The Hawaiian Islands are often spoken of as one place, yet each of the five main islands carries its own character, rhythm and appeal. With insights from our local go-to insider, Debbie Misajon, choosing the right island becomes less about checking boxes and more about finding the Hawai‘i that feels your own.
Oahu
“This is where our capital, Honolulu, is located. It’s the birthplace of surfing. It has a bit of everything from incredible hiking, beautiful beaches, hole in the wall dining, incredible Hawaiian food, and James Beard Award-winning chefs, albeit one retired. There’s the elegance of old Hawaii in the halls of I’olani Palace and Queen Emma’s Summer Palace to the tourist traps of Waikiki. You’ll find a blend of Asia and the West throughout Oahu. The yachts are abundant and sailing at sunset with Diamond Head in the background is something special.
Oahu is for everyone – adventurous, quiet, hikers, lovers, there are so many things to experience. With my background at Aman Resorts, If I used the analogy of Aman in Bali, I think of Oahu like Amanusa, busy busy.”
Maui
“The capital of the Kingdom of Hawaii was Lahaina until 1845. What’s lovely about Maui are the beautiful beaches, up close whale-watching, easy offshore snorkeling, and established restaurants. You can do a lot, but you can also do very little. There’s an abundance of hiking trails that lead to multiple waterfalls, many with swimming holes, including hiking in an inactive volcano, Haleakala. The crater offers numerous trails leading through surreal landscapes.
And if you enjoy helicopter touring, you can explore beyond Maui for aerial views of Molokai’s seacliffs which are the tallest in the world, Lanai which is privately owned, as well as several interesting outlying islands and rock formations. Many come here for the deep-sea fishing and golfing. It offers epic scuba diving sites and the gorgeous drive along the road to Hana.
Maui is a fabulous honeymoon island, wonderful for relaxing, hiking, and beach going. Maui is like Amandari, a bit of bling, but quaint to explore.”
Big Island of Hawaii
“Hawaii Island is the size of all the other islands put together. It has 2 active volcanoes, white and black sand beaches, long drives in between, and just over 100 documented waterfalls albeit most are inaccessible. The Kona side of the island is typically sundrenched, there are more yacht operators, resorts, and private homes, and white sand beaches. But the east side – Hilo – is lush where the waterfalls are, bridges and deep valleys, black sand beaches and coves to swim in, sugarcane history, and of course Hawaii Volcanoes National Park with miles of easy to moderate hiking paths, lava tubes, and more. And it’s famous for deep sea fishing experiences, scuba diving sites and you’ll find many luxury resorts, and golf courses.
Hawaii is all the islands mixed into one with something for everyone. Hilo feels like old Hawaii, Kona is more like the mainland, but most activities are found here. It’s culturally significant as it is the birthplace of King Kamehameha and there are lots of legends to be learned.
Hawaii is for active travelers, explorers, curious, enjoy driving and exploring. Hawaii is like Amankila – wow, out there with some activities.”
Kauai
“Many argue that Kauai is the most beautiful island. And it is absolutely breathtaking. It’s the oldest island, the jagged cliffs along the Napali coastline are millions of years of erosion, it’s dramatic. The helicopter touring and private boat charters are experiences that stay with clients the rest of their lives because it is just that gorgeous. Of course, the most famous hiking trail in the islands is on Kauai – The Kalalau Trail – is a life changer as well. Even segments of it have moved travelers to tears, similarly hiking in Waimea Canyon is a special experience.
Kauai is a wonderful honeymoon destination, but equally suited to wellness, adventure, and active travelers. It’s very laid back, slower of all the islands with quiet nights. Kauai is like Amanwana, hip, laid back, groovy.”
