Warm beaches, cultural experiences and family-friendly resorts make this South Maui community an inviting place for generations to make memories together.

Eating strawberry ice cake is how my husband and I started our visit to Wailea, a gorgeous luxury community in South Maui. The jeweled-toned sculptural dessert is almost too beautiful to cut, but once we did, the flavors stayed with us. This lingering experience is exactly what chef Amber-Lynn Ching was aiming for when she created a version of the dessert for guests at Fairmont Kea Lani’s signature Kō restaurant.

“For many children who grew up on Maui, this dessert brings back a beautiful piece of childhood,” she says. “When I was in elementary school, we would take field trips to the Puʻunēnē Sugar Museum, where we learned about the history of sugar and its importance to Maui. But, of course, the highlight of the trip was the little treat waiting for us at the end — a mini Dixie cup filled with frozen strawberry ice cake.”

Years later, as a chef, she took that childhood memory and reimagined it, honoring the familiar flavors while blending them with new ideas, textures and a more thoughtful presentation. Her twist on strawberry ice cake feels both familiar and new. “The shape, the colors and the way the dessert looks are all part of that experience — a little playful, unexpected and joyful,” says the mom of three.

Those are some of the adjectives I would use to describe all of Wailea. There is something about this dreamy, sunny part of Maui that’s perfect for making family memories. It’s especially ideal for grandparents and cousins to join in on the fun. You’ll find friendly staff ready to help, shaved ice by the pool, lounge chairs on the sand, water slides, fresh seafood brimming with Maui Gold pineapple, guava-glazed meats, sunset cocktails with lilikoi, canoe adventures, hula lessons and, of course, swimming and playing in the clear, warm and usually calm ocean. You can also snorkel with sea turtles, play golf, go kayaking, do stand-up paddle boarding or rejuvenate with a volcanic clay scrub or a lemongrass foot massage.

During our recent visit, my husband and I stayed at three properties along the beach path – Fairmont Kea Lani, Grand Wailea and the Wailea Villas — each spectacular with its own unique personality. We met multigenerational families who have returned to this little slice of paradise year after year to celebrate milestone birthdays and anniversaries, reunions and holidays.

Fairmont Kea Lani: Spacious suites and cultural experiences

We stayed in a one-bedroom suite at the recently renovated Fairmont Kea Lani. With a bedroom, living room and spacious lanai, more than 800 square feet give families enough space to spread out. The resort also offers two- and three-bedroom private villas with full kitchens, plunge pools and in-villa washers and dryers.

Kea lani means “heavenly white,” an ode to the striking all-white architecture of the resort, which is celebrating its 35^th anniversary this December. My husband and I visited during our wedding anniversary, and we were delighted to find the white plumeria, the distinctive flower that grows along Maui’s shoreline, in full bloom throughout the resort. It felt like nature’s tribute to love, joy and family.

The resort’s new oceanfront Hale Kukuna Cultural Center is a celebration of native cultures and traditions. All guests are invited to explore and learn through books, artifacts, exhibits and daily immersive cultural experiences. It offers free morning canoe excursions, lei making, hula and ukulele lessons and ʻŌlelo Hawaiʻi lessons, introducing guests to the Hawaiian language.

Even the nightly torch ceremony that begins at sunset in the resort lobby invites young guests to participate. We watched a group of kids of all ages running behind the torch lighter as he glided through the resort. And just behind the happy crew were the parents and some grandparents soaking in the kids’ joy. I have no doubt that this will be a special memory for these families for years to come.

Resort highlights include all-suite accommodations with a mini fridge and microwave, free laundry on every floor, easy access to the beach (where plenty of lounge chairs, umbrellas and towels await), two family pools with a connecting 140-foot waterslide, an adults-only tranquility pool and a koi pond where kids can feed colorful fish each morning.

Dinner at Kō (which means sugarcane) is another way to immerse in the story of this island. Staff greeted us with fresh sugarcane juice crushed by a traditional press. The menu is a celebration of the sugarcane workers who helped shape Maui’s culture. Executive chef Matt Dela Cruz’s thoughtful creations are a combination of Hawaiian, Filipino, Portuguese, Korean, Japanese and Chinese culinary traditions mixed with local produce, seafood and meat.

Insider tips: Reserve the breakfast package with your room. Kea Lani Restaurant is a large open-air dining room with an extensive buffet. Our mornings started with a swim in the ocean, followed by a leisurely breakfast. For lunch and an afternoon treat, MAKANA Market & Café is great for grabbing sandwiches, pizza and ice cream.

Grand Wailea: A family-friendly resort with a mini water park

Grand Wailea, a Waldorf Astoria resort, is 40 acres of tropical gardens, waterfalls, pools, shops and restaurants. The resort recently underwent a renovation, and its Wailea Canyon Activity Pool remains legendary with nine pools, seven waterslides, six waterfalls, a lazy river, a sandy “baby” beach, a lava tube slide and a Tarzan rope swing.

This is where you want to get a cabana for all-day shade, fresh fruit and cold drinks in the fridge because there is a lot to explore. The beach is just steps away, and you can easily go back and forth. The new Haleakalā Shave Ice is a great addition to the pool fun. Try its Wailea Sunset, a combination of passion orange, mango and guava, and Grand No Ka ʻOi, a concoction of guava, coconut and lilikoʻi.

With expansive ocean views, L.A.’s beloved Nobu has recently opened at Grand Wailea. And make sure to visit Humuhumunukunukuāpuaʻa, the resort’s signature restaurant, which has a thatched roof and magical vibe, especially as the sun begins to set and the surrounding lagoon shimmers in the twilight. As you walk in the open-air restaurant, you’ll find a large, circular glass bar with a built-in aquarium filled with tropical fish. We topped off our dinner with Humu Mud Pie, made with Kona coffee, macadamia-nut ice cream and a delectable cookie crust.

Loulu is a great spot to get grab-and-go items any time of day. You’ll find a little taste of L.A. inside this market and café, including a curated collection of snacks from Erewhon. Hawaiian professional surfer Kelia Moniz’s Love & Lava Sundae adds local dragon fruit, Kula Country Farms strawberries, candied macadamia nuts and a few more local specialties for an L.A.-meets-Maui bliss.

For our cultural immersion, we joined the lūʻau held in Molokini Garden overlooking the beach, which is a great way for families to experience Hawaiian storytelling, music and flavors. The show is focused on Maui legends and the Wailea area in particular. Before the dinner and show, families can play Hawaiian lawn games, take pictures and have some snacks. One thing that’s unique here is that groups sit at private tables, not at long communal tables. And the meal is not a buffet, but rather a three-course meal served family-style.

Insider tip: Reserve your room in the resort’s club-level property Napua, and you’ll have access to the private lounge with a complimentary breakfast every morning, appetizers in the evening and snacks, drinks and fruit throughout the day. It’s a great spot to get out of the sun for a bit, grab an apple or a kiwi and have a little downtime.

Wailea Beach Villas: Private, spacious accommodations for families

The Wailea Beach Villas are privately owned villas and penthouses in a gated community set among 12 acres of lush tropical landscaping. Staying here is going to feel like your own luxury beachfront home. It’s private and quiet with lots of space.

There are no waterslides or restaurants on site. Instead, you have multiroom, spacious homes with gourmet kitchens, living and dining areas, barbecue grills on the lanai and a washer and dryer. Since each unit is privately owned, it is individually decorated and, as the property manager explained, many families come back to their favorite penthouse or villa year after year.

While this is not a hotel, it does offer many resort amenities such as housekeeping and concierge services, two pools (the family pool with a waterfall and jacuzzi and the adults-only infinity beachfront pool and jacuzzi), a family room with ping pong and billiard tables and beach service with towels, lounge chairs and umbrellas.

A fun bonus of staying here is the private entrance to The Shops of Wailea, which are adjacent to the property. With your room key, you can open the private gate of the resort and easily explore the restaurants and shops. The beach path also runs in front of all the Wailea hotels, villas and condos.

We loved having both our morning coffee (and a glass of wine during sunset) on our own private lanai. We ordered takeout from different restaurants in the area, stocked the fridge with fresh fruit and veggies and savored our penthouse with a view. When traveling with kids, space can become the ultimate luxury. Kids can watch a movie or take a nap while parents curl up on the couch to chat or read books.

Insider tip: The Island Gourmet Market at the Shops of Wailea is a great place to grab fresh fruit, cheese, deli sandwiches, salads, yogurt and other snacks to take back to your villa. Having a full kitchen and being within walking distance to a gourmet market is a dream when traveling as a family. Pick up some pastries, scramble some eggs, enjoy a leisurely breakfast on your lanai and then walk to the beach.

Explore Maui’s history at a working pineapple farm

We took a half-day detour and drove 45 minutes to the Maui Gold Pineapple Company’s farm. This is a fun family adventure in Upcountry Maui on the slopes of Haleakalā. The 90-minute tour takes you on Maui’s last working commercial pineapple farm. We learned how pineapples are planted and harvested, saw tiny pineapples and fully grown ones and got to taste freshly cut fruit in the field right after it was hand-picked.

The best part? Each tour guest receives a Maui Gold pineapple packaged for air travel. Back in L.A., we enjoyed pineapple that had been sweetened by the Maui sunshine, volcanic soil and mountain water.

I can see why Wailea is a place families return to again and again. Like Ching’s strawberry ice cake, each experience is a cherished memory. The beach community is more than luxury resorts and villas; it’s a place to connect across generations while savoring shaved ice, floating on a lazy river, watching golden sunsets and hula dancing to your heart’s content.

More Restaurants in Wailea

Matteo’s Osteria is a cozy, traditional and chef-owned Italian restaurant featuring local Hawaiian ingredients, handmade pastas, an extensive wine list and the catch of the day.

Monkeypod Kitchen by Merriman features a seasonal menu, plus an extensive selection of craft beers. Offerings include poke tacos, taro ravioli, pizzas, salads and sweet-and-spicy grilled chicken.

Lineage serves up local ingredients and bold flavors. Dishes include Korean fried chicken, crispy cauliflower with lemongrass and garlic Szechuan noodles.

Lāhainā Brewing Co. offers an array of food to accompany the variety of island craft beers, pretzels with whipped beer cheese, Lōkahi pilsner beer syrup, poke nachos, smash burgers, mahi mahi tacos and a chicken-and-strawberry salad.

Elena Epstein is Editorial Director of L.A. Parent.