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The Ultimate Maui Family Vacation

Updated: Mar 13, 2021

My husband and I made a trip to Maui this year to celebrate our 10 year anniversary (with our two little boys in tow) and it was AMAZING! Despite the hoops we had to jump through due to COVID it was well worth the added pre-travel stress.

My husband and I love a good adventure and although we allocated one entire day to some good old fashioned relaxing, we used most of our time on Maui to explore the island. While we were there we managed to drive around the entire island - it was quite the adventure! If you love beautiful drives, breathtaking hikes and secret beaches all to yourself then read on. I’ve got the ultimate itinerary for you and your family!!

Now I’m all about the details so I’ll be giving you ALL those helpful tips and details you might be thirsting for (I know I was when I was planning our Maui vacation) that will make your planning that much easier.


Arrival, Ioa Valley Park, Makena Cove

1:00 PM Ioa Valley Park

Once you arrive in Maui and get your car rental - I recommend getting a Jeep - take off the roof, buckle up and head over to Ioa Valley Park, just a short drive from the airport. This gorgeous area highlights the steep green rolling mountains that Maui is known for. This makes for a nice first stop in Maui - you’ll get to stretch your legs on a easy short paved hike, marvel at the beauty of Iao Needle (and learn of the interesting native meaning for the needle) and even take a dip into Iao Stream!

To make wading and swimming in the gorgeous array of Maui streams easy be sure to pack the proper footwear. For the boys we bought these Teva sandals which worked well, and I packed my Chacos. Having water sandals that also can work for hiking is a must in Maui.

4:00 Makena Cove “Turtle Town”

After your refreshing dip in the stream head over to the southwest side of the island to the district of Honu’ula. There pick up some dinner to-go (because dinner with a view is much better than eating at a restaurant) and head to this beautiful beach! Makena Cove is an intimate beach that packs a punch with beauty - here we saw whales, sea turtles, impressive tidepools, jumped off some small rocks (because I’m a scaredy cat and wouldn’t dare jump off large cliffs) and shared an unforgettable sunset together. Our boys also played very happily in the small Sandy beach here until the sunset.

5:00 PM Coconut Fish Cafe

After our long day of travel we wanted to get something fast and easy - but delicious - so we picked this local favorite for dinner. Their coconut shrimp was the BEST I ever had, so be sure to buy an order of that (or maybe two). What I wish we would have done is gotten the food to-go so we could enjoy sunset at the beach while having dinner. That’s my tip!

Here’s a little peek into what our first day in Maui was like:

DAY 2 Haleakalā Sunrise & Reverse Road to Hana

4:30 AM Sunrise at Haleakalā National Park

You better believe we woke up at 4:30 in the morning to see the sunrise on a Hawaiian volcano! With a little motivation and a BIG heart for adventure this can be such a fun experience for everyone. Admittedly, my kids weren’t as impressed as my husband and I but when the sun finally began rising over the clouds, the park rangers began to sing the Hawaiian sunrise prayer and then we all saw the liquid gold lining around the fluffy beauties they began to see the vision.

Be sure to wear appropriate clothing - it gets cold up there! Some thick jackets and blankets should do the trick.

Note: You do need to buy your tickets in advance and the sell out FAST. A reservation is required for each vehicle entering the park from 3:00 a.m. to 7:00 a.m. You may book a reservation up to 7 days in advance. For example, on January 1 you can book tickets through January. Here’s the website to purchase the tickets.

7:00 AM Grandma’s Coffee House

After your early rise you deserve a good breakfast. For a local owned off the beaten path option check out Grandma’s Coffee House, which is conveniently a short drive from the park. Well loved by locals, yummy coconut French toast and one of the best smoked salmon bagels I have ever had.

What I wish I would have: I wish we would have ordered lunch here to-go along with our breakfast. On the reverse road to Hana there is NOTHING to stop and eat so you will need to plan ahead. Grab lunch to-go here and some snacks at the grocery store a few shops down. You’ll be glad you did! Our boys were a wee bit hangry at the end of our trip.

8:30 AM Reverse Road to Hana

Are you ready for the most beautiful drive of your life?? Then buckle up, be sure to rent a Jeep (take off the top), pack a lunch and a bathing suit and get ready to have one of the best TWO days of your trip!! This drive takes in the very best of Maui.

Most people start the road to Hana at the opposite end, by beginning on Highway 360 headed towards Hana, however the reverse road begins you at Keokea on highway 37 (which turns into 31). This highway is often avoided by tourists who complain the road is dangerous, scary and too much work. I can’t disagree more.

That being said my husband and I do have a love for driving on rugged roads/taking the road less traveled, even if it means there are no bathrooms in sight, it’s unpaved and maybe a little sketchy. But honestly, it was not the worst road we’ve ever been on. Almost all of it was paved, with just some short dirt road sections, and although there were many sections that were one lane roads we hardly ran into cars coming the opposite way (most people who were there that early in the day were doing reverse road to Hana too).

Since most people do the road to Hana the other direction you’ve got the road almost to yourself. Which means many moments of taking in a unbelievable views (like the one above) or savoring a secret beach all to yourself. There are a lot of Kodak moments on this drive so get ready to be amazed. Beautiful sweeping valleys with grazing livestock, rocky majestic coastal cliffs, magical secret beaches straight out of a postcard, thick lush jungles, bamboo forests, waterfall after waterfall... I could go on and on. There is A LOT to take in on this side of the island which is why I highly suggest breaking it up into two days. It’s worth it I promise!

Disclaimer: We did travel to Maui during February (a less busy time of year for Maui) and during COVID pandemic. So, maybe we got lucky with less busy roads - it’s hard to say.

Note: many people struggle with road sickness on the road to Hana. Surprisingly, I didn’t get road sick despite the fact I’m typically often road sick. Maybe it was all that adrenaline from the excitement of being there - I’m not sure - but I did bring some motion sickness medication just in case. If you get car sick then be sure to bring some just in case!

12:00 PM Laulima Farm

For a unique down to earth fruit stand experience you’ll definitely want to make this stop. Laulima Farms is owned by a couple that have lived there for twenty years and are passionate about Maui sustainable farming and quality agriculture. After your beautiful drive treat yourself to some freshly cut coconut 🥥 water or some delicious fresh squeezed local juice. She cuts the coconuts herself right there and then makes a straw from bamboo shoots! So cool to watch! The owner also had some delicious homemade cookies we scarfed down (remember we forgot to pack snacks... learn from our mistake, pack thy snacks, but also.... buy these cookies too).

Make sure to sit and stay awhile on one of their handmade wooden unique tables. Some of which are surrounded by tall bamboo and give it such an intimate jungle feel. She also encourages people to take the small loop trail around the farm to see the many varieties of fruit trees and plants she has. Lovely little walk!

2:00 PM Pipiwai Trail

Your next stop on the reverse road to Hana is the mind-blowing beautiful trail of Pipiwai. If you love a gorgeous hike and have never been through a bamboo forest don’t miss this! I have been on a lot of memorable trails in my life but this one was pretty special and has made its way to my top ten hikes of all time. Every corner we turned there was something new to marvel at ... lush jungle forests, huge ancient banyan tree, biggest bamboo forest I’ve ever walked through and a 400 foot plunge waterfall that we both took a shower under. This trail is just a series of epic moments. Bring some good shoes, bathing suit, snacks, sunscreen and get ready to be amazed.

Note: there are many warning signs about the dangers of swimming in these pools and under the falls. Flash floods do occur and have killed people unfortunately. I would not recommend getting in the water or under the falls during a rainfall or right after one as the water levels may change drastically. Be sure to keep an eye on the weather and stay safe!

4:00 The Pools of Ohe’o

The highlight of Haleakala National Park for us was most definitely the Pipiwai Trail, but the Pools of Ohe‘o was just a short walk from the parking lot and well worth the view. Occasionally, in the summer months, these pools open up to the public for swimming. However, for the most part they stay closed to the public but are quite a beautiful sight to admire! Don’t forget to get your National Park stamp and Jr. Ranger badges for the kids before you leave (if you collect them).

6:00 PM Hana Ranch

We were starving after our long drive (and not planning ahead for lunch - oops) so after the day we had a delicious dinner at Hana Ranch. If you can reserve a table with a view (or outside) this is a lovely place to share an evening together! We sat right next to bay windows with this stunning sunset view of Kaihalulu Bay - it was dreamy!

Added bonus the boys could run in and out of the large bay windows to enjoy a grassy hill they rolled coconuts down. They were SO happy and my husband and I got to enjoy a quiet(er) dinner. The prawns appetizer were AMAZING - some of the best I’ve ever had - and the the Mahi Mahi with onion reduction was mouth watering (perfect amount of sear and crust).

Our dinner view and evening entertainment for the kids (they happily rolled coconuts down the hill all evening). They also had a pretty impressive ukulele collection!

DAY 3 Reverse Road to Hana Continued

The Road to Hana is just waaaaay too special to do in one day. Honestly, next time when we return to Maui, I’d rather spend our entire vacation over there because that’s the better half of the island in my mind. But at the very least, do yourself a favor and split it up into two days - you’ll feel way less rushed and get to savor all of those waterfalls and beautiful beaches more.

8:00 AM Koki Beach (Red Sand Beach)

We started our day out by having our breakfast at the red sand beaches of Koki. We grabbed breakfast to-go and loved our slow morning here wading in the waters, admiring the gorgeous red sands and looking at bleached coral.

10:00 AM Hana Gold Cacao Plantation

This is a fun stop for any chocolate lovers out there. The owners are really lovely people and unfortunately can’t do their usual routine of sampling and touring of the farms (darn you COVID!!). I was bummed that we couldn’t get a tour of the farms but the chocolate was yummy and the kids were impressed to see the cacao trees nonetheless.

The chocolate is smooth and you can really taste the fruitiness that comes from chocolate made from real beans.

11:00 AM Hana Lava Tube

It started gently raining on us early in the morning so we sought shelter in the Lava Tube and it ended up being a fun little stop on our adventure in Hana. The Lava Tube is a short walk but memorable, with some informative educational plaques as you progress through the underground tunnel. Our two little boys really thought this was AMAZING - inside a lava tube?! Yes Please! So it was a parent win.

12:00 PM Hana Farms Roadside Stand

Highly recommend this place for lunch. So tasty and really hit the spot. It was one of the best plates of Hawaiian food we had our entire stay on the island and the fIzzy fruit drinks, that come in a variety of flavors, were so refreshing!

2:00 PM Wai’anapanapa State Park (Black Sand Beach)

The black sand beach here is quite the sight to see and makes for a lovely afternoon for the kids - and parents! We really loved relaxing here and watching the boys play in the waves. There’s also an impressive blowhole where you can watch huge crashing waves and get splashed.

4:00 PM Coconut Glen’s

Even though it was raining ever so slightly when we got here I was feeling pretty determined to try a taste of this famous Hawaiian ice cream. It did not disappoint! I went with the origional coconut vanilla ice cream - YUM!!

4:30 PM Waikani Falls

When you first jump in it is COLD - not going to lie - but don’t worry you do warm up! The current from the waterfall is quite strong and you work up some warmth just swimming against it. Swimming around right next to a Hawaiian waterfall was well worth the initial cold of the first swim in. Live a little - get in there!

5:00 Honomanu

This has to be the most scenic surf spots I’ve ever been too. Wow. Pictures just don’t do it justice. I wish we could have stayed at this magical beach longer but we had a glorious hour here and I loved it. We didn’t do any surfing ourselves but just watching the surfers was so memorable. They were literally surfing underneath a rainbow!! Made me appreciate why Hawaii’s license plate is a rainbow.

6:00 PM Waikamoi Waterfall

Want to Tarzan swing yourself into a gorgeous Hawaiian waterfall? Then don’t miss this fun stop. It was later in our day and the sun was starting to set but I did NOT want to miss out on this. It was one of my favorite parts of the day swinging into here. SO much fun and once again you warm up quickly swimming around.

DAY 4 Relax

After three very fun filled adventure days it’s time for some relaxing! We stayed at the Hyatt Regency Resort and enjoyed some down time at the beach, LOTS of pool time for the boys and of course some Hawaiian Ice. Although staying at resorts isn’t my usual cup of tea, the Hyatt Regency of Maui is a comfortable, clean, modern and fun stay. We enjoyed the penguin feedings, koi pond, gorgeous beaches, huge pool and on-site restaurants.

4:00 PM Honolua Bay Trail

Before the sun completely went down we took a drive and explored the Honolulu Bay Trail. This is a MUST see and features some of the most impressive forests and old trees I’ve ever seen. It’s a great spot to watch the sunset colors and it is also less busy in the evening. The locals here take great care of these trails growing their own poi plants and papaya trees. Take care not to step on the poi plants or steal the papayas. Treat this place like the sacred and well cared for garden that it is!

7:00 PM Hawaiian Luau

Also, as cliche as it is, if you get a chance to watch a Luau it does add that extra bit of magic to a Hawaiian vacation. The Hyatt Regency puts one on and we simply walked on over after dinner and watched the dancing from afar (hooray for a free luau!). The boys loved the fire dance of course and watching the luau dancers gave me a new appreciation for the beauty of Hawaiian culture.

DAY 5 Snorkeling/Explore Northern Island

9:00 AM Snorkeling at Olowalu Beach

Although hugged right against a highway, this is a very easy accessible place to snorkel where you can find lots of colorful tropical fish! The water is somewhat silty but if you’re patient there’s a lot to see here. I saw loads of fish including Humuhumu-Nuknuku-Apua’a (try saying that fives times in a row), varities of ornate Butterflyfish, Wrasse, Spotted Toby, swam with some sea turtles and loads more! My boys also loved to climb around on the beach trees and collect sea shells here. The big beach trees offer nice shade and a lovely atmosphere.

12:00 PM Leoda’s Kitchen and Pie Shop

YUM! This is a great spot to grab some lunch and eat it back at the beach. It’s convienently right down the road from Olowalu, so you can grab some lunch and bring it back here. Of course, you’ll have to try some pies! Good luck deciding which one to get - it‘s so hard to choose from all those delicious flavors. We liked the passion fruit cheesecake.

2:00 PM Nakalele Blowhole

To complete your circumnavigation of the island it’s time to head up to the Northern tip of the island to Nakalele Blowhole. This is an exciting stop that the kiddos enjoyed thoroughly. The blowhole here can be quite impressive and there’s hundreds of black crabs scurrying around the walls next to the hole. Be careful because the suction from the blowhole can be quite dangerous, so keep a safe distance. However, get close enough to get a little wet - cooling off before the hike back up makes it less of a arduous climb! This hike can get hot as it’s completely exposed to the sun.

5:00 PM Kahakuloa Head Lookout

Grab some dinner to-go (we bought some poke salad at a food truck) and park at this gorgeous lookout spot! This was one of my favorite evenings hands down. We had this amazing view all to ourselves and had a nice peaceful dinner while the kiddos ate there dinner on the roof of the Jeep (and could be as loud and crazy as they wanted to be without some stressed out parents). We were all pretty dang happy. I will always remember this evening - it was pretty special! The lookout isn’t marked on the map but it’s a lookout spot right before you hit Kahakuloa Beach.

6:00 PM Scenic Evening Drive

After you finish dinner, bellies full and happy, then head south on Highway 340 and enjoy a scenic drive. These roads are windy and often only one lane roads so driver be warned. I advise not doing this road in the dark but during sundown/dusk is doable. Don’t be scared though it’s well worth the drive! It’s neat to see the untouched portion of the island where you’ll be rewarded with stunning views all to yourself.

DAY 6 Leaving/Last Minute Beach Time

Sneak in as much time as you can before you have to leave this gorgeous island! We spent a nice morning at the beach (swam with more sea turtles) and the boys caught a few more strokes in the pool. Careful to check for and fruits in your baggage’s before you leave. Our little kiddo tried to sneak some local fruits in his backpack... the disappointment of realizing he had to leave his precious treasures can be seen below...

Hope this blog helps you on your trip to Maui. We LOVED our stay there and know you will too! It’s a magical place. Enjoy!


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