The 100-pound grouper floating to my right looks at me with interest. I stare right back, adjusting my dive mask as I slowly drift above the tank floor.
My husband, Ben, and I are two of three guests in the Maui Shark Dive experience, a scuba diving experience in the 750,000-gallon Open Ocean tank at the Maui Ocean Center. Open to certified divers, the experience allows a few guests at a time to spend 30 minutes with a dive master among the five species of sharks — blacktip reef, whitetip reef, grey reef, sandbar, and tiger — plus Hawaiian broad stingrays and giant trevally (ulua) that call the tank home.
It’s one thing to see amazing sea life in an aquarium — it’s a whole other level when you can join them in their own environment. I never imagined I’d be having a silent conversation with a grouper, but there she is, looking straight into my dive mask. Later, I learned that the grouper’s name is Macnut, and she is known for her curiosity.
Visiting with Macnut and being surrounded by some 20 sharks is a thrill. Many of the sharks swim surprisingly close, paying us no mind — though the tiger shark keeps its distance, which honestly feels about right.
Maui Ocean Center for Families
Outside the tank, my two-year-old granddaughter experiences the Maui Ocean Center in a different way. She shrieks with delight watching the sharks and Manta, then pulls her parents along to the next exhibit. It’s one thing to see marine life in a tank. It’s another thing entirely to watch three generations of your family experience it together, but in different ways.
Shark Dive Maui isn’t the only reason to build a day around the Maui Ocean Center. Known as “The Aquarium of Hawaii,” it’s home to one of the world’s largest displays of live Pacific corals, along with exhibits like the Living Reef, Turtle Lagoon, and the Humpbacks of Hawaii Exhibit & Sphere, a 3D theater experience that brings you eye-to-eye with humpback whales.
Kids can get hands-on at the outdoor touch pools, and complimentary marine naturalist presentations run throughout the day, so there’s always something happening no matter which generation of your group you’re trying to keep entertained.
A Multigenerational Vacation in Maui
The Maui Shark Dive kicks off a week when my family, three generations strong, gathered in Maui for our annual trip.
We started coming to Hawaii when my kids were little, and it’s been a favorite family destination ever since. We choose a different island each year. This time, we’re in Maui, the second-largest of the Hawaiian Islands, in the North Pacific between Oahu and Hawaii Island (the Big Island).
It’s long been one of the most popular multigenerational destinations in the islands, partly because of its range of experiences — reef days and gentle beaches for the youngest travelers, snorkeling and diving for the more adventurous, and resort culture, spas, and fine dining for anyone happy to slow down.
Our own week in Maui ended up touching nearly every one of those notes, starting with a full day poolside on the south shore.
Wailea Beach Resort – Marriott, Maui
Maui has some wonderful family-friendly resorts, and Wailea Beach Resort – Marriott Maui is one of them. The resort is known for its excellent pools and restaurants, so it seemed the perfect place for a Day Pass and family pool day. Our base for the day was a Nalu Adventure Pool cabana.
Our granddaughter made a beeline for the NALU Adventure Pools, home to the longest resort waterslide in Hawaii, along with a swim-through grotto and splash zone built for younger kids. She played in the pools with her parents all morning; later we all relaxed in the cabana, cold drinks in hand, with the Pacific stretched out in front of us.
Set on 22 lush oceanfront acres on Maui’s sunny south shore, Wailea Beach Resort sits between two golden-sand crescent beaches, with 543 residential-style rooms and suites (including new oceanfront villas) that all open onto private lanais.
Guests staying at the resort have access to daily programming for every age group — sunrise yoga, beach boot camp, and coconut yoga each morning, twice-daily movie screenings, complimentary bike rentals, and a Keiki Kids Club for the youngest travelers — plus a full-service spa, beach access, and water activities just steps from the pool.
Te Au Moana Luau
We capped off our day at the Wailea Beach Resort’s Te Au Moana Luau, held right on the grounds. The name means “the ocean tide,” and the show lives up to it — beautiful performances tracing the stories of Polynesian voyaging, fishing, and Hawaiian culture through song and dance, with the ocean itself as the backdrop.
The food was excellent, and the show was polished enough to become one of those experiences that connects you to a place on a deeper level, no matter your age.
Beach Days, the Multigenerational Way
Not every day called for a resort, though. We spent part of nearly every day at one of Maui’s beaches, and each one served a different purpose for our group. Here are a few favorites:
- Kaanapali Beach — Great snorkeling and free parking, with plenty of room to spread out. The surf runs a little rough for young kids, but there’s shade and bathrooms nearby.
- Kapalua Beach — Calm, protected waters and good snorkeling, making it a solid pick for families.
- Baby Beach — True to its name, the calmest option on the island and the best spot for toddlers and little ones.
A Grown-Ups’ Morning at Molokini Crater
Not every part of a multigenerational trip has to include everyone every moment — and that’s part of what makes it work. One morning, Ben and I slipped away for the Molokini Deluxe Snorkel & Sail with Alii Nui.
It’s a five-hour morning sail aboard a 65-foot luxury catamaran, timed to get you in the water at Molokini before the crowds arrive. The day started with dockside boarding and local Maui coffee, followed by a chef-prepared breakfast buffet as we cruised out to the crater.
Molokini is a crescent-shaped, partially submerged volcanic crater and protected Marine Life Conservation District, and the water inside is about as clear as Hawaii gets — it blocks the swells that stir up sediment elsewhere, so visibility can reach 150 feet.
After our first snorkel there, the crew set out a mid-morning snack of ahi poke before we sailed to a second stop, where we swam alongside numerous Hawaiian green sea turtles (in winter, this same second stop shifts to prime humpback whale territory). Lunch was a full island buffet back on board, followed by an open bar and a genuine sail home under the trade winds.
It was a fantastic reminder that multigenerational travel doesn’t mean sacrificing the experiences you’d plan on any other trip — it just means everyone gets a turn. And by the time we were back on dry land, it was time for the whole family to reunite for more time together.
The Road to Hana, Toddler Edition
One activity we wanted to do was to drive the Road to Hana. For anyone unfamiliar, the Road to Hana is one of Hawaii’s most famous drives — a roughly 60-mile stretch of the Hana Highway that winds along Maui’s northeast coast from Kahului to the small town of Hana.
The route is known for its sheer number of hairpin turns and one-lane bridges (roughly 620 curves and 59 bridges, most of them one lane wide), all threaded through dense rainforest, past waterfalls, black-sand beaches, and scenic overlooks. It’s less about the destination than the journey itself, and most visitors plan for a full day to do it justice, factoring in plenty of stops along the way.
No Maui trip is complete without the Road to Hana, and we tackled it as a full family unit. We kept our granddaughter entertained with songs along the winding coastal route, pausing for waterfall views and—the unanimous favorite stop—coconut ice cream at Coconut Glen’s (more on that below).
Shopping and Local Eats Around the Island
Between beach days and big excursions, we also carved out time for the smaller, everyday pleasures of the island. For shopping, Kihei Kalama Village is an easy, open-air spot to browse local vendors, art, and souvenirs without setting aside a full afternoon.
For restaurants, a handful of stops earned a permanent place on our Maui itinerary:
- Humble Market Kitchen by Chef Roy Yamaguchi, at Wailea Beach Resort — Roy’s signature Hawaiian-regional cuisine, right on the resort grounds.
- Burger Shack at The Ritz-Carlton Maui, Kapalua — a north-shore favorite for its beachfront setting, inventive burgers, and cocktail shakes. My pick: Lonnie’s Mai Tai Shake, made with toasted coconut and dark rum. The Ritz-Carlton itself sits on 54 oceanfront acres inside the larger Kapalua Resort, tucked along Maui’s quieter north shore with views stretching toward Molokai. Guests get access to the resort’s championship golf courses, marine sanctuaries, and miles of hiking and coastal trails, along with six on-site restaurants — from the more casual Burger Shack and Ulana Terrace to the elevated Banyan Tree. It’s a great home base if you’re chasing a slower, greener corner of the island.
- Paia Fish Market on the south side, for fresh, simply prepared fish in a laid-back setting — a Maui classic for good reason.
- Kihei Caffe, our go-to for breakfast, with a location in Lahaina and another in Kihei — both reliable stops for a hearty morning meal before a big day of sightseeing.
- Coconut Glen’s is a colorful roadside shack near Mile Marker 27.5 on the Hana Highway and the unanimous favorite stop on our Road to Hana drive. The ice cream here is 100% organic and dairy-free, made from a fresh coconut milk base, with flavors like original coconut, lilikoi, ginger, and banana rum raisin. You can also pick up a fresh whole coconut to drink and eat on the spot.
- Honoapiilani Food Trucks, near the Hilton Vacation Club, for a casual, no-fuss meal between beach stops.
One Last Splurge: A Massage at Serenity Spa Maui
After a week of island time together, my children closed out the trip with a gift to me: a massage from Joel at Serenity Spa Maui in Lahaina. It was, without exaggeration, one of the best massages I’ve ever had.
Joel brings 21 certifications and years of experience to the table, and it shows — I walked out feeling like a million bucks. It was the perfect way to end the trip.
Where We Stayed, and the State of Maui Travel
For the trip, we booked an Airbnb in Lahaina that was large enough for the whole family, using it as our base for beach days, the Road to Hana, and day trips like our day at Wailea Beach Resort.
Maui is fully open for tourism, including the West Maui resort areas, though visitors are asked to be mindful of ongoing recovery efforts following the 2023 wildfires. Most of the island — Wailea, Kihei, Kahului, Wailuku, Paia, and Hana — is open and welcoming visitors without restriction.
In West Maui, areas like Kaanapali, Napili, and Kapalua are open and taking reservations. Lahaina itself remains a community in ongoing recovery from the 2023 wildfires — some areas, like the North End, have reopened with businesses back up and running, while parts of the historic core are still being rebuilt and may be closed to general tourist access. Recovery is progressing, but conditions change, so check the official Maui travel site closer to your trip for current guidance.
The Best Souvenir Was Time
Between the shark dive, the pool days, the luau, the beaches, and the long, winding drive to Hana, our week in Maui gave each generation of our family something different to love.
My granddaughter got sandcastles and pool slides. My daughter and son-in-law got a break by the water. Ben and I got a morning with the turtles at Molokini and a dive with the sharks.
But what we all got, together, was a week of undivided time — the kind that’s harder to come by every year, and worth returning to Hawaii for again and again.
If You Go
- Getting there: Most visitors fly into Kahului Airport (OGG), often with a connection through Honolulu. Rent a car — Maui’s attractions are spread across the island, and a car is essential for beach-hopping and the Road to Hana.
- Best time to visit: Year-round, but shoulder seasons (April–May and September–October) bring fewer crowds and better rates than the busy winter holiday season. Whale season runs roughly December through April, if you want a shot at seeing humpbacks from shore or by boat.
- Book ahead: Shark Dive Maui, the Te Au Moana Luau, and the Molokini Deluxe Snorkel & Sail all sell out, especially in peak season — book these as soon as your dates are set. Certified diver status is required for the shark dive.
- Road to Hana tips: Fill your gas tank before you leave, download offline maps in case of spotty cell service, and start early to beat both the crowds and the afternoon light fading on the return drive. Pack snacks and entertainment for little ones — the drive takes longer than the mileage suggests. We love this Shaka Guide audio guide, which had a fun guide for Road to Hana.
- Pace yourself: The best advice for traveling with three generations is to build in unstructured downtime. Not every day needs an activity, and splitting off in smaller groups (a grown-ups’ morning here, a nap-time excursion there) lets everyone get what they need out of the trip.
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