So I’ve been to two islands in Hawai’i: Maui and Oahu. Of the two I’d say I prefer Maui, but it’s been a while since I’ve been there (guess I have to go back soon!), so I will share my tips for Oahu instead.
I’ve actually been to Oahu twice fairly recently (this decade), once for my cousin’s wedding, and once because the flight was super cheap! Yes, that is a valid reason to go somewhere. I got up to a few different things each trip, but I will share some of my favourites and a few pieces of advice.
Transportation
Flying into Honolulu from the mainland means you’ll most likely be landing in the daytime. If you don’t want to rent a car, there are plenty of options for airport transportation. If you’re heading for Waikiki, and you only have carry-on luggage, you can hop on the public bus for about $3. There are also various shuttles and taxis.
There are lots of places to explore once you’re on the island. The two places I’ve stayed are Waikiki and Kailua. I definitely found Waikiki to be super touristy, and a little on the expensive side, while Kailua, which is on the other side of the island, was a little more relaxed and low key… except for when Obama showed up. But that’s a story for another time…
If you’re really looking to get the most out of the island I would recommend renting a car. A lot of the places you can technically get to by bus but it’s quite difficult the further out you get from the main cities.
Things to do, places to see!
Pearl Harbor Memorial
Unless you’ve been hiding under a rock, you’ve heard of the tragedy at Pearl Harbor. I was impressed by the attempt at balance when they were looking at the tragedy. It’s definitely worth making your way over there. You can actually explore some of the submarines and there are many different exhibits.
Diamond Head Hike
This hike is easy to access from Honolulu. You can take a bus most of the way there. The hike up the crater is only about a mile, but it gets fairly steep and there are a lot of stairs involved. It’s not technical though, so this shouldn’t scare you off. The view is worth it.
Pillbox Hike
This was just a short walk from where we were staying in Kailua, so I took a chance and hiked up. And by hiked, I mean I walked up in flip flops. Slightly more technical than Diamond head as there aren’t nice stairs to get you to the top, but you get a nice view over the other side of the island.
Ahupua’a ‘O Kahana State Park
This park is on the Eastern side of the island, about half way to the North Shore. There are lots of hikes in this area as well. We opted to try to follow a trail that lead back into the lush jungles on the island. I say try because I’m pretty sure we took an older trail for the first portion of it, as we basically had to bushwack for 20 minutes, but we completed the loop and found some great scenery.
North Shore Beaches
You can stop pretty much anywhere along the North Shore and be impressed. Cars line the highway along beaches, so don’t be afraid to join the party. We made two or three different stops. There were also some cute little towns, so definitely take your time to explore the area.
Kaena Point State Park
The place to go for sunsets! Also, there are birds and seals that like to hang out on the beach, just don’t disturb them. It’s a bit of a walk, with lots of beaches on the way. If you head out for sunset, be sure to bring a flashlight to find your way back after dark.
Swimming with Wild Dolphins
This one is tricky. There are a few tours that offer swimming with dolphins, but finding a responsible one is difficult. I ended up booking with Wild Side Specialty Tours and was impressed. Basically, you take a boat out into an area that dolphins like to frequent, jump off, and hope some swim by. No guarantees on sightings here, but you won’t be contributing to dolphins in captivity, which is a major win. You also get to snorkel in the reefs with turtle and fish spotting. It’s a bit out of town, but I did manage to get there on the bus, so you don’t NEED a car to do this.
Hanauma Bay
Sadly, I don’t have great pictures of this area, but it’s another “swim with wild animals” experience. This bay filled with coral is a snorkelers dream. Even though it can be packed with tourists, it’s still amazing. Be sure to wear reef-friendly sunscreen so you don’t damage the ecosystem!
Waikiki Beach
Who hasn’t heard of the iconic beach? Although there are lots of other beaches, it’s worth spending at lease some time here. There are lots of stores and tourist attractions just steps from the sand. If you are so inclines you can take a ride in an outrigger canoe or learn to surf! They also have free hula performances in the evening some days; check out the schedule.
Lanikai Beach
If you’re looking for less crowds, but don’t want to wander too far, Lanikai Beach offers beautiful sand beaches and calm waters. You’ll have to park on the street and walk down a short path to the beach, but it’s much more relaxing than the hustle and bustle of Waikiki.
There are a lot of adventures you can get up to on the island, so don’t take this to be an exhaustive list. These are just the things that I’ve had fun doing, and hope you do too. If you have any questions, feel free to reach out!
zen on a plane 
Nice post Jenn. I tried to ‘like’ it. Not sure I succeeded – but I did like it. I’m in the middle of a travel nightmare. Flying business class and missed our connecting flight in Frankfurt – thunderstorms apparently – Lufthansa did not treat us well – many delays and problems. Not planning to fly Lufthansa ever again! Love Grandma
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