A first timer’s guide to Oahu in just 5 days!
Welcome to Oahu – the heart of Hawaii – where the vibrant city energy meets the laid back island lifestyle and where turquoise blue waters meet luscious green mountains! Visiting Oahu gives you a bit of everything you want on vacation including iconic beaches, scenic drives, adventurous activities, hikes with stunning views, some of the best snorkeling spots in the world, and a diverse, eclectic food scene!
We spent 5 days exploring the island of Oahu where we snorkeled with turtles, went whale watching, hiked to the top of a crater, wandered around Waikiki, and explored the historic Pearl Harbor. No matter how you decide to spend your time in Oahu, you won’t be disappointed!
Where to Stay:
Waikiki:
Waikiki is often the most recommended place to stay while visiting Oahu, and is where we chose to stay during our trip thanks to some free night rewards we were able to redeem for a hotel in Waikiki.
Waikiki is also pretty central to many of the activities you may be interested in doing, with many things only being a short walk and/or drive away. Waikiki is very accessible by walking, Uber, or even public transit. It also has a great food scene with quite diverse offerings!
North Shore:
If you are looking for more of a laid back casual vibe and trying to avoid the busy city area of Waikiki, then we recommend staying in the North Shore. The North Shore has some amazing snorkeling locations, is great for beaches, and for surfing. It definitely has much more of a local feel as there aren’t large name brand shopping centers around every corner unlike in Waikiki. It does have the downfall of not having as much variety in food though as well, however if you plan to stay somewhere where you can cook your own food, then the North Shore may be a great fit for your stay!
Things to do in Oahu:
Hike the Diamond Head Crater Trailhead
Cost: $20
Diamond Head Crater Trail:
- Length: 1.5 miles
- Elevation Gain: 485 ft
- Difficulty: Moderate
With the Diamond Head Crater being such an iconic viewpoint in Waikiki, a trip to Oahu wouldn’t be complete without hiking the Diamond Head Crater trailhead. We hiked this spot at sunrise which was stunning! Please note that reservations for this hike are required in advance and if you aren’t a Hawaii local then you do need to make a reservation and pay a small fee ahead of time to hike and to park here. Reservations open up 30 days prior to your hike date, so be sure to get that reservation in so you don’t miss this stunning hike! To book a reservation, you can click here. Please also note that you need to start your hike within the first 30 minutes of your timed entry to assure that there is enough parking space for the next group of hikers.
Hike the Lanikai Pillboxes Trail
Cost: Free
Lanikai Pillboxes Trail via Ka’iwa Ridge Trail:
- Length: .9 miles
- Elevation Gain: 393 ft
- Difficulty: Moderate
Our favorite hike in Oahu was hands down the Lanikai Pillboxes hike. It felt less like a hike at times, and more like a scramble making for a full body workout along several areas of the hike as you grabbed onto trees, rocks, and roots to steady yourself along the vertical gain. Once getting to the top, you are greeted with the view of the Lanikai pillboxes along the ridge and a stunning view of the Lanikai beach below. We felt like we were on top of the world here and couldn’t believe how stunning the view of the water was.
Visit the Pearl Harbor National Memorial
Cost: Varies depending on what all you want to see. We chose to only pay to see the USS Arizona Memorial, so it was $9 for both of us to visit. ($7 parking fee and $1 per person for the USS Arizona).
To book tickets for only the USS Arizona, you can reserve them here. If you want to book other activities like touring the Battleship Missouri Memorial, there will be additional costs involved. We suggest visiting the Pearl Harbor Website for more details and to figure out what all you want to do during your visit.
Tip: Visit Pearl Harbor early on during your visit to Oahu in case of bad weather! Unfortunately we weren’t able to end up seeing the USS Arizona due to a high wind advisory and therefore the boats weren’t running to take people to the USS Arizona for the day. They did offer to let us come back another day with better weather, however we weren’t able to take advantage of that due to the fact that we left seeing Pearl Harbor to the last day of our stay.
Waikiki Beach
Cost: Free
While in Waikiki, a can’t miss location is Waikiki beach – it’s a great place to watch the sunset! This beach can definitely get crowded though so if you aren’t a fan of crowds you may want to find another beach – luckily all the beaches in Waikiki are open to the public!
Drive through the Ho’omaluhia Botanical Garden
Cost: Free
Note: The Gardens are closed on Thursdays
Nestled in the windward side of Oahu you will find this stunning 400 acre botanical garden that is shockingly free to visit. This garden was established by the United States Army Corps in 1982 as a form of flood protection for the nearby Kaneohe, but also features plants from all over the world. Whether you choose to stay on the main road just driving through the scenery, or get out and walk the trails, this botanic garden is definitely worth a visit on your trip.
Visit the Byodo-In Temple
Cost: Adults: $10 per person
Seniors: $8 per person
Children: $6 per person
Temple Grounds: 8:30am – 4:30pm daily (Last entrance at 4:15pm)
Built as a small scale replica of a World Heritage site in Japan, the Byodo-In Temple is located at the foot of the Ko’olau Mountains in the Valley of the Temples Memorial Park. Visiting here is like you are stepping into another country entirely. You are surrounded by the tall mountain, this unique Temple, and koi fish ponds all around you. You can even ring the bell here for good luck!
Drive to the Halona Beach Cove and Halona Blowhole
Cost: Free
Halona Beach Cove, also known as the Eternity Beach or Cockroach Cove is a small beach accessible by driving to the Halona Blowhole Lookout parking area and taking a short walk downhill. The Halona Beach Cove is known for being a secluded swimming spot, a place to go cliff jumping (small cliffs) and even snorkeling. However, our favorite part was a natural cave like lava tube that leads to the beach. This area is also notable as a filming location for movies like 50 First Dates the Pirates of the Caribbean: On Stranger Tides.
The Halona Blowhole was also created by lava tubes, but is known for having a scenic lookout of the coastline and being one of Oahu’s wonders, often blowing seawater up to 30 feet into the air.
Go Whale Watching in the Winter Months
If you are visiting in the winter you have an extremely high chance of seeing humpback whales as thousands of them migrate down from Alaska to Hawaii every year at this time. The whale watching season in Oahu is from December through May with the peak whale watching season being January through March. We visited in late January/early February and were lucky enough to see a few families of whales on our whale watching tour and even saw a breach! If you are interested in taking the same tour we took, you can book that here.
Where to Dine:
Duke’s Waikiki
Cost: $$
Right near Waikiki beach you will find Duke’s, a lively beachfront restaurant famous for its Hawaiian style dining. We ate the fish tacos which were incredibly delicious, enjoyed the sunset on their outdoor patio, and enjoyed the live music. Although we thoroughly enjoyed our food and drinks, we did feel like the portion size vs the price was a bit crazy for our budget friendly mind set.
Banan Waikiki Beach Shack
Cost: $
This tiny little beach shack is known for their dairy free, soft serve ice cream made from frozen bananas. Located in surfboard alley next to Waikiki beach, this is a great place to stop for a delicious treat on your way to or from Waikiki beach. It’s also perfect for those like HallyAnn who are lactose intolerant!
Leonard’s Bakery
Cost: $
A staple restaurant in Oahu, Leonard’s Bakery has been around since 1952 and is known for their malasadas – a portuguese donut! We found this to be a delicious sweet treat, and definitely worth a quick visit. We suggest grabbing these on the way to another activity as there wasn’t much seating.
Earth Aloha Eats – Vegan Food Truck
Cost: $
Oahu has so many delicious restaurants, but they also have several food truck parks and it wouldn’t be a complete visit to Oahu without visiting at least one food truck on your trip. Our favorite food truck that we visited was just a few minutes walk from our hotel in Waikiki – Earth Aloha Eats! It’s a vegan food truck – but don’t let that scare you away if you aren’t vegan. We ate Mexican street tacos, pulled pork fries, and the teriyaki fries and all of them were amazing! Genuinely, this was our favorite meal of our trip!
Hawaiian Aroma Caffe at Waikiki Walls
Cost: $
We stopped here for a quick drink and some relief from the humidity in the AC, but honestly fell in love with this spot! This cafe had great happy hour drinks and the cutest little wall displays that we took full advantage of with a mini photoshoot. They also serve pizza here as well – although we didn’t eat here so we can’t speak to the food.
Island Brew Coffeehouse
Cost: $
Located right along the water, this little coffee shop is family owned, and has the cutest vibe. With a variety of seating both indoor and outdoor, we enjoyed sitting on the outdoor patio, enjoying the waterfront view, and drinking our lattes. Hint: We visited the Hawaii Kai location and stopped here before heading to the Halona Blowhole and Beach Cove area.
Junpuu Ramen
Cost: $
If you are looking for something savory, but still want to try some Hawaiian style food, Junpuu has a great Hawaiian style Ramen!
Check out our Wanderlog map for a full list of recommendations for things to do in Oahu!
Feel free to download our suggested 5 day Itinerary here. Note that you can also move days around to work better for your itinerary – but note that some of these places are closed on specific dates!