Oahu Itinerary: 5 Days in Paradise

Oahu is one of Hawaii’s most visited islands and good reason! There is so much to do on this island paradise, and it offers some of the most stunning beaches, historic sites significant to Hawaii, and incredible hiking. This Oahu itinerary (5 days) will help you see the best the island has to offer!

This winter, my fiance and I found a cheap ticket to Hawaii from D.C. Southwest had a flash sale and thanks to my companion pass, we paid just $175 each for roundtrip flights. It was an incredible trip, and I’m so excited to share the details! So here’s how to spend 5 days on Oahu. 

Table of Contents

Overview of Costs for this Oahu Itinerary 5 days

  • Flight: $175
  • Hotels: 3 reward nights, 2 nights Airbnb, $130 each
  • *note, short-term rentals ended on Oahu outside Waikiki in Oct. 2022
  • Activities: $450
  • Jeep Rental: $120 (3 days, through Turo)
  • Food: $40-50 a day
Note: You can easily cut the costs of activities by skipping the helicopter tour I discuss OR by using the Go City Pass to cover many attractions and things to do on Oahu.

Night 1

We used a reward night for that first night and stayed at the Lotus Hotel Diamond Head our first night. We knew our first few days we’d be doing things on the East side of Oahu and did not want to sit in Honolulu traffic, which can get really bad during rush hour!

The hotel is charming and right near the beach. It’s on the quieter side of Waikiki Beach, and we didn’t feel the rush of the downtown area, even though we did drive through it!

There are specific rules you need to follow when visiting Hawaii, and you need to be respectful of the people who live there and the protections they have in place. Never visit anywhere you aren’t willing to be respectful of!

We arrived late in the evening on our first night of the trip to Oahu and took an Uber straight to our hotel, ordered take-out, and went to sleep. We knew we’d need to wake up early for our trip to Hanauma Bay the following day!

Day 1: Hanauma Bay and Koko Head

Hanauma Bay

East of Waikiki

Open Wednesday through Sunday from 6:45 am to 4 pm

Hanauma Bay is one of the most popular snorkeling spots on Oahu. It’s gorgeous and part of a nature reserve. We chose to go early in the morning because they have staggered tickets, and you can enter and then stay for the day. The earlier you get there, the fewer people.

Only 1400 guests are allowed each day / 40 guests every 10 min. Parking is also first come, first serve ($3 parking fee).

You need a reservation to enter; with how popular it is to visit and how limited they make the tickets, you should plan ahead. They regularly change the rules on when tickets become available, so check their website. The standard entry fee is $25.00 for each guest.

You can rent snorkel gear from there or bring your own. We chose to bring our own to save some money and because, well, it’s safer in these times! This also meant fewer lines and worries about wasting time while there.

Find your own snorkel gear here! Reef-safe sunscreen options found here too.

The last thing to consider is that you need reef-safe sunscreen and you will have to watch a 9-minute video on safety and how to protect the coral reef.

Our entry time was 9:30 and everything went really smoothly! We were able to walk through quickly, take in the views, watch the video, and head down the hill into the bay. They do have a tram that takes you up and down the hill if you’d like as well that is free. We chose to walk down and take the tram up.

When in Hanauma Bay, you’ll see tons of different fish and beautiful corals. The water is pretty shallow, so you’ll need to be careful not to hit any of it or touch it as you swim!

Coral can die when touched by humans, and so you need to do your part by continuing to swim and stay afloat. If you’re worried this might be an issue for you, you should rent a life jacket or take frequent breaks.

The best snorkel spots are easily accessible from the beach. Unfortunately, we didn’t see any sea turtles while here, but we did see many beautiful and colorful fish!

We spent about 2 hours here really exploring and enjoying the beach. It started to feel a little crowded around 11:00 when we left.

Bogart’s Cafe

After spending the morning snorkeling, we were hungry! We made a stop at Bogart’s Cafe, not far from Hanauma Bay, and on the way to Koko Head. Bogart’s Cafe is known for its sandwiches which is what we were definitely craving. There was also a nice seating area outside where we were able to enjoy our lunch.

Koko Head

The Koko Head Stairs hike is a steep, no-shade climb to the top of Koko Head Crater that includes spectacular panoramic views of the East Honolulu shoreline, Hanauma Bay, and parts of Moloka’i. The 1.6 mile, 1,000+ step walking track consists of abandoned railroad ties that run along the crater’s west side to the top of Koko Crater.

The military used them previously during World War 2 as part of an incline tram to transport supplies to a lookout post at the summit. This is a very unique hike and extremely challenging. Here’s how to hike Oahu’s Koko Head stairs.

This was a very difficult trail. Most people take about 1/12-2 hours to do this hike. We took around 2 1/2 (primarily because of me), but we also spent a decent amount of time walking around at the top of the trail.

Koko Head is stunning and offers fantastic views at the top. Plan ahead with plenty of water, and sun protection, oh yeah… and be in shape!

Read my complete guide on hiking Oahu’s Koko Head Stairs here.

Shave Ice

After our hike, we deserved a reward! So we headed to Kokonuts for some of the famous Hawaiian shaved ice I heard so much about. It was SO good. Kokonuts has hosted some famous visitors and you’ll see photos of celebrities and visitors around their shop.

Drive the East Side of the Island to North Shore

After our exciting and admittedly tiring day, it was time to head around the east side of the island to our Airbnb for the next two days. The drive along the east side of Oahu is stunningly beautiful! We did make a few stops along the way when we saw a pretty spot we felt like stopping at, but we were hungry.

Almost anywhere you stop along this drive is going to have great views and something fun to see. So take your time as you drive, and stop when you see a pretty beach or spot! We chose to make only quick stops for views on this day. On day 3, I’ll share some of the best places to stop on the way back to Waikiki.

Waiahole Poi Factory

For dinner, we wanted to grab some traditional Hawaiian food. Waiahole Poi Factory is a long-standing family restaurant with dishes inspired by the food you would find at a traditional Hawaiian Luau. It was really good and it was easy to try a little of everything while we were there!

I recommend looking up some traditional Hawaiian food before visiting if you’re not familiar with dishes so you know more about the menu before visiting. They are take-out only, so we took our food to our Airbnb after ordering.

Stay on North Shore

When I looked at itineraries, I saw that most people stay in Waikiki when visiting Oahu and miss out on the island by only taking a day trip to the North Shore. Instead, I highly recommend spending a few days on North Shore Oahu to really experience and enjoy its entirely different atmosphere!

As mentioned at the beginning of this post, Airbnb and other short-term rentals are limited on Oahu. While this does restrict affordable options, the short-term rental business has impacted Hawaii in ways that mean it is better for locals to no longer have Airbnb on the island. We chose a shared stay with someone who has lived in Hawaii their entire life. Be careful when choosing where to stay and visit ethically!

Day 2: Surf Lesson, Ka’ena Point State Park, and Beach Time

Acai Bowls at Nalu

Before we headed for our next activity, we needed to relax and grab something to eat. North Shore is full of little Acai bowl spots all along the drive. We stopped at Nalu right by our surf lesson, and before hitting up the beach.

Surf Lesson

North Shore is one of the most famous places in the world for surfing. There are huge tournaments there, and many famous surfers choose to live there. The waves can get huge, especially in the winter, so it’s best to start off with a lesson!

We had another early start with a surf lesson in Kawela Bay at 9 am. We booked our surf lesson through Airbnb Experiences for $80 a person for a two-hour lesson. I had never been surfing before – it was not easy, but it was a lot of fun! I got up just once toward the end of the lesson. My fiance got up a lot!

The instructor changes the beach for each trip depending on the conditions and level of experience of the surfers in the class. It was a lot of fun to try surfing in such a beautiful place so known for its history of surfing.

Laniakea Beach

Laniakea Beach is also called Turtle Beach. You may have guessed it: It’s called Turtle Beach because there are relatively frequent turtle sightings at this beach. So, if you’re looking for a beach on Oahu to visit, it might give you a fairly decent chance of spotting a turtle.

After a surf lesson and some refreshing food, it was time to relax at this beach! We did end up seeing a sea turtle, but it was almost like an attraction or something. There was a barrier up around the turtle and tons of people circling it to take photos.

Luckily, a turtle conservation organization supported and kept people a safe distance away. Getting close was unappealing, to add to the crowd hovering around this turtle… But there is a sea turtle in that pic posted above if you can spot it among all the rocks!

The best time of day to see green sea turtles is between 11 am and 1 pm which made our stop mid-day perfect. Alternatively, just before sunset offers a good viewing experience.

Food Trucks in Halawei

For lunch, we stopped at the food trucks in Halawei. They have several different options to choose from, including the shrimp tacos that North Shore is famous for! Every food truck had a sitting area and space to sit and enjoy your food after.

Ka’ena Point State Park

Ka’ena Point State Park is a relatively remote and wild coastline park with hiking, picnicking, and shoreline fishing opportunities. The park wraps around the northwest corner of the island of Oahu and is composed of two sections: the Ka’ena Point Mokuleia Section (north shore of Oahu) and the Ka’ena Point Keawa’ula Section (west side of Oahu).

Ka’ena Point State Park is the gateway to Ka’ena Point Natural Area Reserve at Oahu’s northwestern point. A large sandy beach at Keawa’ula Bay with board surfing and body surfing for experts and swimming only during calm conditions in the summer.

You need a permit to drive inside the state park, but you can park outside and walk in. There is little to no shade in the area, so you need to be prepared with water and sun protection.

We chose to hike the Ka’ena Point Trail, which is 2.7 miles each way and takes you to the northwestern point of Oahu with stunning views of the coastline the entire way. You can hike all or part of this trial, but the end of the trail is the best. We loved this hike and saw at least a dozen whales while we were hiking as well as sea lions.

All in all, this took us about 3 hours to hike, and we wished we’d brought more water. We thought it was 2.7 miles roundtrip, but were definitely wrong!

Dinner at Seven Brothers in Kahuku Sugar Mill

We headed back toward our Airbnb, but of course, another stop for amazing food! Another area known for its food options is Kahuku Sugar Mill. We went to Seven Brothers and I got the Hawaiian burger. It was so good! We took our food from there and went to Kahuku Beer Garden, where we enjoyed local beers and our burgers with fries. It was a great way to end the day.

Day 3: Drive Back to Waikiki

It was time to head back to Waikiki on our third day, but we had stops to make on the way back! We didn’t have time on our first day to make many stops, so instead, we stopped on day 3 at some beautiful spots.

Stop 1: Kaawa Beach

This beach is beautiful! It offers stunning views of the mountains and calm waters inside the bay nearby. You can watch surfers here and take in breathtaking views of the mountains here. It’s a pretty narrow strip of sand, so be prepared to be close to the water!

Stop 2: Kualoa Ranch

Kualoa Ranch offers a vast range of activities. It’s probably best known for its amazing views of the mountains on East Oahu and as the location for filming Jurassic Park. They have a shop, farm, and tour packages. A few of the things they offer are ziplining, catamaran tours, horseback riding, and movie tours.

We chose to make a fairly quick stop here just to take in the view. It’s honestly stunning! The main reason we didn’t do any activities? They’re expensive, but they look like so much fun, and if you have the budget, go for it.

Stop 3: Ho’omaluhia Botanical Gardens

This is a pretty Instagram famous spot, and for good reason! The gardens are stunning. Please note that you’re not allowed to take pictures along the road where you see all the pictures taken during open hours. So come early and respect the rules. They have signed everywhere telling you not to and we still saw people trying it… don’t be like that people! There are still many other spots you can stop at they allow that are beautiful.

Opened in 1982, this Garden in Kāneʻohe features plantings from major tropical regions around the world grouped geographically.

Geographical regions represented by their botanical collections: Philippines, Malaysia, Tropical America, India & Sri Lanka, Melanesia, Hawaii, Polynesia, and Africa. The Garden was designed and built by the U.S. Army Corps of Engineers to provide flood protection for Kāneʻohe.

9:00 am – 4:00 pm daily

Photo by Ava W. on Unsplash

Stop 4: Lanikai Beach

Known as one of the most beautiful beaches on Oahu, Lanikai Beach is definitely worth a stop. Snorkeling here is easy and will offer the chance to see a lot in crystal clear waters. You can also consider taking a full day to enjoy this area instead of making the other stops and go kayaking to the Mokes.

Nearby is Manoa Chocolate, Hawaii’s craft chocolate brand. They offer chocolate tastings and tours of their factory. This is a great stop after a day at the beach!

Parking can be really tricky here and is one of the surprising things that no one tells you about visiting Hawaii. Be respectful and pay attention to parking signs while here. There is a free parking lot nearby at Kailua Beach.

Stop 5: Halona Blowhole and Beach Cove

The Hālona Blowhole is one of Hawai’i’s natural wonders, created thousands of years ago when molten lava tubes were formed from volcanic eruptions. There aren’t any active volcanoes on O’ahu anymore, but the blowhole remains a must-see scenic stop. It’s an easy stop off the highway, but parking can be tricky. Be prepared to wait for a spot if needed.

Right next to the Halona Blowhole is Halona Beach Cove. This secret Oahu beach is more commonly known as Eternity Beach for an infamous beach scene in a romantic 1950s Hollywood movie. You can walk down to this beach and swim or snorkel here. Be careful as it is a narrow beach and there are jagged rocks all over.

Stop 6: Hilton Hawaiian Village

From here, we headed back into Waikiki to drop off our rental car and check into the resort for our next two nights: Hilton Hawaiian Village.

Thanks to our Hilton points, we spent our last two nights of the trip at Hilton Hawaiian Village located in downtown Waikiki. The Hilton Hawaiian Village on Oahu is one of the most famous hotels in the country — if not the world.

The average stay here is around $300 a night, stateroom tax of around $22.14 per night, a general excise tax of $10.18, and a $50-per-night resort fee — but don’t forget the taxes of $7.49 on top of the resort fee. When all was said and done, it comes out to more like $380 per night. However, with our points, everything was covered.

Note: As you noticed, our travel credit cards made this trip WAY more affordable than it would have been. Travel credit cards are one of the best ways to travel for cheap.

Dinner at Hilton Hawaiian Village

Hilton Hawaiian Village has 8 onsite restaurants for dining, and through the Hilton Amex, we get $30 of dining credit a day per person during a stay at any Hilton property, so naturally, after checking in, we had to eat at the resort! We chose to eat at Tropics Bar & Grill, which had a great sunset view.

Day 4: Helicopter Ride and Relaxation

As you can tell, the first part of this trip is action-packed, so on this day, take some time to relax at your resort and still do something adventurous… a helicopter ride!

Relax at the Beach or Sleep In

Start the day off with coffee in Honolulu and spend some time at the beach right outside the resort, or treat yourself to some time at the spa or sleep in. Find a way to relax before you go on a truly epic adventure.

Helicopter Ride with Magnum Helicopters

$300 each


I wanted to surprise my fiance with a truly unique birthday gift, and boy did he get it! I booked us an open door, 50-minute helicopter tour over Oahu through Magnum Helicopters. We honestly had the best time on this tour and loved every minute of it.

Magnum Helicopters is located at Honolulu Airport and offers a variety of tour options to best fit your needs. They were communicative and did a great job preparing us for the trip with safety information, what to wear, and even taking pictures for us throughout the journey! We sat in the front and saw amazing views of the island for the entire trip.

Our helicopter pilot had his microphone on the whole time, so we could communicate with him, giving us a sense of comfort and providing us with information as we went over different parts of the island. The tour took us over Waikiki, Diamond Head, Stairway to Heaven, North Shore, Dole Plantation, Pearl Harbor, etc.

They also offer a video package where they record the entire flight for you as well as a short video as if you are Magnum P.I. driving our Ferrari and helicopter all over Oahu and lanyards to hold your phone during the flight so you can still take photos. These packages were a fun addition to the trip.

If you’re in Oahu, this definitely should be on your bucket list for the trip. It was such an incredible experience, and they are the nicest there.

Kalia Tower Pool on the left, view from Paradise Pool at Sunset on the right

Pool Time at the Resort

The rest of the day, take it easy There are 5 pools at the Hilton Hawaiian Resort perfect for relaxing. You can also hang out on the beach right at the resort. We spent most of our time at the Kalia Tower pool which was for adults, but also enjoyed the slides and bar at the Paradise Pool!

Kalia Tower Pool – Located on the fourth floor, this pool displays a mosaic-tiled maile lei intertwined with ilima and pikake flowers. This pool is for adults only.

Kalia Pool Hours: 9:00 am-5:00 pm

Paradise Pool – A 5,000-square-foot family activity pool that boasts one of the only slides in Waikiki and overlooks the Duke Kahanamoku Lagoon This pool allows arm band floats for children who don’t meet the height restriction of the water slide rules.

Paradise Pool Hours: 9:00 am-6:00 pm

Outdoor Slide: 11:00 am-2:00 pm, Lava Tube Slide: 2:00 pm-5:00 pm

Towel Stand: 9:00 am-6:00 pm

Super Pool – 10,000 square foot beachfront pool located between the Rainbow Tower and The Ali’i, adjacent to the Hau Tree Cantina. No pool toys or floats are allowed in the Super Pool.

Keiki Pool –A tiered pool off the Super Pool, providing a shallow swimming pool for our younger guests No pool toys or floats are allowed in the Keiki Pool.

Super Pool & Keiki Pool Hours: 8:30 am — 9:00 pm

Towel Stand: 9:00 am — 6:00 pm

Tapa Pool – A tropical pool located between the Tapa Tower and Diamond Head Tower, No pool toys or floats are allowed in the Tapa Pool.

Tapa Pool Hours: 9:00 am – 9:00 pm

Towels are available at the Tapa Pool 10 am – 6 pm

The Ali’i Pool – A private sanctuary with a sun deck, exclusively for the guests of The Ali’i. No pool toys or floats are allowed in the Ali’i Pool.

Day 5: Explore Honolulu

On the last day of the trip, spend your day seeing Honolulu. There are tons of things to do, from shopping to snorkeling to history. We chose to go snorkeling one more time, do some shopping, and have a fancy dinner downtown. Below are things you can do on your last day to explore Waikiki.

Iolani Palace—Iolani Palace is a living restoration of a proud Hawaiian national identity and is recognized as Hawaii’s spiritual and physical multicultural epicenter. Built in 1882 by King Kalakaua, It was the home of Hawaii’s last reigning monarchs and served as the official royal residence and the residence of the Kingdom’s political and social life until the overthrow of the monarchy in 1893.

Pearl Harbor – At the Pearl Harbor National Memorial, learn about one of the most pivotal moments in U.S. history: the attack on Pearl Harbor, and the subsequent entry of the United States into World War II. You do need a ticket and reserved time to visit. We didn’t realize this and missed it on our trip.

Shopping Luxury Row – High-end shopping complex featuring boutiques for apparel & accessories located in downtown Waikiki. Lots of non-luxury shops surround this area as well.

Diamond Head Monument – The unique profile of Diamond Head (Lē‘ahi) sits prominently near the eastern edge of Waikiki’s coastline. Hawaii’s most recognized landmark is known for its historic hiking trail, stunning coastal views, and military history. As of May 12th, 2022, all out-of-state visitors must have an advanced reservation to enter Diamond Head.

Kapiolani Park Beach – Located at the eastern end of Waikiki, this park is green and much more relaxed than the extremely busy central portion. It’s a large expansive 300-acre urban park and green space also hosts an aquarium and a zoo. You can go snorkeling here or watch the surfers on the beach.

Plan your dream trip to Oahu with this 5-day itinerary. Explore beautiful beaches, visit historic sites, and embark on unforgettable hikes.
Plan your dream trip to Oahu with this 5-day itinerary. Explore beautiful beaches, visit historic sites, and embark on unforgettable hikes.
Plan your dream trip to Oahu with this 5-day itinerary. Explore beautiful beaches, visit historic sites, and embark on unforgettable hikes.
Plan your dream trip to Oahu with this 5-day itinerary. Explore beautiful beaches, visit historic sites, and embark on unforgettable hikes.

This Oahu itinerary (5 days) offers the best things you’ll find in Oahu. From the stunning coast and beaches to the adventure and relaxation you need, I know this itinerary for 5 days on Oahu will help you plan your trip!


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