Good question. And to be honest, there is no cookie-cutter answer, as each “side”of the island has so much to offer. That being said, the south shore, windward side, leeward side, and North Shore (the latter must be capitalized) all have their own unique appeal and will differ in the eyes of the beholder.
As kama’aina we have our own insight, but as a service that chariots visitors from the airport to their Oahu destination, we know the varying expectations after numerous conversations with our passengers. We also get their feedback on their return to HNL. Today, we’re applying all of the above to provide you with a quick and succinct guide to each of the four corners of Oahu so that you can make a more informed decision about where you should stay.
Your Guide to Which Side of the Island You Should Stay On When Visiting Oahu for the First Time
South Shore
This is where most everyone stays. It’s home to the city of Honolulu and world famous Waikiki Beach and all of the bells and whistles that come along with it.
Notable beaches include Waikiki Beach (obviously) and area, Ala Moana Beach Park, and Diamond Head Beach. Swimming, snorkeling, surfing, scuba, kayaking, paddle boarding, canoeing, and all other water sports and beach activities are bountiful on the south shore.
Shopping is also top notch, with Ala Moana Center (the largest shopping mall in all of Hawaii) located just minutes from Waikiki, in addition to a hoard of other shops along Waikiki’s Kalakaua Avenue which also counts the International Marketplace and Royal Hawaiian Center.
There is also every imaginable dining option on the south shore, with an eclectic blend that includes mom and pop diners and world class eateries alike, all of which run from Chinatown to Kaimuki and beyond.
Because the south shore is the proverbial center of all things (cultural activities too), there are hotels and resorts everywhere, and even during busy season (all year?) you’ll find a place to stay, although with rates that swing up significantly during high traffic periods (i.e. holiday season, spring break, etc.). Transportation is also plentiful, with numerous buses operating in the area and car rental services every few blocks.
The south shore is perfect for both first time and seasoned visitors that like to be where the action is, and want the conveniences that come along with it, including the ability to grab a tube of toothpaste at midnight.
View flat rates from HNL to Waikiki and other south shore communities
Windward Side
This is undeniably the most breathtaking and diverse side of the island. Some might say it’s so beautiful it’s ridiculous. Coastal recreation and sightseeing are unmatched, as you leave Hanauma Bay (world famous snorkeling) along Kalaniana’ole Highway and watch it all unfold. You’ve got Sandy Beach (a bodysurfing and boogie boarding capital), Koko Crater, Halona blowhole, Makapu’u tide pools and hiking trail, Waimanalo Beach, Lanikai Beach, Kailua Beach, and Kaneohe which is home to Chinaman’s Hat (Mokoli’i island) and Kualoa Ranch aka Jurassic Park.
There are shopping and dining options throughout, with Hawaii Kai and Kailua (learn more) being highlights, but accommodations are certainly more sparse than what you’ll find on the south shore, with most people opting for vacation rentals via Airbnb and the like.
The windward side is perfect for those of you who want to keep the bustling scene of Honolulu at an arm’s length, but still find comfort that it’s nearby if you need it.
View flat rates from HNL to Hawaii Kai, Kailua Beach, and other windward communities
Leeward Side
Ten years ago we’d tell first time visitors to skip staying on the leeward side of the island unless they came for golf and complete relaxation. But fast forward to today, and things have changed. In addition to the golf, beach, and country club styled resorts of Ko Olina, (including Disney Aulani) you’ve got exponential growth in the community of Kapolei which has been nicknamed the new Waikiki. With the recent development you’ve got mainstays such as the Wet n’ Wild Waterpark and a wave of shops and eateries.
For those that want to stay more connected to the local communities of Oahu, the leeward side promises to fulfill those ambitions. You can mingle with the local crowds in Ewa Beach and Makaha, the latter of which puts on quite the display of surfing prowess during the big swells of winter. Here, you will also find some of the best snorkeling at Kahe Point Beach Park.
The leeward side also offers close proximity to Pearl Harbor and the islands most famous luaus, including Germaine’s Luau and Paradise Cove Luau.
The leeward side is a bit schizophrenic, given the fact that it is home to both the islands most grand resorts and impoverished tent communities alike. It’s a tough one to figure out for many, which may indeed be a part of the appeal.
View flat rates from HNL to Ko Olina, Kapolei and other leeward communities
North Shore
There is nothing quite like the North Shore of Oahu, and we’ll do our best to not let the favorable bias shine through. It may be a bit of trek to this crown of the island, but it’s worth it. However, while EVERYONE loves visiting the North Shore, is it a great place to stay, given that it’s much quieter that the rest of Oahu? You be the judge.
The mantra here is keep the country, country. The expression has been coined by the local community in an effort to keep major development at bay, and it also asks visitors to respect this fact by respecting the community when venturing through. And yet, there is nothing off-putting about any of this.
Island country charm exudes from every lush nook and cranny running from Waialua to Kahuku, with nothing but boutique shops and eateries (for the most part) to spend your money at. There are more food trucks than brick and mortar restaurants, and water sport activity shops are located outdoors as much as indoors. Sure there’s a Starbucks and McDonald’s but most people prefer to get their coffee at the locally owned Coffee Gallery and their breakfast at either Kono’s or Breakers, all of which are located within the North Shore Marketplace.
This is a surfing community through and through, but there is also fishing, paddling, shark cage tours, scuba diving, horseback riding, hiking, macadamia nut farm tours, and much more along the seven-mile-miracle. You’ve got Laniakea Beach (aka Turtle Beach), Waimea Bay and Valley, Banzai Pipeline, and Sunset Beach to name a few top spots.
“Big name” accommodations are limited to famed Turtle Bay Resort and Courtyard Marriott (in Laie, towards the windward side) but the North Shore is well known for its bounty of vacation rentals and bungalows, including one real gem – Ke Iki Beach Bungalows which is multi-bungalow property located right next to Shark’s Cove off of Kamehameha Highway.
The only downside, if you can call it that, is that things shut down pretty fast after dusk on the North Shore, with nearly all shops and eateries closing down around 9 or 10 PM. However, if you’re looking for some hard earned peace and quiet in paradise, then the North Shore may be for you.
View flat rates from HNL to Haleiwa and other North Shore communities
Honolulu Airport Transfer can take you to (and back from) any part of the island you decide to stay on. Just give us 24-hours notice and we’ll take care of you and your party. View all flat rates and call us at 1.800.929.1219 or complete the form found here.