Nicknamed the Valley Island, Maui is one of the most beautiful places on Earth. Home to countless waterfalls, gorgeous beaches and amazing food, it is considered one of the best honeymoon destinations on the planet!
This 5-day itinerary is designed to show you how to see the best of Maui while still enjoying a restful vacation. It can be shrunk down to 3 very full days or stretched to 7 more relaxing days depending on your preference. I love to go hiking and exploring all day, and I’m fine with limited resting time. However, I know that’s not most people’s idea of a vacation.
When to go?
There is no bad time to visit Hawaii as the weather is extremely pleasant year round. During the winter months, you may even spot Humpback whales wintering in the warm Hawaiian waters. I would only suggest to avoid school breaks as Hawai’i can get quite busy during those times. Airfare is also much more expensive during the summer and winter holidays.
Where to stay?
I would recommend staying in the Wailuku/ Kahului area on the eastern side or Lahaina, Kihei, and Wailea-Makena area along the western shore.
To ideally follow this itinerary, you would stay on the eastern side the first 3 nights and travel west for the last 2. If you prefer to stay in the same area the whole time, staying near Kahului would be more economical and cut down driving time.
During our time on Maui, we stayed at the North Shore Hostel in Wailuku. This is a great option if you are looking to explore Maui on a budget. I did lots of research on accommodations. Shocking! I know. This hostel was by far the cheapest place to stay on the island. Maui is not cheap, but this hostel goes above and beyond to provide for its guests. They offer free pancake breakfasts, daily excursions, a fully equipped kitchen, towels, and even snorkeling gear. They are also centrally located in the artistic district of Wailuku. You can read the review I gave them here.
Related: 6 Amazing Hawaii Budget Tips
Where to go?
You know I like to see it all. After exploring all over the island, I cannot think of an area that wasn’t worth our time. That’s why this itinerary covers all of the best things to see and do in Maui!
How to get around?
If you stay at the north shore hostel, you will be able to see a lot even without renting a car. However, you’ll be dependent on their schedule. If you aren’t staying at the hostel or want to be more flexible, I highly recommend renting a car. In my opinion, staying in a resort and spending all your time on the beach would mean missing out on a lot of what Maui has to offer.
Day 1 – Kahului/ Wailuku
When you arrive on Maui, you will land at Kahului Airport on the eastern side of the island. I highly recommend stopping at the food truck park near the airport for some poke to start off your Hawaiian vacation. I am partial to the poke from Like Poke, but I’ve never had bad poke while in Hawai’i!
After filling up on some delicious food, head to Iao Valley State Monument for a short 0.4 mile/ 0.7 km hike. This short trail offers breathtaking views of the needle-shaped peak nestled in the thick forest of northern Maui. The entrance fee is $10 per vehicle and $5 per person as it is for most Hawai’i state parks. Note that clouds often cover up the needle, so you may want to skip this visit until it clears up or go early the next morning.
One of my favorite things to do in Wailuku is to go mural hunting. There are tons of painted walls around town, often depicting native Hawaiian life.
After admiring the work of Wailuku’s talented artists, head to Waiehu Beach to enjoy a relaxing evening and watch the sunset. What a perfect way to end your first day on Maui!
Day 2 – Haleakalā National Park
Your Maui vacation wouldn’t be complete without a visit to Haleakalā National Park. I recommend dedicating at least half a day in the park as climbing up Mount Haleakalā takes over an hour each way.
Watch the sunrise
The most popular thing to do in Haleakalā National Park is to watch the sunrise over the crater. If this sounds like something, you would like to do, take advantage of your jet lag, and do this early on in your trip. Make sure to reserve your tickets 60 days in advance at recreation.gov. Much like in Zion National Park, tickets are $1 each. Don’t worry if you missed early reservations as additional tickets are released 2 days prior. One ticket allows one vehicle to enter the park between 3am and 7am.
If you did not get reservations or prefer to sleep in, you can also watch the sunset on Haleakalā free of charge with your America the Beautiful pass.
The parking lot at the summit fills up first. But to be honest, the views are much better near the Visitor Center anyway. Park your car at the second visitor center and watch the sun rise over the Haleakalā Crater there. Chances are it will be less crowded than the summit, and you’ll also be closer to the Sliding Sands trailhead. I recommend arriving no later than 30 minutes before sunrise, so make sure to leave yourself plenty of time to get to the summit.
WEATHER
It will be cold, very cold at the top of Mount Haleakalā. Temperatures typically stay in the low 30s (around 0-3 degrees Celsius), so come prepared.
Hike into the crater
The Keonehe’ehe’e or Sliding Sands Trail is a difficult 11 mi/ 17.6 km out-and back trail. If you parked near the visitor center as I recommended, you will be able to start the trail right after sunrise.
Let me preface this by saying we did not hike all the way down the crater. It takes twice as long to climb back up from where you turn around. You must also take the altitude into account as you are nearly 10,000 ft (3000m) above sea level, and the air is thin. If you do choose to hike all the way down, know that there is the possibility to ride mules on the way back up. However, I cannot vouch for the treatment of these animals, so please do your research before you go if you choose this option!
We hiked for about 3 hours, and the views were breathtaking (literally). As you walk through the crater, you will gaze upon bright red hills and Martian-like landscapes. It is one of the most extra-terrestrial-looking places I’ve ever been. It definitely feels more like Mars than Hawaii.
Other viewpoints and overlooks
After hiking however far you want, climb back up the walls of the crater and get back in the car. Continue driving up to Pu’u’ula’ula Summit, the highest drivable point on Mount Haleakalā. There you’ll see the NASA observatory, but it is actually closed to the public.
After that, you will begin your descent along Haleakalā Highway towards the Kalahaku Overlook. Make sure to follow the speed limit and watch for nenes, the endangered Hawaii state bird. As you near the park exit, you’ll pass Hosmer Grove, a perfect place to picnic! If you did not pack a lunch, consider stopping at Coconut Fish Cafe in Kihei for amazing fish tacos!
Cycle on the way down
Another popular activity in Haleakalā National Park is to rent bikes to cycle down the crater. Many companies will shuttle you up to the summit for sunrise and provide the bikes to ride all the way down.
Related: Hawaiian Food Bucket List
After a busy and exhausting day on Haleakalā, you deserve to rest! The beaches of Wailea-Makena are perfect to lounge in the sun or go for a snorkel. Since I’m not the beaching type, I got all geared up and began exploring life underwater. I had very low expectations when I entered the waters near Makena Beach. Most of the coral was dead, but within two minutes I was inches away from a sea turtle I initially believed to be a rock. Swimming with this honu (Hawaiian sea turtle) made my day!
If you’re up for more adventure, you may want to take a boat to Molokini Crater for some of the best snorkeling on the island. Keep in mind that wearing reef-safe sunscreen is extremely important to preserve the marine life you are admiring on your snorkeling escapades.
Related: 8 Things You Should Never Do in Hawaii
Day 3 – Road to Hana
What is it?
Highway 360 or Hana Highway is better known by tourists as Hana Highway. It stretches along the southeastern coast of Maui and offers lots of roadside pullouts with beaches, waterfalls, local food trucks, and more. As you drive down the Road to Hana, make sure to stop only in designated areas to avoid causing traffic jams and endangering the lives of others.
What we did
After doing lots of research, we opted to drive the back road to Hana. I knew the roads would be rough, but a friend had done it a few months before and reassured me that it was nothing we hadn’t seen in Oklahoma. Do NOT attempt this drive if you don’t have experience driving unpaved roads or without a high-clearance vehicle. It’s also important to note that this road is mostly used by locals, so you must always let them pass.
I cover Road to Hana driving etiquette and so much more in the 10 Best Stops on the Road to Hana.
Highlights
Hiking the Pipiwai Trail (3.8 mi/ 6.1 km) in the Kīpahulu District of Haleakalā National Park is the reason we decided to drive the loop. We wanted to make sure we could complete the trail before it closed at 5pm. This Trail features a majestic banyan tree, a one-mile hike through a bamboo forest, and the towering Waimoku Falls at the end. I am so glad we got up early and completed this hike! Other highlights of Hana Highway include the red sand beach, Wai’anapanapa’s black sand beach (reservations required), and rainbow eucalypti.
Driving the Road to Hana takes approximately 12 hours, so plan accordingly. It is tiring but is also a great activity for families or those on a budget as it’s virtually free. On our way back from Hana, we stopped for some poke at the Food Truck Park in Kahului. It was the perfect end to a successful day on the Road to Hana.
Day 4 – Lahaina
Driving the Road to Hana is exhausting, so today, you earned a restful day in Lahaina! Check out the Old Lahaina’s shopping district and banyan tree downtown or spend some time enjoying the sun on Kaanapali Beach. Great for swimming, Kaanapali Beach features white sand and calm waters.
For your evening in Lahaina, I highly recommend you treat yourself at the Old Lahaina Luau. I researched luaus on Kauai, Maui, and Hawai’i and changed plans more than once when schedules didn’t match with our itinerary. Finally, I decided on Maui’s Old Lahaina Luau. I was very happy with my decision and got ready to book. That’s when I realized their calendar showed no availability for the next 8 weeks. The dates I needed were 7 weeks away. I was so disappointed. I did some additional research but decided that I’d rather be on a waitlist at the Old Lahaina Luau than settle for something else. If you ask Garrett, he’ll tell you it’s the second best decision I ever made after marrying him. Less than 2 weeks before our trip, I got a call from the Old Lahaina Luau and was able to book us a table.
Why choose the Old Lahaina Luau?
- Most authentic luau on Maui
- Constantly voted best luau on the island
- Unlimited food and drinks
- Outdoor setting
- Oceanview
- Fresh lei upon arrival
- Amazing entertainment
- Great service
- Take-home gift
- Cheaper than some other luaus
I cannot recommend this experience enough. It is definitely a budget, but it was worth it for us! The luau made Garrett’s top 3 favorites, and if you’ve read our other Hawaii guides, you know we did a lot! If you want to experience the Old Lahaina Luau on your next trip to Maui, hurry because this luau stays booked for weeks in advance!
Day 5 – Northwest Maui
There are two ways to explore West Maui. 1) You can drive the loop from Kahului and back through Lahaina. 2) You can drive to Lahaina first and turn around where Honoapiilani Highway turns into Kahekili Highway. I recommend the latter, and here’s why.
Kahekili Highway
Kahekili Highway is very dangerous. In fact, Hawai’i State Highway 340 is considered one of the most dangerous roads in the country! Garrett is an absolutely amazing driver, and he did a fantastic job, but I don’t know that I could have done it without him. I never felt unsafe, but we had to keep our speed around 5 mph through innumerable blind, single-lane curves. Cell phone service is also scarce, so if you do decide to drive the northwest Maui loop, you may want to bring a map.
You may think that you should drive the loop because you don’t want to miss out on anything. I get it; I’m the exact same way. However, believe me when I tell you, the sights along Kahekili Highway aren’t worth dying for. I honestly had no idea how curvy the road truly was until we began driving it.
Olivine Pools
We made two stops along the way: Olivine Pools and Nakalele Blowhole. The pools were beautiful, but our visit was tarnished by the irresponsibility of other tourists. If you’ve read my other Hawaii guides, you know I am very serious about water safety. When we began the short trail to the pools’ viewpoint, we came across a sign narrating the sad stories of Steven and Brian who both died tragically at Olivine Pools.
The signs are clear that you should not attempt to climb down to the pool during the winter months. Yet, when we arrived at the viewpoint, our view was spoiled at the sight of swimmers dipping in the pools. I was upset for Brian and Steven’s families, and for the locals whose first responders risk their lives daily to rescue irresponsible tourists who chose to defy the laws of nature. Please don’t let Steven and Brian’s deaths be in vain; learn from their mistake and admire the pools from afar.
Nakalele Blowhole
The Nakalele blowhole was beautiful, but as the Olivine Pools, it was overcrowded with tourists who had climbed down on the rocks to be near the spouting water. By then, I was really annoyed and couldn’t imagine how frustrating this must be for the locals. We didn’t linger long. By the time we got back up, we saw several firefighters carrying a stretcher and beginning the downward climb to retrieve a wounded patient.
Yes, the views along Kahekili Highways are beautiful, but driving down the road takes a very long time; time you could be spending snorkeling, hiking, or admiring the views on the westernmost side of north Maui.
Punalau Beach
My favorite beach was Punalau Beach. The different shades of blue contrasting perfectly with the white sand and lush green of the coast made it one of the best views we caught that day.
Honolua Bay
Driving back to Lahaina from Punalau Beach, you’ll pass Honolua Bay. This area offers some of the best snorkeling in Maui. I highly recommend you stop there for a few hours to relax and enjoy the marine life. Make sure to bring your snorkeling gear! We bought our mask and tube from Walmart on Maui for only $12. You can also rent snorkeling gear all over the island for about $5-10 a day.
Kapalua Bay
Our last stop before reaching Lahaina was Kapalua. This coastal location has so much to offer: a coastal trail, beaches, and cliff diving. I recommend parking at the free public parking to get a quick look at the Dragon’s Teeth. We didn’t go all the way to the maze as this is a sacred native Hawaiian site, and signs request that you do not disrupt the area. We walked a little ways, admired the dragon’s teeth from afar and turned around. Some people were picnicing in the maze, which really saddened me as it is specifically asked of non-native Hawaiians to stay away.
If you would like to hike the coastal trail, you can try parking at the Kapalua parking lot near the beginning of the trail. Unfortunately, this parking lot is quite small and fills up fast. The coastal trail will take you past Kapalua Cliff House, a popular diving spot, all the way to Kapalua Bay Beach. The Kapalua Coastal Trail is an easy 2.5 mi/ 4 km out-and-back trail featuring beautiful views of the shoreline and whale watching. At the end of the trail, you’ll be rewarded with great swimming and snorkeling on the gorgeous Kapalua Bay Beach.
WHAT’S THAT IN THE DISTANCE?
As you drive along Honoapiilani Highway, you’ll see two other islands in the distance. The island on the left is lanai, known for its luxurious resorts and great snorkeling. to the right is molokai. well into the 20th century, patients suffering from leprosy were forced to isolate on the island of molokai in an effort to stop the spread of the disease. father damian, a belgian catholic missionary, dedicated his life to caring for the diseased of molokai until his own death of leprosy in 1889. today the leper colony of kalaupapa is a national historic park open to visitors wanting to learn more about its tragic history.
This concludes our detailed Maui itinerary! I hope you now feel ready to plan that once-in-a-lifetime Maui vacation you’ve been dreaming about. Make sure to check out our other Hawaii articles, and pin this one for later!
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