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Maui with Kids – A Dream Come True

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Maui with kids is a dream come true. Literally. Last year my son, Leo, was given an assignment in his kindergarten class to draw a picture depicting his biggest dream. He drew his vision of a coconut tree beside the ocean. When he brought home his drawing, he said, “My dream is to go to Hawaii! Will you take me there pleeeeease?”

Hawaiian Sunset - Sheraton Maui Resort & Spa

Sunset at the Sheraton Maui Resort & Spa (Photo credit: Colleen Lanin)

A Dream Come True

Leo knows I am The Travel Mama and this means we are lucky to get to travel more than the average family. He also knows that I went to Maui last year and came home with gorgeous photos and stories about warm ocean waves, waterfalls, tropical flowers and dreamy hotel pools.

With a limited budget due to an impending move to another state, the likelihood of a return in the foreseeable future to any of the Hawaiian islands, however, seemed remote. Maui had already hosted me on my Maui Midlife Crisis press trip. Hawaii is kind of the holy grail of press trip invitations. I mean, it’s HAWAII. And what were the chances that even if I received a coveted invitation to visit one of the islands, that I would be granted permission to bring along a kid? Not good.

Still, I told Leo that all dreams can come true. I said if he really wanted to go to Hawaii, he should try to envision the sound of Hawaiian ocean waves and the feel of powdery Hawaiian sand beneath his toes. If he had a hard time falling asleep at night, sometimes we would envision Hawaii together. The question would always come up, “Mom, when will we go to Hawaii?”

Someday, baby, someday.

Then Kaanapali, Maui invited me AND a child to visit their gorgeous 3-mile stretch of paradise. I told Leo, “You envisioned Hawaii and brought this to us!”

Off we went to Kaanapali with our Hawaiian dreams in mind. My mom flew in from Arizona for six days of three generations of ohana (family) bonding, Maui style.

Three generations in Kaanapali, Maui

Three generations in Kaanapali, Maui (Photo credit: Colleen Lanin)

Spirit of Aloha

At breakfast at the Hyatt Regency Maui Resort & Spa’s Swan Court, Leo told our waitress, “Did you know something? It was my biggest dream to come to Hawaii. And now I am here!”

We watched the swans and ducks swimming at the Swan Cafe’s pond and ate our fill of pancakes and other breakfast buffet goodies. Then our waitress returned with a gift for Leo. She handed him a box of chocolate-covered macadamia nuts across which she had written, “To Leo, keep living your dreams!”

She said, “I think it’s wonderful that you dreamed of coming to Hawaii and I hope you will continue to dream because you can do anything you want in life.” (Thank you to our waitress, Debra!) It’s not just the beauty of the islands that makes Hawaii one of my favorite places in the world, it’s this spirit of aloha.

As Leo said, “Everyone in Hawaii is happy. No one seems mean here.”

Hyatt Regency Maui Swan Court

One happy boy at the Hyatt Regency Maui’s Swan Court (Photo credit: Colleen Lanin)

Maui with Kids Dining

Although he is the pickiest of eaters and he had never before tasted a nut of any kind, Leo gobbled up his first chocolate-covered macadamia nut with gusto. A couple of days later at the Hula Grill he even ordered (and loved!) macadamia nut-crusted mahi mahi. (Thank you again, Debra!)

He also fell in love with POG (a combination of passion fruit, orange and guava juices that is often touted as Hawaii’s “official” drink). My fruit phobic son drank cup upon cup of this delicious concoction throughout our stay in Kaanapali. POG continues to be his favorite drink at home, too.

Tobi's Shave Ice North Shore in Paia

Tobi’s Shave Ice North Shore in Paia (Photo credit: Colleen Lanin)

A stop in Paia allowed Leo to taste more fresh Hawaiian fish at the popular Paia Fish Market. Grandma and I got the fish tacos (yum!) while Leo went for straight up fish n’ chips. Afterwards, we stopped across the street to cool off with some of Toby’s Shave Ice North Shore, a Maui must-have!

We went to not one, but two luaus during our six nights in Kaanapali; Drums of the Pacific at Hyatt Maui Resort & Spa and Maui Nui Luau at Black Rock at the Sheraton Maui Resort & Spa. I worried the second luau might be overkill and that my 6-year-old would get bored with the traditional Polynesian music and dance. I couldn’t have been more wrong. He sat rapt in amazement throughout both performances and begged me to let him stay long enough to see the fire dancers. I relented, of course. I even bribed convinced my stage shy guy to get in front of the crowd with other brave audience members to learn the hukilau!

Fire dancers at the Drums of the Pacific Luau

Fire dancers at the Drums of the Pacific Luau (Photo credit: Colleen Lanin)

New Experiences on Maui

Hoping to get my picky eater to open his palate to new flavors, I signed up for a Maui Gold Pineapple Farm Tour. Unfortunately we missed the tour due to a couple of wrong turns along the way. Alas, Leo didn’t try any fresh pineapple in Hawaii. (There’s always next time!)

Our tardiness, however, gave us a chance to explore Hui No’eau Visual Arts Center, from which the pineapple farm tours depart. Here we explored the current art exhibit, which featured local children’s art work. Plus, Leo the boy came nose to whiskers with Leo the cat, the gallery’s resident feline.

Leo the cat at Hui No’eau Visual Arts Center

Leo the boy with Leo the cat at Hui No’eau Visual Arts Center (Photo credit: Colleen Lanin)

During visits to the ocean in his previous hometown of San Diego, Leo spent all of his beach time playing on the shores, afraid of the chilly water. In Maui, however, Leo cautiously dipped his feet in the ocean before grinning and shouting, “The water here is so warm!” Soon, he was bobbing about on his inner tube in Kaanapali’s sweet saltwater.

At the Surfing Goat Dairy, we embarked on a tour to learn all about goats and goat cheese. We got a chance to feed and pet the friendly goats. Leo even tasted (and liked!) the sample goat cheeses…another culinary first!

Travel has a way of pushing people outside our comfort zones. We are more likely to try something new while away from our usual lives. I love seeing how my children react to the unfamiliarity of new destinations. It stretches them and teaches them so much about our vast, beautiful planet.

Surfing Goat Dairy

Feeding goats at the Surfing Goat Dairy (Photo credit: Colleen Lanin)

Dream On

What about Leo…did Maui, Hawaii live up to his expectations? What is his biggest dream now? Leo’s new dream is to someday live in Hawaii.

All dreams can come true, baby.

Have you ever visualized a dream into reality? Tell us about your experience in the comments below!

A Note from The Travel Mama: Thank you to Kaanapali Beach Resort Association for hosting our stay! All opinions are mine, as always.

About Colleen Lanin

Colleen Lanin is the founder/editor-in-chief of As the author of her book, "The Travel Mamas' Guide," she teaches parents not only how to survive a trip with children, but also how to love exploring the world with their offspring. Her stories have appeared online and in print for such outlets as the "Today" show,, Parenting Magazine, Orlando Sentinel, Chicago Tribune, Expedia, San Diego Family Magazine, and more. Colleen gives tips on television, radio, and as a public speaker. She has a master’s degree in business administration with a background in marketing. She lives in Arizona with her husband and two kids.

  1. Leo was so much fun in Maui, making it a very pleasant vacation. There was so much to do that he was never bored., I especially enjoyed playing ping pong at the beach with him and snorkeling for the first time in the ocean.

  2. Your son must have been so excited when you told him about your press trip. Awesome to see all the highlights a family can experience in Maui!

    • Colleen Lanin, The Travel Mama says

      James – Truly…the kid was jumping up & down with joy when I told him we were headed to Maui. SUCH a wonderful place to visit with kids.

  3. Hi Coleen..thank you for sharing us this useful information…:)

  4. you are welcome. I like travel with family too..I have 4 kids…
    And everytime we go together there’s always be a beautiful moment…sometimes surprisingly..haha..
    I guess you must be the same with me…:)
    Have a great day….cheers…:)

  5. Incredible! Hawaii is yet another entry on our family travel bucket list 🙂

  6. It’s like his own vision board come true! Glad he loved it!

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