Oahu, Hawaii’s state capital, is the third geographically largest but most populated island. World-famous for its capital of Honolulu, Pearl Harbor, this island is home to a plethora of activities and stunning nature.

My friend, Cortland, was studying “abroad” spring 2019 semester at the University of Hawaii, Manoa instead of at UC Berkeley. My best friend, Olivia, and I decided to visit her for a few days during a weekend in April. We packed so many activities on the island within a few days. This is a perfect 4.5 day guide for anyone who needs ideas for a quick trip to Oahu.

DAY 1

Olivia and I arrived at the Honolulu airport around noon and took a Lyft to the University of Hawaii, Manoa to meet Cortland. Our reunion was awesome and we all immediately changed into swimsuits and took the bus to Waikiki Beach. The bus system in Oahu is very impressive. Here is a really good guide to important stops.

Before getting to the beach, we stopped by an acai bowl and poke place to get lunch. We went to Maguro Spot for poke. Here, you select your bowl in steps. The sizes to select from are small ($5), medium ($8.50), and large ($12.50). Then you pick your fish, which comes in the usuals (salmon, ahi, yellowfin) and whatever they have as their fresh catch for the day. You choose your rice next (white, brown, sushi), your sauces (spicy, wasabi, shoyu, creamy sesame, Hawaiian, house, oyster), and then your toppings (cucumber, asparagus, seaweed, macadamia, pine nut, avocado, tobiko, ikura). Toppings have various prices. I ordered a salmon and ahi tuna split sushi rice bowl with house and shoyu sauce and cucumber and seaweed. What I liked the most about this bowl was that the fish tasted super fresh and it had simple ingredients.

Olivia and Cortland opted for acai for lunch, so they stopped by Hawaiian Crown Plantation, which was down the block from Maguro Spot. Their acai bowls here are amazing! They use freshly grown pineapple from their own plantation in Oahu. I tried Cortland’s bowl and it was the best acai bowl I’ve had in Hawaii. We walked to Waikiki Beach from the stores and ate our food right on the beach.

We jumped in the water after and spent so much time swimming and just enjoying the cool water. After hanging out at the beach, we walked around the Waikiki area to look for a place to eat dinner. We decided on Duke’s Waikiki, a really popular restaurant right on the beachfront. I ordered the fish tacos, Cortland got the quesadillas, and Olivia just ordered fries since the acai bowl filled her up.

We met up with some of Cortland’s UH friends next to Waikiki Wall to watch the sunset. This spot is right on Queens Beach and has a super clear view of the horizon which serves great sunset colors. We spent an hour or so just sitting on the sand, talking, and enjoying the views before heading back to campus.

DAY 2

We woke up pretty early because we needed to rent a car. For car rental, I recommend Enterprise or Turo. Turo is like Airbnb for rental cars, and if you are planning to rent for a couple of days, this is an affordable option. We settled on Enterprise because the prices turned out to be cheaper. We got our car from Enterprise on Seaside Ave. I also suggest asking nicely for an upgrade if possible. Originally we were provided a sedan, but I asked if there were any convertibles available for the same price. Luckily, a silver convertible Mini Cooper was available and we were so excited to get that one.

Cortland picked up a quick breakfast from Starbucks for us and we ate it in the car on the way to the Moanalua Valley Trail (trailhead). We all really wanted to hike to the Stairway to Heaven (aka Haiku Stairs) but decided to hike the legal route, since we weren’t willing to risk a $600-1000 fine. The Moanalua side is around 12 miles round trip and takes a lot longer compared to the stairway side.

Hiking the Stairway to Heaven

The beginning of the legal trail is in a neighborhood park, so we parked our car down the street right next to the trailhead and began our journey. The small parking lot next to the trailhead gets full fast, so either come early or park on the street - but be respectful of the residents and parking rules.

After entering through the main gate, we walked flat for around 2.5mi and crossed maybe 15-17 small streams. After walking past these streams, we hiked through a more forested area before coming across the Kulana’ahane Trail sign. DO NOT take this trail. Continue a few more feet ahead and there’s a tree with a pink ribbon tied to it. Turn left into the grassy area right before the tree to cross a big stream. After crossing the stream, there is a curved, thick tree branch that is marked “Middle Ridge”, officially indicating the start of the Moanalua Valley Middle Ridge Trail.

This is the recognizable “Middle Ridge” branch!

The hike up is very challenging. I’ve been on many difficult hiking and backpacking trips and this trail was probably one of the most strenuous I’ve done. The reason being is because we didn’t bring enough water and all wore plain Nike running shoes. Despite these setbacks, we enjoyed the hike thoroughly. There was about a 1000ft elevation gain during the first mile of the hike and eventually led into a narrow forested area with trees on the sides and roots all over the ground.

Eventually, the forested elevation led into a more open setting, but with very steep drop-offs on both sides. Luckily, it was a sunny day with just a light breeze, but some rain clouds were creeping over the main mountains and we could feel some drizzle coming in. We stopped at a great lookout point so I could fly my drone around and just enjoy the view. The views up here were SO amazing! We could see all of the valley and part of Oahu from up there.

There were quite a few places on this trail that were so vertical that there were ropes installed to help with climbing. It began to drizzle a bit so we were slipping up muddy walls hoisting each other up the rocks. I got a slight rope burn on my hand so if you are better prepared, I recommend bringing gloves to hike with.

It was almost as if the steep hiking was never-ending, and the drizzle was coming down a bit harder now so we were even considering turning around. But we decided to push through because we had already made it so far. The moment we saw the top of the radio tower peak, we were so excited. The final leg of the hike was pretty steep and muddy, but we made it to the top!

We walked around the top for a bit and then walked down some flights of the stairs. The clouds and fog were rolling in so we didn’t venture too far out since the visibility wasn’t the greatest.

The walk down wasn’t too bad, but we had to be pretty careful since the drizzle made the route a bit muddier. We also ran out of water so we were hiking miles back completely dehydrated. Luckily, we ran into a really nice family who had an extra liter of water that they gave to us.

We were entirely exhausted after this hike, so we decided to treat ourselves to Banan, which is a farm-to-table, non-dairy ice cream shop that directly transforms fresh fruit into ice cream. You can read their cute story here. I built my own bowl with half banana banan and half chocolate mac banana and topped it with dark chocolate balls, shaved coconut, strawberries, and chocolate drizzle. We devoured our bowls and just sat in the store for a long time, chugging water, and relaxing.

After our snack, we went back to UH to change into nice dresses and then went to Waikiki Beach to watch the fireworks put on by Hilton Hawaiian Village, every Friday night around 7:45pm. The firework show was such a nice end to our evening. We lied down on our blanket and just watched the lights above us. There were some people kayaking on the ocean watching the fireworks in clear, plastic, light-up kayaks so we enjoyed watching them as well. We chilled on the beach some more before going out to get drinks.

We decided on going to a small karaoke bar called In Between, which was just a short walk from the beach. Cortland was really good friends with the owner at this point so the bartender let us pick a few songs for free to sing, but usually, you input a song and it’s $1 per song. The drinks at the bar are pretty affordable as well, so we ordered a couple of beers and luckily we made a few friends there who ordered a couple more rounds for us. After at least 10 songs, we called it a night and went back to UH.

DAY 3

We woke up before sunrise around 5am to pick up Cortland’s friend, Libby, to drive to the Lanikai Pillbox Trail to go on a sunrise hike. Parking is a bit difficult, so we found a random spot in an open neighborhood and parked the car there. The hike up was pretty steep but very doable and a nice way to wake up! It was a fairly quick trail and we got to the top of the pillbox to enjoy the last bit of sun rising above the ocean horizon. We climbed to the top of the pillbox and sat there for a while to look at the view and I had fun flying my drone around.

After our hike, we walked down and drove a bit closer to the coast to get to Lanikai Beach. This is probably one of the most beautiful beaches I’ve been to in Hawaii. The waters are a crystal clear turquoise color and the sand is a light yellow, almost white. The ocean is also a very comfortable 80F, so we spent a lot of time in the water swimming and looking at coral from the surface.

We tanned a bit on the beach, read our books, and would constantly switch from chilling on the sand to swimming in the water because the weather was so warm. This beach is also a great location because you can watch kayakers paddle across the ocean to access the Mokolua Islands, also known as “The Mokes”. Moku Nui is on the left and Moku Iki is on the right. Everything about Lanikai Beach was just so picturesque and perfect.

After we got our beach fix, we drove to North Shore to get food from Giovanni’s Shrimp Truck. Cortland kept telling us how amazing the shrimp was here, so we definitely had to make a stop. The line was very long, but we endured it and just hung out while waiting. Cortland and I ordered the half plate shrimp scampi, which has 6 shrimps and 1 scoop of rice compared to the dozen shrimp and 2 scoops of rice in the full plate. This was so delicious! The garlicky sauce and lemon butter is really tasty and hits the spot so nicely.

Since we were on a food bend, we drove a few minutes up to get Matsumoto Shave Ice also in the small town of Haleiwa. This famous (for visitors and locals alike) shave ice spot has been operating since 1951 and is family-owned. You can read the sweet story here. The line here was also very long, but because there are so many flavors, we took a while deciding what combinations to get. I decided on a large size with half coconut and half peach flavors. I also topped it off with condensed milk and vanilla ice cream. Although additions are extra, they are worth it! I highly recommend adding condensed milk and ice cream, because that’s just how the locals love it!

After our food adventure, we kept driving north towards Pupukea. The scenic route along the Kamehameha Highway is just stunning. The mountains were on our right side and the sparkling ocean was on our left, adding to the perfect coastal drive up. Hawaiian weather is pretty unpredictable, with sun and rain battling it out throughout the day, and many times during this drive with our convertible top down, rain poured into the car soaking us all like crazy! It was so much fun and added to the Hawaiian experience.

We got to Sunset Beach a bit before sunset time so we could watch the surfers farther out on the reef. The water here was so calm and beautiful. I flew my drone for quite some time, capturing the light changes of the sunset. The name of this beach is pretty self-explanatory, considering that this spot on the island serves the best views of the sun hitting the horizon.

When we got back, we stopped by the little market on campus and grabbed a couple spam musubis and mini pizzas to finish off our evening.

DAY 4

Cortland had work today, so Olivia and I went out to have our own adventures. Olivia dropped me off at Reef Pirates Diving so I could go on a morning dive. Since she and I both had separate activities, I’ll explain both of our experiences.

My Dive Adventure

With Reef Pirates, I chose the morning dive with the deep wreck and shallow reef options. Since I’m scuba diving certified, my package was $135. Olivia dropped me off at the dive shop at 6:30am and I got my gear all settled. There were only 4 other people diving that morning - the instructor, a mom and daughter, and a really experienced older guy.

We set out on the boat and first went to the Corsair Plane wreck dive. This plane sank back in 1948 during WWII, but the pilot skillfully landed it in the water because he heard the engine sputtering before giving out. Luckily, the pilot was saved and he actually dove out many times after the war to visit his old plane. This dive was absolutely stunning. The day was so clear that at the top of the ocean surface, you could look directly down and see the wreck. The plane sits 33m (115 feet) below sea level, so it was quite a deep dive. We dove around the site for 15-20min, watching swarms of fish and eel swirling around the site. We even saw a sea turtle there looking for food. That was the deepest dive I’ve done to this date and it was incredibly rewarding.

Our next dive was Sea Cave, an underwater cave spot in between China Walls and Spitting Cave. This dive was so beautifully blue with lots of marine life. We first swam through the cave and saw quite a few sea turtles drifting through the surge that goes in and out of the cave. We even saw a white tip reef shark swim quickly by us! We exited the cave and explored the side of the sea walls and saw so many beautiful coral and anemone on the rocks. There was also a fish (maybe 3-4ft long) that died from a shark bite. We could see the huge chunk ripped out of its body. After diving around for almost an hour observing beautiful sea creatures, we came back up and went back to shore. The dive trip ended a bit before noon.

Olivia’s Adventure

Since Olivia had the car, she drove to the Koko Crater Railway Trail to check out the view of Oahu from there. This 1.8mi trail consists of 1000 or so steps made from the railroad track. It’s very steep and is a pretty challenging incline. The railroad was once used during WWII to transport supplies up the mountain to those at the lookout post but now is a super popular hiking spot because the views are just stunning. After hiking, Olivia went to Hanauma Bay to go snorkeling. This beach is popular for snorkeling and has a nice lookout point for a view of the entire beach. Hanauma Bay is currently overrun by tourists, so coral reef and fish life are becoming endangered. It’s crucial to wear reef-safe sunscreen (no oxybenzone and octinoxate). You can find more information about the impact of sunscreen here and a list of reef-safe sunscreen here.

After my dive trip, Olivia came to pick me up and we drove to the Crouching Lion hike. It’s important to park here if you want to do the short route. We walked across the road (be careful because there are cars coming from both sides) to a small opening in the forest. There is a trailhead sign in between a telephone pole and a “Do Not Pass” sign. Don’t worry about the latter sign - the trailhead indicates that you can hike up.

The short trail is fairly muddy and covered with tree roots. There’s even a spot with rope to help you get up a steeper area. Getting up to the top was pretty fast from this point. There were two rocky areas that we walked to, to view the Crouching Lion from different angles.

This view is more inland towards the mountain side

And this view is on a rock peak that is steep to access but very doable!

We spent some time just sitting on the rocks, looking at the view, and flying my drone. It was so serene just sitting here because there really weren’t too many people. We pretty much had this rock to ourselves. After Crouching Lion, we wanted to drive around the east side of Oahu to see some of the popular coastal sites. We passed by Chinaman’s Hat and sat on the grassy beach area in Kualoa Regional Park. We bird watched for a bit and just enjoyed lying down on the grass.

We kept driving down south along the Kalaniana’ole Highway and quickly stopped at the Makapu’u Lookout to see the lighthouse. We drove more to get to the Halona Blowhole Lookout and Halona Beach Cove (aka Cockroach Cove). Cockroach Cove was really interesting! We walked into the water and on top of the shallow rocks to find tidepools. There were lots of urchins, anemone, and small fish in the little pools. We continued down to get to Lanai Lookout, which is a nice scenic spot to pull over your car and check out the view. It started to rain at this point, and Cortland was almost done with work anyway, so we decided to drive back and stop by Leonard’s Bakery before getting her.

Leonard’s, originally family-founded in 1952, is famous for Portuguese malasadas. The line at Leonard’s wrapped around the corner but the way they handled orders was very organized! The order station was on the right-hand side of the counter and the pay area was on the left, so customers generally knew how to follow the line. I ordered a couple of malasada custard puffs and dobash (chocolate) puffs. They. Were. So. Damn. Delicious!

After we picked up Cortland, we immediately drove to China Walls to watch the sunset and the cliff jumpers. The waves there were huge! Some people even catching the swell from the waves crashing on the rocks. The sunset was so pretty from this side. The sun was really bright and although there were clouds, pretty pastel colors peaked through the sky.

It was pretty much dinner time once the sunset, so we went to the Ala Moana Center to go to Shirokiya, which is a Japanese market village walk on the first floor of the mall. The selection here is huge! There’s ramen, sushi, Japanese bbq, seafood plates, spam musubi, and a few more little bites. The decoration here is also insane. There are cherry blossoms and lanterns hanging from every ceiling so you truly feel like you’re in Japan.

Since it was really dark out once we were done with dinner, we drove to Tantalus Lookout to see a panoramic view of Oahu at night. The nighttime views were so beautiful here! We drove back to Enterprise, dropped off the car, then took the bus back to UH. Solid ending to our busy day.

DAY 5

Our last day here...we woke up and went to Moku Hawaii to rent surfboards to surf at Waikiki Beach for a couple hours. Moku is right across the street from the beach, so it’s a great spot to rent boards for cheap. We paid $14 to rent for 2 hours. I got a 9’6 soft-top longboard, which is the size I usually surf with (I’m 5’5). We got to the beach, paddled out, and surfed for so long. Waikiki Beach is crazy crowded with beginners, instructors, and locals alike. It’s pretty difficult to catch a wave because some beginners drop in and ignore etiquette. Regardless, surfing is always so much fun and you can always catch a wave with patience and efficient paddling. If you’re a beginner, here is a great video explaining surf etiquette.

After surfing, we stopped by Honolulu Cookie Company so I could grab a box of Hawaiian shortbread cookies to bring back home. This is one of my most favorite cookie places and I always load up when I’m in Hawaii. We went to Hawaiian Crown Plantation again to get one more Hawaiian acai bowl before going back to California. Our flight was in the afternoon so we took a Lyft to the airport after parting ways with Cortland. This entire trip was such a great taste of Oahu for all of us!

OAHU