Why Families Are Returning to Hawaii
From multi-generational getaways to meaningful moments closer to home, Hawaii is once again becoming the perfect place for families to reconnect, slow down, and travel well together.
Hilton Waikoloa Village on the Big Island offers extensive pools, lagoons, and family-friendly amenities ideal for multi-generational Hawaii vacations.
Over the past several years, many travelers have focused on long-haul bucket list adventures and once-in-a-lifetime international journeys. But recently, we’ve noticed something shifting. More families are once again looking closer to home for meaningful experiences together, and Hawaii is increasingly becoming part of that conversation.
Part of that shift is practical. Some travelers are hesitant about the uncertainty surrounding international travel right now, while others are watching airfare trends and rising fuel costs carefully. Multi-generational families are also looking for destinations that feel easier to navigate without sacrificing beauty, culture, or experience. Hawaii answers all of those needs remarkably well.
But personally I think the renewed interest in Hawaii runs deeper than logistics.
There is something restorative about the islands. The pace naturally slows. Families spend more time together outdoors. Phones disappear during sunsets. Grandparents snorkel alongside grandchildren. Parents finally relax. Even simple moments, whether it’s morning walks on the beach, shave ice after a long pool day, or spotting sea turtles from the shoreline, somehow feel more memorable there.
And while every island offers something different, that is part of what makes Hawaii so special.
Maui continues to resonate with families looking for a classic beach vacation with exceptional resorts, calm swimming beaches, and opportunities to reconnect. Kauai offers a quieter rhythm with lush landscapes, dramatic coastlines, and a feeling of stepping away from everyday life entirely. The Big Island remains one of my personal favorites because no other Hawaiian island feels quite as diverse. Within a single trip, travelers can experience volcanic landscapes, rainforests, black sand beaches, coffee farms, upcountry ranchlands, and some of the best stargazing anywhere in the world.
Jamie and Ashley at Mauna Kea Resort on the Big Island during a meaningful babymoon celebrating family, tradition, and the next generation of travelers.
Last year, my wife and I stayed at Mauna Kea during our babymoon, and the experience carried special meaning for our family. The Mauna Kea Resort was actually Julie Shipley’s favorite property in Hawaii. Julie, Ashley’s grandmother, founded our agency in 1965, so returning there while expecting her great-granddaughter felt incredibly fitting. Standing beneath the palms overlooking the coastline, it was hard not to reflect on the generations of family memories, both personal and professional, that travel has helped create over the years.
That’s also why thoughtful planning matters more than many travelers initially realize. The “best” Hawaiian island depends entirely on the personalities, travel styles, and priorities of the people going. Some families want walkable beaches and easy dining. Others prioritize adventure, privacy, snorkeling, cultural experiences, or a quieter luxury atmosphere away from larger crowds. Even choosing the right side of an island can completely shape the overall experience. Several members of our team also hold Certified Family Travel Advisor credentials through the Family Travel Association, helping families navigate everything from multi-generational resort planning to selecting the right experiences for different ages, interests, and travel styles.
The “best” Hawaiian island depends entirely on the personalities, travel styles, and priorities of the people going. Some families want walkable beaches and easy dining. Others prioritize adventure, privacy, snorkeling, cultural experiences, or a quieter luxury atmosphere away from larger crowds. Even choosing the right side of an island can completely shape the overall experience.
Our team regularly visits the islands, and we’ve recently seen several properties stand out particularly well for family and multi-generational travel. On the Big Island, Hilton Waikoloa Village continues to be incredibly popular with families thanks to its extensive pools, protected lagoon, water slides, lazy river, and even dolphin experiences on property. The expansive resort is especially well suited for larger family groups, and its complimentary Swiss-made air-conditioned tram system makes navigating the property surprisingly easy for grandparents and children alike.
Sunset views from Ritz-Carlton Turtle Bay on Oahu’s North Shore, where families can experience a quieter and more relaxed side of Hawaii.
On Oahu, the historic Moana Surfrider remains one of the best options for travelers wanting a classic Waikiki experience with a swimmable beach, lively atmosphere, and easy access to restaurants and shopping. Meanwhile, the newly refreshed Ritz-Carlton Turtle Bay on Oahu’s quieter North Shore offers a completely different experience, one centered around open coastline, more space to unwind, and a slower pace that many families are increasingly seeking.
For travelers looking for a more relaxed Maui experience, Napili Kai Beach Resort remains one of our favorite family-friendly properties. Tucked along Napili Bay away from the larger high-rise resort areas, it captures the slower and more authentic side of Hawaii that many families are craving right now. Days revolve around snorkeling, paddleboarding, beach walks, and simply being together. The resort’s welcoming atmosphere, spacious accommodations, complimentary amenities, and Kids Eat Free program help create the kind of easygoing experience that turns vacations into traditions.
We’re also seeing more families prioritize value and flexibility when planning travel. Fortunately, many of our travel partners allow travelers to lock in package pricing well in advance while adding protections that provide peace of mind if airfare or pricing changes later. In a travel environment where uncertainty can sometimes make planning feel stressful, having flexibility and trusted guidance has become increasingly important.
As tourism continues to recover across parts of Hawaii, including Maui, respectful travel also remains incredibly important. Supporting locally owned restaurants, guides, cultural experiences, and small businesses helps ensure tourism benefits the communities that make the islands so special in the first place. Thankfully, many travelers today are increasingly seeking those more meaningful and locally connected experiences.
Napili Bay on Maui offers the quieter, more timeless side of Hawaii, where gentle waves, swimmable beaches, and relaxed oceanfront resorts create the perfect setting for family connection and slower travel.
Even closer to home, that same spirit of connection and community is one of the reasons we’re proud to support the Kiwanis Club of Lake Oswego’s upcoming Toast to Community fundraiser on June 7th at Monte Ferro Winery. The gathering brings neighbors together over shared food, wine, and conversation while supporting underserved children within our local school district. As part of the fundraiser, attendees will also have the opportunity to bid on a three-night stay at Napili Kai Beach Resort on Maui, generously provided in support of the event.
In many ways, Hawaii reminds us of something simple that often gets lost in modern travel planning: the most meaningful trips are not always the furthest away. Sometimes they are the ones where families reconnect, slow down, and return home feeling grateful for time spent together.
And right now, that feels more valuable than ever.
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