The mosaic of colors and ecosystems sitting in the middle of the Pacific Ocean belong to the Hawaiian archipelago, a significant location on many traveler’s bucket lists due to their eye-popping landscapes, mesmerizing culture and delicious cuisine. Unfortunately, those who have the opportunity to plan a trip often face a major dilemma: how do you choose which island(s) to visit?
Since they are geographically isolated, located 2,471 miles from the closest point in the United States, planning a trip is time-consuming at best. Each island is also packed with its own unique highlights, which would easily occupy the best of a week to only scratch the surface. Piggyback that thought with the fact that most travelers average 2 weeks of vacation time per year and you can see that there may only be enough time to explore one or maximum two islands during one trip.
Luckily, each island has adopted its own unique personality and travelers can design their Hawaiian vacations by picking those isles that best match their personal characters. Are you a self-proclaimed foodie whose adventurous palate knows no bounds? Or do you prefer passing the day on the water, enjoying one activity after another? Perhaps, Hawaii is your honeymoon destination. Fortunately, no matter who you are, or what your reason is for visiting, there is an island for everyone.
O’ahu
Do you enjoy being around large groups of people, visiting popular tourist attractions and balancing outdoor activities with multicultural events? If so, O’ahu is the place for you! Staying true to its nickname “The Gathering Place,” this major hub is home to the state’s capital city, Honolulu, and holds two-thirds of all Hawaii’s residents.
Common to the entire Hawaiian archipelago, there are no shortages of surfing, snorkeling, hiking and other outdoor activities in O’ahu, but the difference is that visitors can balance these favored pastimes with sightseeing historical and popular locations. And you will want to, considering that this is the home of Pearl Harbor, Waikiki Beach, the USS Missouri, the USS Arizona Memorial and the iconic Diamond Head volcanic cone.
This island is also where you will hear Hawaii’s heartbeat. The isle pumps with music, multicultural and local food, beach walks, clubs, bars and pockets of dancing. And the activity never ends. In fact, it is easy to find a number of 24-hour restaurants, especially around Honolulu, like Sikdorak Korean Restaurant, M.A.C 24/7, and Wailana Coffee House, just to name a few. And if you enjoy food trucks, you’re in luck, because there are plenty scattered around the island, especially many with Latin flair.
Maui
If the options in O’ahu attracts you but the crowds don’t, try visiting Maui for a calm middle ground. This is the island that has something for everyone, and will make a great trip for families looking to accommodate multiple personality types. You can find lively yet calm restaurants and bars filled with flowing drinks, island food and music with a side of breathtaking views. Enjoy a show at the Maui Arts and Cultural Center. Meander through botanical gardens or visit historical churches.
Known as The Valley Isle, nature is the primary reason why people visit Maui. It’s the location of the world’s largest dormant volcano, Haleakala, where you can rent cabin space to get an up-close and personal experience. There is also a plethora of watersports to enjoy, from snorkeling to windsurfing, regular surfing and kiteboarding. Of all the water activities that one can enjoy in Maui, immersing in the underwater world is the most popular, and there are numerous caves, craters, reefs and bays where you can snorkel or scuba dive. What else can you expect from an island with 81 beaches?
And don’t pass the opportunity to indulge in locally-grown crops. The primary exports in Maui include coffee, macadamia nuts, pineapple, and papaya.
Kauai
Would you rather travel to Hawaii for long days exclusively laying on sunny beaches? Are you into luxurious hotels but don’t mind missing a vibrant social scene? Can you lose yourself in mountainous landscapes set against blue ocean backdrops? Then visit Kauai, The Garden Isle.
Both nature lovers and romantics will enjoy escaping to this green and blue paradise painted in reds and oranges. Waterfalls, rivers, steep cliffs and ominous mountains cover the island’s 562 square miles. The food is delicious and tourists can enjoy both top-class restaurants and food trucks as they wish, which both take advantage of the locally-grown ingredients. Tourists can visit four botanical gardens, and there are private premises throughout the island. And it’s been argued that the hiking is second to none. In fact, many people believe that Kauai is the most beautiful of the Hawaiian Islands.
Big Island (Hawaii)
This is the place novice travelers think of when people mention a trip to Hawaii, and as its name suggests, it’s the largest island in the archipelago. The Big Island is perfect for active travelers who can enjoy a wide range of outdoor activities and sports, as well as for those looking for unique hidden spots. Hikers will want to schedule a solid amount of time here, as it’s the most ecologically diverse of the Hawaiian Islands and home to the world’s tallest mountain, Mauna Kea. And in addition to the largest mountain is the world’s most active volcano, Kilauea, a dream for adventurists and volcanologists who want to see live lava flows and their resulting land growth.
Have you ever wanted to attend an authentic Hawaiian BBQ, complete with pig roast, hula dancing and leis? This is the perfect place to go. The Big Island’s economy is primarily driven by tourism, so expect to see stereotypically Hawaiian culture and events.
Lanai
Did you know that one of the Hawaiian Islands is privately owned? Lanai is the place to go if you want to escape to an isolated luxury resort and money isn’t a deal breaker. It’s a quiet paradise with rustic charm, where visitors can stay at one of the top two hotels in the world.
Although pineapples are grown on a few of the Hawaiian Islands, this is the actual “Pineapple Isle”. Thousands of acres were once home to the Dole Pineapple Plantation, one of the largest producers of pineapple in the world. Even though the market has since withered, its reputation remains. Now, Lanai’s reputation includes billionaires and tourists in addition to pineapples.
Molokai
Do you agree that while water sports are fun and hiking adventurous, while clubs are a good way to fill nights and good food can make or break a trip, the real reason to visit someplace new and exotic is to learn about the indigenous culture? Welcome to Moloka’i, The Friendly Isle, where the greatest number of indigenous descendants can be found. This isn’t where you will find the glamorous side of Hawaii, but it is where you will see its authentic spirit.
In this rural island, you will find a lifestyle centered around family, fishing and festivals conducted around picnic tables. Folktales are told around camp sites and you won’t miss the melancholy left over from a sad history (the island was historically home to a leper colony).
Regardless of where you go, this will be the trip of a lifetime
Hawaii has a rich culture thick with mythology and history, modern twists and ambient influences. Volcanoes, craters, mountains and caves are only a few ecosystems that make up these otherworldly environments. Regardless of which island you choose, you can expect gorgeous beaches and plenty of water activities. And by visiting more than one isle, it is easy to gain an idea of the heart and soul that is Hawaii.
Matthew Young is a Boston based freelance writer. As an aspiring automotive journalist looking to make a name for myself in the industry, he is passionate about covering anything on 4 wheels. When Matthew is not busy writing about cars or new emerging tech, he usually spends time fiddling with his camera and learning a thing or two about photography. You can tweet him @mattbeardyoung.
Nice report. The bottom line is that it doesn’t really matter. On out first trip (been there 3 times now), we had no clue. Everyone here on the east coast said O’ahu and Maui. Ok. Thank you, but for how many days? My west coast friends told me to spend 2 nights on O’ahu and a week on Maui. That worked out.
Our second trip took us to the Big Island (a week) and Kauai (3 nights).
Our third trip took us back to Maui for a week (lots of things to do), and Kauai (3 nights).
When we head back, it will be for a week to the Big Island and Kauai (3 nights). Kauai is where the Hawaiians go on vacation.
I’ve been to Oahu, Maui and the Big Island. I liked Maui the best (more tropical than Oahu and much smaller than the Big Island – things are closer together). I still need to visit Kauai (planning a trip there next fall to stay in Princeville). Where did you stay in Kauai?
After moving from Chicago to Florida, we haven’t been back to Hawaii. There isn’t another vacation like it, if you know where to go. We had multiple trips to both Maui and Kauai, which is our favorite. We love the laid back atmosphere. The North Shore is drop dead beautiful and meant for nature lovers, which is our MO. We must go back!
Coming from the East Coast to Hawaii is tough. You are closer to Europe than to Hawaii, plus you have so many island options in the Caribbean.
Our first trip to Kauai, we stayed at the old Princeville (Starwood). The second trip was at the Sheraton in the southern part of Kauai since the Princeville was closed for rebranding. That area has more hotels. Up north has less properties, and more laid back.
I’ve got my eye on the Westin Princeville Villas (timeshare property) so I am hoping to get a week there a timeshare owner who can’t use their week. Price for a studio for a week is ~$900.
Ridiculous article. Sounds like half was stolen from Hawaii Tourist Authority…
Thank you for the feedback. I will pass your comments on to Matthew. Thank you for reading.
Lol, after visiting O’ahu, Maui, and Kauai his descriptions were very good. Next trip we are planning is the big island. The pictures on the first three islands bring back some memories of incredible views that we saw! Some people are never happy nice response grant.
Thank you LJ. Are you planning on staying on the Kona side or Hilo side of the Big Island? Kona is very flat and deserted, while Hilo is much greener.