It was August 4th, 2007. I was in the dress of my dreams next to my favorite person, surrounded by a handful of our closest friends and family on Papa’iloa Beach on the North shore of Oahu. We had already legally been married for a year but decided that we wanted a destination wedding, so we planned it for our 1st year anniversary!

For years, I have wanted to go back to show our kids Oahu and all of my favorite things about the island. In 2023, we finally got the chance over our Fall break and I’m excited to share all the details!

Check out our top picks for lodging, dining and activities below. I have included some great travel deals if you are ready to plan your next trip to the Islands too!

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Oahu Lodging

Hilton Hawaiian Village Waikiki Beach Resort

The Location

We have been Diamond members since our long stint in a Hilton when we first moved to California. We are still riding that wave and have gained a lot of perks because of it! I was hesitant to stay down in Waikiki because the two other times we have visited Oahu, we stayed up on the North Shore at Turtle Bay Resort. I’m happy to report that staying down in Waikiki didn’t take away from the nature-driven experience that I was hoping for!

We were in the Rainbow tower which had an ocean and Diamond Head view and very easy access to the water. The put us on the top floor, which gave us an incredible view of the ocean, coastline and beautiful Diamond Head Crater.

The Pools

Super Pool • This 10,000 sq ft pool has enough space for everyone! It is surrounded by palm trees and overlooks the beach! There is a Keiki pool right next to it that is safe and fun for the smaller kids. We spent all of our time at this pool!

Paradise Pool • The paradise pool is just that, paradise! It is a bit smaller than the Super pool and has a waterslide!

Ali’i • This private pool is exclusive for Ali’i guests. It is smaller, quieter, and secluded for the ultimate experience.

Tapa Pool • The Tapa pool is one of the smallest pools located between the Diamond Head Tower and Tapa Tower.

Kalia Adult Pool • This pool is located on the 4th floor of the Kalia Tower and is for guests 18 and older only!

Duke Kahanamoku Lagoon • If you would like a more natural experience, the Lagoon is for you! It is 5 acres of sparkling salt water overlooking the ocean. You can rent SUP boards here, or try your hand at the aqua cycles.

Onsite Shopping

At Hilton Hawaiian Village, the onsite shopping experience is as vibrant as the resort itself. Guests can explore a diverse range of boutiques and stores offering everything from stylish beachwear and souvenirs to unique Hawaiian gifts and upscale fashion. The Village’s shopping areas are conveniently located, making it easy to find that perfect item to remember your stay or to pick up essentials without leaving the resort. Whether you’re looking for local art, resort wear, or specialty items, the shopping venues cater to all tastes and needs!

Onsite Dining

Onsite dining at Hilton Hawaiian Village offers a delightful array of culinary experiences in the heart of Waikiki. With over 20 restaurants, cafes, and bars, guests can savor everything from casual bites to gourmet meals. Enjoy fresh seafood at Bali Oceanfront, island-inspired dishes at Tropics Bar & Grill, or international flavors at Rainbow Lanai. Whether you’re in the mood for a quick snack, a family-friendly meal, or a romantic dinner, Hilton Hawaiian Village provides diverse dining options, all set against the stunning backdrop of Waikiki Beach.

Bali Oceanfront • This upscale offers a captivating culinary experience, specializing in Pacific Rim cuisine, featuring fresh seafood, locally sourced ingredients, and innovative dishes that celebrate the flavors of the region.

Tropics Bar & Grill • A lively beachfront venue that captures the essence of Hawaii’s vibrant culture. This popular spot offers a diverse menu of island-inspired dishes, refreshing cocktails, and live entertainment. It is the ideal place to enjoy a casual meal, unwind with a drink, or take in the spectacular Hawaiian sunset!

Top Lodging Picks For Other Hawaiian Islands

Maui: Grand Wailea, A Waldorf Astoria Resort

Big Island – Kailua Kona: Hilton Waikoloa Village

Kauai: Koloa Landing Resort

The only other place we have stayed on Oahu in years past, is Turtle Bay on the North Shore. They were recently bought by the Ritz Carlton. It will be interesting to see if/how this changes the Turtle Bay vibe that we all know and love.

Dining

Visit the Food Trucks in Hale'iwa

Besides dining at the Holo Holo Grill on plenty of occasions, we did venture out and have a few great meals elsewhere. Before our Na Pali Coast Catamaran ride got canceled, we planned to have lunch down in Eleele near where we were to catch our boat. While waiting to determine our fate, we sat down and had lunch outside at Port Allen Sunset Grill and Bar. I was pleasantly surprised by the food as it looked more like a bar-centric spot. We tried it anyway and it did not disappoint. As you know, our boat tour did end up getting canceled so we ended up with plenty of time to go shopping nearby!

Get Some Shave Ice From Aoki's

There are a lot of places that you can get shave ice from on the North Shore. You can visit Masumoto’s, which is the most popular (with a longer line), or you can go across the street to visit the more highly rated Aoki’s!

Activities

Take a UTV Tour at Kualoa Ranch

When I was getting ready to book our UTV tour, I planned to have Kyle and I drive. By the time I actually got it together, the self-driving UTV tour was full so we only had the option to ride along. I was initially a little bummed out because we had done something similar a LONG time ago there, drove ourselves, and it was lots of fun!

I was SO wrong to be bummed out. We ended up being in the front UTV with our tour guide. We got the best, unobstructed views and stayed a little bit cleaner than the rest of the crew. Instead of learning just a few minutes of information at each stop, the best tour guide ever, Nathan, shared so many more great stories and exciting details. It was really the cherry on top of the perfect trip. Our kids considered it the highlight of their trip to Oahu.

Take a Train Ride at Dole Plantation

Ok, ok, this is pretty touristy! This was the 3rd time that Kyle and I have been to Oahu so we figured we should probably just knock it off the list already. It ended up being a great time. All of the tickets are first come, first serve, so you can’t reserve anything in advance. The main activities include the Pineapple plantation train ride, the garden maze, and the plantation garden tour. There is also a large gift shop and country store, a few other outdoor vendors, and the Plantation Grill.

We opted to do the train ride and eat some delicious pineapple soft serve while we waited in line.

Have a Beach Day!

There is no shortage of beautiful beaches to choose from on Oahu! Some of our favorites are Kualoa Regional Park, Kailua Beach Park, Sunset Beach Park, Lanikai Beach and of course, right out in front of the Hilton Hawaiian Village, Kahanamoku Beach! There are a few more special ones that you’ll have to find by exploring on your own!

Take a morning to visit Pearl Harbor National Memorial

One of our top priorities was taking our oldest son to Pearl Harbor. We very much appreciate that he has a deep interest in history and feel it is important to nourish it. You will want to reserve your tickets in advance. Be sure that you are logged into your recreation.gov account ahead of time and have the page you are looking for saved to your favorites. Certain tickets, like these, go very fast so you don’t want to fumble around with logging in last minute! Click here to go to recreation.gov to save the link!

Things To Do On Our Next Trip!

Ho’omaluhia Botanical Garden, Byodo-In Temple

Save up to $375 on your next Hawaii SW Vacation Package!

If you are considering a trip to Oahu soon, bookmark this post so that you can check back to see what great deals are going on to get you there!!

Click the Southwest Banner below to find out all the details and book that trip to this Hawaiian paradise or one of the many other destinations they offer great packages for!

Choose Hertz for your next trip

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We have been loyal to Hertz for over a decade now and we haven’t had a single bad experience with them. Even in this weird, ‘not sure if your car will be there’ insanity that is being threatened in the news, Hertz hasn’t let us down! I hope that if you decide to try out Hertz, you will have a similar experience.