How to Pick the Right Hawaiian Island for Your Vacation by Anna Fishman

Updated: Oct 20, 2020

Which Hawaiian island should I visit? Confusing, I admit. It is very confusing. With the five main Hawaiian Islands available for selection, determining which one best suits you can be difficult. Often, this leads to yet another question, which of the Hawaiian island is the best?

There is no best. Simple. All of the major islands of Hawaii have just about everything that gives an island its appeal – calming beaches, soft white sand, lush vegetation and lots of cultural sites. But they also offer different things. Your choice of an island would depend on what you hope to get out of it.

Makena Big Beach, Maui


Maui is home to some of the world’s best beaches. It offers everything that makes Hawaii so special. Golden sunny beaches, majestic whales in the winter, a volcano, and relaxing resorts. Maui is your ideal resting place. If your vacation is meant to be a peaceful, relaxing time, visit Maui. Maui is also a great place if you are visiting with your family. There is also no shortage of things to do from snorkeling and swimming with the turtles, to hiking to the volcanoes and experiencing the luau.



Kauai, the Garden Isle, is the oldest island of the Hawaiian chain. If you wish to enjoy nature in its pure, romantic form, Kauai is the island for you. The grand waterfalls, remarkable coastal trails, unblemished beaches, lush green cliffs, and colorful gardens combine to make Kauai a place to love. Throw in a hiking visit to the Grand Canyon of the Pacific, and your Hawaii vacation is complete.

Waikiki Beach, Honolulu, Oahu


Home to Hawaii’s largest city, the capital city of Honolulu, Oahu is one of the most vibrant islands in the Hawaiian chain. Oahu has just about everything you’d expect from a modern city. A vibrant nightlife, natural wonders, historic feel, and a bustling entertainment industry, you’ll see it all. With all of its high-rise buildings, luxury shops, bustling restaurants, and nightclubs, you’d simply be enjoying a vacation in seemingly familiar surroundings. It’s impossible to miss a visit to the iconic Waikiki, one of the world’s most famous beaches.

Punaluu, Black Sand Beach, Big Island

The Big Island

The last of Hawaii’s biggest, most popular islands. The Big Island is the largest of the Hawaiian island chain. It is big, literally, bigger than all of Hawaii’s other islands when combined. A vacation in Big Island is one you wouldn’t forget in a hurry, and there is no shortage of activities to keep you busy. It is an island with history. Stories of kings, gods, and traditions are sure to grace your stay. Stunning waterfalls, untouched rainforests, silvery beaches, an active volcano, and snow-capped mountains. What’s not to love?

Molokai Coastline


If you want to enjoy the unspoiled and authentic Hawaii, Molokai is the place for you. Much like (and even more than) the Big Island, Molokai preserves a strong sense of history. It is home to the epic Kalaupapa Peninsula (site of a prominent leper colony). Of course, it doesn’t miss the ideals of an island, either, with long stretches of beaches and grassy mountains available for your enjoyment. In keeping with the local style, it’s not uncommon to find resorts with secluded cottages and condos.

Indeed, visiting Hawaii is an awesome way to spend your honeymoon or family vacation. Worried that you don’t have enough time to visit all of the major islands? Why not spend your time exploring just one. By spending time on a single island, you immerse yourself in its culture and its people. On your next visit, explore yet another. The difference is stunning. The beaches, history, and people are sure to keep you entertained. Every island has something for everyone.

Anna Fishman is the owner of Olegana Travel Boutique and plans incredible, unique and authentic luxury experiences around the world for couples and families based on her first-hand experience of traveling through 25 countries and visiting over 200 luxury hotels and resorts all over the world.  Anna promises you a stress-free travel planning process with an easy to follow itinerary that will save you a lot of time and energy so you can relax and escape to your own paradise where you will feel at ease that every detail has been thought out and taken care of exclusively for you. Olegana Travel Boutique is a five-stars rated travel agency, a member of Travel Leaders Network, Destination Weddings and Honeymoons Association, Adventure Travel Trade Association and is featured on The Knot and NJMom.

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