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Travel on Point(s) is an independent, advertising-supported website. This site is part of an affiliate sales network and receives compensation for sending traffic to partner sites like and This compensation does not impact how or where products appear on this site. Travel on Point(s) has not reviewed all available credit card offers on this site. Reviews, analyses & recommendations are the author’s alone and have not been reviewed, endorsed, or approved by any partner entities.

5 Days In Maui

After recently spending 5 days in Maui, I figured I would share what we did during our time there. We packed in a decent amount of stuff, but didn't go overboard. I think that is the sweet spot of family travel right there. I'll share some of the things we did while on the island, which things we really liked and what we thought we could do without. Hopefully this gives you some ideas for your next trip there. If you have done some of the same things then share your experiences with me over in the ToP Facebook Group.

5 days in maui

Stocking Up

The first thing we did during our 5 days in Maui isn't very sexy at all. We landed, grabbed our rental car and headed straight to Target. While many people head to Costco in Maui, we had some discounted Target gift cards banked and wanted to use that instead. The prices were pretty close to mainland prices, which is a reason many people go to Costco. The Costco looked like an absolute zoo though. I think everyone on Maui goes there!

**It should be noted that the Costco hot dog deal is the same price as anywhere else if you need a cheap lunch in Maui!

We loaded up on some snacks, drinks, an inflatable bed (to save on the cost of a rollaway) and some other odds and ends. Strange enough, the Target did not stock their standard Target brand sunscreen (or anything else affordable). That was a strange quirk, but we were able to get everything else we needed.

5 Days In Maui

Pool Time

One of our main goals on the trip was some fun in the sun. We happened to be staying at the best resort for that for the first part of the trip, the Grand Wailea Waldorf Astoria property. If you checked out our recent review on the site, then you know this is a pool person's paradise. We spend a good chunk of two days zipping through the slides and taking in as much sun as we could. While we hung out at the beach for a little bit, the pools were the main draw here.


We even spent some time under water doing some free scuba at the hotel. They also offer paid diving tours right out in front of the hotel which is pretty convenient. The free pool scuba is a way to get you interested in that. My son had fun playing a bit of under water frisbee.

5 Days In Maui

The pool at the Hana Maui Hyatt (our review) was as picturesque as one could hope for. We just wish it was heated a little better during the rainy season. Unfortunately, it was a bit too chilly to spend too much time in.

5 Days In Maui

5 Days In Maui: Haleakalā National Park

Another thing I know I wanted to do was head into the Haleakalā National Park. This was far and away the highlight of the trip for all of us. The drive will take some time, and you will be going through some extreme climate change. It is was mid to low 80's when we started our trek, and it was in the low 40's when we finished it at the top. It was super windy as well, so pack properly if you are heading up. A winter hat and gloves are a good option that won't take up a ton of space in your carry on. You will want some pants and something warmer on top, like a sweatshirt or jacket.


We downloaded an app that talks you through the history, gives you directions and gives some info on the nearby towns on the way up and down. It was well worth the $10. If you are going to do the Road to Hana (more on that in a bit) then you can buy a package deal for them both. Entry into the park will cost you another $30. Time it up within a few days on the Road to Hana and you may be able to double dip the ticket, since there is an entry to the park just past Hana and the ticket is good for 3 days.

A lot of people want to go for sunrise, which is supposed to be beautiful. The problem is you need to get up mighty early, and you have to have a timed ticket for it. You will want to be sure to plan ahead if you are going to do the sunrise viewing. You don't need a ticket for sunset, but the parking is limited and can fill up. We headed up early afternoon and still got some amazing views, and it was pretty empty. It looks like Mars up there and is well worth the effort in my opinion.


Visit Smaller Towns

One of the things we like to do as a family is check out smaller towns. So we were sure to make a few detours while driving around to check out some of them. If going up to the Haleakalā National Park then stop in Makawao on the way up or back. It is a cute little town with quite a few little shops.

You can continue on to Paia from there for some great dining options. If you don't have time to fit it all in, you will get another chance at Paia on the Road to Hana.

Hana itself is a cute little town that we enjoyed hanging out in during our two night stay.

5 Days In Maui

5 Days In Maui: Eat Around The Island

Our second favorite thing about Maui was the food. Most everything we had was pretty amazing (besides Polli's in Makawao). While a good portion of the food scene is out of food trucks, they were all outstanding. Unfortunately, we were not able to get into Mama's Fish House, but I have heard amazing things. I know people that have planned their entire trip around a reservation there. Book far in advance if you are interested.

We went to one of the famous MonkeyPod restaurants in Grand Wailea. They have an amazing happy hour that drops the prices of things to non Maui prices. Everything we ate there was great (ravioli, pizza, chicken wings, fries etc.). If you like Mai Tais then this is your spot too!

We also waited over an hour for some shave ice. While I wanted the kids to try it, I have always thought it is a bit overhyped. We should have just tried again at another location when the wait wasn't so long too.

We found two groupings of food trucks that bookend the Courtyard Marriott by the airport. I am not ashamed to say we went back there a few times during our travels for lunch. They had around 10 food trucks on each side of the hotel and everything we had was amazing. My favorite of the bunch was Ono a teppanyaki food truck. My wife loved the poke place (pictured above).

The food truck scene wasn't quite as good in Hana but we had some decent food there. We actually preferred the trucks to the The Ranch Restaurant in Hana. I will say the breakfast and pool bar did stand out for us at the Hyatt Hana Maui though.

5 Days In Maui

Road To Hana

After a few days at the Grand Wailea we headed out towards Hana to finish up our 5 days in Maui. We stopped at the food trucks above on our way out. Normally you want to start the road to Hana earlier in the morning to give yourself enough time to see and do stuff along the way. There will be a turn off, or visitor spot, every few miles on the road to Hana. You will need to decide which ones you want to do, and which ones you feel like skipping. This is where the audio app we downloaded came in very handy.

5 Days In Maui

We headed out after lunch since we knew we didn't need to drive to Hana and back in the same day, since we were staying at the Hyatt Hana Maui. I think that makes the entire thing more enjoyable, because you don't feel rushed at all. I would encourage anyone doing the road to spend a night in town at the resort. You can book it with Hyatt nights, and as I said above, the breakfast is pretty good too.


This is a great chance to unplug, unwind and relax a bit. At least if it doesn't rain a ton! It is also a much needed rest from driving the Road to Hana. Had we not stayed overnight I don't know that I would have found the drive worth it. I know many do, but it wasn't worth a full vacation day on its own to me. A lot will depend on if you don't mind driving tight turns and one lane crossings for a few hours, or if you can find someone else to drive at least. I would probably hop the quick flight and hang at the resort a few days instead if I did it again, but we aren't big hikers etc.

5 Days In Maui: ToP Thoughts

That about does it for our 5 days in Maui. We were able to get in some great pool time, eat amazing food, check out natural wonders and got a little peace and quiet towards the end of it all. Hana really can feel like the edge of the world for a few days.

Maui has a lot to offer, especially if you are into hikes and nature. It goes well beyond the beach life and ocean paradise you see on TV. It has vastly different terrain and ecosystems across the island, so be sure to head out and see some of it. The people are pretty amazing as well!

I would say hands down that Haleakalā was the most unique thing we did during our 5 days in Maui, and it was everyone's favorite from the trip.

Share some of your favorite things to do while visiting Maui over in the ToP Facebook Group.


We promise to keep things short, sweet, and packed with awesome insights!