When I set off for Molokai, I wasn’t 100% sure what the experience was going to be like. This isn’t as popular an island as most of the more accessible parts of Hawaii. I also didn’t really find any itineraries that fit my preferences – e.g. an itinerary for a hiker. So, after visiting and having a wonderful time, I wanted to put together a 5-day Molokai itinerary for hikers. This will take you to several different, unique ecosystems that characterize the island, and give you space to enjoy some of the culture and history of Molokai as well.

Who Might Like This Itinerary

molokai itinerary

(c) ABR 2019

This definitely isn’t the 5-day Molokai itinerary for everyone, mostly because I think it is pretty high energy. And not everyone is looking for that on vacation. Furthermore, two of the day’s trails are pretty hard to get to and require both a 4WD vehicle and some careful drivers. You need to know when to turn back if things just aren’t safe on the road, on the trail, or due to weather.

Now that I’ve told you why you might NOT like this itinerary, why don’t I tell you why it’s awesome.

(1) This schedule features some of the most unique environmental and cultural experiences on Molokai.

(2) You will get a workout everyday. Believe me, even shorter trails in Hawaii will really take it out of you. (Unless you are a Hawaiian hiker, then I am sure it is old hat). Whether you are trekking across a beach, or navigating rainforest trails, there is no shortage of physical activity here.

(3) Every day is completely different than the last. You will never feel like you saw the same thing twice. And when you leave, you will definitely be feeling like you made the best use of your limited time on this amazing island.


While I have set up this 5-day Molokai itinerary day-by-day, please plan for some flexibility when you arrive. You will need to work around the weather conditions for safety and accessibility of the trail. You will also need to adjust to fit the hours of museums, restaurants, and shops, because this is a smalltown situation, so things won’t be open 24/7.

Day 0 – Getting There

molokai itinerary

(c) ABR 2019

Getting to Molokai is no joke, especially if you aren’t from Hawaii. Of course, the first thing to do is get to Hawaii from where-ever you call home. As of 2022, Hawaiian Airlines no longer flies to Molokai and there isn’t a ferry service either. So, I would suggest booking through Mokulele Airlines. Check out their website to see where they fly to Molokai from and what the schedule is. Then, plan your arrival flight to Hawaii around that.

I flew into Kahului Airport (OGG) in Maui when I jumped onto my last leg to Molokai. I had to learn the hard way that the little planes left from a different terminal. So, when you arrive, be sure to ask for directions on how to find the right departure spot. Skip wandering around the airport like I did!

If you can afford it, I would also suggest renting a Jeep, otherwise, these trails will only be accessible if you can join the group hikes.

Day 1- Explore the Town

molokai itinerary

(c) ABR 2019

The first day of my 5-day Molokai itinerary is a day for some rest and prepping. This is the perfect day to visit the Nature Conservancy’s office to check on trail conditions and visit the town of Kaunakakai. Stop by some of the local shops and restaurants, and grab your groceries for the trail.

If you like burgers, please be sure to stop by Molokai Burger.

Outside of town, close of Kalaupapa Lookout, is the Molokai Museum and Cultural Center. This is a great day to stop by and learn more about the island and her people. It’s only $5 to visit.

It’s also a good day to take a drive around the island to explore and check things out as well. Just be sure to be a polite driver. Some of the paved roads of Molokai are 1 lane and you will need to be mentally prepared. Be sure to pull over when there are other cars coming and it is safe to do so.

Spend the evening enjoying town and some good food (if you have the energy).

Day 2 – Beach Hiking at Mo’omomi Preserve

Mo'omomi Preserve

(c) ABR 2019

For a day that isn’t the hottest, or a day when you are comfortable waking up early, beach hiking at Mo’omomi Preserve is perfect. This preserve is managed by the Nature Conservancy, so be sure to stop by their office before you head out for directions and to check on the conditions. You will also need a 4WD vehicle to access this trailhead, unless you are willing to walk several extra miles. In either case, there is no shade on this trail, so please be prepared with sunscreen, hat, water, etc.

Once you get there, you will have the opportunity to walk down a beautiful beach. It will likely be pretty quiet and wild out here. Down the beach, you will also be able to hike up into the grassy coastal hills.

This place represents an environment that is disappearing. Please be sure to protect it when you visit. Don’t drive your car off the road, or hike off trail. And please close all gates that you hike through.

For my full guide to this hike, visit my post on the Mo’omomi Preserve.

Day 3 – Kalaupapa

Kalaupapa National Park is often referred to as the leper colony of Molokai. This settlement was created initially when King Kamahameha V started sending people afflicted by the introduced Hansen’s disease (leprosy) into isolation. The National Park Service says that since 1866, more than 8000 people have called Kalaupapa their final home. For many years, people were basically imprisoned here due to their affliction, but thanks to science, we have a cure to Hansen’s disease in modern day. Now, Kalaupapa remains a small community of people who were cured of Hansen’s disease, but who have chosen to remain in this now peaceful place.

This is a location that can be visited (outside of pandemic conditions). But you must do some research before leaving, because you will need to connect with a tour. See NPS’s website here for more information: https://www.nps.gov/kala/planyourvisit/directions.htm.

Of this 5-day Molokai itinerary, this is the most somber stop, but it is an important part of history as well. Please remember, if you are able to stop by Kalaupapa, come with the utmost respect for the people living here. And let’s not forget the suffering that happened here in the past. While Hansen’s disease has been cured in our time, there are other health conditions that still cause people to be isolated from others – if not in such an extreme way.

Day 4 – Kamakou Preserve

kamakou preserve

(c) ABR 2019

Shifting gears from painful, but important history, this part of the 5-day Molokai itinerary is back to hiking. This trail is completely different from Mo’omomi, however, as Kamakou is a tropical mountain preserve with a bog at the top.

This area is also run by the Nature Conservancy (TNC) though, so do make sure to check in about this preserve when visiting their field office as well. Road and trail conditions will be must-knows.

Getting here isn’t easy. It’s about a 10 mile drive up a rough, dirt road to a lookout. I would suggest parking here, instead of continuing down the road to the actual trailhead. From here, you will hike a few miles up the muddy, rutted and steep road. You will know when you are at the trailhead when you see the gate to the trail. Please be sure to close this after you have passed through.

Past the gate, you will be hiking on a small boardwalk through the bog. The trail will end at an exceptional overlook of the mountains.

This hike will require hiking boots, pants, and a 4WD vehicle. You can try to join a monthly TNC hike if you think this sounds a little too wild for you.

You can learn more about this trail via our guide to Kamakou Preserve.

Spend the evening enjoying town and some good food (if you have the energy).

Day 5 – Beach Day

molokai itinerary

(c) ABR 2019

After three days of hiking and exploring the history and culture of Molokai, spending your final day of the island relaxing on the beach is the perfect conclusion to this 5-day Molokai itinerary. Soak it all in. Eat good food. Grab some souvenirs.

How I Designed This 5-Day Molokai Itinerary

I “field tested” this 5-day Molokai itinerary when I visited on my own in 2019. As a traveler, I am introverted, but dedicated to seeing as much (responsibly) as I can. So, I am fairly driven when I travel and try to make the most out of the time I have anywhere. Usually, my mornings and days are really busy, but I turn in early to rest and write or work.

molokai itinerary

(c) ABR 2019

My goal for my trip was do as much hiking as I could, but I had to learn the hard way that getting to trails in Molokai was not like accessing trails in Arizona. It was much harder. Luckily, I did research enough ahead of time to rent a Jeep, which was a huge help. I also made sure to stop in to the Nature Conservancy office to ask them questions about the conditions of the trails and how to get to them. It was because of their help that I knew to park at the lookout for Kamakou instead of trying to drive to the trailhead. I wouldn’t have made the last few miles due to one section of the road that was extremely deep, rutted, and slippery.

I was also unable to visit Kalaupapa because I didn’t have the money for a helicopter tour and when I went, the trail had been damaged by a landslide. This was disappointing, and that’s why I’ve included visiting the historic national park here. If there was one thing I could go back and do on Molokai, it would be this.

Land Acknowledgement

When visiting Molokai, please keep in mind that this is the ancestral and current home of the Hawaiian people. They’ve been stewarding and living on this land for hundreds of years. And today they face some major challenges due to the cost of living in Hawaii and the housing crisis (among other things).

Please remember to respect their home and the laws of Hawaii when visiting. Do not hike on private land unless specifically allowed or with a guide. Do not enter sacred land if told not to.

Do your best to support Hawaiian-owned and small businesses on Molokai. And be the polite visitor on the road, on the trail, and everywhere else. If you have the resources, you might also consider contributing to organizations that support the Hawaiian people and their culture. 

More Travel Guides from Nightborn Travel

Nightborn Travel specializes in active, solo/small group itineraries like these. In particular, with an entire lifetime of experience in exploring Arizona, we have guides to trails, towns, and restaurants throughout the state. Check out our guide to Arizona learn more!

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