How to Spend 5 Days on Oahu Hawaii
Hawaii is one of the most dreamt after holiday destinations in the world and I have been dreaming of visiting for what feels like my entire life! I finally managed to persuade Dave for us to go and we jetted off on an epic 2 week trip to Oahu and Kauai.
Our trip to Hawaii is one that I will never forget because it is the trip that I left to go on with a boyfriend and came back from with a Fiancé! I’ll go into more detail on how Dave proposed further down in this guide. 💍
This guide will provide details on a 1 week Oahu Itinerary which is taken from our exact trip including all of the hikes that we did and beaches that we went to. I will also give you a list of some of the best hotels to stay at while you are on the island.
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📍 Where is Oahu, Hawaii
Oahu is the main island in Hawaii and also the busiest one. If you are flying to any of the Hawaiian Islands, you will most likely fly into Honolulu International Airport on Oahu first, before transferring.
Click here to open the map in Google Maps!
🚗 Do I Need a Car for Oahu
If you are planning on driving around the island and visiting any of the places in this list, then I recommend you hire a car. If you are only wanting to stay in Waikiki for your time in Hawaii, then you don’t need to hire a car unless you want to do any day trips around the island.
🏄♀️ Things to Try in Hawaii
- Poke Bowls
- Garlic Shrimp from a Food Truck
🛏 Places to Stay
I highly recommend booking your accommodation far in advance for anywhere in Hawaii because accommodation books out fast!
- Turtle Bay Resort – This is where the movie “Forgetting Sarah Marshall” was filmed.
- Takanoha Condo
- Ocean Villas at Turtle Bay
- Cute Plantation House in Kailua with AC
- Delightful & Spacious 2 bedroom 2 bath Apartment with full Kitchen AC
- Lanikai Ohana Hale
- Outrigger Reef Waikiki Beach Resort
- Hilton Hawaiian Village Resort
- DoubleTree by Hilton Alana – Waikiki Beach
🗺 Oahu Itinerary 5 Days
Day 1 – Flight to Hawaii, Turtle Bay Resort and Garlic Shrimp
Your first day in Hawaii will likely be your travel day so you probably won’t want to go too wild with adventurous activities on this day.
We flew into Honolulu International Airport early in the morning after a night flight from Sydney Australia, which neither of us were able to sleep on and went straight to pick up our hire car. We then drove from the airport all the way to Turtle Bay resort which was a only a bit over a 1 hour drive. Instead of 1 hour, the drive felt like 3 hours because of how tired we both were. Dave started driving, couldn’t handle the tiredness, we stopped at Maccas (Australian slang for McDonalds) for ice coffees which we both found way too sweet and I drove the rest of the way to the resort.
On the way, we stopped off at the Polynesian Culture Centre for a small nap in the car and a very yummy crepe from one of the food trucks. Guys, if there is anything we learnt about Hawaii, it’s that food trucks are HUGE. Food trucks are everywhere, kind of replacing cafes and keeping the islands nature intact which is super nice. Hawaii definitely had a very natural, hippy feel about it, especially the North Shore, which is where Turtle Bay is located.
Turtle Bay and North Shore Food Trucks
We didn’t actually stay at Turtle Bay Resort because we were trying to keep our trip fairly budget but I would absolutely love to stay there one day. Instead we stayed at an Airbnb at a villa complex literally just down the road from the resort, meaning that we could walk into the resort and swim at their beach, go to the restaurants and bars and have a sneaky look around pretending to be richer than we were.
As our room wasn’t ready until after midday, we went straight to the beach at Turtle Bay, lay down on the grass under the palm trees and both fell straight asleep. It was glorious. Then once we had had a dip in the water, we were ready for some cocktails so we went to one of the outdoor bars (this one was on the beach side) at Turtle Bay.
While you are staying on the North Shore, you should definitely go and try some of the food trucks for lunch or dinner. We came across a bunch of food trucks at Pupukea which was only around a 12 minute drive from Turtle Bay Resort. If you use google maps to direct to “North Shore Shrimp Truck,” this will get you there. I have included it in the above map.
Here we had our first Garlic Shrimp and me oh my it was delicious! If you are going to try anything new in Hawaii let it be the Garlic Shrimp! There is also a Food Land next door for any groceries that you may need.
The food trucks are right across the road from Shark’s Cove which we went back to the very next day to snorkel.
Day 2 – Snorkelling at Shark’s Cove and Sunset Beach
Go Snorkelling at Shark’s Cove
Shark’s Cove is a great snorkel spot on the North Shore of Oahu and only a 12 minute drive from Turtle Bay Resort. Don’t let the name deter you as we did not see any sharks but did see turtles and loads and loads of fish. There is also a cool Aloha sign written with shells underwater. I’m not sure if this would still be there now though. We brought out own snorkelling gear with us from Australia because we knew that we would be doing lots of snorkelling and thought it would be easier than having to hire every single time.
If you do need to hire snorkelling gear, you can do so from Surf N Sea which is right near Shark’s Cove.
Catch the Sunset at Sunset Beach
If you are staying on the North Shore of Oahu, I recommend checking out Sunset Beach for sunset. This was Dave’s original spot that he planned to propose at, but I was more in the mood for cocktails than chilling at the beach so I made the beach trip a little too short for him and he had to wait and pick another spot. Gotta keep em on their toes! 😉
Sunset Beach is about a 13 minute drive from Turtle Bay Resort and is gorgeous. You will not regret catching a sunset or two there. It is quite popular so as long as you are not expecting to have the beach to yourself you will love it!
Day 3 – Travel to Kailua (East Coast) + Crouching Lion Hike
After our stay on the North Shore for 2 days, we ventured down the East Coast to Kailua where we stayed in a lovely Airbnb. Kailua is a very modern beachy town and we absolutely loved it there. From the North Shore to Kailua, it is around a 1 hour 15 minute drive. We would love to go back for an anniversary one day as it will always be very special to us, being the place where we got engaged.
Crouching Lion Hike
Distance: 0.8km / 0.5 miles | Elevation Gain: 90m / 300 ft | Time: 1-2 hours
Just less than half way to Kailua from the North Shore, was the Crouching Lion Hike which we decided to do on the way. The trail is located on East Coast of Oahu in Kaaawa with incredible views at top of Kahana Bay. We decided to hike the Crouching Lion trail because photos that we had seen of the views from the top looked like those classic Hawaii views that you see in all of the movies.
The Crouching Lion Hike is a fairly short (around 30 minutes of hiking/scrambling up) but steep hike as shown in the above picture of me struggling to climb down. We did this hike smack bang in the middle of the day but from what I have heard, it is best done at sunrise or sunset.
We didn’t have any issues but we came across other blogs that recommend to not to leave valuables in your car as the area is prone to break ins. The small carpark for the Crouching Lion Trail is across the road from the trail head. I have to say, the trail is hard to find if you don’t know what you are looking for. Type Crouching Lion Hike into google maps to get to the general area. Heading North, you will want to keep driving after you reach the google maps spot and you will drive around a bend You will see a bunch of parked cars on the side of the road on a patch of dirt. Not an official carpark but this is the spot.
Alternatively you can use the map above, which has a pretty close location of the trailhead spot which is also very close to the parking lot.
Once parked, you will need to cross the road and walk back towards the direction you came in. Here you should see two signs, One says “danger hazardous cliff” and the other says “Area closed.” This is where the trail starts.
The hike is a bit of a scramble but the views from the top are awesome! We both want to do it again at sunrise or sunset next time we are in Hawaii.
Rope Swing Near Crouching Lion Hike
After our little hike, we explored the area a little bit. From where we had parked our car, we walked towards the ocean a little and came across a couple of rope swings which were fun to mess around on for a while (We are all just big kids at heart).
Kailua has some lovely beaches. We were staying pretty close to Kailua Beach Park and so once we had arrived in Kailua after the Crouching Lion hike, we hung out at the beach and had a swim.
If you are looking for a good bar or restaurants in Kailua, I can recommend Buzz’s Original Steakhouse, which is right next to Kailua Beach Park. They have some awesome cocktails there however, if you are there at dinner time, you may have to wait a while for a table. Alternatively, you could try to get there for an early pre-dinner drink and some snacks.
Day 4 – Lanikai Beach (The Proposal) & Wiliwilinui Hike
The day Dave proposed was a big one and my favourite of the whole trip. We got up for sunrise and went to Lanikai beach to take some photos. Dave proposed while we were taking photos (He sneakily set the camera to video instead of photo and got a video of the whole thing!). The full video is available in our stories on our Instagram if you want to check it out. We then went for a quick swim and then decided to do a hike and check out the nearby Botanical Gardens followed by celebration cocktails our favourite beach cocktail bar, Buzz’s Steakhouse. Then, after calling our parents to tell them the good news, we finally went out to a Japanese Restaurant for dinner. This restaurant was called Tokoname and was so delicious!
Lanikai Beach in Kailua is one of the most popular beaches for wedding and elopement photography and has been rated as one of the best beaches in the world! It has electric blue water and perfect soft sand and you will understand why it is so popular the moment you see it.
Wiliwilinui Ridge Trail
Distance: 7.6km / 4.7miles | Elevation Gain: 493m / 1,617ft | Time: 3 hours
This is one of the easier ridge hikes on Oahu, from what we gathered and will take you around 3 hours return. This didn’t stop us from freaking out slightly before starting the hike and leaving a note for our Airbnb hosts to come looking for us in case we didn’t return. 😆
We saw a few other people on the trail but not too many which was nice. The beginning of the hike was along a fire trail for quite a long time, which did get slightly sleep in sections and made me worry about it raining as I can imagine that the clay-like mud would have gotten extremely slippery. The fire trail was surrounded by trees on either side so we couldn’t see the views yet. This section of the trail probably lasted around 45 minutes.
Finally, we reached the spot where the stairs started with a spot to brush off your shoes. This is where the views start getting good and the definition of “Ridge” trail comes from. There are a few spots where there is a steep drop off on one side but for a lot of the hike, we were surrounded by shrubbery which kind of makes you feel a little more at ease.
There are sections of the hike closer to the top where you have to pull yourself up using a rope but they are not too bad. Please take care and note that this hike would be treacherous in the wet as the mud would be extremely slippery!
From the top, you can see views of the sea and of Waikiki which is pretty awesome. The views from the top show you that you are in the middle of the island with mountains all around you which is an incredible feeling! We were going to stay for sunset but ended up going back down because we were scared it would start storming and didn’t want to slip down the path on the way back. Conditions in Hawaii change frequently due to the tropical nature of the island which we were not used to.
Ho’omaluhia Botanical Gardens
The Ho’omaluhia Botanical Gardens are so beautiful! I’m sure you have seen a picture of this place on IG, the iconic road with the jagged Hawaiian mountains in the background and beautiful palms on either side?
Unfortunately, when we arrived at this iconic spot to take our own photo, the guard at the gate was very quick to tell us that taking a photo here is now illegal and so we needed to keep driving through to the gardens. We had no idea of this until we got there, as we had seen so many photos on IG so the disappointed hit us hard. But that’s okay, the rest of the gardens are free to take photos in and they are just as beautiful. The first photo pictured below is the iconic IG spot, however taken from our moving car.
Entrance to the gardens is free and you can walk around for as little or as long as you like.
Day 5 – Snorkelling at Hanauma Bay and Kahe Point (Electric Beach)
Day 5 is a snorkelling day! Once again I recommend you purchase your own snorkelling gear if you want to snorkel as much as we did while in Hawaii. From Kailua to Hanauma Bay, it is a 30 minute drive and then from Hanuama Bay to Electric Beach it is a 1 hour drive.
Hanauma Bay is a very touristy beach and marine park that you can snorkel at that you do need to pay an entrance fee to visit. The reason for this is that the bay is a protected Marine Sanctuary and I can confirm the amazing snorkelling at Hanauma Bay is 100% worth the entry fee!
We arrived very early before the opening time and were able to get in for free as some sort of “you are the first visitors for the day thing.” I’m not really sure if this is something they do every single day but we obviously did not complain. Our favourite fish at Hanauma bay was definitely the Humuhumunukunukuapuaa (pictured below) which is the State Fish of Hawaii! We also had a ton of fun learning how to say it! 😆
Kahe Point (Electric Beach)
We ended up going to Kahe Point (Electric Beach) twice, actually by accident, (one was on a boat tour) but it was so worth it! If you plan on snorkelling anywhere on the island of Oahu, do it here.
Kahe Point got its nickname, Electric beach because it is situated next to a power station. The power station outflows warm water through its pipes. The warm water from the pipes makes the ocean a few degrees warmer than normal, which attracts an abundance of sea creatures.
When we went to the beach the first time, we were snorkelling in the wrong spot and later realised on the tour that you needed to be out at the spot where the pipes end. Here you will find load of fish swimming into the outflow and get pushed away and then coming back again almost like its a game. We saw so many sea turtles at this spot too. Please take care as the water is fairly deep where the pipes end.
Bonus – Waikiki
If you have time to add an extra night onto your trip, I recommend staying in Waikiki for at least a night before flying back out of Honolulu International Airport.
We stayed at the Waikiki Resort Hotel for one night only which was around USD$200. Once thing I have to note is that Hawaii is not cheap! We did it as cheaply as possible with some splurges here and there for dinner and cocktails and we probably spent around USD$3,300 for our two weeks there as we also spent a week exploring Kauai.
While we were in Waikiki, we spent our time at the beach, rented some surf boards from the beach surfboard rental and completely failed at surfing and then chilled out at our resort pool, before heading to the restaurants on the beach for some sunset cocktails and our last dinner in Hawaii. We made the mistake of being in the restaurant while the sunset was putting on an awesome show. The sunsets in Waikiki are incredible!
We love Oahu and are so keen to make a return visit some day soon! We love the beachy vibes of the island and also that there is so much in the way of outdoor adventure!
You might also enjoy:
- Crouching Lion Hiking Guide
- How to Find the Best Snorkelling Spots in Oahu
- How to hike the Wiliwilinui Ridge Trail
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