A Beginners Guide to Oahu

I thought I would begin this whole “travel blogging” thing by writing about a place dear to my heart. A place I’ve called home for the last two and a half years (on and off due to work visa issues but that’s a story for another day!).

When I first came to Hawaii in 2012 to study, the islands had such a hold on me that I had them tattooed on my foot when I left. I just knew that Hawaii would be in my life forever.

Fast forward almost five years and I am back in paradise, working full time and exploring as much of Oahu as I can in my spare time.

It would be near impossible to write details about everything I have done here, and let’s be honest, not very interesting to read. So I thought I would split the island into four parts and document the best things to do in each area.

Side note: I would recommend hiring a car for exploring Oahu. It’s cheap (Discount Hawaii Car Rentals has the best deals; tip: book online for the smallest car and you usually end up with an upgrade) and the best way to see everything. The local bus (it’s legit called Da Bus) is often late, slow and you don’t want to spend your entire vacation simply on public transport.

Now for the fun part…

North Shore

My all-time favorite place in Oahu, and where I have resided the last year and a half.

Known as the “Seven Mile Miracle”, with famous surf breaks such as Banzai Pipeline, Sunset Beach and Waimea Bay, it is a surfers paradise. But it’s not just for surfers!

Summer time on the North Shore brings calm, glassy ocean, perfect for snorkeling and swimming.

The local town of Hale’iwa is an attraction in itself. All buildings in Hale’iwa have to be built in a certain rustic style, making it feel like you’ve stepped back in time. While it is a smaller town, it can get crazy busy both in summer time and in winter (summer weather brings the visitors for the beach, and winter weather brings the surfers and the visitors to watch the surf). Traffic is a constant issue in both seasons so keep that in mind if you are driving from elsewhere on the island.

I like to adapt the Hawaiian mindset of being on “Aloha time” which means never rushing to be anywhere and enjoying the view on the way. This is an easy way not to get upset at the traffic

My favorite beaches to swim at on the NS are Waimea Bay and Sunset Beach. While often overcrowded with tourists, they can be the most beautiful beaches I’ve ever been to (on good days). I also have another favorite beach spot that is tourist free but I’m going to keep that one a secret so it stays that way – sorry!

One thing that the NS is abundant on, is places to eat. Sometimes I feel like there is too many places to choose from because I can never make a decision! Food trucks are everywhere here and often serve the most delicious meals you’ll ever have.

I can’t write about the NS and not mention garlic shrimp from a food truck. It’s almost a rite of passage for anyone visiting the NS. However, I’m not a huge fan of seafood so I prefer other places.

Here’s a few of my favorite places to eat on the NS:

Uncle Bo’s restaurant – their big nachos are amazing (and huge!), and definitely try the Hobos (taro beignets). Everything on their menu is ono (delicious) and also reasonably priced.

Surf n Salsa food truck – a REAL Mexican place to eat in Oahu (don’t try any of the other Mexican places, trust me!). They make absolutely everything by hand (including the tortillas), and on Tuesdays have $1 tacos and elotes available.

Thai Bo’s food truck – my favorite Thai food truck although a lot of people like The Elephant Truck. I always go for a curry or a noodle dish which has never disappointed.

Il Gelato Hawaii – favorite place on the NS for breakfast/brunch and dessert. Sweet and savory waffles, sweet and savory crepes available and the best coffee I have had (Italian style, and not American!). Also amazing gelato, obviously.

Other than eating out, my next favorite past time is hiking and exploring. There’s not a huge number of trails around the North Shore area; I prefer to go to other areas around the island for my favorite hikes.

Disclaimer: a number of hikes I will mention in this blog post will be illegal. Majority of the good ones in Hawaii are (the legal ones are full of tourists and generally boring). For all hikes I mention: enter at your own risk, be careful and always “malama the aina” (respect the land).

Recommended hikes for the NS:

Ehukai Pillbox Hike – easy short hike (approx. 20-30 mins up and 20 mins down), with views from Kaena Point to Pipeline and Sunset Beach. Pillboxes are all over the island, leftover from the World Wars as lookouts. The hike starts in the parking lot of Sunset Beach Elementary School and I would not recommend if it has been raining lately. Tip: make sure you keep going past the first pillbox as the second pillbox has the best views!

Kaena Point Pillbox hike – Kaena Point is a popular trail from both the west side of the island and the North Shore (it meets at the point). You can see monk seals and a number of birds all year round on this trail. It’s a flat but bumpy hike to the point, approximately an hour one way. If you want to make it a little harder and also get some great views, stay inside the fence near the point and head up the hillside in an unmarked (but obvious) trail to the pillboxes. There’s about three pillboxes and the higher you go, the better the views! Tip: Try for a clear day and see all the west side too.

East Side

People will argue what is considered “east side” of Oahu til the cows come home, but for simplicity, east side in my post will be from Laie to Kaneohe/Kailua and all the way down to Hawaii Kai.

Whenever friends come to visit, I make sure I take them for a drive from Kaneohe to Laie. The mountain ranges on that side are some of the most incredible I’ve ever seen, and the close proximity to the bluest ocean is so magical.

Kualoa Ranch is a tourist hot spot, but is also where a number of famous movies have been shot. Pearl Harbor, Jurassic Park, Lost, 50 First Dates and of course Hawaii 5-0 have all used Kualoa Ranch for set locations.

My absolute favorite beach in all of Oahu is on the east side. Lanikai Beach, near Kailua, has sand that is as soft as clouds, the most beautiful blue/green ocean water and unfortunately has been in every tour guide recently meaning the number of tourists has increased. Ah well, life in paradise right?

If you’re up for an adventure, rent a kayak or SUP (stand up paddleboard) in Kailua and head over to the “Mokes”. The Mokuloa Islands just off Lanikai Beach are an easy paddle to, however I would be cautious as there have been a couple shark attacks here (to swimmers, not paddlers). My first experience ever paddle boarding was to the Mokes and I went okay – but I wouldn’t suggest it as you may fall in a lot. Kayaking is a lot safer!

Another beautiful beach (I know, I know. You’re probably sick of hearing about them all. But they’re just all so nice!) is in Waimanalo. Now, this area is a little on the rough side. So be cautious with your gear on the beach, as well as leaving valuables in your car. On a sunny day, the ocean here is second to none.

Hanauma Bay is a VERY popular snorkeling spot on the island. It costs $7.50 to go to, and is closed on Tuesdays. I’ve been twice and do not rate it – I think there are other places around the island that are better, less touristy and also free (I’m a cheap person at heart which you will probably realize soon!).

Unfortunately, I haven’t eaten at many establishments on this side of the island. But where I have eaten, has been amazing.

Guadalajara Grill – another Mexican food truck to rival my favorite one in Haleiwa. The horchata here is the best I’ve ever tasted.

Cinnamons – a popular breakfast/brunch spot in Kailua. The red velvet pancakes are a novelty and the cream cheese sauce is to die for.

I might seem like I have seen and done a lot on this island, but I still have my own bucket list that I am slowly working through. There are a number of hikes on this side of the island that I haven’t done yet but I have heard are great, such as Three Peaks, Maunawili Falls, and the Koolau Summit Trail.

Instead I will tell you about the ones I have done and would recommend! Again, some of these are illegal so enter at your own risk.

Lanikai Pillbox Trail – a short and easy hike with scenic views over Lanikai Beach. Again, make sure you go onto the second pillbox. Not recommended after rain. Tip: parking in Lanikai is difficult to find. Park near the beach and walk a little bit to the trail and then head straight to the beach after your hike!

Crouching Lion Hike – located near Kaaawa, you’ll have to do a little research on the trail to find the beginning of the hike. Approx. 30 mins up to the top and has a tiny bit of rock scaling. Tip: pick a sunny day and you’ll have incredible views from the top. But be careful as it can get really windy at the top.

Makapu’u Lighthouse Trail – easy and paved hike to a summit above a lighthouse. Tip: do this hike for sunrise time (as the sun rises on this side of the island) and also in winter for prime whale watching times.

Makapu’u TomTom Trail (just to the puka) – the entire TomTom trail can take up to 6-7 hours which is why I recommend only going to the puka (hole). The best views are from the beginning to the puka and is about two hours one way. It is more difficult than any of the other hikes I’ve mentioned and you’ll have to do some research on where the trail starts. Tip: early in the morning is the best for this hike.

South Side

For this blog post, south side will refer to the area from Kapolei to Hawaii Kai and everything in between.

Waikiki is by far the most popular place to visit in Oahu. Waikiki Beach is famous in its own right; it often makes lists of top beaches in the world, but once you’ve been there, you’ll wonder why the heck it’s on any list. The ocean is dirty, there’s a million people on the beach and it’s just not a great experience overall. However, I do tell visitors to Hawaii to check our Waikiki area for two days (max!) as it is a must-do. The best thing about Waikiki? The clothing stores are open until 11pm-midnight.

Waikiki is known for its upmarket dining experiences – there are a large number of restaurants to choose from and all serve pretty great food. I don’t venture into Waikiki often anymore (I lived there for six months and that was enough!) but when I do I tend to eat at these places:

The Cheesecake Factory – if you’re American and you’re reading this blog then you’ve probably already rolled your eyes at this. However, coming from New Zealand where The Cheesecake Factory doesn’t exist, this place is heaven! Tip: the meals are huge so always expect to be taking some home. And make sure you leave room for cheesecake of course!

Lulu’s Waikiki – indoor/outdoor restaurant that serves breakfast as well. Again, portions are pretty big. They also have live music in the evenings. Tip: their nachos are the biggest I’ve ever seen in my life. Try with the kalua pork for a delicious Hawaiian twist.

Leonards Bakery – One word: malasadas. If you don’t know what that is, you are missing out big time. Tip: go later in the evening for less crowds.

Kaka’ako Food Truck area – formally a once a month event, this now permanent food truck area has a range of delicious food to pick from. Tip: bring cash as most places don’t take card.

I know I have given limited places in such a huge foodie area but anywhere you go is bound to serve amazing food.

There are a large number of hikes in this area – a lot of them going up into the valleys with views over almost the entire island. Here’s a few of my favorites:

Kaau Crater – a long, and tough hike. Approx. 6 hours round trip. It starts off in a jungle and you make your way past three waterfalls; the third one you actually climb up (with the help of ropes). Tip: be careful near the waterfalls. I fell into the first one and had wet feet for the next five hours of hiking, not ideal.

Koko Head – a short but VERY intense workout. Obama is known to do this one when he is in Hawaii. Climb up can take anywhere between 20mins-1 hour (depending on your fitness level). I do not recommend this hike if you have a beginner’s level of fitness. Tip: do not do this in the heat of the day. First thing in the morning or after 4pm is the best time. Sunset views are pretty amazing!

Diamond Head Crater – I have to be honest and tell you this is not one of my favorite hikes. But it is almost a “must do” for someone visiting Oahu. It gives views over Honolulu and the south side area. It’s easy and short; I did it in jandals/thongs/flip flops once but I wouldn’t recommend it. Tip: bring cash. It costs $1 per person to enter.

Kalihi Ice Ponds – there’s a few waterfall hikes around the island that I like to explore after a good pouring of rain, but I would recommend the Kahihi Ice Ponds for visitors as it’s an easy hike. It’s about 20-30 mins of walking, with a steep incline at the end and a little bit of downhill towards the falls. Tip: you can go up the first waterfall to more falls behind!

West Side

From Kapolei all the way up until Yokohama Bay/Kaena Point is the beautiful West Side of Oahu.

West side often competes for best side of the island in my heart. I think the only thing that holds it back is the lack of good food which you’ll read about later in this post. But the mountain ranges, the views from the hikes and the ocean are all to die for. My favorite beaches to swim at on this side are Makaha Beach and Yokohama Beach (aka Yokes).

West Side can be a sketchy part of the island. Keep this in mind when leaving your car at a hike or at the beach.

One of my favorite things to do out here is go swimming with dolphins. Now there are reputable snorkeling companies you can do this with; however we’ve found it easy enough to just swim out from the beach and follow these boats and you’ll see dolphins! They tend to hang around Makua Beach really early in the morning (7am early) and summer time brings clear water. Tip: take a snorkel mask and fins to help with the swim.

As I mentioned, West Side is seriously lacking in good eateries. Because of the low income residents, you’ll find a lot of fast food chains over this side (think Taco Bell, McDonalds, KFC etc). So if you’re into that sort of thing then you’ll love it! However I’m not a huge fan of eating this food (although Taco Bell does hit the spot sometimes) and try to find alternatives.

Kahumana Farm – an organic farm and café a little out of the way (about ten mins drive from the main road). But it is a “farm to table” style café and everything is super fresh and delicious. Tip: they also serve Il Gelato Hawaii sorbetto for dessert which is super refreshing and compliments all of their meals.

Monkeypod Kitchen – a restaurant in the Ko Olina resort area which is a little pricey but damn, it is delicious. Tip: try their pumpkin ravioli – by far one of the most amazing dishes I have ever had.

My Café – I’ve found it really hard to find good brunch places here in Hawaii, until I found My Café in Kapolei. Their “flight of pancakes” is the best thing on the menu – a short stack of cookie butter, a short stack of lilikoi and a short stack of taro haupia (coconut) pancakes. Oh. My. Lord. I’m drooling writing this. Tip: there can be a long line for this place so be prepared (study the menu while you’re waiting!)

Hiking on the west side has the best views in my opinion. Here’s a few of my favorites:

Pu’u’ohulu Kai (aka Pink Pillbox) – another pillbox hike! But this one is a little longer than the others. Tip: go early in the morning before the sun has reached over the hill. Or do it at sunset time as the views from this side of the island are beautiful for sunset.

Mt Kaala – full disclosure: I haven’t done this hike. But it’s on my bucket list! My friends have done it and the views look absolutely incredible. I think it’s the highest point on Oahu? It’s approx. 7 hours round trip. Tip: I would not recommend for people with beginner fitness levels.

Upper Makua Cave – less of a hike and more of a rock scaling adventure. I’ve seen dogs and young kids do this before but I definitely wouldn’t recommend. Also if you’re afraid of heights, this one’s not for you. Tip: sunset time is great for this one also. Oh and that sign at the beginning that mentions live ammunition is in a different area to where you hike – promise!

I have a few extra places that don’t really fit in with my “hiking and eating” theme I have been following so far, but are worth a mention.

Pearl Harbor – a must do for every person visiting Hawaii. It’s absolutely incredible and I’ve been twice! Tickets to the USS Arizona and Pearl Harbor are free, however they are sometimes hard to come by. You can arrive at Pearl Harbor early and hope there are spare tickets that day (which myself and some friends have done and been successful) or you can pay for a tour that picks you up from your accommodation and drops you back afterwards. Either way, definitely make it happen! A 20 minute film is shown to every visitor before you are shuttled over on a boat to the USS Arizona for approx. 15 mins. Tip: they don’t give you much time on the USS Arizona so be quick with reading the information around the memorial and taking photos.

Ala Moana Center – Ala Moana shopping center was the largest mall in America when it was built in 1959, and is still the seventh largest mall in the USA today. It is also the largest open-air shopping center in the world! While it’s stores can be seen as more ‘upmarket’ (think Gucci, Versace etc), there are some rare gems in here also. Tip: the food court has almost every type of cuisine you could think of. I was speechless when I first went there!

Polynesian Cultural Center – growing up in New Zealand, I learnt about the Maori culture and the other Polynesian cultures around the world. I never ever would’ve thought I would visit a tourist attraction based a culture from my home country – but when you’re offered free tickets and your mom is in town, how can one say no?! This place is voted Oahu’s number one tourist attraction every year and they aren’t lying. It is amazing. And the food at the end, so so ono. Best part would have to be the performance at the end. Tip: start early. You’ll want to see and do everything. I would recommend getting there at 11am, and you won’t be done until after 10pm. It’s worth it though!

Mahalo for reading this long but I hope helpful guide to visiting Oahu. If you have any questions, please do not hesitate in contacting me – either on the contact page of this website, on Facebook (Antipodean Adventurer) or on Instagram (@antipodean.adventurer).

Aloha nui loa