Planning a Trip to Hawaii • Amazing 10 Step Hawaii Vacation Planner

Planning a Trip to Hawaii • Amazing 10 Step Hawaii Vacation Planner

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 have a clear idea of 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. With their own unique selling point choosing the right spot can be pretty difficult. We had two weeks to galavant around and ended up going to the four most popular islands of Hawaii. 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 a ton of sights, beaches, 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, that 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 near 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 happens to have 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 to be the cheapest of the islands (though that’s not to say that it’s cheap). If you’re in search of beaches, Kauai is not known for its beaches, diving, or snorkeling.

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 a fantastic idea 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?

Plan Tip To Hawaii - Waikiki Sunset

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 humpbacks 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 around the world 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. The vast majority of arrivals will be into 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 a number of 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 in between the islands, so you’ll need to take inter-island flights, which the majority of are 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 the convenience. With a large number of direct flights from many US hubs to Hawaii it 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 go back. It started off beautifully with lay-flat seats and delicious food. The flight attendants were a delight 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 travel blog guide is to consider 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 without a doubt see them everywhere. When it comes to 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