Five Nights in Oahu

It is completely and utterly sad to me that its been two months this week since we left for Hawaii. Dan and I planned a totally spontaneous, last minute trip in March where we conceived the idea, booked and traveled to Hawaii in less than three weeks!

Those who know us well know this was totally unexpected and out of character for us, but maybe that goes to show how necessary a trip like this felt… Dan has been immensely stressed with work and I was finally starting to feel like myself again after a little more than a year of anxiety really wreaking havoc on my life.

With no time to research, we called Hilton for available hotels and days and basically let them tell us where we were going. I think we both would say we are glad our first trip was to the island of Oahu.

For those unfamiliar with Hawaii, Oahu is the home to Honolulu, Pearl Harbor, the North Shore (where the big surfing competitions are held), and Waikiki Beach. Needless to say, there was so much to do and see on the island. We spent ZERO time on the beach. This is hard to believe for a lot of people, but for two people who don’t love sand, it was sort of perfect.

My favorite thing about Oahu was that in a fifteen minute drive you could see dramatically different settings. The island has mountains and valleys, a dormant volcano, bamboo forests, rainforests, waterfalls, farmland and obviously beaches galore.  The only downfall is that this is an insanely populated island, we were told a million residents on what is a pretty small island. The populated areas are crowded to say the least.

We look forward to returning to Hawaii in the future, but we will be anxious to check out other more remote islands on our next trip! Keep reading for our trip highlights, and a guide to some of our favorite foods and activities.

Steal our trip! No really, here’s some links to places and things we loved!

Our Best Meals: 
Breakfast: Il Gelato Cafe,    For the best Acai bowl…. I’d eat this every day if I could.
Lunch: Sprout,  The sandwiches were so amazing (and affordable) we went back twice!
Dinner: Uncle Bo’s Pupu, really amazing drinks. Fun atmosphere, and oh- Pupu = appetizer 😉 Order in abundance and skip the main meal!

Accommodations: The Grand Islander, This newer hotel located in Hilton’s Hawaiian Village Resort on Waikiki Beach had enough going on you’d never need to leave…. It was amazingly beautiful and we feel very privileged to have been some of the hotel’s first guests as March 2017 was the month it opened!

Excusions: We had so many trip highlights, I hope some of these insider tips will help you with planning your trip. While these were not the only things we did, they were the most memorable…
Hike Diamond Head: I read before our trip that this is one of the longest land views in the world, and I don’t doubt that.. It was totally worth the heavy breathing it took to get to the top. It’s called the Stairway to Heaven,  245 stairs  to the actual top. I know this thanks to the child who was counting aloud behind me, while I felt like I was dying and trying to breathe…. This was one of those times you challenge yourself physically and are just completely thankful to have done so!
Hike Manoa Falls Trail: This is a decently hard hike in my opinion. It’s super humid as you get closer to the waterfall and the rocks are very slippery. Other places I read listed it as easy, and I don’t know who this is easy for! It’s a beautiful hike…..but its in the rainforest. Wear bug spray. Also, don’t feel like you need to pay for a guided tour. You don’t. The trail is clearly marked and its well traveled. Lots of locals with their pups when we went. 🙂
Kualoa Ranch ATV Tour – Okay, confession. We found out about this place from watching Mike & Dave’s Wedding Dates and we needed to go. It was legitimately SO MUCH FUN! I am so happy we took the two-hour tour, an hour wouldn’t have been enough. And don’t forget to apply sunscreen…. learn from my mistakes!
Ko’Olina Dolphin & Whale Snorkel Tour: Sadly, no whales, but we saw plenty of dolphins! This tour was well worth the money, the land views from the boat were gorgeous! and they feed you two very good meals, which you’ll appreciate because Hawaii is expensive A.F.
Explore the North Shore Marketplace:  This area felt way more authentic and way less touristy than other parts of the island..
Paradise Cove Luau– Unless you have kids, you don’t need to get there until 7 PM. If you get there at 5 as suggested, you might be over the festivities before the show even starts…. That’s how my husband and I both were. Listen, luaus are super touristy. I think it was cool, and the performers are super talented, but I wouldn’t go back. Also something to note…. we bought the VIP tickets, you definitely can do the regular and get the same experience. I didn’t think the extra cost was justified. It’s the same food, someone else just goes to the buffet line to get it for you.


We are super bummed to have planned poorly and missed touring the U.S.S. Arizona and U.S.S. Missouri at Pearl Harbor. Note: you need to get there early for a chance at tickets.

Are you familiar with Oahu? Feel free to leave comments toward your favorite places 🙂





  • This trip looks amazing. What a special spot for a couple. I bet you both really were able to connect in spirit.
    • Ashley Rae
      Thank you so much- it really was! Vacationing is such a personal experience and it really is crazy to me how much the experience bonds people together..
  • Your photos are beautiful! I would love to visit one day. I had a friend get married there but I could not make it to the wedding :( so sad! Michelle | She's Not So Basic
    • Ashley Rae
      Thank you so much! How lucky for your friend to have such a beautiful destination wedding! I hope you are able to visit another time when it is better suited for you! Thanks for stopping by!
    • Ashley Rae
      Thank you- it was an amazing experience- I hope you are able to enjoy it! Will absolutely check out your site :) Thanks for stopping by.
  • Chemady
    I have not been to Oahu. Beautiful pictures you have there, I can also see that you had fun.
    • Ashley Rae
      Thank you so much! We had an amazing time, ready to go back already!
  • Cristina Leau
    Wow, the images are amazing. Good for you for taking this trip. I love instant trips more than the ones we plan a lot. It's something about them, they feel more real in a way. I hope I will be able to go to Hawaii.
    • Ashley Rae
      Thank you! It was a very cool experience to be able to separate from my tendency to over plan. We relied a lot on advice from the locals and it worked perfectly! I hope you get to go as well!
  • Agentszerozerosetter
    What a beautiful place to visit, I would love to have a relaxing vacation here! You sure had fun!
    • Ashley Rae
      It was lovely! Thank you :)
  • This looks like you had such a beautiful trip. I have had one trip to Oahu, but unfortunately that wasn't my experience there. But I would like to go sometime again because it was beautiful.
    • Ashley Rae
      It was amazing! Were you on a work trip? Sounds like you didn't get to enjoy it, you should definitely return if given the chance!
  • Laura
    What a tropical paradise! 5 days doesn't seem enough!
    • Ashley Rae
      It truly was paradise! Five days was okay for the one island (though I could have stayed forever!) but if you are island hopping you definitely need more time!
  • Elizabeth O
    Everything about Hawaii says rest and relaxation to me. I have a few friends who live on the islands and should visit them some time soon. Beautiful photos.
    • Ashley Rae
      I Agree! I think everyone needs to visit at least once! With friends there you are a lucky lady!
  • You are such a beautiful couple. I love the idea of just making a decision and booking a trip! It must have been quite an experience
    • Ashley Rae
      Thank you so much, you are very kind! It was truly AMAZING! We really did love every second of it.
  • Sorry to hear about the anxiety hope you are ok. Oahu is beautiful and it sounds like it was an amazing getaway but shame about the overcrowding. Beautiful photos though x
    • Ashley Rae
      Thank you so much! A good therapist and some meds and I am feeling so much better! We absolutely LOVED it, but definitely want to check out other islands! :) Let me know if you have any recommendations.