The Perfect 5 Day Maui Itinerary

I have dreamed of visiting Maui for a while, mainly because I was itching to get to the Haleakalā National Park. Maui is one of the most accessible islands to see, and there is so much to do! Hiking, waterfalls, beaches galore, so many restaurants, and snorkeling. It is the perfect place to vacation, and with over 275 sunny days a year, I can see why so many people want to come here! After exploring for a week, I have come up with the perfect 5 day Maui itinerary! This itinerary is ideal for anyone that wants to explore and have an action-packed vacation. Enjoy!

Disclosure: This post contains affiliate links. If you click one of them, I may receive a small commission (for which I am very grateful for) at no extra cost to you. 

Download my free Outdoor Photography Guide

Download Now!

Maui Itinerary Map

When To Visit Maui

There is no wrong time to visit Maui! The weather is pretty fantastic most of the year. But if you want to avoid certain things like crowds, you might want to plan it during a specific time of the year. I went in September, and there weren’t many tourists and the planes were pretty empty.

Going in Spring and Fall is a great time to avoid the crowds. Winter can be crowded, and this is technically their rainy season (November – March), but if this is the only time you can go, don’t stress as the rain doesn’t last all day. The summer months can be pretty crowded and expensive as this is when kids are out of school.

Read More: How to Plan a Trip to Hawaii

Where To Stay In Maui

  • Lahaina Shores Beach Resort, a Destination by Hyatt Residence: Features an outdoor pool and hot tub and beachfront accommodations. >>>Check Prices Here
  • The Kulani Maui: The cabin is beautifully designed and is located in the city, but you feel like you are in the middle of the jungle.>>>Check Prices Here
  • Hotel Wailea, Relais & Châteaux – Adults Only: Nestled on a cliff overlooking the southern coastline and it features luxurious facilities and spacious suites. >>>Check Prices Here

How To Get Around Maui

If you are going to the Road to Hana and Haleakalā National Park (the two most popular activities on the island), then you need to rent a car. I usually rent cars from here. You will be doing a lot of driving on this trip, but it is so worth it!

What To Pack For A Maui 5 Day Itinerary

  • Sunscreen: Super important, and it is part of the ten essentials!   >Buy Sunscreen
  • Chapstick: This one has SPF so your lips won’t get burned! >Check Out This Chapstick
  • Hiking Boots/Shoes: It is pretty muddy in Hawaii. It is best to have waterproof hiking shoes.  >Check Out My Hiking Shoes
  • Hiking Sandals: If hiking shoes are not your thing, then hiking sandals are amazing, especially on the Road To Hana. >Buy Some Here
  • Hiking socks: Having the correct socks helps you prevent getting blisters. Smart Wool is probably my favorite brand out there. >Buy Hiking Socks
  • Water Reservoir: Water reservoirs help prevent me from getting dehydrated while hiking. The great thing about this reservoir is that it doesn’t have the plastic taste. >Here Is My Water Reservoir
  • Water: Stay nice and hydrated.
  • Sunglasses: It can get pretty sunny! >Check Out These Sunglasses
  • Snacks: The best snacks are jerky, nuts, and energy bars. >>>Check Out These Bars
  • Camera: The Sony A6000 was one of the first cameras I started traveling with. The Sony A6000 is an excellent camera for people that want to start improving at travel photography.  >Buy Sony Camera Here
  • First Aid Kit: This is one of the first things I bought when I first started going on adventures. It is super portable. >Buy This Awesome First Aid Kit Here
  • Day Pack to carry all your things: To carry all your gear, water, and food, you need a good backpack. Osprey is known to have some of the best backpacks in the market. >Buy This Great Quality Backpack
  • Leggings or Hiking Pants: I usually wear leggings while hiking because it is what I feel most comfortable with! >Click For My Favorite Hiking Leggings
  • Breathable sweat-wicking shirts: Cotton shirts soak up your sweat when hiking, so make sure to wear something breathable. >Check out this awesome breathable shirt here.
  • Sports Bra: For women. >Check This One Here
  • Rain Jacket: There is a chance of showers! It did start raining when we were in one of the state parks.  >Check Out My Rain Jacket Here
  • Tripod: This is an optional item, but it is excellent for getting the ideal sunset pictures. >Check out this tripod
  • Jacket: You need this for the national park. It is cold during sunrise and sunset! >This is the one I wore
  • Bathing Suit: This is for sure needed! >Check This One Out
  • Cover Up For Beach: >Check This One
  • Dress: >Another Dress Here
  • Sandals: >Cute Sandals Here
  • Shorts: It can get pretty hot so wearing shorts during hikes can help! >Check These Out

Claim your FREE Hiking Checklist

Ready to start hiking? Grab my free hiking checklist and never forget anything at home!

Sign Me Up

5 Day Maui Itinerary

Day 0: Get To Maui

When you get to Maui, I recommend having a relaxing day bacause you have to get up pretty early the next few days! Stop at the food trucks near the airport if you are hungry. The Geste Shrimp Truck is pretty good, and there is a shaved ice food truck right next to it.

Day 1: Haleakalā, Kihei, And Makena

Watch Sunrise At Haleakalā National Park

Haleakala National Park Sunrise

The Haleakalā National Park was probably my favorite part of Maui! Being on top of the clouds was so memorable. The best part is that it is pretty much guaranteed you will experience a cloud inversion if you go during sunrise.

A cloud inversion is a layer of a low-level cloud of thick fog with a clear sky above it. It is something that I try to experience in Washington State, but it is never guaranteed. Here in Maui, it is assured, so do not let that chance slip!

You have to plan for this in advance as you have to get a permit to enter the national park for sunrise. Do not attempt to “wing it”. We saw people get denied entrance to the park, which would be terrible, especially because the drive is so long and you have to get up around 3 am.

This National Park has to be added to your Maui 5 days itinerary

You need to log into the NPS website and reserve two months in advance to guarantee a spot. I made sure I had it in my calendar to get on right at 8:00 am HDT 60 days before the date. I also recommend getting on the website around 70 days before to make sure you understand how the website works and when your permit will go on sale. That is what I did, and I was able to plan easily.

The cost is only $1 per car, and sometimes they open more reservations throughout the next month, so if you didn’t grab one, two months before, I would still check back daily to see if more permits open up.

If you still can’t get a permit, I would opt-in for sunset. My friend went for sunset, and her photos were still pretty epic! You don’t need a permit, it is less crowded, and it looks pretty similar.

You also don’t need to go for sunrise or sunset. You can go during the day and do some epic hikes like:

  • Pa Ka‘oao – 0.4 miles
  • Leleiwi Overlook – 0.5 mile
  • Hosmer’s Grove Nature Trail – 0.5 mile
  • Halemau‘u Trail (Switchback Trail) – 7.5 miles

I had the sunrise on day one of the itinerary because you have to get up pretty early to experience it. If you are coming from America, it is pretty simple because of the time change.

For sunrise, leave no later than 3:30 AM. It takes one hour to reach the summit when leaving from Kahului, 1-1.5 hours from Kihei, and 2 hours from Lahaina. I do want to say that the drive made me very nauseous. So be prepared for the windy road.

Credit to NPS

Eat Breakfast At Kihei

One of the best breakfast spots in Hawaii is the Kihei Cafe. I will warn you that the line will be long, but it is well worth it. The food is pretty good, and they have options for sitting outside.

Shop At Wailea

Wailea has a great selection of shops! Head on over to The Shops at Wailea and buy some bathing suits or dresses. Once you are done, you can head to the Wailea Beach or eat lunch at the many restaurants located at the shops like Tommy Bahama Restaurant, Bar & Store, Longhi’s Wailea, and Waikiki Brewing Company, South Side.

Check Out Mākena State Park

This is probably the prettiest beach I have seen in Hawaii. The water is bright blue, the crowds are pretty small, and the waves are pretty wicked! You have to pay an entrance fee and parking, and there is someone watching everyone, so don’t think you can skip out on payment. There are also volleyball courts, and you can bring a boogie board. Be careful when boogie boarding, as the waves in the area are pretty intense!

Get 35% off of AllTrails+

With offline maps, wrong-turn alerts, and extra planning features, AllTrails+ helps you make the most of every minute outdoors!

Sign Up Now!

Sunset At Makena Cove

If you are a photographer, this is a great place to end the day! The palm trees, black rocks, and colorful sky make this a perfect spot for sunset or sunrise. You don’t need to pay for parking, just park on the side of the road.

Dinner At Monkeypod Kitchen

My favorite restaurant at Maui was Monkeypod Kitchen. It is worth all the hype! We didn’t have reservations but decided to try it out anyway. We put our name on the list and had drinks next door in another restaurant and waited 30 minutes. The wait was worth it! I loved Bulgogi Pork Tacos, and everyone else ordered fish, and they loved it.

Day 2: Road To Hana

The Road To Hana is probably the number one thing to do in Maui! This was one thing I did not want to miss when going to Hawaii, and I am so glad I didn’t!

The most useful thing we bought when traveling here was buying an app that told us when and where to stop. You can download it here. I highly recommend it! It really made the road to Hana less stressful! We also learned the history and he also took us to some spots that were not crowded.

Waiʻānapanapa State Park (Black Sand Beach)

I suggest going to the Road To Hana on the second day because you have to get up early again. The road to Hana is an all-day thing. And the road is so windy and long.

We got to our first stop (which was breakfast) at 7 am in Hana Picnic Lunch Company Paia. I ordered a lunch box as well and took it all to go.

Here are the best spots to stop at in the Road To Hana:

  • Ho’okipa Beach Park
  • Twin Falls
  • Huelo Lookout – Loved their coconuts!
  • Ke’anae Arboretum
  • Keanae Lookout – Get Auntie Sandy’s banana bread!
  • Nahiku Viewpoint And Wayside
  • Upper Waikani Falls
  • Kaihalulu Red Sand Beach
  • Wailua Falls
  • Pipiwai Trail

Read More: The 19 Best Stops On The Road To Hana

The only thing on the list I would worry about beforehand is the Waiʻānapanapa State Park (Black Sand Beach). You have to make a reservation two weeks in advance to get entry. You can make a reservation here. Please note that you have to pick a time when you want to enter the park. Also, the time when you have to make a reservation might change, so check well before the two weeks.

Once you get to Hana, make sure you eat dinner like at Thai Food by Pranee or at the many food trucks across the street from the Hana Ranch Restaurant.

Please respect the locals, try to let them pass when driving, and try not to block anyone when parking.

Nahiku Viewpoint And Wayside

Day 3: Kaanapali, Kapalua, and Lāhainā


Lāhainā Banyan Court

I loved walking around the town of Lāhainā as it was lively, energetic, and cute. There are many local shops here and restaurants. Down The Hatch is an excellent restaurant with an outdoor patio and after you are done make sure to stop at the Lāhainā Banyan Court as the tree there looks pretty wild!


Magical Enchanted Forest

Kapalua is a magical area and has a forest called the “Magical Enchanted Forest”. It feels like a real enchanted forest when walking through the trail, and my pictures do not do it justice! The forest is vibrant, exotic, and humid! So bring bug spray because they were eating us alive!

Take pictures while walking the trail and then walk on over to the Honolua Bay. This is a fantastic spot for snorkeling, and you can even see many surfers in the distance. It is a hidden oasis.

It is close to private property, so make sure not to explore too much of the area. Parking can also be a pain as there are limited spaces on the side of the road.

Afterward, head on over to Kapalua Bay Beach and snorkel some more or walk the Kapalua coastal trail! This is a great place to spot sea turtles and if you are hungry, eat at Kitchen 5315 Restaurant & Tiki Bar.


Hula Grill Kaanapali

Kaanapali is a fantastic area to explore during the late afternoon! Head on over to the Whalers Village mall and park there. There are a ton of shops here and places to eat. Just make sure to get your parking validated at a restaurant or shop.

Hula Grill is a great place to eat dinner. There is also another MonkeyPod restaurant in this area. Afterward, walk on over to the Kaanapali and watch the sunset and relax!

I will warn you that Kaanapali is probably the most touristy area in Maui. It can sometimes feel a bit crowded and overpriced.


Day 4: West Mountains, and ʻĪao Valley State Park

Eat Breakfast At Stillwell’s Bakery & Cafe

The bakery is located in the heart of Wailuku town, Maui, and has so many good pastries and breakfast plates! If you don’t want to stop anywhere for lunch, you can also order a boxed lunch.

Waihe’e Ridge Trail

  • Distance: 4.0 miles round trip
  • Elevation Gain: 1,600 ft.
  • Route Type: Out And Back
  • Difficulty: Hard
  • Trail Guide : Link

Ok, if you have been following me for a while, you might know that I am obsessed with hiking. One of the things I had in mind when returning to Hawaii was doing a hike that resembled Jurassic Park, and the Waihee Ridge Trail did that for me. It is so stunning! The trail is pretty steep, though, and hot! Bring sunscreen and plenty of water. Parking can also be a pain, so get there early.

ʻĪao Valley State Park

ʻĪao Valley State Park is definitely worth a stop! This state park doesn’t take long to explore. The trail is pretty short, and the lush green mountains, rivers, and gardens make you feel like you were transported to another planet. You have to pay for parking.

Eat At Mama’s Fish House

The most popular restaurant in Maui is, of course, Mama’s Fish House. Everyone that has been to Maui recommended me this restaurant. Getting a reservation is pretty tricky, so make sure you do it well in advance. I loved the Oyster dessert as it was so beautiful and yummy. For people that love fish, this restaurant is fantastic!

Day 5: Molokini Crater Or Whale Watching Or Helicopter Tour

Eat Breakfast At Brekkie Bowls

Brekkie Bowls food truck serves up healthy Açaí, or Pitaya (dragon fruit) bowls to locals and visitors. So yummy!

Molokini Crater

Molokini is a crescent-shaped volcanic crater located in between the islands of Maui and Kahoʻolawe. You can only get here by boat, so it is best to take a tour! There are options to snuba, scuba dive, or snorkel. Make sure to bring snacks as this can be an all-day thing. However, some tours do offer food.

Whale Watching Or Helicopter Tour

If you don’t want to snorkel, you have other options like a helicopter tour or whale watching tour. It all depends on your budget and the time of year you go. Below are some tour examples:

Final Thoughts On 5 days in Maui Itinerary

Thank you for reading all about the best Maui itinerary. I had so much fun on the Hawaiian islands! Make sure to check out some of my other blog posts in the United States:

  • 5–7 Day Kauai Itinerary
  • How to Plan a Trip to Hawaii
  • The 19 Best Stops On The Road To Hana

Claim your FREE Hiking Checklist

Ready to start hiking? Grab my free hiking checklist and never forget anything at home!

Sign Me Up

Pin For Later: Maui Itinerary 5 Days

Leave a Reply

Your email address will not be published. Required fields are marked *