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Family-Friendly Hotels & Outdoor Activities in Wailea, Maui

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Hawaii is a very popular travel destination for families, and many hotels can look alike. Family-friendly travel writer Margot Black recently visited Wailea in Maui, which is home to several neighboring resorts. Keep reading to learn more about the resorts, family-friendly outdoor activities, and where you can eat local fish and fresh fruit. 

Wailea in Maui comprises 1,500 acres of yellow sand beaches, sprawling hotels resorts, and many outdoor activities, Wailea has a fascinating local history. Ancient lore says that Lea, the goddess who watched over the canoe builders, was transformed into a small forest bird and would fly down from the Haleakala volcano to the shoreline of South Maui, which is how the area became known as Wailea, meaning “the waters of Lea.” Much later, during During World War II, the Wailea shores became a training area for the Marines in the Pacific Theater.

Now it’s home to six major resort hotels, and I stayed at two of them for two nights each; the Grand Wailea, a Waldorf Astoria Resort, and its neighbor the Marriott-owned Wailea Beach Resort.

Only 35 minute drive from Kahului airport, Wailea’s beach expanse offers opportunities for swimming, kayaking, snorkeling, paddle boarding and hiking around the bays. There are also three commercial centers in the area plus an award-winning tennis center and three golf courses.

With my husband and ten-year-old son in tow I was determined that for this short but mighty Moana-style vacation we were going to do something new together as well as learn something new together.

I had big plans for us all to learn to surf and paddle board, but once we hit the resorts I barely wanted to move. Despite the fact that we hardly wanted to leave the hotels, we managed to fit in sailing, kayaking, and paddle boarding. Unfortunately surfing lessons were fully booked, which is why it’s best to plan key activities in advance at popular destinations.

When we weren’t out on the open water our kid was happy to play in the pool, and by pool, I mean their insane, on-steroids fantasy water-wonderland for children. There really was something for each family member to enjoy.

The Waldorf Astoria Grand Wailea Hotel

The Grand Wailea resort is so enormous we almost needed a map and compass to explore. But we loved our room with an ocean view, and also the family-friendly bathroom with a bathtub and shower, which meant that we could all get dressed in double the time.

If a kid could ever find nirvana in a pool it would be the one at the Grand Wailea. It was the size of a village and he was happier than I’ve ever seen him. It’s 2,000 feet long sprawling over 25,700 square feet, and consists of nine individual pools on six levels, connected by a river that carries swimmers along whitewater rapids and gentle currents.

There are also four jungle pools, five intertwining slides, a whitewater rapids slide, a Tarzan pool with rope swing, a sand beach, six waterfalls, caves, an infant pool and the world’s first water elevator.

Their newly updated 262 foot Lava Tube slide offers 14-second thrilling seconds of sheer adrenaline with the potential to reach 22 MPH! There is also an adult pool, the Hibiscus, for 18 year-olds and over, which features a swim up pool bar and two Jacuzzis.

The water slides open from 10 a.m. to 5 p.m. and our kid was delighted to stay right to the very end. The hotel staff give you wristbands to wear at the beginning of the morning and all the kids wore them as cute badges of honor, collecting them throughout the week. 

Where To Eat

On our first night, we ate at the Monkeypod Kitchen in the Wailea Gateway Center, which is a five-minute shuttle ride from the hotel lobby. It’s the epitome of laid-back, island chic atmosphere with a lively, jumping vibe. There’s a long communal table for either large parties or for making new friends.\My husband dined on the daily special, the local Monchong fish, which is seasonal, and was served over rice and arugula in a green curry sauce with macadamia nuts. It took great restraint for me to not keep digging my fork into his dish.

I tucked into their signature spicy tacos that didn’t disappoint with fresh flavors and a beautiful presentation. There was a simple kids menu and our son was happy with the comfort of a wood fired pizza. It was very family friendly, and I could see other families around enjoying their food as well.

Our second night’s food choice was completely different as we’d booked to join a Luau, which is a traditional Hawaiian party and feast. Yes, it’s touristy and a tad cheesy, but it’s exceptionally delightful and family friendly. If you are wondering if you should go to a Luau while on Maui, I say do it!

The one we saw, the Te Au Moana Luau dinner show, was located at the hotel next door so we enjoyed a beautiful walk along the ocean first. The evening kicked off with an ocean side show that featured hula dancers, singers, fire dancers, and an extraordinary dinner while watching a glorious sunset over the ocean.

There was a pig roast cooked by their traditional underground oven method and lots of pre-show activities for the kids. An open bar kept everyone in good spirits, and the show offered lots of audience participation. 

Outdoor Activities

We booked a trip with Maui Kayak Adventures, which was a great way to explore the waters of Maui. Our guide Matt was informative, capable, and friendly. He was knowledgeable about the marine life, filled with snorkeling and wildlife tips, and was great with our ten year-old.

We were a tiny group and kayaked at our own unhurried pace. We were impressed with the abundant marine life and stumbled upon turtles within minutes of jumping overboard. Matt took some stunning photos I will forever cherish that were all included in our tour (I appreciated the added value).

The kayaking went at a nice pace and none of us ever seemed to get tired. I was most concerned about myself figuring I’d be the weakest link, but was able to do it all with no problem. I was initially concerned getting back in the kayak after taking a swim, but it was very easy once the guide showed me.

Since I had read that sunscreen is deeply damaging the coral reefs, we prepared for all our open water adventures by purchasing sunscreen clothing from Tuga Sunwear. The 50 SPF clothing made it easy and safe for all our water play, and I didn’t have to chase our kid around with a tube filled with sunscreen like a crazy zealot mom.

My sunscreen clothing was so fashionable, utilitarian, fast drying and comfortable, I wore it constantly throughout our stay. I never knew waterproof pants existed, and in a moment of mom modesty I was very grateful as I got in and out of the kayak that I wasn’t wearing a regular bathing suit or bikini. 

On our way back to the hotel we were starving and looked for somewhere to eat that would host a bedraggled, post-kayak ocean-drenched family and found a relaxed restaurant in a strip mall. It had a bunch of bikers that were meeting and eating, as well as roosters running around. We ordered giant juicy burgers and my son made eye contact with a very large chicken who was enjoying a stroll inside the restaurant. It was a delightful stop and one of those unforgettable and wonderful travel moments.

On our final morning at the Grand Wailea we learned how to paddle board in a trip that was organized by Aqualani, who are based at the hotel. I like to make sure each of my travel destinations includes learning something new as a family—it gives us all an experience of stretching out of our comfort zone together, and in Maui it was stand-up paddle boarding.

I expected to spend a good deal of time getting dunked in the water and trying to get up, but we were blessed with a great instructor and near still waters. As a family, we took a brief 10-15-minute lesson on shore and were then sent out into the water with our capable and experienced instructor Lucas. I was impressed that Lucas managed to keep track of all three of us even as the currents changed and more impressively, keep us on top of our boards.

The waters of Maui are so incredibly clear that stand up paddle boarding was an invigorating way to further enjoy them. This hotel even comes with its own paparazzi on hand—if you desire to book a session.

The Wailea Beach Resort

On our third morning, we drove less than five minutes to the Wailea Beach Resort next door. The hotel, which is part of the Marriott group, was the first to be built in the area but has been recently renovated and now bills itself as the “newest” hotel in the area. 

Our room faced the adult-only infinity pool that overlooked the ocean and I was constantly blown away by the beauty at this hotel. An impressive, open air lobby greets you upon arrival. There’s also a yard with a swing, a large chess set, and a couple of quirky and beautiful areas tucked inside a massive tree to lounge in while you wait for your room.

The hotel has three distinct pool areas across their 22 acres, offering four water slides, one of which is the longest in Maui (measuring an incredible 325 feet).

When we first saw the big water slide it was nearly empty and we ran up the stairs, which felt to me like being on a cross trainer for an hour, and slid down. We did that about 20 times in the first hour. My kid loved it, my husband loved it and so did I. It was super fun. Not for those with a fear of heights, these slides had me screaming with joy when I went down. I only stopped because my legs were trembling while my son went on at least another 50 times throughout our stay.

There are also splash zones for younger kids and other amenities, including a swim-through grotto, waterfalls, family cabanas, a pool bar, and food truck that serves kid-friendly favorites and local treats such as shaved iced and poke.

They also had a restaurant that we really loved called the Humble Market Kitchin where we enjoyed our breakfast buffet every morning.

Open for lunch and dinner, it was a great breakfast spot serving up fresh papaya and pineapple, as well as tasty lava pancakes. We sampled a variety of fresh made jams here, and while eating a huge breakfast (you need energy for all these adventures) a large, bright rainbow appeared over the ocean.

Later that day we stumbled upon one of the resort’s coin-operated laundry rooms, which we took full advantage of and were grateful to use after a few days at the beach. We have now deemed a laundry room a family travel essential.

The next morning we set out very early for an eight-hour catamaran and snorkeling tour to the island of Lanai with Sail Trilogy. We were greeted on board in the early morning light with giant cinnamon rolls, juice, and coffee. The crew provide all the snorkeling equipment, but take towels and a change of clothes, and definitely some kind of jacket as the early mornings are cooler.

Lanai is the sixth largest island in Hawaii but has a tiny population of just 3,200. Its current owner is the Oracle billionaire Larry Ellison, who bought a 97 percent stake in it for a reported $300 million, in 2012.

Previously it was owned by the famous Dole fruit farming family, which is how it earned its nickname “Pineapple Island.” There are 30 miles of road but no traffic lights and no public transport, as all that is supplied by the local hotel resorts.

We had time to swim and snorkel and also dock for a while and enjoy pretty Lanai town and beach. While we were on the boat Spinner dolphins followed us spinning into the harbor, which was amazing. We had a lovely casual group plantation-style barbecue lunch at a pavilion overlooking the harbor. On our way back to Maui we had a crazy, scream-worthy time riding the big waves.

I would recommend building in time to relax around the many pools or room balcony into your itinerary. You could easily fill every minute of the day with activities, but don’t. It’s a great place to chill out, enjoy the ocean views and soak up the sunshine.

For more family-friendly travel tips and destinations from Margot Black, check out: 

Text and images by Margot Black for