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!

  • We are going to Hawaii and Kauai for our honeymoon! I love Maui too, especially Haleakala. Such a beautiful place.

    • It really is so beautiful! We wanted our 5 year anniversary trip to kind of be like a second honeymoon, so that’s why we ended up choosing Hawaii. Y’all are going to have such a great time on your honeymoon!

  • ugh i need to go back. i did a week on oahu and a week on the big island (hilo) and i just loved. maui next time! oahu was nice bc i really really liked kailua and north shore – so diff than honolulu! and the black sand beaches on the east coast of the big island from the volcanos – can’t beat it! oh this brings back memories!

    xoxo cheshire kat

    • The black sand beaches were by far one of the most amazing things that we saw when we were there this past time. I pretty much freaked out when we were there! I really wanted to go to Oahu, but it just didn’t work out time wise this time. Maybe next time we’ll go there! I think that you’d love Maui, so I hope that you get to go back!

  • This is a fantastic guide for planning a Hawaii trip! I’ve never been but hope to go within the next couple years. It looks and sounds amazing! I’ll save this post for when I get to plan my first Hawaii trip. 🙂

    • I hope that you make it there sometime soon! It really is so beautiful, and there’s so much to do! I know that I usually think of beach vacations as relaxing vacations, but I really enjoyed all of the activities that each of the islands offered.

  • Jen

    I spent 10 days in Maui several years ago with my family and it was absolutely amazing! We went horseback riding through pineapple fields, whale watching, and did the Road to Hana. It was such a wonderful experience and I would love to go back again.

    • I hope that you do get to go back soon! Each island is so beautiful and there’s so many different things to do on them as well. The horseback riding through the pineapple fields sounds so amazing, and whale watching is something that I’d love to do as well. It sounds like I need another trip back too!

  • Living on Cloud Nine

    Too funny, my husband and I were just talking about how we want to go to Hawaii for our Anni in two years! I’ve heard so many different things but I trust your travel advice the most so I am saving thus to refer to!

    • I really hope that you make it there for your anniversary trip! It’s so beautiful, and there’s so much to do and see! Plus all of those things combined make for a really great anniversary location too!

  • This is so interesting! My parents visited Maui a few years back, and my mom still talks about The Road to Hana all the time. I guess it’s definitely something to experience. Can’t wait to hear more about your trip!

    • The Road To Hana really is so beautiful, and worth a trip! I’m really glad that we didn’t drive it ourselves though because it was scary just being in the car during some of those curves. I can’t wait to recap the rest of our trip!

  • Hawaii is so far away from Norway, I guess I would just stay where it’s the cheapest 😀 But to be honest, all the islands looks absolutely gorgeous so I’d just be glad if I could visit any of them 🙂

    • They really are so beautiful, and well worth the trip! I still haven’t been to Oahu, so I’m hoping to make it there too! It was expensive for us to fly there as well, but we used hotel points to stay for free on the islands, which was really nice.

  • Ah go to Haleiwa around where Turtle Bay is on Oahu. You’ll get that island feel!!

    • I know that there are places on Oahu that will feel more Hawaii, and I know that I would still love to experience the other stuff too! I think that Oahu will be on my list for when we go back.

  • this is fabulous! i have only been to Oahu and it was an okay trip (other things happened to drag it down, the place itself was fine though not what I was expecting) so I’d love to go back and visit more of the islands.

    • I hope that you do get to go back and experience some of the other islands! They’re so beautiful and they all have their own personalities too. And hopefully on your next trip there won’t be other things that happen!

  • Hawaii is so much more than I give it credit it for! I think I would have to choose Kauai–it just looks so stunning! 🙂

    • It really was so beautiful and so incredible to visit! I hope that you get to visit sometime soon because it’s an extraordinary part of the United States!

  • Ashley Angle

    Loving this post! I want to Hawaii one day! Kaui sounds the best… just total relaxation!
    Ashley @ A Cute Angle // A Cute Angle

    • Kauai was definitely my favorite island, and I would love to go back one day! It was the perfect mix of relaxation and doing too!

  • Oh wow, what an amazing post! Do I have to choose just one? tehehe.

    • I don’t think that it’s possible to choose just one, which is the main reason why we ended up on both Maui and Kauai during our last trip!

  • Such beautiful photos! I have never been and it has always been on my list. Thank you for a thoughtful thorough review! I will definitely be using this as inspiration for when I finally get to go!

    • I hope that you get to go soon! Hawaii really is so beautiful and it’s totally worth the money that the visit will cost.

  • This is such a great breakdown! I’ve done Oahu, Maui, and Big Island, but I really want to go to Kauai! I can’t wait to see your posts about it.

    • I hope that you make it to Kauai sometime soon! It was so beautiful and I thought that it was definitely the less commercialized of the Hawaiian Islands. I’m hoping that we’ll make it Oahu one day!

  • Hawaii has always been on my bucket list but I know very little about each island. My idea for visiting Hawai has always been enjoying the beaches and relaxing in paradise but the canyons look really cool and there’s so much outdoor sites and scenes that I didn’t know about.

    • It really is amazing how much there is to do in Hawaii that doesn’t involve laying on the beach, and I know that we didn’t even scratch the surface of everything during our last visit. The beaches are still perfect for relaxing, and I loved that we got the best of relaxing and doing on this vacation. I hope that you make it there soon!

  • Rachel

    What a great guide to all the Hawaiian islands, Ashley! I went with my parents when I was in kindergarten and we stayed in Maui. From what I can remember about it, I loved it! We were talking about going to Hawaii this year for our anniversary, but coming from the east coast, it takes FOREVER to get there! Not sure we want to spend two+ days of traveling! It is a beautiful place, though!

    xo, Rachel
    A Blonde’s Moment

    • Really the only bummer about Hawaii is how long it takes to get there and how much money it ends up costing. But it really is worth it when you see how much each of the islands has to do! I hope that you’ll consider it one day, even if it’s not this year for your anniversary! I’m hoping that we’ll go back and maybe visit Oahu our next trip!

  • These pictures have me dreaming of Hawaii!! I so wish we could have gone there for our honeymoon, but it just didn’t work in our budget. Hoping that we can go for an anniversary trip sometime in the future :)! Maui and Kauai are definitely the 2 islands I would love to visit!

    • Maui and Kauai definitely make for the most perfect trip, in my opinion, and I hope that you make it there for a future anniversary! It’s totally worth the time and money it takes to get there!

  • very nice! We are debating going to Hawaii right now (vs. another vacation locale). If we do, we definitely feel in the mood for Maui!

    • Yes! I hope that y’all end up choosing Hawaii for your vacation spot! Maui is so much fun, and you really do get the best of both worlds with island life but also a little bit of city as well.

  • I haven’t visited Hawaii before, but Maui or Kauai sound like my kind of islands. I’m excited to hear about the details from your trip!

    • Hawaii really is amazing, and I hope that you make it there sometime! Maui and Kauai were so much fun, and I think that it’s the perfect pair of islands for a Hawaii trip!

  • Christina Sotherden

    The perfect spot to celebrate five years! This is so informative – we might have a wedding coming up soon in Hawaii and it’s great to know a little bit about each island, we’ve only done the main one and Maui, both of which we loved.

    • A wedding in Hawaii would be so amazing, and talk about the perfect way to get a vacation along with getting to see your friends get married! My first trip to Hawaii we visited Maui and The Big Island and loved them both, but I’m glad that we got to visit Kauai this time around.

  • Oahu was my least favorite of the islands and I think Kauai or the Big Island were my favs. Hawaii is so gorgeous! Definitely an awesome place for a 5 year anniversary… or any trip 🙂

    • Exactly! Chris had never been to Hawaii before, and I figured that a 5 year anniversary would be the perfect time to explore! I’ve heard from a lot of people that Oahu wasn’t their favorite, but I’d still love to visit one day.

  • it’s nice in Hawaii… 😉 I met up with my parents there a few years ago, but we were just in Honolulu. And back when I was a kid, we hit up Maui. I’d love to go back and check out Kauai..!

    • I hope that you make it to Kauai one day! It’s so incredibly beautiful and still has an untouched feel about it. Hawaii probably is a great middle meeting point for you and your parents! Y’all should do it again!

  • I’ve only been to Kauai when I was about 15. It was absolutely beautiful and we saw so much, but I’ve always heard that of all the islands Kauai is one of the more relaxed islands. I’d love to see the other islands one day! #WanderfulWednesday

    • I hope that you make it back! It really is so crazy how each of the islands can have its own personality, so getting to visit multiple islands makes for an even more exciting vacation! I still haven’t been to Oahu, but I’d love to visit!

  • I’ve only been once, and went to two islands, so this is good reference!

  • ooh good to know! I would love to go there someday! 🙂 I always do find it tricky to decide where we would want to go. So many islands, so many choices. XO – Alexandra

    Simply Alexandra: My Favorite Things

    • Exactly! I feel like even when you decide where you want to go, the hardest decision is still figuring out what exactly you want to do and see. That’s why I thought that the island breakdown would be so useful!

  • Such a helpful guide! Hawaii is so far from the UK that we don’t really know anyone who’s been, so it’s good to get tips from people in the know. I’d definitely be on for Kauai, it looks beautiful! Can’t wait to read all about your trip, what a fantastic way to celebrate 5 years 🙂

    • It really was the most perfect way to celebrate our 5 year anniversary! We had decided to go two years before our anniversary, so I thought that it was nice to have enough time to save for it because it can be expensive to visit even living in the States. Maybe it’ll be closer with you living in Australia and you can visit!

  • Such useful information! I have never been to Hawaii but I would love to go. I think it would be fun to take a Hawaiian cruise so we can see multiple islands in one trip.

    • We had friends that did that and they said that they loved it! It really did give them the opportunity to see all of the islands and see the highlights. I hope that you get to visit one day!

      • I’m sure we will. It’s just a matter of when. There are so many places we want to go to that we have to prioritize. 🙂

  • I love this post Ashley! I went to Hawaii for spring break my senior year in college. We stayed right off of Waikiki and had a great time. I would love to go back (now that i’m not on a college student’s budget).

    • I think that’s awesome that you were able to visit while you were in college! We started planning our trip a couple of years in advance so that we could make sure that we could utilize points for our trip. I hope that you get to go back sometime soon and visit some of the other islands!

  • So pretty! I visited Maui (and a quick Honolulu stop) years ago! I think it’s time to plan another trip back!

    • I think that you’re right! There’s so much to see and do on each island that it’s fun to visit all of them!

  • Great job on this post!! And thanks for plugging my blog! When people are going to visit Hawaii I usually tell them that my picks would be Kauai and the Big Island, but like you said, it all depends on what you want from your vacation. I haven’t been to Maui yet so I really can’t say what it’s like there. I will add that Oahu has some incredible restaurants, probably since Honolulu is the biggest city we have. There are influences from all over the world in one little spot.

    I love that Kauai has such an islandy feel, especially since buildings aren’t allowed to be that tall. I want to go back!! The Na Pali coast is one of the most beautiful places I’ve ever seen! I only went to the Big Island for 2 days but I want to go back to see more volcanoes and go stargazing.

    • You’re so welcome! I love that I can go to your blog and your instagram and get some Hawaiiness whenever I need it! I really want to go back to The Big Island because I don’t think that I fully appreciated it when I visited with my family when I was in high school. We probably would have done Maui and The Big Island if it hadn’t been for my parents visiting Kauai this past year and talking about how amazing it was and how we needed to go! That being said, I still really want to visit Oahu! It would be awesome to visit Waikiki and the North Shore, but I also really want to pay my respects at Pearl Harbor. It’s just something that I feel like I need to do.

  • My brother in law is planning this for their 5th anniversary too! I’m going to shoot this over to them. I’ve only been to Oahu, but I’d love to visit Maui or the Big Island for sure!

    • I hope that he has a great time on their anniversary, then again, they are visiting Hawaii, I feel like it’d be hard to not have a good time! I think that all of the islands are worth a visit, so a trip back would be awesome!

  • Ahila Thillainathan

    Have wonderful memories of Oahu, Big Island and Maui! Hope to visit Kauai, if I do get to revisit Hawai’i.

    • I hope that you get to revisit Hawaii soon! Kauai is so incredibly beautiful and there’s so much to see on that one island, that it’s totally worth a trip!

  • My cousin went to Kauai on her honeymoon and she absolutely loved it! I would love to visit Hawaii someday, and I’ll remember your info!! 🙂

    • I hope that you do get to visit one day! There’s a reason that so many people visit for their honeymoon, it’s a beautiful and romantic destination for sure!

  • Ever since my coworker has gotten back from her trip to Hawaii I have been wanting to go! She mainly explored Honolulu and the north coast of Oahu and it all looks so gorgeous. Great post Ashley!
    Evelina @ Fortunate House

    • Thank you! I hope that you do get to visit one day! I would say that Hawaii is even more beautiful in person than pictures or people’s descriptions would ever be able to show!

  • I know very little about Hawaii so this post was incredibly helpful! If I could teleport there it would definitely be on top of my travel wish list– all of the islands look so beautiful!

    • I know, when are they going to invent teleportation so we can visit all of the beautiful places quicker! Hawaii really is beautiful and a perfect location for any vacation! I hope that you get to make it there soon!

  • LOVE this comparison! We’ve only done Kauai which we loved because of the Na’Pali Coast, but we’d love to see the other islands as well someday!

    • The Na’Pali Coast was one of my favorite parts about Kauai. It was just so stunningly beautiful! We haven’t done Oahu yet, and I’d really love to make it back there one day to visit!

  • I always have a hard time choosing! As a child my parents took us to Oahu. Then my husband and I went to Oahu/Kauai in our honeymoon. We went back to Oahu/Kauai for our 10th anniversary and then Oahu/Maui for our 11th. LOL! We obviously love it there. We’re thinking Maui/Big Island this year. 🙂