The ULTIMATE Guide to Planning a Trip to Hawaii

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This is a guest post that is very close to my heart. Oahu is one of the most beautiful places I’ve been, and planning a trip to Hawaii was so much fun. The friendly people, the beautiful water, the stunning nature, and the awesome acai bowls. There are so many things to make you fall in love with Hawaii, and if you’re lucky enough to be planning a trip there sometime soon, this post is for you! Once you’ve booked your flights, you’re ready to start planning your trip to Hawaii!

Guide to planning a trip to Hawaii

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Planning a trip to Hawaii

When we think about this wonderful island paradise the first thing that comes to mind is; Waikiki, Pearl Harbor, luaus and beaches. Right? These are just a mere surface of what Hawaii has to offer. Hawaii is a chain of islands consisting of eight main islands. The most populated island is Oahu. This is where Honolulu, Waikiki Beach and Pearl Harbor is located.

While planning a trip to Hawaii there are a couple of things you need to consider. Start with these:

How long is your trip going to be?
What types of activities do you want to partake in?

Once you’ve answered those basic questions you can start figuring out which and how many islands you want to see during your trip. Each island of Hawaii has its own distinct reason to visit.

What island in Hawaii should I visit?

Below you’ll find some of the main activities for each island that would make you want to visit!

Oahu

  • Historical sites like Iolani Palace and Pearl Harbor
  • Waikiki Beach and Honolulu city
  • Brand name shopping
  • Some epic (and famous) hiking trails
  • Neat guided tours like the Food Tour and the Haunted island tour
  • 2nd biggest fish auction in the world

Big Island

  • VOLCANOES!
  • Some of the most epic snorkeling ever
  • Stargazing on dormant volcanoes (a bucket list activity for many)
  • Papakolea Beach, also known as ’Green Sand Beach’
  • A Macadamia Nut factory for those who are interested

Planning a trip to Hawaii green sand beach

Kauai

  • Beautiful caves
  • Waimea Canyon (the largest canyon in the Pacific)
  • Breathtaking views at the Napali coast
  • White sand beaches galore
  • Some rugged and hard core hikes

Maui

  • Waterfalls galore through the Road to Hana
  • Epic sunrise or sunset at the dormant volcano Haleakala
  • Neat farms to visit with produce such as goat cheese, local wine and even vodka
  • Black and red sand beaches
  • Snorkel with turtles
  • Easy access to Lanai or Molokai via ferry

Lanai

Molokai

  • Some gorgeous snorkelling (worth a day trip for those who love underwater life)

Planning a trip to Hawaii shipwreck beach

As you can see, the types of activities you want to do will determine which islands are worth visiting for you. Each island has its own distinctive look. Big Island has lots of volcanic rocks and shrubbery on the dry Kona side, while the Hilo side is very wet and almost like a jungle. Maui is filled with beautiful valleys and waterfalls, and Kauai has one road that encircles the island and is known as the ‘garden isle’ because of its greenery.

Now what we figured out what types of things are available on each island, I will give you my top recommendations for when you are visiting Hawaii!

Where to stay in Hawaii

Whenever you go on vacation, you will need a place to call home and catch some zzz’s. The type of place you want to stay depends entirely on what type of vacation you have planned and what is your budget. If you are planning a pool/beach lounging vacation with occasional sightseeing and have a bigger budget you can stay at some of the nicest resorts you’ll ever feast your eyes on. These types of resorts can be found on every island.

If you still want something more relaxing but can’t afford these luxury resorts there are still hotels that offer beach front access that are mid ranged in price on each of the Hawaii islands.

If sightseeing if your main focus and not sticking around in your room or hotel, your best and most budget friendly option is doing a range of AirBnB, a HomeStay or a traditional Bed and Breakfast. If you are into meeting people and don’t mind a bit of noisiness, hostels are always an option, too.

Lisa’s comment: On my trip to Hawaii I spent 2 weeks staying in a lovely AirBnB, and a weekend splurging on a stay at Disney’s Aulani!

What to do in Hawaii

The Polynesian Cultural Center (Oahu)

The idea of grass skirts and coconut bras may be what you thought Hawaiian Hula is supposed to be like, but it couldn’t be further from the truth! One of the most beautiful things about these islands, other than its natural scenic beauty, is the culture! There is no point in coming to these islands if you don’t try to appreciate and understand their unique island culture! At the Polynesian Cultural Center you follow a journey through all the major islands in the Polynesian Triangle, learn about their customs, food and attire. This will take an entire day, but is completely worth it! If you want to have the luau experience you can give it a go here.

Polynesian Cultural Center Hawaii What to do in Hawaii Planning a trip to Hawaii

Beaches

Coming to an island paradise like the Hawaiian islands doesn’t make any sense if you don’t experience the beach! Be warned, however, that not all beaches are created equal! There are certain beaches that have extremely rough shore breaks that have been known to seriously injure even seasoned swimmers! The beaches below are my recommendations for swimming.

There are tons of beaches on each island for whatever suits your need. Snorkelling, body boarding, actual surfing, or just watching people surf – you name it!

Top Tip: Decide whether or not you are comfortable with a beach with no lifeguard, since a lot of the beaches in Hawaii do not have one on duty at all times.

Awesome beaches for swimming in Hawaii

Waimanalo beach (Oahu)
Lanikai beach (Oahu)
Hanalei Bay ( Kauai)
Kapalua beach (Maui)
Wailea beach (Maui)

Planning a trip to Hawaii PLan a trip to Hawaii guide

Food

Hawaiian food is super unique. You’ll find a mash up of Korean, Hawaiian, Japanese, Chinese and even Portuguese food. I would highly recommend checking out a food tour if you find yourself in Oahu, as learning about local cuisine is a must!

Foods to try in Hawaii

  • Poi
    Mashed up taro – this dish looks like purple mashed potatoes, and is meant to be eaten like a side dish. You’ll find the best Poi in Kauai.
  • Loco Moco
    Always ask the locals, there are certain restaurants that are known for their Loco Moco. I personally advise you to stay away from L&L BBQ. This chain uses very subpar ingredients and completely will ruin your experience of having local cuisine
  • Spam Musubi
    This is actually great at 7-Eleven! The dish is made from spam and rice and seaweed, it tastes way better that it sounds, I promise!
  • Lau Lau
    Pork wrapped in steamed taro leaves, absolutely divine!
  • Sushi
    Did you know? Some of the best Tuna is caught in Hawaii and exported to the rest of the world. Japan included! Get some of the freshest and tastiest sushi while you are on the islands.
  • Saimin
    Noodles and soup, you can’t get this type anywhere else in the world!
  • Haupia
    The most delicious coconut based dessert ever!
  • Poke
    You can get a huge variety of this all over the Hawaiian islands. It is basically marinated raw tuna, and absolutely delicious!
  • Malasadas
    This is a deep fried custard filled dessert from heaven! If on Oahu, a trip to Leonard’s Bakery for Malasadas is a MUST!

Hikes in Hawaii

The gorgeous mountains on the Hawaiian islands are simply begging for you to visit, if only to enjoy the views. Each mountain top boasts of views you will see nowhere else on the island. I can’t stress enough how epic the hiking in Hawaii is!

The ocean and views from the different mountain tops will leave you absolutely mesmerized. You don’t have to be in top physical shape to complete some of these hikes, as there is something for every level!

Planning a trip to Hawaii Guide to Hawaii Plan a trip to Hawaii

The best hikes in Oahu, Hawaii

  • Diamond head
    This is a super easy hike where you can get a great view of Waikiki. You actually get to start this hike from the inside of a crater.
  • Judd Trail
    This hike’s surrounding environment changes around you as you go, making it a super fun and interesting hike! Did I mention there is a sweet, sweet spring at the end to swim in?
  • Lanikai Bunkers aka the Pillbox Hike
    On this hike you get to explore some World War II bunkers while staring at the gorgeous beaches of the area.
  • Olomana aka 3 Peak Death Hike
    Okay, maybe I am exaggerating the nickname a bit… But this hike isn’t for the faint of heart. You should be in top physical shape to try and attempt it, but the view is oh so worth the sweat and tears, I promise.
  • Makapu’u lighthouse
    This is an easy hike with a lovely view at the end.

Sightseeing in Hawaii

What is the point of hauling yourself to the most isolated island chain in the world if you don’t see some of the unique and epic sights it has to offer? Here are some of my favourite things to check out on the Hawaiian islands.

  • Tantalus Lookout
    If you find yourself on Oahu, make sure to take this gorgeous drive up and see a view of Honolulu you can’t get anywhere else on the island. You should go before 5pm to avoid the gates closing on you.
  • Museums
    Iolani Palace and the Bishop Museum will give you a unique view into the history of Hawaii.
  • Waimea Canyon
    An absolute MUST when on Kauai! The view is unlike anything you have ever seen before, trust me.
  • The Road to Hana
    This is my top tip for visitors to Maui. This epic drive checking out waterfalls takes up an entire day and you’ll be able to experience the red sand and black sand beaches on the way.
  • Volcanoes National Park
    One of the coolest things on all of the islands, if you are lucky you may see some lava spewing out!

Planning a trip to Hawaii Beautiful Waimea Valley

Is Hawaii a ‘fragile destination’?

As you may or may not know, Hawaii is very vulnerable to flooding. Being a low-lying island chain, with global warming, scientists are not sure how much longer we will be able to enjoy this beautiful paradise. Since the islands are so isolated, almost everything consumed is shipped in, so the island is far from self sustaining.

It isn’t just Hawaii that is vulnerable; it is our lovely home planet as a whole. With rising sea levels and ever-growing piles of garbage on both sea and land, we are pushing the limits of what our home can handle.

We are passionate about travel because we want to see all the beautiful sights, tastes and sounds this wonderful place called earth has to offer. It would be a shame if generations after us never get the experiences we get through travel, because we failed to take care of the place we call home.

This is why whenever we travel, we should try and tread lightly, leave as little a footprint as possible, so these lovely places we travel to will be around for many generations to come and enjoy.

You might be wondering; how? I love travelling but I have no idea what I can do to make a difference. Below I will list some things you can try while you are checking out Hawaii.

Travel without a trace

As I mentioned above, everything in Hawaii is shipped into the islands. So when eating or buying souvenirs try to be as local as possible with your purchases.
Be as efficient as possible when travelling on the islands. For example, if you wish to do and see things on the west side of Oahu, try staying in a place close to those sights to cut down on driving/transportation.
Avoid buying bottled water when you can. It is better to take a water bottle with you that you can fill up before you go.

These are just a few tips for visiting Hawaii. I am giving away a free packing list to make your trips even more sustainable, so you know you are having the time of your life and not harming the planet.

Planning a trip to Hawaii green sand beach


About the author: Jen is crazy passionate about two things, seeing the world and how to save our planet. She started travelling when she was less than a year old, and got hooked on jet setting ever since! She has lived in 4 different countries including Canada, India, U.S.A (Hawaii) and South Korea. The thing that she loves so much about travelling is learning from other people by seeing and experiencing how they live. About the age of 11, she picked up a book called ‘Oceans in Peril’ It changed the way she looked at the world forever. She realized how much we mistreated not only our oceans, but our planet as well. Just because we didn’t live in the ocean or in the forest, didn’t make it right for us to pollute, pillage and destroy it. It was a horrible feeling, soon she realized if things kept going this way, we won’t have a home to live in for much longer. The beautiful sights and sounds we take for granted at home and when we travel will not be around for future generations to come. 
She started educating her friends and classmates through fun plays, showing everyone that being more sustainable in our everyday lives didn’t have to be super difficult or expensive. It starts with the willingness to try and to make small little change which later become habits. Learn how you can change the way you travel @ http://green-travelling-101.com/

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  • This is great – I really love the breakdown of the different things on each island, since I’m not sure where I would want to go! I will find this useful someday I’m sure, so I’ll be saving it!

    • Agreed, and I’m so happy to hear that you may find it useful, Becky! Hawaii has so much to offer!

  • I love this! I live on Oahu and Jen nailed it. I’m planning a trip to the Big Island and am hoping to get to Maui sometime, so I’ll be referencing this list!

    • I’m so glad you think so, Carolann! And you’re so lucky to live on Oahu! I spent 2 weeks there in October and absolutely loved the island! So beautiful! I’m sure you’ll have a great time on Big Island and I hope you get to go to Maui soon! 🙂 Thanks for reading!

  • I’ve always wanted to go to Hawaii ever since I was a kid, mostly because of Lilo & Stitch. I didn’t know everything was shipped in to Hawaii. Wow, the things I learn from reading blogs. 🙂

    Teesh || Adventures of Cupcake Girl

    • I love Lilo & Stitch! Going to Hawaii was a dream of mine, too – I was so excited when I finally went! 🙂 Glad you enjoyed the post! 🙂