Oahu Off the Beaten Path: The Perfect 5 Day Itinerary

If you’ve already been to Oahu before, or are just looking for an off-the-beaten-path itinerary, we have lined up the perfect 5 Day Itinerary for you!

Oahu is Hawaii’s most populated island and definitely the busiest.  Considering it is a major tourist destination it can sometimes feel like it is hard to “get off the beaten path” and really get away from it all.

Luckily since Ryan’s family is born and raised on Oahu we have always been fortunate to explore the island “off the tourist trail” and experience the more local, off-the-beaten-path spots.  Below are our suggestions on how to spend the perfect 5 days on Oahu!

Last Updated On: April 24, 2020

Oahu Off the Beaten Path Itinerary

Day 1: Honolulu

Lunch: Chubbies Burgers

If you are an In-N-Out lover (yassssss) you will love Chubbies Burgers!  This food truck is outside the main touristy area, near Ward Center.

We went for the 50s burger and bacon fries and were not disappointed!  Both were absolutely delicious.

Hours: 10:30am-9pm every day

Wander around Kaka’ako

Close by Chubbies Burgers is the super cool neighborhood of Kaka’ako!  There is so much awesome street art to wander around and see.  If you love graffiti and street art you will definitely enjoy strolling around this area.

Check out Iolani Palace

If you continue walking on from Kaka’ako you will eventually reach the beautiful Iolani Palace.

There are some great photo opportunities in this area with the surrounding buildings and cool banyan trees.

Go Paddle Boarding at Ala Moana Beach

Finish off your first day with a relaxing paddle at Ala Moana Beach Park.  We love this beach for paddle boarding as it is so calm, making it perfect for beginners.

Dinner: Zippy’s

This is Hawaii’s chain restaurant and it is always a must whenever we go back to visit.  It is simple, affordable local food with lot of choices.

Where to stay in Honolulu:

Mid-range: Ala Moana Hotel

The Ala Moana Hotel is a good choice if you are looking for something a little less-expensive (hard to find in Hawaii!).  Being outside of Waikiki saves you a little bit of money, but the hotel is still well-located, sitting between the massive Ala Moana Shopping Center and the Hawaii Convention Center.

We enjoyed a comfortable stay at the Ala Moana Hotel and appreciated being close to the mall (and its food court!) and Ala Moana Beach.  The rooms are not very large and not very luxurious, but it is comfortable and clean!  And there is a refreshing outdoor pool as well.

Luxury: The Kahala Hotel and Resort

If you really want to get away from it all, but at the same time not be too far from the comforts of the city, The Kahala Hotel is a fantastic choice.  It is about a 15 minute drive outside of Waikiki, close by to the Kahala Mall.

The hotel sits on its own perfect stretch of beach which is perfect if all you want to do is spend an afternoon lounging.

We’ve always enjoyed a relaxing time staring out at the calm, turquoise waters, while sitting under the palm trees swaying in the breeze and sipping on some refreshing cocktails.

Of course, if you are more of a pool person, the Kahala Hotel also has a lovely outdoor pool.

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Check out: 76 Hawaiian Slang Words and Pidgin Phrases You’ll Want to Know before your trip!

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Day 2: Honolulu and Waimanalo

Hike Makapu’u Lighthouse Trail

Get yourself up as early as possible and head over to Makapu’u Lighthouse Trail.  It’s best to go early to ensure there is parking and to beat the heat!  The trail is paved the whole way and it is a steady incline on the way up, but there is no shade!

It is a good hike for all fitness levels (I’ve even done it in flip flops) and there are benches and lookout points along the way.  If you make it there super early, it is a nice spot to take in the sunrise.

Swim in the Makapu’u Tide Pools

Just before you reach the lighthouse there is a steep and rocky trail on the right, which leads you to the beautiful tide pools!

If you’ve always wanted to float in tide pools, here is your chance.  BUT BE CAREFUL.  You need to watch the waves very carefully and if the swells are too big do not go into the outer pools.  You are at huge risk for being knocked over by the waves and being pulled out.

The rocks are really sharp so it would definitely be best to go with some water shoes.  We didn’t and our feet got cut up.  The rocks are also very slippery with algae so you need to walk slowly and carefully.

On your way back up from the tide pools, look for the spray-painted arrows on the rocks which will help you find the easier way up.

Brunch: The Nook

The Nook is open for brunch until 2pm and dinner is served from 5-9pm.  We went for brunch and highly recommend it.  Especially the Lilikoi Cheesecake Pancakes – they are to die for!!  The whipped lilikoi cream cheese smothering the pancakes is one of the most delicious things I’ve ever tasted.

The mochi waffles were also pretty unique – I loved the texture.  And, with a sweet tooth like mine, the condensed milk on top is a tasty bonus 🙂  You can also get the mochiko chicken and waffles – another great choice if you want a little protein!

Check out the view from Tantalus Lookout

A 15 minute drive up the winding mountain side will take you to the beautiful Tantalus Lookout.  From up here you will have fantastic views over all of Honolulu!

Dinner: Fresh Catch

For another simple and tasty, local-style dinner, head over to Fresh Catch.  You can find some of the best poke and seafood here!  It’s definitely a local favorite.

Dessert: Uncle Clay’s House of Pure Aloha

You’re in Hawaii so you gotta have some shave ice.  Uncle’s Clay’s is famous for their homemade syrups made from all-natural, Hawaii-grown/Hawaii-made ingredients.  No artificial flavors here!

Day 3: Kalihi and Kaneohe

Breakfast: Liliha Bakery

Everyone seems to know Leonard’s, but not everyone makes it to Liliha Bakery as it is a bit of a drive out from the main tourist spots.  But Liliha Bakery is on the way to our off-the-beaten path destination for today so you are in luck 😉

Stop in for some delicious pastries, particularly their famous coco puffs!  Just be prepared for a possible wait in line, as this is a popular local spot.

Hike and Swim at Kalihi Ice Ponds

This is a truly hidden gem and is so off-the-beaten-path that even many of our relatives who live in and grew up on Oahu didn’t even know of this spot.  And I’m sure the locals want to keep it that way.

This is not an official hike and it is on private land so unfortunately we can not share the details of how to get to the falls on here. (Sorry!!)

Remember: If you do make it here, RESPECT THE LAND.  This is private property and people live nearby.  Do not leave anything behind and be mindful of the residents who live nearby and don’t make too much noise as you hike in.

The hike in is a peaceful and easy one.  You will feel like you are in another “Lost World” with downed power lines and trees and abandoned shacks.

The final hike down to the falls is steep and muddy so be prepared for that.  Your shoes will get dirty and you will need to hold onto the ropes to help you down.

Once you get to the falls you will find yourself in a peaceful paradise.  Beware that the water is pretty cold (hence the name Ice Ponds).  But if you are from Canada like us, it isn’t as bad as our waters back home!

Wander through Ho’omaluhia Botanical Garden

After your hike and swim at Kalihi Ice Ponds, head windward on the Likelike Highway towards Kaneohe.  After you’ve passed through the tunnel you will descend down into Kaneohe and eventually come to an intersection with signs for Ho’omaluhia Botanical Garden.

The gates are open from 9am-4pm, but you are still able to walk in outside of those hours.  There is no cost to enter.  The entire area is huge (400 acres!) so you can spend a lot of time here.  For a detailed map, click here.

This garden has recently become famous for the iconic shot of people walking down the tree-lined driveway with the Ko’olau Mountains in the back.  Unfortunately, due to the popularity of all the Instagrammers coming here just to get this shot and clogging the road, the park is now heavily enforcing a new law of no pictures allowed on this road.  There are signs everywhere and even guards that sit there all day to ensure no one takes photos on the driveway.

Note: We had figured that if we went before the gate opens at 9am, or after it closes at 4pm, that we would be allowed to take photos.  But NO.  NO PHOTOS ON THIS ROAD AT ANYTIME.  Very disappointing but those are now the rules.  We tried three different times and days and at no point were we able to take a photo.  I guess we could have broken the rules and got yelled at, but I didn’t have the heart to do so after the guard went through the whole spiel when we entered.

If you are interested in camping, this is a wonderful choice for a mountain view campsite.  More information on staying here can be found under “Where to Stay in Kaneohe”.

Dinner: KJ’s Local Grindz

This little hole-in-the-wall restaurant is located in the back of the Windward City Shopping Center (not to be confused with Windward Mall).  KJ’s is most famous for their fried chicken!  Their furikake chicken is so ono as well.  The menu is good ol’ simple, local food and super affordable.  A great choice in Kaneohe.

Where to Stay in Kaneohe:

Budget: Camping at Ho’omaluhia

If you really want to get off the beaten path and be one with the stunning Hawaiian nature, there’s no better place than camping below the Ko’olau mountains in peaceful Ho’omaluhia Botanical Gardens.

A camping permit is only $32 for 3 days (Friday-Moday) or $52 for 5 days (Friday-Wednesday).  You need to book in advance online and pay the fees.

High End: Paradise Bay Resort

This charming resort on Kaneohe Bay is the perfect little place to unwind and get off the beaten path.  Paradise Bay Resort is truly a peaceful and rejuvenating place to stay.  They even offer complimentary yoga and mediation classes, as well as free kayak and snorkel rentals and sandbar boat excursions!

Day 4: Kaneohe

Morning stroll at Byodo-in Temple

You will be amazed at what beauty lies hidden behind this turn off from the highway.

The gate to Byodo-in Temple opens at 9am.  If you come a bit early the guards will not let you pass.  You will drive through the beautiful cemetery grounds until you reach the end of the road at Byodo-in Temple.  The entrance fee is $5.

This magnificent Buddhist temple is a smaller scale replica of the Byodo-in Temple found in Japan.  The location in the lush, green paradise below the Ko’olau mountains is breathtaking.  It is so peaceful to stroll around the beautifully landscaped grounds.

The huge koi fish are lovely to see.  You may also see the rare black swan – a first for me!

There is also a gift shop with some interesting items if you’d like a souvenir.

Hike Crouching Lion

After your relaxing stroll, get ready for an intense hike!

Follow Google map directions to Crouching Lion and park on the right side of the road.

On the left you will see these signs.

Now, this is the important part.  DO NOT take the first trail you see.  Keep walking towards the left and you will see more sets of these signs.  You want to take the left-most trail.  If you take the first one, which we unfortunately did, you will be in for a steep and scary hike involving ropes and a bit of rock climbing.

The hike up is not long, maybe about 45 minutes, but it is steep, no matter which way you take.  The trail can be pretty muddy so wear good shoes and be careful!

Once you reach the top and see the fantastic views over Kahana Bay, you will forget the tough climb – it will all feel worth it.  Beware that it can be quite windy (and rainy) at the top so again, be careful and watch your step.  People have died here and you will see a cross at the top which serves as a reminder just how careful you need to be.

Once you’ve made it back down, cross the road and just to the right of the parking area (pictured below), walk towards the beach where you will find this rope swing 🙂

Relax at the beach

After your strenuous hike it is time to relax on the beach and grab a bite to eat.  Hopefully you have packed a picnic to enjoy on the beach, but if not, there are a few places to stop along Kamehameha Highway.

There are many beach parks along the highway not far from Crouching Lion.  Just choose whichever one you can find parking at and enjoy!  You really can’t go wrong.  We love these beaches because they are way less crowded than the more popular ones in Honolulu and Kailua.

You can also go on a little hunt for one of the many “hidden” beach swings. 😉

Dinner: Waiahole Poi Factory

For some authentic Hawaiian food, you gotta stop in at Waiahole Poi Factory!  Obviously they are famous for their hand-pounded poi, but they’ve also got the Hawaiian favorites such as Lau Lau, Squid Luau, Kalua Pig and Chicken Long Rice.

Day 5: Kailua

Hike the Lanikai Pillboxes

Start the morning off with an early hike up the Lanikai Pillboxes.  I wouldn’t say this is exactly off the beaten path as it is now a very well-known hike (thanks, Instagram!) but it is also a local favorite.  It’s best to go early to beat the heat as this is another hike that does not offer any shade.

It is a fairly easy hike, good for beginners, and the rewarding view at the end is well worth it.

Breakfast: Cinnamon’s

Refuel yourself after your hike with a hearty breakfast at Cinnamon’s!  This is not really off the beaten path, either, as this restaurant is well-known, but for good reason!  Their pancakes are amazing.  My personal favorites are the red velvet and guava chifon pancakes!

Breakfast Option #2: Boots & Kimo’s

This place is tied as my favorite breakfast spot in Kailua.  Boots & Kimo’s is actually where Ryan took me on my very first visit.  I love their pancakes smothered in their famous Kimo’s macadamia sauce, while Ryan loves their corned beef hash.

Relax at Lanikai Beach

This is personally our favorite beach on the island!  Ryan used to come here with his family as a child, when it used to be just a local spot and still a hidden gem.  This is also the first beach he ever took me to when I first visited Oahu.  It has now (somewhat unfortunately) become very popular among tourists (again, thanks Instagram!)

Despite the popularity, it is still a wonderful choice and you can not beat the super fine white sand and perfectly clear turquoise waters.

Note: There are no restrooms or changerooms so come prepared.  There is also no parking lot so you will need to search for parking along the residential roads.

Grab a Shave Ice at Island Snow

This is a classic Kailua spot, albeit a bit unusual at first as it is half clothing store/half shave ice stand.  It is so good that even Obama took his fam here.

What I personally love about Island Snow is I can get a snowcap topping on my shave ice, which is a topping of condensed milk!  It is really so delicious.

Eat a Papaya Bowl

Yup, more eating!  But it is hard to resist all the delicious treats to be found in Kailua.  Head to Nalu Health Bar for some delicious acai bowls, or, my favorite, a papaya bowl!

Dinner: Fatboy’s

I hope you still have some room in your stomach!  Grab some local-style mix plates at Fatboy’s for dinner.  They are most famous for their ono garlic chicken so make sure you order some!

Where to Stay in Kailua: Airbnb

Kailua is mostly a residential area so your best bet is to stay in one of the many Airbnb’s.  You can find some affordable options all the way to some very pricey vacation home rentals right on Lanikai beach.  Choose something within your budget and enjoy the laid back vibes of Kailua.

New to Airbnb?  Sign up through our link and get $45 in travel credit!

Note: There are still many more off the beaten path areas to explore on Oahu and we’ve only touched on the areas of Honolulu, Kaneohe and Kailua.  If you have more time, definitely check out the North Shore and the West Shore, which is very off the beaten path!

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Want to extend your stay in Oahu?  Check out our other add-on itineraries:

The Perfect Oahu Itinerary for Terrace House Fans

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