
Palm trees dotting the shore line, sunlight glistening off the endless blue water in front of you, mountains to your back, a cool ocean breeze against you skin. Surfers, like ants floating upon the water, waiting for the perfect wave. Beach-goers, Mai Tai in hand, relaxing along the shoreline. If this is what you think of when you think of Hawaii, you are absolutely right. Yet not quite.

What do you think of when you think of Hawaii? Why is this a place that is at the top of so many bucket lists? What is it that draws so many people to this set of islands in the middle of the Pacific?

Hawaii, O’ahu specifically, is both exactly like I imagined yet so much more.

To be honest, I always thought of O’ahu as a quick stop on the way to another island. Everyone wants to stop by, see the famous Waikiki Beach and visit Pearl Harbor then move on to “bigger and better” islands.
Yet, O’ahu, the second oldest of the main 6 Hawaiian islands, is so much more. It is a unique mix of east meets west, town and country, beach and mountains, energy and relaxation. There is so much diversity, history, culture, and adventure on this island that you could stay for a week and barely scratch the surface. It is a destination in its own right, not meant to be just a stopover point on your way elsewhere.

In future posts, I will touch on some of my favorite parts of the island but for now, I want to give you a little overview of this island and help you figure out if this is a place to add to your bucket list.
Let’s start with the type of traveler for which O’ahu (and Hawaii in general) is NOT a good match-
- The budget-conscious traveler– Hawai’i is not a cheap destination to travel. It’s not inexpensive to fly to, especially from the east coast. Lodging, food, and excursions are not cheap. We will talk about the value later but if you have a very strict budget, I would not recommend placing this high on your list. You will be frustrated by not being able to fully experience everything Hawaii has to offer.
- The time-strapped traveler– If you have a limited time to travel this may not be your best option. From the US mainland you will have a minimum 5-hour flight each way, 10-hours from the east coast. To truly experience all O’ahu has to offer, I would plan no less than a week. If you want to island-hop I would spend minimum 10 days but preferably closer to 2 weeks or more.
So, who is the ideal traveler for O’ahu?
- The Culturally and Historically Conscious Traveler- this island has so much to teach its visitors. If you arrive on the island with an open mind ready to learn from her people about their history and their way of life, your life will be truly enriched. Traveling is truly one of the only few experiences where you become richer the more you spend.
- The Experiencer– I made up this title but this is the person who wants to experience the place in its fullness. They don’t want to just sit on a beach with a mai tai in hand, though that may be part of the experience. They want to dig deeper than the surface, get to know the place more thoroughly. On O’ahu this may mean starting at the Bernice Bishop museum to learn a little of the history of the way-finding people and the Hawaiian royalty and then follow that up with a visit to Iolani palace to dig deeper into the stories of the Hawaiian royal lines. A visit to Pearl Harbor to learn about the history of the US involvement in World War II is a must-do. This type of traveler would enjoy some time in the busy Waikiki district for shopping and dining and people-watching on one of the most famous stretches of beach in the world but then they would escape to the north shore for quieter beach sitting. This traveler would enjoy the mountains of O’ahu by foot, horseback, or ATV. This person wants to move beyond just the instagrammable shot to really immerse themselves in the place.
- The Adventure Seeker– This piggy-backs on The Experiencer but focuses more on the adventure side of those experiences. O’ahu has much to offer on land and water. From soft adventures like snorkeling, hiking, and stand-up paddleboarding to harder adventures like surfing, zip-lining, and off-roading on an ATV. This traveler is on the move and wants to experience the island with all of their senses but especially through hands-on activities.
- The Giver– No, not the Lois Lowry book, this is the traveler that wants to give back to the land and its people. They are conscious of their actions while traveling and seek to truly get to know the people they encounter in order to offer something in return. This may be as simple as respecting the land and using reusable water bottles and straws. It may mean seeking out family-owned restaurants (that are amazing! Highway Inn and 12th Ave grill were some of the best food and owned by the sweetest families!) that may be a little more off the beaten path. It may look like doing research to find the best company to take you snorkeling that will honor the animals and water as you enter their environment.
I am hopeful that this gave you a glimpse into the island of O’ahu. Is this a good fit for you?

If not, it is totally ok. If you want a quick, less-expensive escape to disconnect on the beach with a drink in hand, there are other amazing places I with which I can connect you.

But if you want to travel to a place rich with history, culture, nature, wildlife, adventure, food, energy, and more, let me tell you more about O’ahu. Let’s work together to craft the perfect itinerary for YOU. Your trip will look different than your best friend’s or your sister’s or your neighbor’s or the well-meaning facebook acquaintance.