Hawaii Trip Planning 101: Which Island Should You Visit?

Hawaii is many people's definition of paradise for obvious reasons. What many people don't realize is that there are eight main islands to pick from. After visiting all of them, I will tell you a bit about each island and help you plan your perfect vacation!

One hundred thirty-seven officially recognized islands make up the state of Hawaii. Most of these are tiny and uninhabited. The eight main islands are Hawai’i, Maui, Koho’olawe, Moloka’i, Lana’i, O’ahu, Kaua’i, and Ni’ihau. Traveling between islands cannot be done by boat or ferry except Maui and Lana’i. Although flights between islands would probably be the cheapest part of your trip, you may want to pick one or two islands for your vacation.


O’ahu: The Gathering Place

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If you’ve seen Hawaii-based TV shows, they were probably filmed on O’ahu. At only 1,546 km² (597 squared miles), O’ahu is the third biggest Hawaiian island by size. However, it is the busiest, most populated, and most popular island to visit. It is famous for Waikiki Beach, the North Shore, and Pearl Harbor.

O’ahu has some of the best nightlife in Hawaii and endless opportunities for hikers, beachgoers, and natural area explorers. Honolulu is a fun but busy city that quickly feels like any other bustling metropolis.


  • Best nightlife in Hawaii
  • Live music and social events
  • Many restaurant options
  • World-famous beaches
  • Lots of activities to pick from


  • Very crowded and busy
  • Lots of car break-ins, even in public parking lots
  • Expensive accommodation and car rentals
  • Too touristy


Hawai’i: The Big Island

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Since the name of this island is the same as the state, which can be confusing, most people refer to Hawai’i as The Big Island. This nickname is very fitting because Hawai’i is the largest island by far. In fact, all the other islands can fit inside it with plenty of room to spare. It is the youngest of the Hawaiian Islands and has two active volcanoes, one of which is currently erupting lava.

There are many popular places to visit on The Big Island, including Hawai’i Volcanoes National Park, the Green Sand Beach (yes, the sand really is green), Black Sand Beach, and Mauna Kea, to mention a few.


  • Many natural places to explore that are unique to Hawai’i
  • Home to world-famous Kona coffee
  • Laidback lifestyle
  • Not crowded or too touristy
  • Peaceful – you might be the only one at a beach or on a hiking trail
  • Cheapest island to visit


  • Most of the island feels desolate
  • It takes a long time to travel between cities and tourist hot-spots
  • Public transportation is not reliable
  • Fewer things to do than on other islands
  • Very little nightlife, live music, etc.


Maui: The Valley Island

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I like to mention Maui after O’ahu and Hawai’i because it is the perfect balance of both. Maui is a little larger than O’ahu, making it the second-largest island; however, you can still drive around the entire island in a day. While it is one of the more popular islands to visit, it is a lot less busy and touristy than O’ahu, yet more crowded than The Big Island.

Maui is known for the Road to Hana, whale watching during the winter months, and spectacular sunrises and sunsets from Haleakala.


  • Good balance of things to do yet not overcrowded
  • Lots of activities for every interest
  • Some nightlife and live music
  • Easy to see sea turtles, seals, whales, dolphins, etc.


  • Sparse nightlife and live music
  • Many one-lane roads make driving to some places dangerous
  • Expensive accommodation and car rentals
  • Can get touristy and crowded at times


Kaua’i: The Garden Island

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Kaua’i is also one of the more popular Hawaiian islands to visit. It is only slightly smaller than O’ahu and has a humble population of 72,000. What makes Kaua’i unlike the others are the many caves that you can explore, plus a breathtaking Nā Pali coast! It is a lot more laid back than the larger and more populated islands yet still offers many fun activities.


  • Not too busy or crowded
  • Many natural places to visit
  • Lots of white sand beaches to choose from
  • Laidback atmosphere


  • Very little nightlife and live music
  • The accommodation can get expensive
  • Not as much to do as on the bigger islands


Kaho’olawe, Moloka’i, Lana’i: Maui Nui

Kaho’olawe, Moloka’i, and Lana’i islands are all part of Maui Nui or greater Maui. These three islands were interconnected with Maui by limestone bridges creating a super-island.



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Koho’olawe is almost impossible to visit because it is a protected island. Long-term bombing training by the US military made the island uninhabitable. It is possible to visit via a restoration project, but only skilled and lucky volunteers are selected to go. It is possible to see the island via helicopter, but it can be challenging and expensive to arrange.



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Moloka’i is a small island with fewer than 7,000 residents. People like to come here for the beautiful cliffs, coral reefs, and beaches. With so few people living here, there really aren’t many activities or amenities, but there is a raw beauty that can’t be found on other islands. Moloka’i is also home to the leper colony that you may have seen a documentary about.



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Lana’i is even smaller than Moloka’i, with just over 3,000 residents. People mostly come here to enjoy the natural beauty almost untouched by humans. There are very few paved roads, so you need to be comfortable renting an off-road vehicle to explore. Those who visit have nothing but good things to say. If you are a social butterfly, these smaller islands may not be the right fit for you, plus the few hotels available are costly.


Ni’ihau: The Forbidden Island

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Ni’ihau is a tiny privately-owned island with just about 170 residents. You technically can’t visit unless you are Hawaiian, and even then, it’s complicated. However, there is one company that makes visiting possible. It costs a lot of money and needs to be booked in advance via email. Even then, there are many strict rules and restrictions.

If you do get to go, you’ll experience a unique and almost untouched island. The few residents who live here don’t have running water, and all their electricity is produced via the sun or by a generator. This isolated community is helping preserve Hawaiian culture and loves to live away from the chaos and problems of the modern world.


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No matter which island you pick for your Hawaii vacation, you’ll find yourself in paradise. Every island has beaches, rainforests, cliffs, volcanoes, and extraordinary flora and fauna. If you can only visit one island, I’d recommend going to Maui. It offers the perfect balance of activities, nightlife, crowds, and is fun-sized, meaning you can see the whole thing in just a few days.


Photo: Shane Myers Photography/shutterstock.com

If you are planning a trip to Hawaii you might also want to check this out:

Five Tricks to Get Great Flight Deals

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