Couple’s Vacation Guide to O’ahu, Hawai’i


This post was originally written in 2016 when I was still working in a corporate job and saved up a week of vacation days to visit this magical island. I knew I had to be back one day for a longer period of time, and I’m so happy to say I have since spent 6 amazing months in O’ahu and have updated these recommendations (2021 edition) accordingly! Feel free to DM me on Instagram if you have any questions, I hope you have an amazing trip!

Tune into Episode 21 of The Wanderlover Podcast: Hawai’i Reflections 2016 vs. 2021

Hawaii is infamous for being a couples destination and we now know why! My boyfriend and I fell in love with its beautiful beaches, romantic atmosphere, kind locals, and luscious greenery. I’m definitely more of the planner in the relationship when it comes to travel so I had all the to-do’s, to-see’s, and to-eat’s all mapped out beforehand for our week in O’ahu.

We rented a car (which ended up being a smart car, that we at point strapped a kayak on top of haha!) to get around the island and highly recommend you do too because public transportation, or lack thereof, isn’t very convenient.

Here are our favorite things to do on the island:

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1) Waikiki Beach

Waikiki Beach is arguably one of the most well-known beaches in all of Hawai’i – and also the most touristy – but hey, if it’s your first time you should check it out! We stayed at an Airbnb right next to the beach with its own surf shop, so surfboards, beach umbrellas, and snorkels were all included with our stay. Score! The waves are perfect for beginner surfers, and there are tons of restaurants and shops nearby.

Haven’t signed up for Airbnb yet? Here’s $40 off your first stay, and it never expires!

Longboarding in Waikiki Hawaii
Longboarding in Waikiki with Diamond Head in the background

*Update: Take a surf lesson!!! I promise you’ll have so much fun if you go out with an instructor who knows what they’re doing. I recommend lessons from Moku, where they also offer 2 hour surfboard rentals for $5 USD. Much less expensive than board rentals on the beach. The first time I visited Hawai’i I didn’t surf, and regretted it for years after really understanding how amazing the conditions are at Waikiki for beginners. 

Don’t know where to stay in Waikiki? Check out The Surfjack Hotel located in the heart of Waikiki. They also have chill, live music every night.

Haven’t signed up for Airbnb yet? Here’s $40 off your first stay, and it never expires!

2) Kayak to Chinaman’s Hat

Drive up the east coast (stop at the Poi Factory if there’s not a huge line!) and strap some kayaks on for a beautiful paddle to Chinaman’s Hat. You’ll get a beautiful backdrop and have the option to hike to the top. You’ll see turtles, fish, and at low tide there are a few sandbars nearby to explore!

Kayaking to Chinaman’s Hat

3) Hanauma Bay

Hanauma Bay is famous for its diverse marine wildlife. Enclosed in the southeastern area of the island, Hanauma Bay is home to a big reef and hundreds of species of fish. If you get lucky you may even see turtles! The water is crystal clear and I really recommend bringing your own snorkel mask for this one

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4) Manoa Waterfall

150-foot Manoa Waterfall is at the end of a 1.5 mile hike through the island’s lush, green, tropical rainforest. Put on your sneakers and get active! Honestly can’t decide whether the rainforest or the waterfall was more breathtaking so you just have to see both for yourself!

5) Ka’au Crater Trail

If you have a full day to spare and want to check out the hardest hike I’ve done in my life, look up Ka’au Crater Trail. Since Hawaii has closed the famous “Stairway to Heaven” trail and it is now illegal to hike it, we tried out some of Oahu’s other amazing hikes. The whole hike takes around 6-8 hours, and you have the option to go around the entire crater at the top. The views are absolutely breathtaking and it’s by far the one that is worth alllll the effort. This trail is not easy!! Under no circumstance should you do this trail on a rainy day as the trail can get very slippery. There are many sections when you will be climbing near vertical sections. Pack lots of water and wear proper hiking shoes. Even on dry days, you are going to get dirty on this hike.

The steep climb above Ka’au Crater

6) Diamondback Trail

Diamondback is a historic 1.0 mile hiking trail up an extinct volcano with an amazing viewpoint overlooking Oahu. If you’re up for some sightseeing, this hike is definitely a to-do!

7) Makapu’u Tide Pools

Makapu’u trail is fairly easy to get up to the lighthouse, and you have the option to hike down to the tide pools! If you’re feeling super adventurous, you can actually park and start around Lele’s chair, and scale the cliffs to arrive at the tide pools first, then hike up to the lighthouse viewpoint! Just look how blue the water is!

How blue is the water at the Makapu’u tide pools? Very blue

8) Kahana Bay Beach Park

As you guys can probably tell by now, yes, we are an active couple! And we loved our kayaking adventure at Kahana Bay Beach Park. This is when we learned that yes, it is possible to strap a 12-foot long kayak above a 2-person smart car. It was amazing kayaking through the low-hanging plants and seeing all the different varieties of plant-life.

9) Luau

The most popular luau on Oahu is at the Polynesian Cultural Center. Luau tickets are pricey, upwards of $100 per person but so worth the experience! You get lei’d as soon as you walk in the door, all local dishes are served at dinner, and the performance is nothing short of entertaining, including fire-dances and traditional island dances from other Oceanic countries.

10) Food trucks: Pupukea Grill + Giovanni’s Shrimp Truck

Drive up to Oahu’s north shore and stop by some of their many food trucks! You will not be disappointed by Pupukea Grill or Giovanni’s Shrimp Truck, serving the best garlic shrimp plate on the island. There may be a line but it’s well worth the wait – literally finger-licking good.

11) Tamura’s FIne Wines & Liquors

Now onto my favorite Hawaiian food that I ate every single day: poke. Cubes of the freshest raw fish, marinated in so many different varieties I couldn’t try them all. The fish is so fresh that even gas stations (my favorite at Kuhuku Superette), supermarkets (Foodland is not bad!), and even liquor stores had poke for sale! Crazy right?! My favorite was the poke at Tamura’s Fine Wines and Liquors and it was so good I went back two more times to get more.

I would go back to Hawaii just for their poke

12) Leonard’s Bakery

I didn’t know what malasadas were before coming to Leonard’s Bakery, but now I will never forget. Malasadas are a Portuguese doughnuts without a hole, lightly fried, and coated in sugar. Another line absolutely worth the wait, and I of course had to try every flavor filling. The custard was my favorite!

13) Dole Plantation

Dole plantation is a pineapple plantation home to the world’s largest maze, and the well-known pineapple ice cream they serve with chocolate.

14) Pipeline on North Shore

If you’re visiting during north shore swell season (Around October – February), check out Pipeline on the North Shore where waves get massive and it’s always incredible to see pro surfers killing it out there in the water! For beginner surf spots, Pua’ena Point is always an option, and for a more intermediate break try Chun’s or Freddie’s!

Hawai’i is a magical place and we will definitely be back! Let me know if you have any questions about the island of Oahu in the comments below!

Are you ready to start planning your next  Hawaiian vacation?!

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