Hawaii is quite far from the east coast, so you don’t often hear about east coasters visiting outside of a honeymoon. But I turned 40 this year and YOLO - so we took the kids and did it. I’m so very glad we did. Hawaii is pure magic and is NOT “just like the Caribbean but farther.”
If you are looking for relaxation, world class resorts, slow paced island living and gorgeous beaches, with some breathtaking vistas, lush vegetation and volcanic craters thrown in, then Maui is your spot.
Maui was the second island we visited on our trip. After five nights in Oahu, we took a quick 30 minute flight over to Maui- piece of cake. To read about our time in Oahu, check Part One.
Wailea Is Where You’ll Find the Fancy Maui Resorts
Wailea is a heavily manicured development area in Maui known for having the best weather, golf and resorts on the island. With the exception of the Hotel Wailea, a stunning adults-only hotel, the resorts of Wailea are enjoyed equally by honeymooning couples and energized toddlers. The Grand Wailea boasts a large onsite water park and the Four Seasons Maui, where we stayed, caters to families and keiki (Hawaiian for “child”).
The Four Seasons was luxurious and gorgeous and though definitely a splurge, it made for a perfect “milestone trip.” And the Four Seasons Maui knows how to treat its youngest guests. My girls received presents from the hotel upon arrival and they adored the hotel’s wonderfully run and completely free (WOO HOO!) Kids For All Seasons kids club, open daily from 9am-5pm.
The resort also offers fantastic and complimentary family friendly Hawaiian cultural activities throughout the week, such as lei making and hula dance lessons. And every night, you can catch hula dancing and live Hawaiian music in the hotel’s beautiful lobby bar from 5:30-6:30pm, followed by a tiki torch lighting ceremony, where kids are invited to join along in the fun.
And do not miss the resort’s glorious Serenity Pool - a gorgeous adults-only pool and swim bar overlooking the ocean. Head there after dropping the keiki at the kids club!
The Four Seasons Wailea is indeed lovely, and you could easily spend your entire visit inside the resort grounds. But alas, you have come all this way, so you should very much leave from time to time to explore Maui.
We Ate Most Meals in Kiehi
Most of the food options within Wailea feature absurd pricing, especially if you’re going to be spending said meal with unruly kids. One notable exception to this rule was Monkeypod, a casual and really great Peter Merriman restaurant within Wailea that was reasonable, tasty and family friendly. Their Mai Tai with a lilikoi (passion fruit) foam on top was legendary, and I will most definitely be craving it all summer.
We ate most of our Maui meals in Kihei, a town just about 10 minutes from Wailea where locals reside. Here, you can find many counter service spots with cheaper and better food than what is offered in the Wailea resorts.
Popular and tasty options that we enjoyed in Kihei include Kihei Caffe for breakfast (banana macadamia nut griddle FTW), Paia Fish Market for dishes like grilled fresh fish and seafood pasta and Outrigger Pizza, a roadside mobile pizza truck. I had the Lilikoi Pork pie (Garlic aioli, kale, pork, sweet bell pepper, sweet onions with mozzarella, Romano, and grated parmesan cheese and finished with a lilikoi drizzle) at Outrigger and it was heavenly.
On the sweet side, there is a location of Maui’s famed shave ice joint, Ululuani’s, open from 10:30-6:30pm (so make sure you visit at lunchtime!) in Kihei and right next door, you can get malasadas (from 8am to 10am) and other baked goods at Sugar Beach Bake Shop. Maui Pie also makes wonderful pies from apple to strawberry mango and, unlike the other two sweet treats mentioned, Maui Pie stays open until 9:30pm. Kihei is also home to the flagship location of Maui Brewing, which makes for a fun visit.
Leave Your Resort to Visit the Mill House
Tucked inside the Maui Tropical Plantation and an easy drive from Wailea as well as the resorts in Kaanapali Beach, is the gorgeous and delicious Mill House restaurant. A“farm to table” restaurant, Mill House was super yummy and managed to be beautiful but still casual enough for kids. Everything we ate was excellent and the restaurant has a huge sugarcane focused cocktail menu, too.
Save time before or after your meal at Mill House to walk around the Maui Tropical Plantation. Besides all the beautiful plant life and scenery to gawk at, there is a notable roasting company, a few shops and a zip line course on site. It’s a fun way to spend a sunny day in Maui.
Leave Your Resort to Visit the Iao Valley
Just past the Maui Tropical Plantation is the Iao Valley, where you can hike among lush greenery to visit Maui’s iconic Iao Needle monument. That “hike” up to the monument is really more of a 10 minute stroll, but with pretty scenery and nice vistas, it makes for a nice visit and good activity to pair with the Plantation.
and DEFINITELY Leave Your Resort to Do the Road to Hana
Standing in stark contrast to the manicured opulence of Wailea is the tiny, isolated town of Hana, accessible mostly by the long, windy and one-lane Hana Highway (aka the Road to Hana). You can spend the night in Hana, or you can simply enjoy the iconic ride there and then head back (or even past Hana).
The Road to Hana is a truly beautiful drive, along stunning cliff-sides, passing ocean views and gorgeous greenery. Many blogs and travel guides will suggest where along the Road you should stop, but, I suggest going with a local guide if you can, because many stops are not clearly marked and some can be downright dangerous if you don’t know the area. Plus it’s more fun to be a passenger enjoying the scenery than the driver. We did the Road to Hana with Charlie of Blue Soul Maui and it turned out perfectly. He picked us up at our hotel and worked with us to plot out a great day.
The first stop we made along the Road to Hana was a truly memorable hike through the “Bamboo Forest.” It happened to start raining during our hike, which made for some slippery, muddy pathways, as well as a more exciting and adventurous trek. It was utterly magic walking through beautiful, towering bamboo trees in the rain. And when we finally reached a waterfall, having gotten practice at Oahu’s Waimea Falls, this time, our family jumped right in.
After the Bamboo Forest, we drove about another hour and a half along the same lush path to Nahiku Marketplace, a roadside collection of food stalls, a coffee shop and a store selling local Maui products and art. We ate poke and charbroiled chicken, drank coffee and fresh smoothies and enjoyed buying some souvenirs. It was a great stop.
Just about another 20 minutes from Nahiku brought us to the enchanting (and popular) Black Sand Beach. This beach was so strikingly beautiful. It was perhaps my favorite beach of all time. I could watch the blue water crash against the black sand with bright green vegetation on the shoreline all damn day. The beach also had a small lava tube that our girls loved exploring.
The Black Sand Beach is only about 5 minutes from Hana Town, which we drove through, and then began our trip back to Wailea along the same one lane road. We made one last stop near the very southern tip of the Hana Highway at Hookipa Beach to see the sea turtles that lounge along its shore.
This was an unforgettable day full of adventure and natural beauty. And it was made all the better because we did it as a family and with an experienced guide. The Road to Hana is most definitely a Maui Must Do.
We Missed the Haleakala Crater But That’s OK
Along with the Road to Hana, visiting the Haleakala Crater, particularly in time to watch the sun rise, is a big tourist attraction in Maui. We decided against a visit on this trip, given it takes about 2 hours from Wailea to get there, and to make it in time for sunrise, we would have needed to leave our resort around 3am. It just seemed like too much with the kids.
Maui is a wonderful place to relax and enjoy its natural beauty. We adored being pampered at the Four Seasons and the family memories we made, especially on the Road to Hana, will last forever. I am so glad we visited Maui.