For Cheri DeWitt, owner of Sol Escapes Travel Agency, Hawaii isn’t just a vacation destination—it’s where her heart lands. A former flight attendant and now seasoned travel advisor, Cheri has found her family’s second home on the island of Maui, where sunsets, sea breezes, and shared memories have woven themselves into her most treasured moments.
Cheri and her husband, John, have visited the islands with their four children—Stephanie, Lhandri, Josh, and Saryn—and their niece, Michelle, and while coordinating everyone's schedules doesn’t always allow for full-family trips, the ones they’ve taken together are unforgettable. “There’s something magical about every day in Hawaii,” she says. “Even the rain brings a rainbow.”
Kid-Friendly Adventures with Cultural Roots
Despite what some might think, Cheri believes Hawaii is one of the best places to bring children. “Some of the world’s best learning happens here. Ecosystems, native culture, history—it’s vacation wrapped in discovery," she says.
Her top picks include snorkeling, visiting butterfly farms, touring tropical gardens, and stopping by libraries where keiki (children) can learn their names in Hawaiian. “Mine is ‘Keli,’” she shares with a smile. “And my brother Steve? ‘Kiwi.’” Add in night crab hunts on the beach and watching a turtle drift by while swimming, and the memories start to stack up.
Families with a bigger budget can explore Aulani, Disney’s Oʻahu resort, where character experiences meet Hawaiian cultural programming. But you don’t need a five-star property to create five-star memories. “Many of our best moments came from low-key days—picnics on the beach, catching waves, spotting whales,” she says.
Hidden Gems (That Stay Hidden)
Ask Cheri about her favorite family beaches and off-the-beaten-path spots, and she’ll give you a knowing smile. “That’s the perk of using a travel advisor—especially one who’s been a flight attendant. We know the places the guidebooks don’t.”
Still, she’ll spill one secret: whale tours during Maui’s December to April season. “You see the mamas and their babies [and] the males showing off. It’s beautiful and kind of emotional watching these majestic giants move through the ocean with the grace and elegance of ballet dancers," she says.
Smart Travel, Happy Wallet
Hawaii can be a splurge—but with Cheri’s tips, it doesn’t have to break the bank. She recommends short-term vacation rentals with kitchens to help families save on dining and walking-distance lodging to reduce or eliminate the need for rental cars, which can be expensive and limited in supply.
If you do need a car, consider booking it for only half the trip—use it early on for adventure days, then return it and soak up beach time near your condo or resort. Many tours offer transportation directly from hotels, so skipping a car altogether can be surprisingly easy.
For food, she swears by local farmers’ markets. “You’ll find fruits you can’t get fresh on the mainland—like papaya boats drizzled with honey and topped with yogurt," she says. "And don’t skip the Loco Moco; it’s a local favorite that’s oddly satisfying and super filling.”
And when it comes to gear, pack smart. Reef-safe sunscreen is a must (and pricier if bought on-island), and if you’re heading to higher elevations like Haleakalā on Maui, bring layers. “It can be downright freezing up there at sunrise—even in Hawaii," she says.
A Moment in Maui
Cheri’s connection to Hawaii goes beyond beach days and travel plans. In 2019, surrounded by 40 friends and family members, she married John during a sunset ceremony on the lawn of the Westin Kā‘anapali. Her brother walked her down the aisle in honor of her late father. Just as they paused to remember loved ones who had passed, a gentle rain fell—and then, a rainbow appeared.
“The pastor said it was a gift from my dad, giving his blessing,” Cheri recalls. “We said our vows as the sky turned pink and orange. It was perfect. It was Maui.”
Travel with Heart
Now, through Sol Escapes, Cheri helps other families discover the kind of joy her own has found. Whether it’s a first-time trip or a long-awaited return, she specializes in customized Hawaiian adventures that reflect the rhythm of each family.
“Tourism is vital to the islands, but it has to be done with care,” she says. “Learn a little of the language, honor the traditions, and treat Hawaii with the respect it deserves.”
With Cheri’s guidance, a Hawaiian escape becomes more than a vacation—it becomes a legacy.
Ready to Plan Your Own Hawaiian Escape?
Let Cheri be your personal “escape artist.” From packing tips to planning magical moments, she’ll help you design a trip that fits your family, your pace, and your dreams.
Visit SoleScapesTravel.com to start planning your unforgettable journey today.
“There’s something magical about every day in Hawaii.” – Cheri DeWitt