While you could make the drive around Oahu in a couple of hours, you probably didn’t come to Hawaii to quickly zip around and rush through your vacation. Why not spend a full day (or several days) exploring the island, taking in the natural beauty, and visiting some of the hidden gems it has to offer.
This template of a road trip will give you ample opportunity to see all the best the island of Oahu has to offer. You’ll have to plan your own accommodations at a hotel or Airbnb, and then apply this list to your own personal timeline. The island is small enough that you can either stop for the night along the way or stay in Honolulu each night and branch out from there. It only takes about 45 min. by car to go from Honolulu (which is on the southern part of the island) all the way to the north shore, so wherever you stay, you’re sure to have a great time.
This is by no means a definitive list. I encourage you to do your own research and modify this itinerary as you see fit. Just make sure you plan on renting a car in Hawaii in advance. As it is (obviously) an island, and if all the cars are rented already, there isn’t a way for any additional vehicles to be brought to the island at the last minute for you.
Leaving from the Honolulu Airport
We’re going to be driving counterclockwise around the island. If you land at Honolulu International Airport and are picking up your rental car from there, you’ll initially be heading east and then southeast to meet up with the coast.
First stop: Waikiki Beach
Whether you’re interested in surfing, canoeing, sightseeing, having a picnic, or just relaxing on the beach, this stop has everything you could want. It’s one of the most famous beaches in the world (so not necessarily a “hidden gem”), but it is absolutely a must-see during your stay on the island.
From here you’ll be able to have a spectacular view of Diamond Head (a famous geological feature) from anywhere on the beach, and you will be able to drive to the trailhead and hike the trail and be treated to even better views of the beach below.
Waikiki Beach itself is actually made up of four smaller beaches that all interconnect into one larger beach. If you so desire, you would be able to visit several beaches in one stop. Of course, while you’re here, you would also be able to enjoy all the amenities that the classic Hawaiian beaches have to offer both tourists and locals.
Stop Number Two: Pali Lookout
After Waikiki, you’ll continue to drive counterclockwise around the island until you reach the southeastern corner, where you’ll begin to head north. On the way north, you’ll be stopping at Pali Lookout. Only five miles northeast from downtown Honolulu, and with only a $7 entry fee for cars, you’ll be able to drive up over a thousand feet above the coastline through thick trees and dense forests until you reach the peak. At the top, you’ll be able to view all of the natural beauty Hawaii has to offer.
This lookout has special historical and local significance. The people of Oahu were united after a fierce battle here in 1795, with many of the defeated soldiers being forced off this cliff at spearpoint.
The Third Gem: Kaliua Beach
Heading all the way north, along the eastern highway, you’ll arrive at Kailua beach, which has a very local and hip vibe to it. It’s much more laid-back and relaxed when compared to Waikiki - if you can even imagine such a thing. Tons of local restaurants, eateries, turquoise green water, white sand - what more would you want in a beach destination? It’s a favorite spot of former President Obama, so if you get lucky, you might be able to spot him (and about a dozen Secret Service agents).
Much like other beaches on Oahu, you would have the option to paddleboard, kayak, surf, canoe, kitesurf, or just relax on the beach. There is plenty of available parking at all times of the day. Prepare yourself for stunning views of the surrounding mountains and some nearby islands.
Final Stop
On the way back to Honolulu, you’ll be heading south through the interior of the island. This is Oahu’s “west side”, and where you come across the Dole Plantation. A “must try” is the hybrid banana-pineapple crossover fruit. Imagine a shorter, fatter, banana that retains the texture of a banana but has the taste of a pineapple. I guarantee you’ve never tasted anything quite like this, and you’re sure to remember it for the rest of your life.
Journey’s End
Now that you have a basic guide for a road trip around the island, I encourage you to add in more stops and take as many days as you would like for this trip. There is so much to see and do here that it would be impossible to fit everything worth seeing in one article. It will be a journey that you’ll never forget, and even more so if it’s personally tailored by you to your specific Hawaiian island destination checklist.
