Trip to Hawaii | Things to do in Oahu and Kauai

Overall Itinerary and Highlights

I’ll start with some of my favorite pictures and a summary of our trip! Then, if you want to see more images, you can keep scrolling.

Oahu Highlights

Total time spent in Oahu: 4 days, 3 nights

Things that we enjoyed and would do again:

• Stay at the Surfjack Hotel. It is a boutique hotel lodging experience that has an excellent happy hour. It also looks like you would run into Donald Draper going through a midlife crisis there. 10/10.
• Diamond Head Crater Hike – an easy hike (but hard enough to feel like a workout) with panoramic views of Waikiki! Shorter Uber ride from Waikiki, too. Please throw away your pineapple smoothie in a trash can, though. We saw a lot of pineapple litter. 8/10
• Makapu’u Lighthouse Hike – we did this hike at sunrise and I highly recommend it! There is no shade on the path, so sunrise or sunset will keep the sun from beating down on you the whole time. This is another easy hike on a paved road, with a pretty good incline the entire time. We found the trail was super quiet at sunrise, too. The view: 180 degree views of the eastern coast of Oahu with a pretty lighthouse. It is a slightly longer Uber right, but worth it! If you have a rental car, even better. 9/10
• Snorkeling on Waikiki Beach. It was better than I thought! That said, I thought I wouldn’t see anything. We actually saw a huge sea turtle and some cute fish! 6/10
• Visit Kailua Beach. You can walk around the neighborhood, pick up some coffee or a bottle of wine at the local market, and enjoy a quiet and stunning beach! It is more off the beaten path, and a great place to go if you want to get away from Waikiki Beach. 8/10

Things I wouldn’t do again:

• Eat at Duke’s. Duke’s used to be good (I think), but now it has relied on becoming a check in the box of things to do, so the food is overpriced and reminiscent of an Outback Steakhouse. If you do want to go to Duke’s, I recommend going for happy hour. It does have a nice beach view. 2/10
• Luau at the Hale Koa. This probably isn’t an option for most people anyway, but this felt like the furthest thing from an authentic experience. The dancers were great, but the experience wasn’t. We went back to our hotel afterward, which has live music every night, and we saw a mom get up and hula with her daughter. It was free, and it was more authentic and special than the entire time we spent at the luau. 1/10
• Heads up: drinks on Waikiki beach are $20 a pop.

Kauai Highlights

Total time spent in Kauai: 4 days, 4 nights

I will preface all of this with the fact that I absolutely love Kauai. If I did this trip over again, I would only go to Kauai (or maybe I would try Maui). It is so beautiful and unlike any other place I have ever been. There is no big city, only a big canyon. Also, if you do go to Kauai, I highly recommend getting a rental car. We stayed in Poipu on the south side of the island, but I also hear Princeville on the north side is very nice. Poipu is a bit more quiet with some rockier beaches.

Things I would do again:

• Waimea Canyon. It’s a must. It is like the Grand Canyon but smaller, and greener. The best view is obviously at the start of any trail, so it’s hard to find the motivation to hike here. Stop at different overlooks and see what you find. Each one is different! Also, to get to the canyon you drive through the town of Waimea, and it’s a cute little beach town. We passed by a guy selling tuna from his driveway. We didn’t buy any, but we wish we did! 9/10
• Boat Tour of the Na Pali Coast with snorkeling. This was definitely a highlight. I don’t think you can really appreciate how beautiful the Na Pali coast is without being in a boat. We went through Captain Andy’s, and rumor has it they have the best boats. It was truly excellent. We saw a school of dolphins, and at least three wales. And an open bar on the way back! 10/10
• Day of hiking and kayaking to a waterfall. We booked it through Ancient River Kayak, and our guide was great. It is about 5 hours total. You start by kayaking two miles, then you hike along a physically easy but geographically medium difficulty trail to get to a super cool waterfall and watering hole! Then you come back the way you came. I felt so relaxed doing this, and it felt amazing so see more of the nature in Kauai. 10/10
• Stay at the Grand Hyatt. This is tricky because it was so expensive to stay there, but also any resort in Kauai is expensive. The Grand Hyatt had great food, incredible customer service, and might be the most beautiful resort on the island and on the most beautiful beach. That said, the food there is a bit expensive because they charge for convenience. If you want to stay somewhere that will take your breath away, it’s a great option. If you want to keep on a budget, I am sure there are little air bnbs somewhere around that are more affordable. Just because it is so expensive, 7/10

Now, to the pictures! And the finer details of our trip! Most of these pictures are Portra 400 film, and I brought one roll of black and white film that I had a lot of fun with!

How it started

We decided since it’s such a long trip, and we haven’t taken a vacation like this since pre-COVID, we would fly First Class! Honestly, the lay flat seats were a GAME CHANGER. Just make sure you actually have lay flat seats, and not regular seats. Our layover was through Chicago where it was -6 degrees. And then we landed in Hawaii!

First stop: Oahu

We checked into our hotel at the Surfjack! While there are many resorts on the ocean, we opted to stay in a boutique hotel a few blocks from the beach. We loved it! Waikiki Beach is a super commercial place that is like any other city, so we enjoyed staying at a place with personality.

Hiking Diamondhead in Waikiki Beach

The views from the top of Diamonhead are beautiful! You literally have a panoramic view of Waikiki Beach. It felt like a short workout getting to the top, but nothing too difficult.

Day 2: Makapu’u Lighthouse Sunrise Hike

We arrived at the trail almost an hour before the sun would rise just so we could see it rise at the top. Hence the sleepy eyes. It was worth it!

After we finished our hike, we took an Uber to Kailua where we enjoyed breakfast and walked to the beach! The beach was super quiet and beautiful. It was a deep contrast from the crows of Waikiki Beach. We took a quick dip and enjoyed the sunshine before heading back to the hotel to get ready for our portraits!

We treated ourselves to a portrait session with Meredith Sledge Photography! I am usually always behind the camera, so this was super special to me. It’s a great way to remember this trip.

During our last day in Oahu, we soaked up the sun rays and hung out by the beach. We did a little bit of a snorkeling and enjoyed an extended happy hour! We had dinner at Duke’s and it was… fine.

Next stop: Kauai

Welcome to Poipu

We stayed in Poipu, on the southern part of the island, while we were in Kauai. There is so much green and so many mountain views! There was a light leak that got into my camera when I photographed Poipu beach, and it ended up being a happy accident. It was completely unintentional, but I love how it made the image look. We enjoyed the poke at Brennecke’s a few times, and had amazing burritos at Da Crack, recommended to us by friends. I should mention– we had ahi tuna every single day of this trip! It was to die for. Other than the amazing tuna, I loved all lush greenery and flowers.

The Grand Hyatt

We splurged and stayed at this beautiful oceanfront resort in Poipu, and it was amazing. Their customer service was incredible! Our room wasn’t ready at check in, so they gave us a free appetizer and two free drinks by the pool while we waited. The views from this resort simply cannot be beat. The grounds were immaculate with so many different flowers. It was breathtaking.

I felt so at peace here. Thomas and I played cards outside as we always do on our trips. We love cribbage. Below is my favorite picture from the entire trip. It perfectly encapsulates how I feel playing cards with him.

The Waimea Canyon

The Waimea Canyon was spectacular. You definitely need a rental car in Kauai to see things like it. It’s not great for hiking since the best view is at the top, but we really enjoyed stopping at the different overlooks. The views were incredible. I transitioned to a roll of black and white film on this day, and I love the mood of the images as we strolled through the town of Waimea. We literally stopped to take pictures of this cool car parked on the side of the road. And then we enjoyed some fresh shaved ice (amazing!).

Outdoor Adventure with waterproof disposable cameras

We booked this through Ancient River Kayak and had the best time. Phones away, sun in our faces, and a beautiful waterfall. These images were taken with a cheap disposable and waterproof camera meant for really harsh light, so the images are of lower quality. The waterfall was completely shaded, so that is why they appear a bit dark.

Na Pali Coast

This was definitely a highlight of our trip. There is no better way to see the Na Pali coast than from the water. I took a lot of pictures and managed not to drop my big, bulky camera in the ocean!

I hope you enjoyed this post! If you found any of it helpful, or even just liked the pictures, please leave a comment and let me know!