Two-Weeks in Oahu, Hawaii

This time three years ago, I was getting home from a dream vacation to Oahu, Hawaii. I had always wanted to go to Hawaii ever since I was young and when I found a great deal on flights I thought “this has to happen!” And I’m so glad it did. Our trip to Oahu was the first big trip my husband and I had taken where we were staying in vacation rentals, where we needed to rent a car for the duration of the trip, and where we didn’t have direct flights. You can refer to my tips for renting a car on vacation, and also my carry-on only packing list for more information on those topics.

I only knew a little about the island of Oahu before booking our flights, so I spent hours of time researching and planning how we would spend our two weeks. Here’s an overview of our vacation and a few tips learned on the way.

Day 1: Arrival & Car Rental Pick-Up

The first day of our trip was long and exhausting. We flew from Toronto to Los Angeles, had a three-hour layover and flew from there to Oahu. It was nice to have a break to stretch in between flights, but it did make the day feel longer. When we got to Oahu we collected our bags, found the shuttle to the car rental agency and we picked up our car. We drove out of the parking lot and as soon as we were on the road the check engine light came on. Car exchange #1 happened – we went from a Chevy Cruze to a Ford Focus. After loading up, we hit a grocery store and a Costco before heading to our (awesome) vacation rental.

Tip: Hindsight being 20/20 I would have only picked up a few items like water, snacks and dinner before heading to the vacation rental. When we got there we were exhausted, cranky and didn’t even want to eat anything we bought.

Day 2: Exploration & Pool Day

On our second day we were exhausted, but still wanted to explore. We also had an issue with our new car rental and had to go find somewhere to exchange it. This brought us to Aulani. In all of my research and planning I don’t know how I didn’t stumble upon this resort… not that we would have stayed there. It is something insane around $600 USD per night… and there’s not even a theme park! We quickly looked around the resort, exchanged our car for car #3 and carried on our way (after I saw Mickey and had to get a photo of him of course). We drove around the area, did some sight seeing and then went back to the condo to lounge (sleep) by the pool.

Day 3: Aulani

After seeing the Aulani resort, I thought it would be fun to go and explore it. The next day we paid for parking at Aulani and wandered around the resort and beach area. Since we came prepared, we also lounged by the pool for the afternoon (and swam in the pool!)

Tip: I don’t think you’re actually allowed to use the Aulani resort facilities unless you are staying there. But we didn’t know that until after our visit, and no one asked us to leave. We clearly looked like tourists that belonged there… I think it was my husband’s explorer hat and UV shirt that made us fit right in with the guests. Also, the gift shop (as expected) was seriously over-priced.

Day 4: Dole Plantation & Turtle Bay

On our fourth day we went to the Dole Plantation to do a tour on the Pineapple Express, wander through the gardens and got lost (big time!) in the maze. It was a really interesting experience and we learned a lot about pineapple farming, shipping and the history of Dole. I also had a Dole Whip which was absolutely delicious, and got some really cool photos while we were there. After Dole we continued going north to explore the beautiful north shore. Our main destination was the Turtle Bay Resort for two reasons: 1) I loved the movie Forgetting Sarah Marshall and had to see where it was filmed, and 2) I wanted to see turtles. We accomplished the first, but unfortunately there was not a single live turtle in sight.

Tip: If you want to see the pineapple demonstration, make sure you check when it is in advance. We missed it and didn’t want to wait for the next one.Turtle Bay Resort had a luau the night we were there and we could have stayed if we wanted to – I didn’t think we were dressed up enough so we didn’t – but it would have been fun! Also, research to know when you may actually see some turtles to avoid disappointment.

Day 5: Polynesian Cultural Center

The fifth day was spent entirely at the Polynesian Cultural Center, and this was one of the highlights of our trip. We had an excellent tour guide who provided us with the history and cultural information for the six Polynesian island villages represented in the center. After touring around we had a buffet dinner at the luau and then saw the evening show Ha: Breath of Life.

Tip: With the tickets we purchased (guided tour, luau, and evening show) we were able to go back the next day to experience the center again.

Day 6: Polynesian Cultural Center & Sunset Beach

We had such an amazing day at the Polynesian Cultural Center, we decided to go back to explore on our own for the morning and early afternoon. There was a lot of things we didn’t have enough time to see with our guided tour so this was an excellent option for us. Also – why wouldn’t you take advantage of free admission the next day!? After we finished we went to a few different beaches to take photos and walk along the north shore and on our way back to the condo.

Tip: The Hukilau Marketplace is a great place to grab something to eat and do some shopping after your visit. We didn’t have time to do this on our first day so we were glad we went back.

Day 7: Pool Day & Packing

On our seventh day, we decided to to relax by the pool. The condo we stayed at had a lovely pool area with lounge chairs, umbrellas and tables. There were also barbecues and picnic tables behind for the tenants of the condos to use. After our relaxing day we packed up our suitcases to head to Waikiki for the next week of our trip.

Day 8: Makaha Beach Park & Waikiki

Before leaving the Makaha area, we went to the Makaha Beach Park to take some photos of the lovely beaches. In comparison to the Waikiki area, these were not busy at all! We drove to Waikiki and checked into our vacation rental at the Aqua Palms Waikiki – some of these suites were owned by the hotel and some were owned independently. Our rental came with parking and we thought the hotel was conveniently located. Once we unloaded, we had to go get another car because car #3 had another issue. I’m happy to say, the fourth car was our last! We spent the evening walking around the Waikiki area and taking photos.

Tip: We really didn’t need a car in Waikiki, but had already paid for it. We had day trips planned outside of the immediate downtown area which made having a car very handy. I still would have wanted a car, but could have gone a few days without it if we were staying in the immediate area only.

Day 9: Waikiki

We set out on our second day to explore Waikiki and leisurely walked as far as we could to see as much as we could. We started at the Hilton Hawaiian Village and made our way down the beach to explore other hotels. Along the way we stopped for photos, shopping and most importantly for food. It was a great walk and very neat to see some of the more historical hotels along the beach.

Tip: Waikiki is a very touristy location and restaurants were fairly pricey. We found that most restaurants had happy hour where you could get discounted drinks and food, typically between the lunch and dinner crowds. We took advantage of this during our week here. Plus, being on vacation means you can make your own schedule so we weren’t really tracking when it was “lunch time” anyways!

Day 10: Pearl Harbor Tour

The Pearl Harbor Tour was an incredible experience. The tour included a visit to Pearl Harbor WWII Valor in the Pacific National Monument, Battleship Missouri Memorial, USS Bowfin Submarine Museum & Park, National Memorial Cemetery of the Pacific, USS Arizona Memorial and the Pacific Aviation Museum. The day was full of history and something that should not be missed. Our tour was a full day, picked us up at the hotel across the street from us and we had an incredibly knowledgeable tour guide which made it that much better.

Tip: If you are going to Pearl Harbor, look into a tour that will allow you to skip the lines and take you to all of these historical sites. It’s worth the money and very educational.

Day 11: Diamond Head Hike & Pool Day

Our adventure to Diamond Head was quite interesting. We started the day by heading to Leonard’s Bakery to try some of the famous malasadas (it was worth the detour!) we had heard so much about. These donuts are plain, custard-filled or chocolate-filled. We naturally had to try them all and I must say – go for the custard! After we filled up on malasadas, we made it to Diamond Head. In short, it was worth the hike to see the views of island from the viewing point. Read my full post for more tips here! After our hike we decided to take it easy and relax at our hotel pool before going out on the town for dinner (like we did every night that week!)

Tip: Avoid hiking on a weekend, the crowds are larger and parking is harder to get.

Day 12: Ho’Omaluhia Botanical Gardens, Hanauma Bay Nature Preserve, Halona Blowhole

On day 12 of our trip we drove around Oahu aimlessly looking for pretty photo opportunities and enjoying the island. This day we got lost a number of times, but ended up finding some pretty cool sights.

Hanauma Bay Nature Preserve

It started by us looking for the Hanauma Bay Nature Preserve. It was a beautiful location for snorkeling and swimming and for the nature lover to take some photos. It’s a fairly long trek to get down to the beach area from the parking lot, but there is an accessible ramp to go down. Once you pay the admission you have to watch a little presentation on the nature preserve and learn about the site. We didn’t do any snorkeling or swimming but walked around and took photos while we were there.

Halona Blowhole

Next on our drive we ended up finding the Halona Blowhole by accident. We pulled off the road at what looked like a busy photo area, and were very pleased to find out that this was actually a tourist attraction we just hadn’t heard about. While we were there we saw a pod of humpback whales out in the distance swimming by. This is apparently a sanctuary for whales and we were just lucky to be in the right place at the right time to see them and get a few photos.

Day 13: Ala Moana Center, Waikiki Sunset Cruise

We spent our second last day shopping at the Ala Moana Center (mostly browsing, since we had no room in our luggage for souvenirs!). The shopping experience is pretty standard for a mall, there were higher-end stores among regular department stores and the food court had regular fast-food chains. It was quite busy, but it was a nice leisurely way to spend our morning. Afterward we walked through the Ala Moana Beach Park where there was some sort of festival taking place. It was a long walk from our hotel and there were a number of areas where tent-cities had formed throughout the park. We didn’t spend too much time here as a result. In the evening we went on an all you can drink sunset cruise. They played great music, we met a number of interesting tourists and locals and we saw a stunning Waikiki sunset.

Tip: Book a sunset cruise in advance! They fill up quickly and the views from the water are simply lovely.

Day 14: Beach Day

Our last day was spent at a beach. The wind was very powerful that day, so I can’t say it was very enjoyable! The sand was flying everywhere and completely covered our towels and beach bag while we were (trying to) taking photos.

Tip: Look at the weather reports before heading to the beach! If it’s too windy I’d suggest sticking around the pool.

And there you have the gist of our two-week Oahu adventure. I haven’t included any of the restaurants we ate at throughout the trip here, but for the entire second week we ate at different restaurants for all of our meals. The first week we had a full kitchen and made breakfast and dinners. Looking back, our itinerary seems pretty packed. We didn’t rush through anything on the trip though, and had a lot of time to wander about and explore the island. If you’re planning a trip to Oahu, make sure you do your research in advance! There is so much to do and see we probably could have spent an extra week in Oahu just to relax from all of our activities during the first two weeks.

Have you visited Oahu? Share any of your Oahu itinerary tips below!