First Time To Hawaii? Discover Which Island to Explore First With This Easy Guide

Maui by Alberto Lama I First Time To Hawaii? Discover Which Island to Explore First With This Easy Guide I The Wander Life

Find your perfect island match.


Above photo via @albertolamanyc

Planning your first trip to Hawaii and unsure of where to start? With four main islands to choose from in this Pacific paradise, the decision of which one to tackle first can be an overwhelming feat. Armed with numerous visits to the islands myself (including for my wedding!), I’ve put together the below flowchart to help streamline the process. Whether you’re looking for culture, off-the-beaten-path adventure, bustling nightlife, a solid case of rest & relaxation or a combination of everything, follow the questions to find your perfect Hawaiian island match – then jump below for an intro into these magical stretches of sun, sand and sunsets.

 

Hawaiian Island Flowchart, Copyright The Wander Life I First Time To Hawaii? Discover Which Island to Explore First With This Easy Guide

Oahu

Photo via

The hub. This is where the prime action takes place with the bustling city of Honolulu and the thriving beaches, restaurants and nightlife in Waikiki. Pearl Harbor is definitely a site to see and experience given its historical significance, and while most of the action takes place along the south coast, you’ll also want to spend time exploring the more serene North Shore – especially if you’re a surfer.

The majority of the state’s population resides on this island, so you can get a taste of local life and immerse yourself into the aloha spirit of Hawaii’s culture. For those who like to shop, Oahu offers A LOT of options, including premium outlets featuring high-end designer brands.

Maui

Maui sunset, photo credit @karenlyuen I First Time To Hawaii? Discover Which Island to Explore First With This Easy Guide I The Wander Life

Photo via @karenlyuen 

If you think that you’ll be overwhelmed by the densely populated big city on Oahu, and that Kauai and the Big Island may be a bit too quiet for your liking, Maui is your island! There’s truly something for everyone to enjoy – whether you like beach and water activities, nature walks, scenic drives, cultural and educational sites, or ticketed entertainment.

One of the most breathtaking experiences you can have on Maui is to watch the sunrise above the clouds at Haleakala, a dormant volcano that sits 10,000 feet above sea level. The fun town of Lahaina offers lively action, while the hippie beach town of Paia offers a totally different, laid-back vibe. Looking for adventure? Drive the windy Road to Hana with its numerous stop-offs to hidden beaches, cave systems and scenic overlooks. There’s plenty to do on Maui and many choose this island as their honeymoon destination!

Kauai 

Kauai, photo credit @karenlyuen I First Time To Hawaii? Discover Which Island to Explore First With This Easy Guide I The Wander Life

Photo via @karenlyuen

They call this the Garden Isle for its lush greenery, and the beauty of Kauai makes it a prime location for filming. Jurassic Park, Hook, The Descendents, and Tropic Thunder are just a few films that have captured scenes from this island.

Home to Waimea Canyon, often described as the Grand Canyon of the Pacific, Kauai offers the most stunning coastlines of all the Hawaiian islands. The famed Nā Pali Coast is not accessible by car, but you can embark on one of the most beautiful coastal hikes you’ll ever go on, take a helicopter tour (highly recommended!), or cruise along the water to see some incredibly majestic views. (I’ve done all three!)

While it may rain a bit almost daily – how do you think the land stays so green?! – your days will be filled mostly with sunshine.

Big Island

Big Island, photo credit @karenlyuen I First Time To Hawaii? Discover Which Island to Explore First With This Easy Guide I The Wander Life

Photo via @karenlyuen

This island is actually named “Hawaii,” however is more commonly known as the Big Island. There’s definitely a lot of land to drive through – it’s twice as big as all of the other Hawaiian islands combined!

You’ll likely be staying in Kailua-Kona on the west, which offers more accommodations than the rest of the island. Venture east (a 3.5 hour drive) to the Hawaii Volcanoes National Park, where you may get to see a volcano erupt. Don’t miss the chance to see Papakolea Beach, also known as Green Sand Beach. There are only four green sand beaches in the world, so while this beach isn’t one for surfing or swimming, it’s definitely a unique sight at the base of the Pu’u Mahana cinder cone.