With nearly two-thirds of the Hawaiian population residing in Honolulu and the surrounding areas, it can feel as though the entire island of Oahu is one huge city. Luckily, it’s not – technically. Whenever you want to escape the hustle and bustle of Honolulu, you can head to any of the island’s charming small towns. These small Oahu towns are full of old-world Hawaiian charm, history, adorable shops, and positively breathtaking views. Let’s explore the best towns in Oahu! 

From coastal communities to inland cities, this epic Oahu road trip measures in at 76 miles, just under two hours of driving time, and stops in eight of the island’s most charming and picturesque small towns – from Wahiawa to Hawaii Kai.

Screenshot/Google Maps
1. Wahiawa
Surfing The Nations/Flickr
Wahiawa, HI 96786, USA
Damon A./Yelp
Home to more than 16,000 residents, Wahiawa is located between the island’s two volcanic mountain ranges on Route 99, the road most commonly taken by those traveling to the North Shore from Honolulu. But if you were to stop in town and take a look around, you would see that there is more than meets the eye in this small inland city.
2. Waialua
brookpeteerson/Flickr
Waialua, HI 96791, USA
brookpeterson/Flickr
Located on Oahu’s north shore, past Haleiwa is the small community of Waialua. With a population of 3,800, this rural community has little more to offer than gorgeous beaches, charming farms and the always delightful Waialua Sugar Mill.
3. Haleiwa
BOMBTWINZ.COM/Flickr
Haleiwa, HI 96712, USA
tdlucas5000/Flickr
Voted as the state’s favorite small town by HAWAII Magazine, Haleiwa seems like a world away from bustling Waikiki. This sleepy surfer town on Oahu’s north shore has a laid-back vibe and charming aesthetic, but also luxuries like killer beaches, mouthwatering restaurants, art galleries galore, adorable shops, and stellar vacation rentals.
4. Laie
Daniel Ramirez/Flickr

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 The 'Road to Hana' is an adventure. Many parts of this winding road narrow to just one lane as it goes through one of the truly last undeveloped tropical areas of the island of Maui, Hawaii. You can see the road winding around the sea cliffs of this picture, as the powerful ocean waves create a misty spray.

Hana Highway Practically Runs Through All Of Maui And It's A Beautiful Drive
Laie, HI 96762, USA
Floyd Manzano/Flickr
This small town on the northeast shore of Oahu is home to two major institutions: the Polynesian Cultural Center, and Brigham Young University’s Hawaii campus. Other than that, you’ll find basic necessities, beautiful beaches, and a retreat from the bustling capital city of Honolulu – even though it’s just an hour’s drive away.
5. Kaneohe
NASA Earth Right Now/Flickr
Kaneohe, HI 96744, USA
Puneet Abbott/Flickr
Located on Oahu’s breathtaking windward coast, the picturesque seaside city of Kaneohe experienced an increase in popularity of 324 percent on Airbnb, but the lush oasis is home to some breathtaking beaches, truly incredible hiking, and several hidden gems – both natural and man-made. Must-visit stops include the Byodo-In Temple and the Ho’omaluhia Botanical Garden.
6. Kailua
Jordan/Flickr
Kailua, HI, USA
Annie/Flickr
Located on Oahu’s windward shore is the breathtaking – and award-winning – Kailua Beach and historic Kailua Town. The beach is a haven for water sports enthusiasts, and an influx of residents and visitors alike have caused real estate prices to skyrocket. But there’s still a sort of charm in this bustling community – and the adjacent beach’s crystal turquoise waters and white sand.
7. Waimanalo
David Siu/Flickr
Waim?nalo, HI 96795, USA
jai Mansson/Flickr
World-renowned for the amazing Waimanalo Beach, this census-designated place is as about as country as it gets on Oahu. The community is so small that the public library is actually housed inside of the local school.
8. Hawaii Kai
John Colby/Flickr
Hawaii Kai, Honolulu, HI, USA
Lawrence Wong/Flickr
This residential community on the island’s eastern tip is not only one of the most upscale areas on Oahu, but is home to endless natural beauty, including the stunning Ko’olau mountains, a picturesque marina, and Koko Head. Home to nearly 30,000 Hawaii residents, there is a ton to explore in this magnificent "town."

Is there anything better than a good road trip? Perhaps a budget road trip around Oahu, or an Oahu waterfalls road trip?

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Best Towns in Oahu

Tori Jane | July 05, 2022

What are some of the best towns in Hawaii to get away from it all?  

Hawaii is an astonishingly beautiful state with so many things to do and see on each island; it can be hard to know where to begin. Well, why not begin by checking out some of the most delightful small towns in Hawaii? Some of them are adorable beach towns and others are more inland (though they’re all on islands, so they’re all destined to be amazing). Among our favorite beach towns in Hawaii are Lahaina, on Maui, which is an excellent place for history buffs and lovers of the ocean alike thanks to its rich and fascinating history. Another excellent town in Hawaii to escape to is Kailua-Kona, on Big Island, which is a resort town and often simply referred to as “Kona”.  

What are the cute towns in Oahu I should add to my bucket list?  

So, that being said, what about Oahu? Surely there are adorable towns there, right? There are (of course)! Some of our favorite cute towns on Oahu include gems like Haleiwa, which is one of the most popular getaway locations in Hawaii, where you can check out local culture, history, and more – all with a jaw-droppingly beautiful view pretty much no matter where you are. Of course, we couldn’t get away with talking about getaways in Oahu, Hawaii without mentioning Waikiki, which is the most popular destination for visitors and locals alike and easily one of the most scenic places in Hawaii. It NEEDS to be added to that bucket list ASAP.  

Where are the best towns in Oahu Hawaii for a romantic getaway?  

Hawaii is easily recognized as one of the best states for a romantic getaway, and it’s pretty obvious as to why. It’s truly the picture-perfect image of paradise, and to think it’s one of the states in our beautiful country (how lucky)! Some of the best small towns in Hawaii for a romantic escape include Princeville’s North Shore, on Kauai. It’s home to some of the best resorts in Hawaii and some of the most incredible beaches in Hawaii as well. You can’t miss that one – it's perfect for anniversaries, weddings, and more, though you’ll want to book well in advance due to its overwhelming popularity. North Shore Oahu is also picturesque and breathtaking – definitely worth a trip!  

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