Hawaii is one of my favourite places on Earth. It’s one of those places that I could visit over and over again, and still not get tired of. Whether you’re looking to relax and spend time on the beach or hike a volcano, there is something for everyone to do! The state of Hawaii is actually made up of 137 islands, with Oahu being the third largest of the Hawaiian chain of islands. I first visited Oahu January of 2020, and fell in love with it so much I went back in December. There is so much to explore, and there’s something about the island life that’s so attractive and enticing. After spending over a month in Oahu, I decided to write up a little blog post to make planning your trip a little easier. Here is the perfect 5-day itinerary for Oahu, Hawaii!
Day One: Exploring Waikiki
Good morning! We’re going to start the trip strong with some surfing at Waikiki Beach. Waikiki is tourist central so we won’t spend too much time here, but it’s a must-do, and it’s a great spot to practice surfing. Surf-shops open up around 7:00, so if you’re up for it, go for a sunrise paddle. If you are not up for some surfing, you can drive to Sandy Beach Park and watch the sunrise. You don’t want to miss a single sunrise here in Oahu!
You can rent surfboards at the surf-shops for ~$10 an hour, and if you have never surfed before, grab a lesson! Oahu is where I learnt to surf, and I instantly fell in love with it even though I s u c k. I usually go for about an hour or two, and afterwards, you’ll be starving, which is perfect because Waikiki has many great restaurants! My personal favourite breakfast spot is Bogart’s cafe. You have to try the açai bowl or fried rice; it’s a tad pricey (as most food options are in Waikiki), but it’s SO worth it. I think an açai bowl goes for $14. There’s also Sweet E which is fantastic as well. If you’re going for something less expensive, I like The Sunrise Shack, but their portions are smaller.
Spend the rest of the day exploring around Honolulu. There are plenty of boutique shops around Waikiki, and if you aren’t into shopping you can go for a hike at either Koko Head or Diamond Head, or you can relax on the beach
For sunset, make your way to China Walls and watch people cliff-jump! If you are brave enough definitely go out for a jump, it’s exhilarating! If you’re not up for it, you can enjoy the sunset from Waikiki Beach or Ala Moana Beach. There are also plenty of excellent restaurants at Waikiki with outdoor seating, and you can enjoy a meal next to the beach during sunset as well.
Day Two: Surf and Turf
Choose your own adventure time! If you loved surfing, start the morning off with a paddle. If you want a more relaxed time, rent a stand-up paddleboard and watch the sun rise on the waters. You can also head towards Hanauma Bay and go for a morning snorkel! If you are interested in hiking, you have a couple of options. Starting with the easier hikes, there is Koko Head or Diamond Head. They are both relatively easy, but there are a lot of steps. I haven’t been before, but I’ve heard great things about those hikes from friends who have done it.
If you want something more challenging but rewarding, check out Pali Notches, which is right off the Pali Highway. It’s pretty sketchy, so go if it’s not windy or raining. Pali Notches is excellent for both sunrise and sunset but be warned: if you go for sunset there might a be a chance that the parking lot will be locked by the time you get down. Last time I went, we got locked in the parking lot for two hours before the cops came to let us out! The most challenge option is Olomana. Olomana takes 2-3 hours to get to the best viewpoint (photographed), and it’s extremely difficult. I almost died slipping off a ledge, so wear proper footwear and only go if you feel confident in your hiking skills. Some people have died on this hike! You'll want to start around 2AM to get to the top for sunrise, and you'll want to park in a safe neighbourhood.
After your morning workout, grab some breakfast and spend some time relaxing at your hotel. If you are looking for a place to stay, I would recommend staying at Waikiki Beachcomber. I stayed there for a few days in December 2020, and you can get 20% off using this link here (3-night minimum stay), and it’s right in the heart of Waikiki, so everything that you need is walking distance!
Day Four: Hiking and a Luau
It's time to hike again! We're starting early in the morning, and depending on where you are staying you'll have to wake up EARLY to get to there. It's about an hour or so away from North Shore, so budget the driving time. Crouching Lion is a relatively easy hike, but difficult if it rained or is raining. You will want to start an hour or so before sunrise, and the best place to park is either at the pull-off on Kamehameha highway or the residential area nearby. The trailhead is a bit hidden, so use AllTrails. I cannot stress how important it is to wear proper footwear. The trail is extremely muddy and slippery, so be careful! Don't forget to bring snacks (or breakfast), and a headlamp!
After your morning hike, make your way back towards North Shore and grab brunch at a food truck. Spend the afternoon exploring North Shore, and around 14:00 make your way to the Polynesian Cultural Center for a luau. A luau is a traditional Hawaiian feast accompanied by entertainment. From what I’ve heard, the Polynesian Cultural Center has the most authentic one, and it’s a great way to experience some Hawaiian culture while eating your heart out. The experience is about $100-$200 depending on which package you get, but the “Ali’i Luau package” is the best option. You can also show up earlier and explore the area, and partake in their VIP canoe experience. Click here for more information regarding hours, prices, and availability.
Day Three: Dolphins, Snorkeling, and North Shore
It’s another early wake-up call! If you are staying at North Shore, get up around 6:00 and drive down to Waianae for a dolphin and snorkelling excursion. There are plenty of tour companies that operate, and most of them start around 7 in the morning. It costs around $150.00 per person, but swimming with dolphins is definitely one of those once-in-a-lifetime bucket-list things that you just HAVE to do. Some tour companies have multiple tours throughout the day, but from what I heard the earlier you go, the more chances you’ll have amazing encounters with dolphins. After the morning tour, head back to Waikiki, freshen up, grab some lunch, check-out, and make your way towards North Shore. Driving in Oahu can a bit annoying as everything is so far away, but the views along the way make it okay. Instead of driving the recommended route that Google suggests, take the Pali Highway. That drive is one of my favourites. Check in to your next accommodation, and spend the rest of your day exploring the town, beaches, and the popular surf spots.
Day Four: Hiking and a Luau
It's time to hike again! We're starting early in the morning, and depending on where you are staying you'll have to wake up EARLY to get to there. It's about an hour or so away from North Shore, so budget the driving time. Crouching Lion is a relatively easy hike, but difficult if it rained or is raining. You will want to start an hour or so before sunrise, and the best place to park is either at the pull-off on Kamehameha highway or the residential area nearby. The trailhead is a bit hidden, so use AllTrails. I cannot stress how important it is to wear proper footwear. The trail is extremely muddy and slippery, so be careful! Don't forget to bring snacks (or breakfast), and a headlamp!
After your morning hike, make your way back towards North Shore and grab brunch at a food truck. Spend the afternoon exploring North Shore, and around 14:00 make your way to the Polynesian Cultural Center for a luau. A luau is a traditional Hawaiian feast accompanied by entertainment. From what I’ve heard, the Polynesian Cultural Center has the most authentic one, and it’s a great way to experience some Hawaiian culture while eating your heart out. The experience is about $100-$200 depending on which package you get, but the “Ali’i Luau package” is the best option. You can also show up earlier and explore the area, and partake in their VIP canoe experience. Click here for more information regarding hours, prices, and availability.
Day Five: Last Day
It’s your last full day in Hawaii! For sunrise, make your way up Kaiwa Ridge (Lanikai Pillbox) for a wonderful view. It’s a 30-40 minute walk up, and it’s fairly easy. If you’re not up for a hike, you can also enjoy the sunrise from Lanikai Beach. After sunrise, make your way towards Kualoa Ranch around 10:00. You’ll want to jump on either a two hour horseback walking tour, or their two hour ATV adventure. Click here to join a tour!
At noon, grab some lunch in Kailua, the nearby town. I absolutely loved this pizza place called Pieology Pizzeria. It’s super healthy, and you can also put as many toppings as you want! There’s also Over Easy, which is a great spot if you’re in the mood for some breakfast food. It’s a bit pricey, but it’s honestly one of the best breakfast spots on the island. Once you’re filled up, make your way towards Makua Beach. It’s about an hour’s drive, and you’ll want to start before 14:00 as the traffic will get terrible around 15:00. Fun fact: Makua Beach is also known as “Pray for sets” beach, as many surfers pray for sets of good waves. A decade ago a graffiti artist wrote “Pray for Sex” on a boulder, and ever since then it’s been called that.
Makua Beach is perhaps the best place to watch the sunset on the entire island, so spend your last evening enjoying the beach. It’s also great for snorkelling and swimming. As a warning, make sure to leave no valuables in your vehicle. I cannot stress this enough; the west side is the sketchiest area of Oahu, and many people have had their vehicles broken into. I actually had my tires stabbed the last time I went! Please be careful, and maybe go and check on your vehicle every couple of hours just to make sure.
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