Planning a Trip to Hawaii • 10 Steps to an Awesome Hawaii Vacation

Aloha! Need help planning a trip to Hawaii? We just spent an incredible two weeks exploring the best of the Hawaiian islands. The trip wasn’t completely seamless to plan, though. Even though you’re traveling to the United States, the 50th state almost feels like another country.

There are few destinations in the world that attract quite as many people as Hawaii. This means tourism is big business, and there are many options that can feel overwhelming at times. It doesn’t have to be that way if you clearly know what you want to do and where you want to travel. Here’s how we suggest planning your first trip to Hawaii.

Planning a Trip to Hawaii

Step 1: Pick An Island

The first step in planning your trip to Hawaii is to know what you want. It’s great to do research on which islands you would like to visit. Each island has its own flavor, landscapes, and experiences. Choosing the right spot can be pretty difficult with their unique selling point. We had two weeks to galavant around and went to Hawaii’s four most popular islands. Here’s an overview of each island and what we thought.

O’ahu – The Gathering Place

Plan Hawaii Trip - Oahu

Oahu is probably the first island you’ll come across when Hawaii vacation planning. This is the classic island of Hawaii. It’s home to Waikiki, Pearl Harbor, the North Shore, Lanikai Beach, and some very infamous hikes. It’s often referred to as the “Heart of Hawaii.”

The island packs a punch with many sights, some of the best beaches in the US, and hotels. It is also the most popular island and prone to horrendous traffic and waves of tourists. It’s the primary hub in Hawaii, with 85% of the state population living here on the island. Daniel K. Inouye International Airport is situated in Honolulu and is the main access point in/out of Hawaii. There is no shortage of hotels and resorts to enjoy while on vacation on Oahu either.

Maui – The Valley Isle

Plan Hawaii Trip - Maui

One of the most popular Hawaiian Islands, and for good reason. Maui has just about everything in a convenient size, which means you don’t have to drive for hours like its neighbor, the island of Hawaii.

Maui is sometimes referred to as the “honeymooner’s island,” and we can attest to that after witnessing four weddings in an afternoon on one small beach. It’s well known for having some fantastic beach resorts, golf courses, the Road to Hana, and Molokini Crater. One thing is for sure; you won’t get bored as there are so many things to do in Maui.

Hawai’i – The Big Island

Plan Trip Hawaii - Hawaii Island

This is the youngest and largest island of the Hawaiian Islands, and it’s nearly twice as big as all the other islands combined.  It should be self-explanatory why Hawaii is better known as the “Big Island.”  It also has the most volcanic activity and is where you will find Hawaii Volcanoes, National Park

An impressive island, no doubt, with a massive amount of climate zones.  Due to its unique geology, you can find all but four of the world’s climate zones.  It’s truly impressive that one day you can go from black sand beaches to rolling pastures or snow-capped peaks to lush rainforests. There’s also Kona, one of the coolest main towns in Hawaii.

Kaua’i – The Garden Isle

Plan Hawaii Trip - Kauai

Kauai has become more popular in recent years, enough to the point that it was the main island we wanted to visit on our trip to Hawaii.  It’s known for being one of the prettiest islands and the most laid-back vibe of the four main islands. 

The main points of interest are Waimea Canyon, Hanalei Bay, and the Na Pali Coast.  We also found it the cheapest of the islands (though that’s not to say it’s cheap). Kauai is not known for its beaches, diving, or snorkeling if you’re searching for beaches.

Other Islands

The two other main islands for visitors are Moloka’i, dubbed the “friendly isle,” and Lana’i dubbed “the pineapple isle.”

Step 2: Decide if You Want to Visit More Than One Hawaiian Island

Plan Trip Hawaii -Oahu

The second step in planning a trip to Hawaii is to decide on your Hawaii island itinerary. Visiting more than one island is fantastic if you have the time. There are no ferries between the islands which means you have to fly. 

Hawaiian Airlines links all of the islands for an affordable price, but the time involved with checking out of your accommodation, arriving at the airport, check-in, flight time, car rental, and then arriving at your next destination can eat up an entire day (we would know we did it four times!), so you should assess your time wisely. 

While flights are not expensive, $150 on average does eat up a bit of the budget if you do a lot of hopping between islands.  Generally, we would say spend at least three days on each island but recommend even more time to not feel rushed.

Step 3: Decide When Should You Visit Hawaii?

If you’re still wondering how to plan a trip to Hawaii, it’s best to decide when to visit. Hawaii is generally very busy. Its reputation and location in the middle of the Pacific draw in visitors from the States, Asia, and Australia. It’s good to know when Hawaii vacation planning that the high season generally runs from the end of November until April, with the peak being the holidays. During this time, accommodation, airfare, and rental cars can be extremely high.

The draw is the opportunity to escape the cold in the Northern Hemisphere and see humpback whales from October to May. The weather during this time sees more rain and cooler temperatures – granted, still very mild. The winter also brings epic surf to the Northern shores attracting pro surfers from around the world; it’s great to see but dangerous for inexperienced swimmers. The next busy period would be the summer months when many take their summer holidays.

If you’re looking for shoulder season “deals,” look for the months of April, May, September, and October. We almost always recommend September worldwide as the best month for travel, which is still the case with Hawaii. Keep in mind that Hawaii enjoys a mild climate and temperatures all year round, so there really is no bad time to visit.

If you’re set on the busier periods of time, it’s still possible to find some solace and space on the islands, but it just requires staying away from the main points of interest and resorts. Kauai in July was quiet away for us when we were away from the resorts. The same goes for Maui and Hawaii. In contrast, Oahu is busy year-round with plenty of military personnel and an island of one million people.

Step 4: Book Your Flight

planning a trip to hawaii
The plane that brought air travel to Hawaii!

The next step in planning a trip to Hawaii is booking the flights. Most arrivals will be at Honolulu International Airport (HNL) on the island of Oahu. It’s Hawaii’s primary commercial airport and serves domestic carriers along with many international carriers. There are several direct flights from the U.S. mainland that still include Oahu, Maui, Kauai, and Hawaii Island. Once you arrive in Hawaii, there are no ferries between the islands, so you’ll need to take inter-island flights operated by Hawaiian Airlines.

When we were younger, we loved to book the cheapest fare we could find. This often leads to multiple layovers and long days, which gets exhausting. We like to opt for more direct routes and avoid layovers, even if it involves paying a bit more for convenience. A large number of direct flights from many US hubs to Hawaii makes flying more hassle-free. We were stoked to fly with Hawaiian Airlines Honolulu to JFK.

Since it was such a long flight between Honolulu and New York, we decided to fly first class for the first time ever and now don’t want to return. It started off beautifully with lay-flat seats and delicious food.

The flight attendants were delighted and embodied the “mea ho’okipa” spirit. Mea ho’okipa translates to “I am host” and refers to the warm hospitality given to guests on the Hawaiian Islands. We had a wonderful in-flight experience, including unlimited Mai Tai’s to get us in the mood.

Step 5: Rent A Car

Plan Hawaii Trip - Rental Car Kauai

Next up on this Hawaii trip planner guide is considering your means of transport on the islands. In the early days of Hawaiian tourism, it was popular to stay on Waikiki Beach. As the secrets of the outer islands have become revealed, every traveler should spend some time exploring the islands on their own.

We’ve often talked about how much we love having a rental car to travel because it allows us to explore properly. For our time in Hawaii, we used Avis across all four islands and had a good experience aside from the location in Oahu, where Avis was painfully slow.

We even received two free complimentary upgrades to a convertible Mustang and Jeep Wrangler. These are arguably the two most popular rentals in Hawaii, and you will undoubtedly see them everywhere. Regarding rental cars, we like to decline insurance because we have primary CDW with our Chase Sapphire Reserve card, which is the travel credit card we recommend most.

Additionally, being a member of rewards programs through companies like National or Avis increase your chances of scoring a free upgrade. We’re rarely loyal to one brand of a car company and find it varies from widely branch to branch – I like to look locally at the branches’ Google reviews to get a good feel for their service. You can also compare rates online on these sites:

  • Provides comparisons for car rentals in Hawaii.
  • AutoEurope: I can often find deals here for car rentals in Hawaii.
  • Discover Car Hire: Searches rental car prices around the globe – great for planning your trip to Hawaii

Step 6: Pick Up a Guidebook

how to plan a trip to Hawaii

If you’re looking at a short weekend getaway, then you probably won’t run out of things to do or places to eat. However, you’ll want to dig a little deeper and explore once you spend several days in an area.

One of the best Hawaii trip planners we had available was the Hawaiian Airlines Insider’s Guide, written entirely by people who know the islands very well.  The island guides have detailed information on their favorite establishments.

Lonely Planet guidebooks are another accessory we love to pick up and make for a great Hawaii travel planner. They are great for plotting points of interest to each unique traveler. If you want to find the best spots to go snorkel on your own or where to find a poke bowl, this is where they can provide great insight.

We used these resources to plot points of interest and then planned our days as they came. Or you can check out awesome travel blogs (like ours) to help plan your days.

Step 7: Plot Your Points of Interest and Activities

Activities in Hawaii

You’re definitely going to want to decide on some things to do when thinking about planning a Hawaii vacation. We are not big fans of planning our days out in advance. Instead, we implement a different strategy of plotting points of interest and having many options to pick and choose as we please.

how to plan a trip to Hawaii

We like to do this by using custom Google Maps. It’s pretty simple to do if you have a Google account and the application installed on your smartphone. Simply save the points and add any notes that you see fit. Planning your days as they come avoids the stress of feeling you need to stick to an itinerary and lets you check out saved places based on your location.

Plan Trip Hawaii - Outrigger Canoe

When planning a trip to Hawaii and tours and activities, we recommend booking those in advance. The best tour companies often sell out well in advance, especially in the high season.

However, you never know. In July, we got two spots last minute on a Napali Coast tour but struck out of luck for Molokini Dive. I would recommend not planning a tour or activity for every day as that will be tiring and leave little room for exploration. You have to be careful not to overwhelm yourself as there are many enticing activities on the Hawaiian Islands, like surfing, snorkeling, sailing, hikes, bikes, zip lines, quads, and food tours.

Step 8: Consider Adding A Few Days

hawaii packing list

You will never feel like you stayed too long in Hawaii – that’s one thing we learned through planning a trip to Hawaii. There is simply too much to do and see. If you can swing it, consider adding a few days to your itinerary. It’s too long of a flight to miss out.

Step 9: Choose Your Hawaiian Accommodation Wisely

Hawaii Packing List

Accommodation can have one of the largest impacts on your trip, so it’s important to get it right. There is a wide range of options and budgets to fill your accommodation needs around Hawaii. Options range from luxury beach resorts to a tent on a public campsite.

The location will also greatly impact the accommodation you choose as you’ll typically find some of the best beaches blocked off by private resorts. We’re big fans of self-catering accommodation and enjoying our time in quieter local areas, but it means we have to drive to popular attractions.


Plan Trip to Hawaii - Maui - Glamping Hub

On the islands of Maui, we had an amazing experience in one very unusual property through Glamping Hub. A bamboo cabin in the nice Haiku community on Maui island. It was so relaxing, and our place had a full kitchen, a living area, and a private hot tub. Mornings were spent sipping Kona coffee and listening to the birds far away from the distractions of resorts.

Self Catering

Waimea Plantation Cottages

You have a lot of options to stay in self-catering in Hawaii. On the island of Oahu, we spent our time in a yurt with Ohana Yurts near Haleiwa. We loved chatting with Jenny and Nathan about their yurt project – check out their TV show! With properties like these, you have a much more personalized experience that you won’t find at hotels or resorts.

Booking these through the various sharing economy sites like Glamping Hub or Airbnb is easy! Or you can seek out resort-style self-catering options like Waimea Plantation Cottages on Kauai. That is where we stayed on the Garden Isle and had a fantastic time in their refurbished cabins in the small town of Waimea. Self-catering options allow for more privacy away from the big resorts and allow you to cook your own meals. Food costs in Hawaii are high, so the ability to cook your own meals can save you a lot of money.


Plan Trip Hawaii - Resort

While you’ve been planning a trip to Hawaii, you’ve probably seen a lot of resorts. If you’re looking to relax in the lap of luxury and sip mai tais by the pool, there are plenty of resorts on the Hawaiian Islands to enjoy. Most resorts are built in certain neighborhoods together and offer direct access to a semi-private beach – you can’t own the beach but the land around the beach.

These resort communities are built so guests never have to leave with golf courses, shopping malls, coffee shops, movie theatres,  and chain restaurants. On the island of Hawaii, we stayed at the Hilton Waikoloa, a massive resort with multiple restaurants, pools, waterslides, and activities. Maui is most known for its resorts with the Four Seasons, Grand Waimea, Sheraton, and Westin if you’re interested in staying at a beach resort. Some of the best resorts in Hawaii are:


There are plenty of traditional hotels in Waikiki scattered throughout all the islands. You won’t find many of the standard big chain hotels like Comfort Inn, Holiday Inn, DoubleTrees, or Residence Inn. Instead, there are several smaller boutique and independent hotels around Maui, Hawaii, and Kauai islands.


Camping on the beach

I bet you never thought about camping when planning a trip to Hawaii, but it’s possible! There are plenty of places to camp with amazingly beautiful landscapes, hiking trails, beaches, state parks, and even national forests.

Most sites require prior reservations and planning in advance. I suggest having a good idea of where you intend to camp before heading to Hawaii. You will need a car to embark on a camping adventure. Trucks are a good option for families who need lots of space for supplies.

Step 10: What to Pack for Hawaii

Best Travel Alone Quotes

Lastly, when you’re thinking about how to plan for your Hawaii vacation, you need to consider what to pack. Here’s a start!

  • Sunscreen: You’ll definitely need sunscreen for Hawaii. Please use reef safe sunscreen if you plan to go into the ocean. We don’t want to kill our corals. Thank you!
  • Allbirds Travel Shoes: Allbirds are the best travel shoes out there. I highly recommend getting the Tree Runners for Hawaii!
  • Rainbow Sandals: You’ll definitely want sandals for Hawaii too! My favorite is Rainbow Travel Sandals – they will last forever!
  • Sundress: Bring at least one nice dress to Hawaii for special occasions. I love Salty Crush dresses as they are floral and fit great.
  • Travel Insurance: We don’t travel without travel insurance and don’t recommend you do either!
The Full Detailed Hawaii Packing List!

Hopefully, this helped you determine how to plan a Hawaii vacation! If you have any other questions about planning a trip to Hawaii, leave a comment!

Plan For Your Trip

About Cameron Seagle

Cameron Seagle is one of the principal writers and photographers for The World Pursuit. He is a travel expert that has been traveling the world for the past decade. During this time, he established a passion for conservation and environmental sustainability. When not traveling, he's obsessed with finding the best gear and travel products. In his free time, you can find him hiking, mountain biking, mountaineering, and snowboarding. His favorite countries are Scotland, Indonesia, Mozambique, Peru, Italy, and Japan.

You can learn more about Cameron on The World Pursuit About Us Page.

1 thought on “Planning a Trip to Hawaii • 10 Steps to an Awesome Hawaii Vacation”

  1. Thank you so much Cameron for this piece!! This trip is to celebrate my husband’s 50th birthday and I want to make it special for him. Please if you have time email me and let’s discuss my options.
    Mrs. Terri Jones

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