1 In All/ Hawaii Island (Big Island)/ Hawaiian Islands/ Kauai/ Maui/ Oahu

How To Choose Which Hawaiian Island To Visit

Are you planning a trip to Hawaii, but aren’t sure which island or islands to visit? You’re not alone! This is the #1 question people have when planning a trip to Hawaii, as it can be quite overwhelming with an archipelago of 8 unique tropical islands (6 main islands) to choose from! In this blog post, I’ll break it down by island, to help you decide which is best for you and your style of travel.

Ka’ena Point, O’ahu

I feel uniquely qualified to write this post, as my family was born and raised in Hawaii, and I grew up on Oahu for 11 years. When people ask me where I’m from, my response is Hawaii because even though I’ve lived in other parts of the country and the world throughout my life, I connect the most with the Hawaiian Islands and will always be a kama’aina (local) at heart. In addition to being a travel blogger, my career is in the travel industry (I graduated from the University of Hawai’i), and worked as a Travel Concierge for Expedia Local Expert’s activities division for many years. In this role, my job was to help travelers plan trips of a lifetime on the Hawaiian Islands, so I frequently traveled to neighbor islands both for work and for pleasure, getting to know each island very well. I also got to partake in all the activities that I sold, which means I did a lot of ziplining, ATVing, snorkeling, hiking, and other popular tours and activities to truly experience fun on the islands from both a local’s and a visitor’s perspective.

At the summit of Haleakala, Maui

So, you’ve decided that you’d like to visit Hawaii; now the question is – which island(s), and for how long? Each island has their own unique vibe and nature landscape, and in this blog post I’ll help you narrow it down, by comparing each island’s unique features and characteristics, including the type of traveler they’re best suited for.

There are 8 Hawaiian Islands, which I will order from West to East (and North to South):

  1. Ni’ihau
  2. Kaua’i
  3. O’ahu
  4. Moloka’i
  5. Lana’i
  6. Kaho’olawe
  7. Maui
  8. Hawai’i (Big Island)

Ni’ihau is known as “The Forbidden Island” and got its name during a polio epidemic in 1952. To this day, the island remains off limits to all outsiders unless you’re a relative of the Robinson Family (the owners of the island) or if you’re invited.

Kaho’olawe is also by law, off limits to the public, however, you can visit the island through volunteer work opportunities. Kaho’olawe was a training ground and bombing range for the military after WWII, and is therefore deemed uninhabitable and has no permanent residents.

Lana’i is one of the lesser visited islands, and is a bit more off the beaten path and far less developed than the main islands. Lana’i tends to attract wealthy visitors, because of the beautiful Four Seasons Resort and world-class golfing.


Hawaii is truly a beautiful year-round destination with mild climate. Peak tourist season is from April – May for spring break, June – August for summer, and from November – January during winter holidays. The best time to visit Hawaii to avoid the crowds, is September – October and January – March. Rainy season is from January – April, but don’t fret, as the islands are a giant microclimate, and the weather forecast is almost always wrong. It rarely rains for an entire day (like you’d see in Seattle), and you can easily drive half an hour to another part of the island and it will likely be sunny there.

Sunset over the Na Pali Coast, Kaua’i


One of the most common questions I receive working in the travel industry is “how can we get from island to island?” The answer is, by plane. There are no ferries between the islands, and you’d have to know a local to take a boat, though the water can be extremely rough in between the islands, so don’t expect a smooth nor comfortable ride. There are daily flights from airlines like Hawaiian and Southwest, and can cost anywhere from $75 – $250+ round trip per person to fly between the islands, depending on the season. The shortest flight is 18 minutes (From Oahu to Molokai), and the longest flight is 45 minutes (from Oahu to the Big Island). While there are snorkeling and diving sail trips that can take you from Maui to Lanai, these are not meant for transportation and are only day activities.

Snorkeling at Honolua Bay, Maui


This all boils down to three factors:

  1. How much you want to see
  2. What kind of traveler you are (backpacker, luxury resort-goer, independent traveler, etc.)
  3. How much time you have

My rule of thumb that I recommended to my guests, is if you have under six full days of vacation, stick to one island. If you have more than six days in your vacation, you can look at visiting two or more islands. I recommend spending at least 3 – 4 full days on each island. By “full day”, I mean not a travel day. Keep in mind that spending 3 days on an island will be a very quick-paced trip and not very relaxing. If you’d like to pair adventuring with relaxation, I recommend that you pick only one island, otherwise your trip will feel too rushed.

Now this leaves us with the four main islands that people typically choose from (Kauai, Oahu, Maui and the Big Island), plus the lesser-visited Molokai. Let’s dive in!

Green gecko – a common colorful critter you’ll find on the islands


Ha’ena Beach, Kaua’i

Nickname: The Garden Isle
Size: 552 square miles
Best For: Adventure, raw natural beauty, hiking, waterfalls, honeymoon couples, solo travelers, backpackers, camping
Fun Fact: The wettest spot on Earth is found on the island of Kauai
Length of Time to Drive Around The Island: Assuming no stops and no traffic, it will take approximately 3 hours. One thing to note is that there is no connecting road at the Northernmost tip of the island, so the road ends where the Na Pali Coast begins on one side and on the other side hugs Waimea Canyon. This means that you cannot make a full circle around the island by car.


  • Helicopter ride over Waimea Canyon (the Grand Canyon of the Pacific)
  • Riding an ATV across the film sites of Jurassic Park
  • Tubing down old sugarcane flumes
  • Sailing along the Na Pali Coast
  • Hiking the Kalalau Trail

Kauai is the oldest of the Hawaiian Islands, and is named The Garden Isle for its lush, tropical vegetation and heavy rainfall. Mt. Waialeale is the wettest spot on earth, averaging 450 inches (37.5 feet / 12.5 meters) of rain each year. Kauai is ultra laid-back and has a mixture of both locals and transplants, both from the U.S. mainland, other islands, and other countries. It’s got a bit of a hippy-dippy 70’s free love vibe, and yoga and kombucha are kind of a big deal. There is a plethora of things to do, both paid activities and free, and many stunning hikes which will reward you with outstanding views. Kauai is a popular backpacking destination because of the rugged Na Pali Coast, one of the most dangerous yet rewarding brag-worthy hikes in America. The Kalalau Trail is 22 miles round trip and is typically hiked over several days. A permit is required to do this hike and to camp. Kauai is personally my second favorite island and the one I have visited the most times (after my home island of Oahu.)

If you are looking for a more active and adventurous vacation where you’re keen to be exploring on the go, and your idea of a fun night out includes chill live music under the stars rather than partying at a club, then Kauai is for you.


The Ultimate Kauai Guide: Top 32 Things To Do on Kauai
Top Kauai Hiking Trails
Kauai Food Guide – Best Places To Eat on Kauai


Nickname: The Gathering Place
Size: 597 square miles
Good For: City life, nightlife, history, museums, families, first-time travelers to Hawaii
Fun Fact: Oahu is home to the only Royal Palace in the United States (I’olani Palace)
Length of Time to Drive Around The Island: Assuming no stops and no traffic (which never, ever happens unless you start at 5AM), it will take approximately 3 hours. One thing to note is that there is no connecting road on the West Side between Waialua and Ka’ena Point, so, like Kauai, you cannot make a full circle around the island by car.


  • Pearl Harbor
  • Diamond Head
  • Waikiki
  • Hanauma Bay
  • The North Shore / Haleiwa
  • Turquoise waters of Lanikai and Kailua

Oahu is my home island and is where I have spent the most time exploring. Honolulu is the capital of Hawaii, and Waikiki is the main tourist hub where most of the big hotels and resorts are located along the coastline. Oahu is where most first-time visitors to Hawaii come, as it provides a diverse array of beautiful nature, historical museums, and city life. Oahu is great for solo travelers, couples, families, and luxury travelers, as it has something for everyone. The main downside to Oahu is that it is extremely crowded all year long and it is NOT cheap. Due to Hawaii becoming one of the most popular destinations to the visit in the U.S. over the years, unfortunately beautiful sights such as Hana’uma Bay and Diamond Head have become overrun to the point of non-sustainability, stripping the authenticity and magic of the island and turning it into what can often feel like waiting in queue for a Disneyland ride. Thankfully Covid has put some boundaries around crowd control with introductions to timed ticketing systems, which seem to be improving visitor experience and reducing negative impact to locals.

One of the main draws of Oahu is of course, the historic Pearl Harbor and Bishop Museum for history and art lovers respectively. Oahu is home to the only Royal Palace on U.S. soil, I’olani Palace, and the famed North Shore is where people flock from all over the globe to view the biggest wave competitions in the world at Pipeline. (Read more: Things To Do On Oahu’s North Shore From A Local’s Perspective.) If you’re into architecture, you’ll love a tour of Doris Duke’s Shangri La. (Read more: Touring Doris Duke’s Shangri La.) Oahu is also home to the artsy Kaka’ako where the colorful wall murals have been made quite the popular Instagram draw. (Read more: Kaka’ako – Oahu’s Vibrant Arts & Foodie Neighborhood.)

If you don’t like crowds, queues for sights and restaurants, and are turned off by commercialism and mass tourism, then Oahu is not the island for you. However, if you’re able to plan your visit during an off-season month, it can be a much more pleasant experience.

If you’re considering a move to Hawaii, have a look at my raw and honest blog post on 18 Reasons Living in Hawaii Isn’t Always Rainbows and Butterflies. This has been to-date, the most popular post since I began my blog in 2016.


A Local’s Ultimate Oahu Foodie Guide
17 Best Hikes On Oahu
Kaka’ako Farmer’s Market Food Tour
Cacao Farm & Chocolate Tour in Waialua
Tasting Tour of Ko Hana Rum Distillery


Labyrinth near Dragon’s Nostrils, Maui

Nickname: The Valley Isle
Size: 727 square miles
Good For: Whale watching, luxury resorts, families, relaxation, laid-back vibes, golfing
Fun Fact: There are over 700 hairpin turns along the famed Road To Hana
Length of Time to Drive Around The Island: Assuming no stops and no traffic, it will take approximately 4 – 5 hours, though due to the unique shape of the island (it looks like a man’s head and shoulders tilted downwards – once you see that image, you won’t be able to un-see it), it’s not an easy circle.


  • Road To Hana
  • Whale Watching (during season, which is November – April)
  • Snorkeling
  • Haleakala Crater
  • I’ao Valley

Maui is a popular choice amongst families with children, or folks looking for a more relaxing vacation. Though Maui has plenty of adventures, it tends to draw people who have fast-paced, stressful jobs back home and just want some quiet time to unwind at a resort and relax with a Mai Tai in hand by the beach. Maui is home to some world-class snorkeling, which is best done off of a boat on a tour. Haleakala is one of the biggest draws; a dormant volcano crater with its summit at an elevation of 10,023′ (3,340 meters). Because of its high altitude, during the winter, temperatures can actually dip below freezing and it can snow! So come prepared with layers and a warm jacket if you’ll be visiting during winter. Other fun activities include rappelling, ziplining and driving the famed Road To Hana, which is all about the journey rather than the destination.

Maui is personally my least favorite of the main islands, simply because it’s a bit too slow for me, and all-inclusive resorts aren’t my style. I prefer unique boutique accommodation and fast-paced adventure with lots of hiking and outdoor nature, and while you can absolutely find that on Maui, it just isn’t the draw of this island.

READ MORE: A Perfect Three-Day Itinerary On Maui


Honaunau (Two-Step) – West Side, Hawaii

Nickname: The Big Island (locals simply refer to it as “Big Island”)
Size: 4,028 square miles
Good For: Luxury resorts, active volcano, hiking, black sand beaches, unique landscapes, geology lovers, spiritual energy
Fun Fact: The Big Island has 8 of Earth’s 13 different climate zones, so you can visit a desert, a lava field, a tropical rainforest, surf the Pacific Ocean, and ski on a snow-capped volcano, all in one day
Fun Fact #2: You can fit all the other 7 Hawaiian Islands into the Big Island, it’s that large!
Length of Time to Drive Around The Island: Assuming no stops and no traffic, it will take approximately 8 hours, and will be one of the most stunning and peaceful drives you’ll ever do.


  • Seeing active lava at Kilauea Crater in Volcanoes National Park
  • Black Sand and Green Sand Beaches
  • Snorkeling & SCUBA Diving
  • Stargazing
  • Mauna Kea (14,000′ / 4,665 meters) elevation!
  • Waipio Valley
  • Waimea – the center for ranching activities and paniolo (cowboy) culture – Hawaii’s own Big West!

The Big Island is by far, my favorite Hawaiian Island. Not only does it have an incredibly diverse climate and exquisite nature, but it has some of the strongest positive mana (energy / life force) I’ve ever felt in a place. There is something special…something magical about the Big Island, that cannot be described – it must be felt in order to form your own personal connection with it. I have heard many stories of people who have come to the Big Island for spiritual retreats, volunteer work on a farm land, or simply just to find themselves, and everybody has positive stories and special memories about this island.

The Big Island has the most local feel to me, because (with the exception of Lanai and Moloka’i), it feels like the only island that hasn’t been completely “touristified” and still holds on to the authenticity that embodies Hawaii as a whole. Big Island is where I feel Hawaiian culture the strongest, and people who are from the island are very proud of their roots – as they should be! On the Big Island, there are still families who grow and cultivate kalo (the Hawaiian name given to the taro plant) the traditional way, and food and farming is celebrated as a tradition. Locals still host Lūʻau in their backyard, not as a paid show for tourists, but because this is a celebration, passed down by generations of ancestors. A Lūʻau is a traditional feast, celebrating anything from a baby’s first birthday, to a wedding, or an anniversary. The star dish from this feast is kālua puaʻa (roasted pig) underneath a hearth in the ground, covered with ti leaves and naturally delectably smoked (usually all day long.)

Because of the diverse climate zones and accommodation offerings, the Big Island truly has something for everyone and attracts a wide range of visitors from backpackers on a budget who stay in hostels and are looking to spend under $1,000 on their entire 7-day trip, to high net worth wealthy individuals who spend $10,000 per night on a room at the Four Seasons Hualalai. So if you’d like a taste of the real Hawaii, whether you’re keen to stay at your resort the entire time, or traverse the island by car, foot, horseback, ATV, zipline or hiking with a local, The Big Island is for you.


Cultural Foodies’ Guide To Visiting Hawaii’s Big Island (Kona & West Side)
How To Spend A Day At Volcano’s National Park
14 Fun Things To Do in Hilo
Hiking To Active Lava On The Big Island of Hawaii
Hilo Foodie Guide


The Tallest Sea Cliffs in the World – Kalaupapa, Moloka’i

Nickname: The Friendly Isle
Size: 260 square miles
Good For: Off-The-Beaten-Path Travel, remote
Fun Fact: Moloka’i boasts Hawaii’s longest white sand beach
Length of Time to Drive Around The Island: Assuming no stops and no traffic, it will take approximately 75 – 90 minutes


  • Kaunakakai
  • Kalaupapa National Historic Park – Father Damian’s Statue & The Former Leper Colony
  • Viewing the Tallest Sea Cliffs in the World (at 3,030′ / 1,010 meters high)
  • Drive the Coastal Road to Halawa Valley (the “Road To Hana of Moloka’i”)
  • Phallic Rock
  • Deep Sea Fishing

Moloka’i has a vastly different vibe than the rest of its neighboring islands. In fact, when you land on the tiny strip of asphalt that is the airport, you may suddenly feel as though you’ve been transported to a different planet, or taken back 200 years in time. Over 45% of the local population of Moloka’i are of native Hawaiian decent, and it truly feels as though time has stood still here. This island is the least built up, meaning you won’t see any chains – no McDonald’s, no Starbucks, no big resorts, and no high-tech gadgets, and the locals prefer it that way. There’s even a rule that no building can be taller than a palm tree – granted, there are some pretty tall palm trees on Moloka’i, but as you drive around the island, you’ll see that a five-story building is considered a skyscraper to locals. The highlight of this island is Kalaupapa Historic Park, where from 1866 to 1969 the peninsula formed an open-air quarantine “prison” for sufferers of leprosy. The only way to visit is with a tour company, as a permit is required to enter. From the floor of this sacred valley, you’ll marvel at some of the tallest sea cliffs in the world, jutting straight up from a turquoise ocean; an emerald mountain majesty with carved formations like fingers from the cascading waterfalls which caress the curves of their textured ridges.

Another highlight is visiting phallic rock – yes indeed, there is a rock in the natural form of a you-know-what, and if this is one of the highlights of visiting Moloka’i, well, then, that should give you an idea of what the pace of life is like here and what people get excited about. So if you’re coming to Hawaii expecting big crowds, crazy nightlife, and good-looking surfers everywhere, you’ll be disappointed if you come to Moloka’i. However, if you’re after a truly authentic, fully local, immersive experience and to experience life as it was 100+ years ago, you will love Moloka’i. Any flight from neighbor islands will allow you to see some of the stunning cliffs from the low altitude of the airplane, so be on the lookout from your airplane window with your camera ready.


I hope that after reading this post, you now have more confidence in selecting which island(s) will be be the best fit for you on your next trip to Hawaii. May you enjoy your time on these beautiful Hawaiian Islands that I am so lucky to call home. Please remember to respect the islands when you visit; respect the locals, respect the culture, respect the Aina (land), the sea (remember that ocean conditions can change on a dime, and Mother Nature is a far more powerful force than you think she is). Allow Hawaii to make its mark on you, but please leave no trace of your mark on it (no graffiti, no trash, no taking sand, rocks or lava home with you.) The islands are truly a special place; may you fall in love as so many do; whether with another human being, with the food, with the locals, with the melodic and uplifting Hawaiian music, with the ability to let go of life back home and embrace Hawaiian time. May you fall in love and always remember Hawaii.


You Might Also Like

1 Comment

  • Reply
    A Local's Ultimate Oahu Foodie Guide - Cultural Foodies
    May 2, 2021 at 10:26 pm

    […] If you’re planning a trip to the Hawaiian Islands (or are a local in search of other islands to visit!), be sure to read my blog post on How To Choose Which Hawaiian Island To Visit. […]

  • Leave a Reply

    %d bloggers like this: