Which Hawaiian Island to Visit First

While there are eight main Hawaiian Islands, two (Niihau and Kahoolawe) are forbidden, and two others (Lanai and Molokai) make more sense for those who have already experienced the other more populated among the archipelago. These final four are primed for first time visitors, with each boasting its unique own offering for the uninitiated. Today. we’re providing succinct but informative break down this quartette so that you can make a more informed decision about which makes sense for your first foray into the island chain.

Breakdown for Which of the Four Most Popular Hawaiian Islands First Time Visitors Should Consider

Oahu – For Those Who Don’t Want to Leave the Comforts of Mainland Behind

Oahu is known as the “Gathering Place” for a good reason. It has something for everyone which is why everyone comes to the island which is packed with a population well passed the million mark. Most people lose their island virginity in Waikiki, which is quickly becoming the Las Vegas of the North Pacific, without the casinos (yet).

For some, it’s a little off-putting to now find H&M and Forever 21 at the very same place King Kamehameha landed a huge fleet of war canoes to slaughter opposers and unite the islands. But in the end, it fills a demand for those that feel a little wary about being marooned on an island for seven to ten days. Waikiki Beach, Honolulu, and South Shore have every imaginable amenity at your disposal. Need some dental floss and a can of Macadamia Nuts at 11:53 PM? You’re set, with nearly two dozen ABC Stores ready and willing to sell you everything from that to $20 ukuleles.

But don’t run for the mauna of the less densified islands below quite yet, because within a quick Uber or bus ride away you’ll find the Hawaii you saw on the brochure that brought you here. The windward side, for instance, boasts what may very well be the most breathtaking stretch of rugged coastline you’ll ever see. Running from Halona Cove (and blowhole) up through to Sandy Beach, Makapu’u lookout, Lanikai Beach, Kailua Beach (including the Mokes) and Kaneohe which is home to Kualoa Ranch (aka Jurassic Park), the windward edge of Oahu is incredible. On the flip side, the leeward cousin may not be as awe-inspiring with it’s scorched dry landscape and tent cities with never ending multi-residential construction to displace them, but it’s also home to the world famous Kapolei resorts, including Disney Aulani, Four Seasons Ko Olina, and the Marriott Beach Club. The leeward side is also known for having some of the best open ocean snorkeling at Kahe Point, and located further north is the legendary surf spot, Makaha. However, the BEST part of Oahu, is the fabled North Shore, which is true to the #islandlife you came for. Collectively, the North Shore’s census designated rural zones of Waialua, Haleiwa, Pukukea, Kawela Bay, Kahuku, and Laie (sort of) deliver the most diverse stockpile of sand, surf, food trucks, vacation rentals, and shave ice syrups on the island.

View activities, attractions, accommodations and more on Oahu.


If Oahu has a nemesis, it’s Maui. Of course, this is only in the eyes of visitors, who like to debate about which of the two is better. Pundits for Oahu will quip about how Maui is too slow for them, while those in the corner of the “Valley Isle” like to complain about Oahu’s over saturation of bloated and sun charred tourists. While Maui has its fair share of resort communities (Kaanapali, Kihei, Wailea) the island is more sparse, artsy, and more known for it’s banana bread than shopping malls.

Quaint Lahaina Town is exactly like an old whaling village that was pillaged by missionaries two-hundred years ago should be, while neighboring Kihei is more “rural” than touristy.

More info coming soon.

View activities, attractions, and more on Maui.


Coming soon.

View activities, attractions, and more on Kauai.

Big Island Hawai’i

Coming soon.

View activities, attractions, and more on Big Island Hawaii.

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