How To Maximize Your Hawaii Vacation!

Two friends enjoying sunny coastal scenery.

If you’re anything like my wife, “winging it” won’t work for you. So, how does one maximize their Oahu vacation?! Hopefully we can show you some ways to do so here! Please feel free to add to the list!

This may seem obvious but we’ll say it anyway; figure out what you and your party want to do. Some people simply want to “have fun” but what kind of fun are you aching for? There are so many things to do here on Oahu from parasailing and surfing to museums and sight seeing!

Speaking of sites, if you are here for the views, there are TONS of places to whet your appetite! In this case, I would – unbiasedly – start off with a Oahu Circle Island Tour! Even if it’s not with us at The Pineapple EXP, it’s still highly recommended. I say this because, with this tour, you’ll be able to see many of the go to scenic places here on Oahu. You will even get information about the places that we pass by like The Polynesian Cultural Center, Sea Life Park and The Bishop Museum. The Oahu Circle Island Tour is even good for people that want to take an overall look at what Oahu has to offer while making some friends along the way. All while not having to worry about driving!

So, you’ve done the Oahu Circle Island Tour, now what? Get out of Waikiki! Get out get out get out! There is way too much Oahu to see for you to stay more than a day in Waikiki. Even if you take the bus. Oahu has one of the top ranked public transportation systems!

Note; if you are planing on going to the North Shore via Bus, plan on a 2 1/2 hour one way trip. Which brings me to the next suggestion; rent a car!

There is an app called “Turo” wherein you’re able to rent directly from locals here. It’s safe, easy, efficient and cheap! Also, it’s another way of supporting local! Driving around Oahu is amazing. We used to do it every weekend in high school (when we could borrow our parents car) and college. Still do it every now and then to this day!

How the clouds slowly crawl across the tips of the Ko’olau mountain ranges’ sharp edges. How it’s many cliffs demand your gaze and never disappoint. A couple of reasons why we always say “No” to the inevitable question; “Do you ever get sick of driving around everyday?”. We will create a whole blog about the places you should visit in your rental car!

Time your trip correctly! By far THE BEST time to come to Hawaii in general is Whale season, hands down. This is December though May. During these times we see many Kohola (Humpback Whales) on our Oahu Circle Island Tours. Not only that, Spinner Dolphins, too!

When you come to Oahu, you’ll feel it. Her history. It hugs your body at every beach. Every landmark. There’s no escaping it. Even in the modernized Waikiki there are flashes of its past like the Moana Surfrider and it’s glorious pillars that date back to 1901. So embrace it. Embrace the history like an old friend you had a crush on in high school. Learn about how this place came to be even before you come here. I promise you it will make your trip all that better!

The most important tip on how to maximize your Oahu vacation is to remember; this is Hawaii, relax! Kick off your shoes and walk barefoot a few places (you’ll see this a lot with the college kids in the Manoa area). I’ve never seen a sign that said “no shoes, no shirt, no service” so take advantage! Give it a shot, go to a fast-food place -barefoot. Go to a sit down restaurant -barefoot. Go to Gucci and try on a new pair of paints -barefoot. I don’t know anywhere else in the United States where you can do that, so hey, might as well.

Don’t be so stressed! Get excited! You are, OR are almost, here! Now, get ready to enjoy Hawaii! -barefoot!