward coast of Oʻahu in Hawaiʻi. Its sacred land and iconic mountain scape can be recognized in everything from Jurassic Park, Lost, to the newest kid-friendly movie on Netflix, Ohana. Kualoa Ranch is perfect to visit with kids. Kids ages 3 and older can participate in the Kualoa Ranch Movie Tour, Jungle Expedition. The ATV tour is for kids ages 5 and older and the zipline tour is for kids ages 6 and older. The Secret Island boat ride and the catamaran cruise are for all ages. Kualoa even has an on-site Cafe, perfect for quick eats when your kids get in the, “I’m hungry right this second” mode!
Pearl Harbor Memorial: If anyone in your party is a history buff or enthralled with the history of WWII like my husband and I, then visiting the Pearl Harbor Memorial is a must. Pearl Harbor is easy to visit with kids, but make sure you bring your stroller! You can walk through the museums, listen to an audio tour as you walk along the harbor, take a boat ride out to the memorial, and more. Kids can even visit the Pacific Fleet Submarine Museum, including walking onto a real submarine!
Dole Pineapple Plantation: The Dole Plantation, found in central Oahu, has been growing pineapples since 1900. It is the best attraction if you’re traveling to Oahu with young kids. You can enjoy gardens, a train tour, local foods, and everyone’s favorite, the signature Dole Whip pineapple ice cream. Try to go early, it gets extremely busy as it gets later in the day.
Our favorite hotels are the Hilton Hawaiian Village and if you’re willing to splurge, Aulani, Disney Resort & Spa. The Hilton Hawaiian Village is Waikiki’s only true resort destination located on 22 acres along the widest stretch of beach in Waikiki. It has sprawling pools and a children’s program, Camp Penguin, that runs every day with half- or full-day programs starting at $60 per child. It is also a short distance from all of the attractions and shops of Waikiki. Moms be wary though – it’s a large resort so definitely bring your stroller with you, especially if you plan to walk toward Waikiki.
If you’re in the Working Moms Club, then you know Disney does things right. Aulani is no exception. Aulani, Disney Resort & Spa is a magical resort located in a more secluded part of Oahu where you can hurdle down water slides, float along a lazy river, snorkel in a private lagoon or simply admire the view from a romantic infinity-edge pool. And around every corner, Disney Magic is sprinkled abound.
Traveling with Older Kids: Kaua’i & The Big Island
Kaua’i and the Island of Hawai’i (Big Island) are more adventurous, rugged, WAY less busy, and have way less attractions than its brothers and sisters. This makes them absolutely perfect for traveling with your older kids where you’re looking for surf-friendly beaches, helicopters, ziplines, and hikes, oh my.
Kauaʻi is called the “Garden Island,” which is an entirely accurate description. The oldest and northernmost island in the Hawaiian chain is draped in emerald valleys, sharp mountain spires and jagged cliffs. Mt. Waialeale is one of the top 3 wettest places on the planet. All of these elements make it one of the most beautiful places I’ve ever visited on earth.
Things to do in Kauai:
Nāpali Coast: The Nāpali Coast is definitely one of the most famous and stunning things you can see while visiting Kauai. Spanning 17 miles along Kauaʻi’s North Shore, the Nāpali Coast is a sacred place with extraordinary natural beauty. The only way to see it is by air, sea, or by foot. We’ve taken a helicopter tour and hiked along it via the first section of the Kalalau Trail. (If you want to do the full 11-mile hike, you need to obtain a permit.) This is a perfect activity to take older kids looking for something adventurous, and a perfect backdrop for their Insta and TikTok content!
Ziplining: Due to its jagged terrain, zipline is a popular activity across many of the Hawaiian islands including Kauai. Outfitters Kauai has the island’s most experienced, longest, and unique ziplines — ten lines, four tours — include tandem, single, superman, seated and even water-zips. Each zipline tour is unique as our lines vary by size, skill-level, and terrain, so there’s a tour for every family. Fly over lush valleys, tumbling waterfalls and forest canopies — landscapes made famous by movies like Jurassic Park, Pirates of the Caribbean, and Indiana Jones.
Surfing: Known as the Crown Jewel of the north shore, Hanalei Bay is one of the best places to surf along the two-mile picturesque coast. Beginner surfers flock to Hanalei Bay for the shallow sandy bottom, gentle swells, and perfect conditions. It also houses some coastline without reef breaks for more experienced surfers. The Hanalei Surf School gives a 90-minute course that includes a surfboard, rashguard, and leash. Instructors teach individual classes or private party bookings with friends. Along the eastern shore, Kahili Beach is one of the best surfing spots in Kauai, with huge swells due to the lack of an outer reef. However, this can mean greater risk on certain days, so beginners should always go in pairs with a more experienced surfer.
The Big Island
With 12 of the world’s 14 climate zones, the Big Island of Hawaii has one of the most dynamic landscapes on the planet. You can drive to the top of Mauna Kea and see snow (and even ski and snowboard certain times of the year!) and in the same day, drive to Kileaua and see an active volcano.
Things to do on the Big Island:
See a waterfall: Waterfalls are pretty easy to get to on The Big Island, unlike Maui which involves the long (and beautiful) Road to Hana. The 422 ft tall ‘Akaka Falls are part of the ‘Akaka Falls State Park, located just north of Hilo. The admission fee to the park is $5 per car. To get to the waterfalls you need to make a pleasant and short 0.4-mile hike through the lush rainforest filled with wild orchids, bamboo groves and draping ferns. The hike is suitable for the whole family and takes half an hour if you take your time. The trailhead is easy to find – just off the parking lot. The Rainbow Falls are the easiest waterfalls to see on the Big Island! This broad waterfall in the Wailuku river is conveniently located within Hilo town. The best time to visit the rainbow falls is in the early morning because this is when you have the most chance to see rainbows in the spray of the waterfall.
ATV Tours: ATV tours are an adventurous way to explore the wild forests and cliffs on the Hamakua and Kohala coast. These tours typically take you on a 10+ mile drive through private lands with stops on the way at scenic points, historic sites, and waterfalls.
Hawaiʻi Volcanoes National Park: The Hawaii Volcanoes National Park is the most popular destination on the Big Island. You can hike over recently solidified lava fields, see the lava glow over the Halemaʻumaʻu crater at night, and much more! As of June 2023, Pele, the Hawaiian Goddess of Fire, can be seen erupting again at Kileaua!
My favorite place to stay on the Big Island is the Hilton Waikoloa Village. It is located on the sunny, scenic, volcanic, Kohala Coast, within close proximity to shopping and great restaurants. The complex is huge, the pools are sprawling and the slides are a ton of fun. On-site, there is a Dolphin Quest where kids can swim with the dolphins or sit along the lagoon while the crew conducts morning wakeup rituals with them everyday.
While writing this, I realized again that Hawai’i is such a sacred, magical place that is worthy of visiting time and time again with your family. As a member of the Working Moms Club, our time with our kids is precious and shouldn’t be spent stressing over finding things to do to please the entire family, and I can’t think of a place better to check these boxes. I’m excited to hear about some of the memories you make with your kids here, too.
Hawaii Travel Tips
✨ Renting a car is a MUST (there’s still a rental car shortage due to COVID so check availability as soon as you’re ready). The different sides of the islands look so different so you have to drive to experience them!
✨ First thing: Walk out to the beach to get some sunlight after you check-in for a few minutes. Always the cure for any jet lag! The leeward (west) side of the islands don’t get much rain and are always pretty sunny and warm.
✨ Make restaurant reservations if you can – many restaurants are still recovering from COVID staffing losses.
✨ November – April are the best months to see whales! Whale watching excursions or dinner charter cruises are popular this time of year. You may even be able to hear/see them from your lanai!
✨ Speaking of a lanai – BOOK IT! Having a room with a balcony in Hawaii to unwind and watch the sunset is priceless.