Oahu, the third-largest Hawaiian island, is where beach life and city living combine in stunning fashion. It only takes one trip to fall in love with Oahu, so be warned — this will likely be the first of many family vacations. It’s something to look forward to; understanding the island’s history and appreciating the plethora of diverse activities available to traveling families grows stronger with each return visit to the isle sometimes called “The Gathering Place.”
Oahu boasts more than 100 miles of coastline, but Waikiki Beach is the spot toward which a majority of folks visiting Oahu gravitate to enjoy long days of soaking up sunshine and surf lessons. Warm sand, sparkling blue water and views of Diamond Head (Mount Leahi) crater make for stellar beach days.
Less than a 10-minute drive from Waikiki, Diamond Head State Monument is known for its hiking trail and the scenic views a little sweat can provide. On the eastern tip of Oahu, the paved, 2-mile (round trip) Makapu’u Lighthouse Trail makes for a stunning family stroll. Be on the lookout for the spouts of migrating whales from December through May.
Some of Oahu’s best-known foods are perfect for families. Hawaii-grown bananas are turned into soft-serve ice cream at Banán. Since 1953, Leonard’s Bakery has been churning out golden brown malasadas. These Portuguese fried doughnut holes are traditionally rolled in sugar, but all sorts of coatings and fillings are available; think cinnamon sugar, guava and chocolate. In addition to the original location in Honolulu, a number of Malasadamobiles are scattered around the island.
When you make your way to the North Shore, stop in Haleiwa Town. There will be a line for the sautéed shrimp at Giovanni’s — land lovers can opt for the jumbo garlic hot dog. Reward the kids (and yourself) for being patient with shave ice at Matsumoto’s.
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Continue your circle around the island to the Windward Coast to visit Kualoa Ranch Private Nature Reserve. Best known as the backdrop for more than 300 movies, including Jurassic Park and Jumanji, it offers a variety of experiences including horseback riding, ziplining and kid-friendly (age 5 and up) all-terrain vehicle tours. The Malama Experience is a fun way to protect and take care of the land (Malama Aina in Hawaiian) and learn about local history and traditions.
Set aside an entire day for a visit to the Polynesian Cultural Center. Along with a half-dozen island villages that highlight the way of life in Tonga, Tahiti, Samoa, Aotearoa, Fiji and Hawaii, this cultural theme park offers a fun luau experience and well-produced evening show called Hā: Breath of Life that includes a mesmerizing cast of twirling fire knife dancers.
A vast majority of Oahu’s hotels are located in Honolulu along Waikiki Beach. That said, even though they share the same geography, they all have their own distinct personality.
Halepuna Waikiki by Halekulani wins the prize for what could be the most restful stay along Waikiki Beach. A moment’s walk away from the beach and directly across from its iconic sister property, Halekulani, the Halepuna name means “House of Welcoming Waters.” One look at the intimate but stunning pool, with breathtaking views of the Pacific Ocean, was all it took my daughter and me to drop all our plans and simply enjoy our days at the property.
Halepuna features 284 rooms and four suites, but has the feel of a much smaller hotel. In addition to the pool, families will be drawn to hotel’s private garden. Located on the 8th floor along with colorful plants, there’s a stretch of grass perfect for shaking out any wiggles or to enjoy a picnic from onsite Halekulani Bakery & Restaurant. Parents will also appreciate the modern fitness center, hospitality center, and that laundry facilities are available.
Health protocols are taken very seriously at Halepuna; of all of my hotel stays during the pandemic so far, I felt the safest here.
You can’t get much closer to the beach then the Outrigger Reef Waikiki Resort. Emerging from an $80 million renovation, the property offers 658 rooms and suites. Guests staying in club-level accommodations enjoy access to the resort’s Voyager 47 Club Lounge – offering complimentary breakfast and evening Hawaiian pupus (appetizers) and cocktails. At the end of the day, shift the kids from the beach to the pool, where live music is offered daily from 6 pm to 8 pm.
There’s an Instagram-worthy shot at seemingly every turn at the Waikiki Beachcomber by Outrigger. Located on Waikiki’s bustling Kalakaua Avenue, the 498-room hotel is loaded with coastal décor and local art. It has a vibe most kids love, especially the teen set. The small pool area, flanked by Maui Brewing Co. and the Hawaiian Aroma Caffe, boasts dive-in movies.
The only luxury resort on Oahu’s North Shore, Turtle Bay Resort stretches over 1,300 acres, offering 410 rooms and suites, all with ocean views. Along with multiple beaches, there are two golf courses and miles of trails for hiking, biking and horseback riding.
With striking views of the leeward coast, the Four Seasons Resort Oahu at Ko Olina boasts 371 rooms and suites. Along with swimmable beaches, there’s a pair of family pools and the complimentary Kids for All Seasons program open to children ages 5 to 12.
Editor’s Note: For review purposes, Dana received media packages from some of the properties mentioned. As always, our thoughts and opinions are our own on Ciao Bambino. Photos by Dana Rebmann except where noted.
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