Oahu, home to Honolulu, is by far my favorite Hawaiian island. It may not be the largest of the Hawaiian islands, but it is the most populous and in my opinion, has the best mix of things to do. Boasting gorgeous beaches with insane waves, staggering cliffs and mountains, amazing food, and cultural sites, Oahu is packed with lots to see and enjoy. Here is my ideal five-day Oahu itinerary that’ll let you see it all.
– Covid Travel Information –
In order to arrive in Hawaii from another state, you must follow the guidelines as outlined by Hawaii Safe Travels. If you want to bypass the 10-day quarantine upon arrival, the current steps as of April 20, 2021, are as follows:
- You must get a negative COVID test from one of Hawaii’s approved partners within 72 hours before your arrival in Oahu, and it must be a NAAT test.
- Upon getting your negative results, make an account to register your trip on the Hawaii Safe Travels portal under the “Trips” section, and upload your negative covid test results to the “Documents” section. Make sure that under the STATUS column next to your test results it says “COVID NEGATIVE.” If it says “Verification in Progress”, there might be an issue with your document.
- Within 24 hours before your flight, you must take the Health Questionnaire in your Hawaii Safe Travels account. This will ask if you have symptoms, have received a positive test result, or have recently been exposed to Covid.
- After taking the questionnaire, you will receive a QR code to the email you signed up with. Save this QR code and present it upon landing.
Of course, be sure to visit the official Hawaii state website for the most up-to-date guidelines and restrictions. These are just the steps that I took when I went.
– Itinerary –
This itinerary is perfect if it’s your first time on the island; it’ll take you all around the island, from Waikiki to the North Shore. I’ve tried to make sure you get the best of Oahu – from beaches to mountains, from the best food to the best viewpoints. There is some light hiking, but nothing too strenuous or over an hour. Also, most of the attractions on this itinerary are free, so it’s great if you’re on a budget.
For the most part, I’m assuming that you’re staying in Waikiki/Honolulu area; however, it’s not strictly necessary if you’re planning on following the itinerary. Also, in order to follow this itinerary, you’ll need to rent a car. There is a public transit system, but it’s not great, so a rental car is well worth the investment.
For your convenience on the road, here is a map of all of the spots on the itinerary!
Day 1
HAWAII KAI
Diamond Head
This is the most popular hike in Oahu! The entire thing is paved, although it gets steeper and uneven towards the end, it’s a great family-friendly hike that takes around 45 minutes round trip. It’s now $5 per person, but the views at the top are entirely worth it. Take note that Diamond Head is closed on Wednesdays, so plan accordingly.
Spitting Cave
This spot is right off the street in Hawaii Kai. Park along the side of the road, and make your way down a short but steep path down to the rocks. The textures in this shoreline are absolutely incredible, and the main attraction is a small cove at the bottom of one of the cliffs which will literally “spit” water out when the waves hit it just right.
Lunch at Fatboy’s
For lunch, I’d recommend the Fatboy’s location in Koko Marina. Fatboy’s is a great place to get local Hawaiian food for a really great price. Some of our favorite local dishes included the Loco Moco (a hamburger patty covered in gravy), the Kalua Pig (delicious smokey roasted pork) and the garlic chicken.
Makapu’u Lookout
This is a quick stop along the side of Kalanianaole highway. There’s a paved walkway to a gorgeous lookout over Makapu’u Beach Park. It’s not worth the trip on it’s own, but given its proximity to the next spot on our itinerary, it’s worth the stop.
Makapu’u Tide Pools
These tide pools were one of my favorite attractions from the entire trip! Crystal clear waters are pooled within pockets of lava rock, with waves crashing along the outside. However, the hike to these pools has potential to be dangerous, so I would avoid bringing children! Start off along the Makapu’u Lighthouse Trail; there’s a parking lot for this trail, but it’s often full so we parked along the highway. At the third rest stop on the lighthouse trail, there will be a sign that talks about the whales and a caution sign that veers behind the rest point – this is where you’ll begin your descent. Although many people have traversed this trail before, you still will probably have to wing it a bit. Follow the white spray paint as far as you can as you scale down the cliffs to the pools. This trail took us about 20-30 minutes one way, so plan accordingly. And if the sun is high in the sky be sure to bring a lot of water and sunscreen and wear proper footwear. Some rocks on the path can be loose, so be careful to watch your footing.
Image Credit: @kevin.moyannaise
Maguro Brothers
This restaurant was founded by two brothers, Junichiro and Ryojiro Tsuchiya, in 2014 and has slowly gained popularity in the Hawaiian food scene, largely in part to their dedication towards creating simple yet high quality meals. Raw fish is not my favorite, however my friend referred to this spot as the best fish he’d ever had in his life so I have to highly recommend! Their store in Waikiki only opens at 5PM and has no seating, so this is a perfect quick dinner stop.
Day 2
WINDWARD COAST
Kona Coffee Purveyors
Hawaii has some of the best coffee in the entire country in my opinion. Kona Coffee Purveyors gets all their coffee beans sourced from Kailua-Kona on the Big Island, and the quality is absolutely unmatched. With their cafe located at the front of the International Marketplace in Waikiki, it’s the perfect morning stop.
Waiahole Poi Factory
This famous spot is the perfect place to try poi! Poi is a traditional food in the Polynesian diet, made from starchy vegetables, usually breadfruit, taro or plantain. Waiahole Poi Factory has been selling poi for over 100 years now. The poi comes as a side for any one of their combo plates with meat or rice. Unfortunately, there is no seating here, but it’s easy to pick up some poi and drive to my suggested dining location further below in the article.
Kualoa Ranch
Kualoa Ranch is one of the most popular attractions on the island, known for their Jurassic Park-like landscapes. There are a number of tours and activities you can book here, including a Jurassic Park raptor tour, a horseback riding tour, zip-lining, ATV rides, and there’s even a secret beach that you can buy a pass to for half or a full day. You can easily spend an entire day exploring the park, however we decided to pass on it due to the fact that in order to access the park you have to pay for an activity, and they’re all rather expensive.
Kualoa Regional Park (Chinaman’s Hat)
Instead of paying for any of the aforementioned activities, we decided to make a stop at the Kualoa Regional Park right next to Kualoa Ranch. There’s a stunning view of Kualoa Ranch and the island Mokolii, colloquially referred to as Chinaman’s Hat. There’s also a parking lot, picnic tables, and a public restroom at this stop, if you want to enjoy the poi from earlier at a real table.
Kaaawa Beach
This might be the beach that has the most dramatic views of Oahu, in my opinion. It’s a very narrow beach right on the side of the highway, and at high tide nearly the entire beach is swallowed by the ocean. But if you come right after low tide, you’ll be greeted with a stunning stretch of sand, with picturesque palms and a dramatic mountain in the background. It’s a great spot for photos!
Crouching Lion Hike
After relaxing at the beach, it’s time for a hike! This hike is along the side of Kamehameha Highway between a ‘Do Not Pass’ sign and a telephone pole. You’ll see a small patch of dirt on the right side of the highway to park in, and then you can backtrack to the trailhead. It’s around 45 minutes round trip from the bottom to the top, and it’s quite steep! However, it’s not dangerous unless it has recently rained, in which case I would try to come back another day. The view at the top overlooks Kahana Bay and the surrounding ridges.
Leonard’s Bakery
This is an absolute must-try spot! Leonard’s Bakery is famous for their malasadas, which are a type of Portugese doughnut without a hole. This bakery in particular has been open since the 1950’s, and still has their original sign from the 60’s. Not only is the entire location extremely charming, but the malasadas are to die for.
Day 3
HONOLULU
After two days full of hikes and driving, day three is a chill beach day to spend mostly in Waikiki/Honolulu and the surrounding area. If you’re more of an adventurous type, feel free to swap this day in for more outdoorsy activities (the Koko Head hike is definitely worth checking out), but I know that at least for me, I needed a break at this point.
Brunch at ARVO
This super cute brunch spot is a must visit in Honolulu! Unfortunately, I didn’t get the chance to go, but it was very highly recommended by the locals that we know. It can get kind of busy, so I would try to come on the earlier side.
Shopping at Ala Moana
This is the world’s largest open-air shopping center. Filled with shops that would satisfy anyone’s tastes, you could spend an entire day in this mall. As it is, I recommend browsing the stores for about an hour or so before heading back to Waikiki.
Waikiki Beach
Waikiki Beach is the most touristy beach in all of Oahu, however, it is still worth the visit! The vibes are always nice here. You can lie on the beach sunbathing, take a dip in the waters, take a surfing or paddleboarding class, or even take a boat ride. I personally enjoy the proximity to shops and food spots.
Optional: Koko Crater Trail
If lying around on the beach all day sounds like a waste of time to you, try hiking the Koko Crater Trail! It goes up an old abandoned railway track, and to get to the top you’ll need to scale 1048 “stairs.” It’s a relatively short distance, but the incline is absolutely brutal. This hike is not for the faint of heart! It’ll take 30-45 minutes one way depending on how many breaks you take along the way. I would try to go as early in the morning as possible to avoid the harsh sunlight. The views at the top are stunning; however, whether or not it’s worth it is up to interpretation. I passed a number of people who were near tears towards the top. The trailhead is at Koko Head District Park – you park in the parking lot and then walk around a baseball diamond to the start of the trail.
Waiola Shave Ice
Whether or not you hiked the Koko Crater Trail, you’re probably going to want some shaved ice to cool off. Waiola Shave Ice is a local-owned spot that is famous throughout the island and has a ton of flavors – all the classic ones, and also a bunch of local Hawaiian flavors such as li hing mui (dried Hawaiian plum), lychee, P.O.G. (passionfruit-orange-guava), and lilikoi (Hawaiian yellow passionfruit)! I recommend trying some of the local flavors while you’re here.
Tantalus Lookout Point
Located in Puu Ualakaa State Park, this lookout point offers amazing views of everything from Diamond Head to Pearl Harbor. It’s just a short walk up to the lookout, and is a great escape from the city.
Sunset Drinks at Deck.
Back to Waikiki for sunset, I highly recommend checking out Deck. at Queen Kapiolani Hotel. It’s a rooftop bar/restaurant with stunning views of Diamond Head.
Day 4
NORTH SHORE
Image Credit: @kevin.moyannaise
Sunrise Shack
Head to this spot to start off the day! The Sunrise Shack is famous on Instagram for its bright yellow color but the food is also really good. Choose from a number of healthy options such as acai bowls or salads or sandwiches.
Banzai Pipeline
If there’s one thing that North Shore beaches are known for, it’s surfing! Located at Ehukai Beach Park, the Banzai Pipeline is world-famous among the surfing community, and if you’re there in the wintertime, you might be able to catch a surfing competition! However, the conditions can be extremely dangerous, even in the summer, for swimming so be sure to check with the lifeguard before taking a dip. I’d recommend just checking it out to spectate the surfers. If you’re coming during the summer months, I’d skip this stop.
Waimea Bay
This bay is also known for large surfing waves in the winter, but in the summer it’s a great beach to just chill and swim. There’s a large rock formation sticking out of the middle of the bay called “The Rock,” and you’ll see many people climbing the rock and jumping off the side. Be warned that it can be dangerous to jump!
Waimea Valley Falls
This is probably the most accessible waterfall on the island that you can swim in! Waimea Valley is a park with an admission fee of about $20 ($16 for college students and $12 for kids). It’s just a short walk from the entrance of the park to the falls, and then you’ll see changing rooms. You need to wear a life vest in order to swim in the falls, but you can take it off for photos in front of the pool.
Shark’s Cove
This is a great spot for snorkeling in the summer! The cove is protected from the intense waves of the North Shore, thus making the water decently still. And it is filled with all types of sea life, including various species of fish, coral, octopi, and even turtles. Be sure to wear proper footwear, as the rocks can get pretty sharp!
Giovanni’s Shrimp Truck
I’m giving you two options for lunch today, just because there are so many amazing foodie spots on the North Shore that I couldn’t narrow it down to one! If you’re traveling with a group, try splitting items from both places so you can try them both. Giovanni’s Shrimp Truck is known as the best shrimp truck on the island. They are known for their garlic shrimp with rice, and while you can get this at other food trucks, it just isn’t the same. Unfortunately, this usually means that there is usually a really long line!
Haleiwa Bowls
This is the second lunch stop. Again, this spot is the best of the best, known for having the best acai bowls on the island, served in an adorable little shack.
Sunset Beach
This is yet another famous North Shore beach that also gets huge waves in the winter. Depending on any dinner plans you might have, you might want to stay until sunset – as the name would imply, it is absolutely stunning here. Otherwise, just come for a short visit before heading back to Honolulu.
Day 5
KAILUA
Lanikai Pillbox Hike
I would do this hike as early as possible – right at sunrise if you’re able to get up early enough. Because this hike is on the east side of the island, the sunrise from the top of this hike is absolutely phenomenal, and has been said to be the best on the island. As it is, even if you miss sunrise you’re going to want to go before the sun is at its peak. This is a pretty short hike, around 45 minutes round trip, and it’s not too strenuous. There are two pillboxes; one earlier in the hike, and the other takes another 20 or so minutes to get to. The view from both is fantastic – we spent longer sitting on the pillbox and taking in the view than we did hiking. The trailhead is easy to find from the road, and we just parked on the side of the road in the surrounding neighborhood.
Lanikai Beach
After your hike, walk right down to Lanikai Beach. This, in my opinion, is the best beach on the entire island. The sand is soft, the water is crystal clear, and the view of the Molokua islands is amazing. It’s also technically a “local” beach, meaning it’s not going to be nearly as crowded as other great beaches such as Waikiki. However, this also means there are no public facilities such as bathrooms or changing rooms nearby, nor any places to get food or drink. Nevertheless, I could spend hours at this beach.
Ho’omaluhia Botanical Garden
I’ll confess, I mainly came here for the extremely popular picture opportunity that is all over Instagram; however, you’re not allowed to take pictures on that stretch of road anymore due to how many people were blocking the traffic. But I ended up really enjoying my time here anyway, and there are plenty of other photo spots! My favorite spot was just past the Sri Lankan plant section; there should be a spot to park, and a small hill that you can walk up. The view from here is gorgeous and makes for a great Instagram pic.
Fresh Catch Kaneohe
I’ve got another two spots for lunch today, because I couldn’t choose between the two. Fresh Catch Kaneohe is a great spot for poke, but they also offer options for those who don’t like fish! At the moment there’s no indoor seating, so you’ve got to eat while baking under the sun, but the food is worth it.
Tamura’s
Tamura’s is another local favorite spot for poke. It’s actually a liquor store, but in the back of the shop there’s a poke counter, with tons of amazing options. You can get combos with rice, or just get the fish on its own, but either way it was delicious.
Byodo-In Temple
Byodo-In is a non-denominational Buddhist temple that was dedicated in August 1968 to commemorate the 100th anniversary of the first Japanese immigrants to Hawaii, and is actually a replica of a temple by the same name in Kyoto, Japan. It is architecturally breathtaking, located in between a stream and a mountain. The admission fee is only $5, and while inside you can ring a giant peace bell, and go inside the temple to see a giant statue of the Lotus Buddha. The entire experience is extremely peaceful. The temple is actually located within the Valley of the Temples Memorial Park, and this entire park is highly worth exploring if you have the time.
Hideout at the Laylow
I highly recommend going to the Hideout and Laylow for drinks at their rooftop bar to celebrate your last night in Oahu! The vibe is really chill – they usually have live music playing – the drinks are really pretty, and it’s just a great place to relax.
Looking to extend your Hawaii trip? Consider adding a trip to Maui.
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