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How You Can Enjoy a Stress-Free, Luxurious Family Vacation on the Island of Maui

If you happen to follow our family adventures, then you already know I’m all about sweet, suite deals. Me and my crew are always on the hunt for family-sized vacation suites that give the most bang for our buck! But, when it came time to plan our trip to Maui, we decided to splurge on a luxury resort experience this time.

After all, Maui would be our second island stop on a 16 day trip to four islands, and we wanted to sneak in some pampering and resort extravagance on this leg of our journey.

vacation on the island of maui 

Don’t get me wrong, however. We still searched for the best suite deal we could find in the luxury category. And, we ended up using a Platinum Business Amex to get a free upgrade from a basic room to an oceanview suite (complete with a living area and mini kitchen). With that, we also got our hands on a free buffet breakfast every morning ($100 daily credit), early check-in (12 am) and late check-out (until 4 pm), and free WiFi. Therefore, while Fairmont Kea Lani was truly a splurge, we still got a ton of value for our vacation dollars and secured a seriously suite deal.

vacation on the island of maui

Now, while this stop was inevitably different from the rest in our island hopping experience, I’m here to unveil my top tips on how you, too, can enjoy a stress-free, luxurious vacation just as we did while on the island of Maui.

1. Splurge on a resort with a kids club.

Family vacations offer the perfect opportunity to connect with our children and savor our time with them. After all, when we’re free of schedules, rushed trips to school activities, homework, and houses littered with toys and dirty socks, we can be the mom we all desire to be. The fun, relaxed, patient, nice mom, happppppyy mom. And, “Happy Mom” (aka “Vacation Mom”) can truly enjoy playtime at the pool, a walk on the beach, or an exciting adventure outside of the resort without feeling frazzled, drained, or short-tempered.

vacation on the island of maui

I also believe that stress-free family vacations should give us time to connect with ourselves and our spouses, too. For that reason, supervised kids clubs are THE best. I’m not talking about just any kind of kids club, however. Instead, I’m talking a guilt-free, action-packed, creative kids club that allows your mini-mes to learn something new, meet some new friends, and have fun!

And, Fairmont Kea Lani in Wailea on the island of Maui is a splurge that offers all that and then some! Our daughter, Mallory Grace, was thrilled to spend either the morning (9am-12pm) or afternoon (1-4pm) at the Keiki (which means kid in Hawaiian) Club where she could hunt for lizards, take a beach hike, make a craft, or play make-believe with her new friends. Meanwhile, I was able to start the day with a yoga or boot camp class, walk on the beach with the hubs, or simply read a book and take a nap – my personal heaven on earth!   

In the end, full-service resorts that offer a really good kids program are a definite splurge (even many of the resorts in our Tripbound portfolio offer them!). But, they always end up being worth it when the entire family leaves feeling relaxed, nurtured, and ready to dive back into “real life”.   

2. Stroll through the town of Lahaina.

One of my family’s favorite things to do on any vacation is to stroll. In no hurry, without any place to be, just stroll and see what we see at a leisurely pace. There are few things I enjoy more than this and Lahaina, is perfect for strolling!

Lahaina is located off of Highway 30 (Honoapiilani Highway) in western Maui. The town is best known for its rich history as a whaling port. But, it’s also home to wonderful art galleries, shops, restaurants, and the giant Banyan Tree in the town square. Planted in 1873, it now consumes an entire city block.

vacation on the island of maui

One of our best discoveries while strolling was the Paia Fish Market on Front Street. This cool, funky, casual place offers the best, most affordable fish tacos on the island. I’m still thinking about the tartar sauce and the freshly-made coleslaw. Delicious!

vacation on the island of maui

The second discovery was the small market with local artisans where we found and purchased our hand-carved totem pole, which was designed to bring joy, prosperity, and luck to our family for many years to come. We couldn’t think of a better souvenir to bring back home with us.

There’s also plenty of shaved ice vendors, surf shops, and art galleries to discover during your stroll along this waterfront town!

3. Sneak out for some “Mom time.”  

Remember tip #1 where I encouraged you to connect and pamper yourself without any guilt on your Maui family vacation?

Well, if you heeded my advice on splurging at the Fairmont Kea Lani, then you’ll love this. The Shops at Wailea is just a couple of minutes up the road. And, the resort’s shuttle service will take you and pick you up upon request. Stop into SoHa for the cutest souvenirs to take home, Keliki for something new to wear to dinner back at the resort, and Mahina for cute, affordable jewelry made local. A dreamy, kid-free shopping experience, for sure!

vacation on the island of maui

4. Take the GyPSy with you on the Road to Hana.

You can’t go all the way to Maui and not leave the resort. You’ve got to experience a little adventure, and the Road to Hana is the perfect way to do just that!

vacation on the island of maui

Don’t get me wrong. It is not for the faint of heart, and you need to be prepared for the more than 600+ hairpin turns and 59 single lane bridges. BUT, if you come to terms that it’s about the journey, not the destination, and you plan accordingly, you can have quite the semi stress-free family adventure!

vacation on the island of maui

vacation on the island of maui

The first step to doing just that: download the GyPSy App. This guy (aka GyPSy) was like having your wise Uncle Steve riding shotgun with you the whole way. My husband was beyond relieved to have another man (whom we called the voice of reason) with him as he navigated the road. He keeps you calm, while also guiding you to all the best stops. And, he somehow knows exactly where you are even when cell service is lost, which is quite honestly still a mystery.

Oh, and remember my love of strolling? Well, this is like the car version of that in one of the most beautiful places on earth. There are literally dozens and dozens of possible stops along the way—from waterfalls and roadside stands to hikes and scenic overlooks. The fun is stopping along the way, and no two journeys are often the same!

Our journey included: giant shaved ice at the Halfway to Hana stand, must-order coconut shrimp at the Island Chef truck, a kid-friendly hike for an up-close encounter with rainbow eucalyptus trees, and a swim in the “Three Bears” waterfall

vacation on the island of maui

vacation on the island of maui

vacation on the island of maui

vacation on the island of maui

I have a feeling that the swim in the waterfall will be the memory our daughter keeps from her vacation to Maui, making it completely worth the trip. If you choose to follow in our footsteps, just be sure you bring water shoes to wear!

5. Connect with your inner child.

While you’re there in the middle of the Pacific Ocean being your fun, happy, relaxed mom self, make sure to take some time to play with your kiddos. If you’ve decided to splurge on a stay at Fairmont Kea Lani, you’ll have loads of opportunities to do so!

Rent a boogie board or stand-up paddleboard at the resort and take to the waves, ride down the waterslide a few dozen times, have an underwater tea party, or do cartwheels on the beach while the sun goes down. It doesn’t matter what you’re doing. All that matters is that you’re in the moment having FUN!

vacation on the island of maui

vacation on the island of maui


In the end, if you choose to splurge on a luxury family vacation to Maui as we did, consider using a travel expert. You’ll save yourself loads of time planning, researching, and worrying about whether or not things will go smoothly.
And, speaking of travel experts, give the Tripbound Resort Specialists a call at 1-888-816-5214. We can help match you with the perfect suite deal on one of the Hawaiian islands!

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