When we were planning our big 5 year anniversary trip to Hawaii one of the biggest questions that we constantly asked ourselves was which islands we were going to visit. While you might think that an island is just an island and they’re one in the same you would be very wrong about about Hawaii. Each of the Hawaiian Islands has their own personality, which means that a vacation on one island will be very different than a vacation on another island. It also means that one island might be for one type of vacationer but not for another.

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

Because each of the Hawaiian islands is so different and has different things to do, I thought the I’d break it down for y’all so you can see why we chose the islands that we chose.


Definitely the most popular of the Hawaiian islands, Oahu is home to the capital city of Honolulu. Millions of people flock to Oahu every year, and it’s also where the majority of the Hawaiian population lives as well. You will definitely get the bustling and big city feel if you stay in Honolulu or near Waikiki Beach.

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

Besides the busy city of Honolulu and Waikiki Beach, Oahu is also home to some other pretty amazing things as well. For the history buff a trip to Pearl Harbor is not to be missed, the surfer will definitely love a trip to the North Shore to try and catch the perfect wave, and the adventure lover will jump at the opportunity to snorkel at some pretty spectacular beaches as well as go on some pretty breathtaking hikes as well. If you want some ideas on what you can do on Oahu, definitely check out Carolann’s blog at Finding Ithaka. Her husband is stationed there right now, and her blog has me daydreaming about a trip to Oahu!

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

While there are definitely some positives to exploring Oahu, the one main negative is that because it’s the most populated and definitely the busiest island, it’s perhaps the island that has lost some of the “Hawaiian” feel. There are definitely still areas that are not as touristy as Waikiki and Honolulu, but by and large a lot of the major attractions are naturally centered around Honolulu. While Chris and I would have loved to spend a day paying respects at the Pearl Harbor Memorial, it just didn’t seem possible to fit in Oahu on our trip. My fingers are still crossed that we’ll make it there one day in the not too distant future!

The Big Island

Hawaii’s largest island, and consequently the island named Hawaii or simply “The Big Island”, is definitely another island to consider when you’re making your travel plans to Hawaii. What brings the millions of visitors to The Big Island every year is one of the two National Parks in the State, the Volcanoes National Park. The Big Island is currently the only island in Hawaii with active volcanoes actually on the island (there are some volcanoes that are active under the ocean), and at Volcanoes National Park, you have the opportunity to come face to face with that live volcano. It’s a truly extraordinary experience that is not to be missed!

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

Besides Volcanoes National Park, The Big Island offers a lot of the same things that Oahu and many of the other Hawaiian islands will offer, hiking, snorkeling, and all sorts of other adventuring, but it has one thing that the other islands don’t have, a ski mountain. That’s right, you can snow ski on a tropical island! Mauna Kea is a very tall mountain on The Big Island that sometimes gets a skiable amount of snow. It doesn’t happen all the time, which means that there’s no lifts or all the normal ski gear on the mountain, but it’s definitely still worth mentioning!

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

Before we left on our anniversary trip, I actually wrote about the time that I visited The Big Island with family when I was a senior in high school. While I enjoyed my time on The Big Island, I don’t think that I truly understood or appreciated the fact that I was actually getting to see active volcanoes on our trip. To my sister and I the volcanoes were kind of boring and we just wanted to go to the beach, Looking back on it, I know that Chris and I would have enjoyed visiting Volcanoes National Park, so I guess that means that while I’m writing this post, I’m also planning our next trip back to Hawaii where we’ll visit Oahu and The Big Island!


The third island that you should consider for your trip to Hawaii is the island of Maui. Often considered a good middle ground of both city life and country life, Maui has a lot to offer for any traveler. From great beaches, hiking, and snorkeling, Maui also offers some great shopping and resorts as well as great restaurants. It’s no surprise that there are actual several celebrities that own houses on the island from Oprah, Clint Eastwood, and even Willie Nelson.

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

Besides what I’m quickly starting to refer to as the “normal” Hawaiian activities, Maui has some very unique experiences to the island itself, including another National Park. Haleakala National Park is a dormant volcano that most tourists visit in the wee hours of the morning to watch the sunrise. It’s a beautiful and stunning experience for sure.

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

The other main attraction for the island of Maui is the infamous Road to Hana. A beautiful and treacherous road that is filled with more hairpin turns and blind curves than probably any other road in the United States, it’s an adventure, and a little scary at the same time! But all of that stress is totally worth it when you see the most amazing views, including a black sand beach!

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

Both The Road To Hana and Haleakala were the main reasons that Chris and I chose to visit Maui on our trip to Hawaii. It was so incredible and I can’t wait to share it with y’all!


Probably considered the most untouched of the Hawaiian islands, Kauai is one of the islands that still very much feels like Hawaii. In fact, there are no buildings that are taller than 4 stories on the island, which not only means that the resorts are smaller, but that there’s no big cities either.

Untouched is definitely a word that comes to mind when I think of Kauai, and nothing brings that word to life more than the Na’pali Coast. These stunningly beautiful and rugged cliffs have no roads through them, and literally the only way that you can access this remote part of the island is by foot, by boat, or by sky.

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

Another unique feature of the island of Kauai is Waimea Canyon, which the Hawaiians have affectionally nicknamed “The Grand Canyon of The Pacific”. This huge and beautiful canyon is quite a stark contrast to the pristine and beautiful beaches of Kauai. It’s a must see for your trip to Kauai.

The Wandering Weekenders- Which Hawaiian Islands Should You Visit?

Both the beautiful Na’pali Coast and Waimea Canyon combined with the practically untouched feeling of the island of Kauai, is the reason why this was the second stop on our Hawaiian anniversary trip. It was stunning, and the perfect way to end our time in Hawaii!

As you can tell, each of the islands is so incredibly different than the other, and while they all have amazing beaches, snorkeling, and hiking, each of those experiences on the different islands will be vastly different. Which is exactly why it’s so hard to pick which island or islands to visit on a trip to Hawaii! I’m so excited to be linking back up with these Wanderful Women from some Wanderful Wednesday- Lauren of Lauren on Location, Van of Snow in Tromso, Isabel of The Sunny Side of This and Marcella of What a Wonderful World!

Have you visited Hawaii? Which island or islands would you want to visit on your Hawaiian vacation?

Other Hawaii Posts

My First Trip To Hawaii- Maui
My First Trip To Hawaii- The Big Island
10 Things I Learned While Visiting Hawaii
Hawaii In Instagram Photos

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The perfect breakdown the differences of all the Hawaiian Islands for your next visit! From Oahu, The Big Island, Maui, and Kauai, I've got you covered!