10 IMPORTANT Steps for Planning a Trip to Hawaii in 2023

Planning a trip to Hawaii blog cover image.  Text overlaying an image of Hawaiian hula dancers at sunset.

While it can feel a bit overwhelming arranging so many things all at once when planning a trip to Hawaii, this guide has been created to simplify the process and break it down step by step.

Things like finding cheap flights, choosing the right island or islands for your visit, time of year, things to do, and so on will all be covered in detail.

If you have already arranged portions of your trip or do not have flexibility, simply browse the table of contents first and skip to the sections that will be most useful.

Need help budgeting for a trip to Hawaii? Read the complete guide:
Trip to Hawaii Cost Review: How to Budget for a Hawaii Vacation

Disclosure: In order to keep providing you with free content, this post likely contains affiliate links. If you make a booking or purchase through one of these links we earn a small commission at no extra cost to you. So a HUGE thank you to you if you click one of these links πŸ™‚

πŸ“‹ How to Plan a Trip to Hawaii: Step by Step

The 10 Important Steps for planning a trip to Hawaii in the order in which you will want to address them are:

  • Step 1: Choose which Hawaiian island(s) you will visit.
  • Step 2: Review current Hawaii travel restrictions (currently none, Jan 2023).
  • Step 3: Book your arrival and departure flights to/from Hawaii.
  • Step 4: Book any inter-island flights.
  • Step 5: Find the best place to stay within your budget.
  • Step 6: Create your Hawaii itinerary.
  • Step 7: Book tours and activities.
  • Step 8: Establish how to get around (car rental highly recommended).
  • Step 9: Pack for your vacation.
  • Step 10: Enjoy a well-deserved Hawaiian vacation!

This guide will go through each step providing travel tips for being as time and cost efficient as possible.

In addition, we will provide links for recommended tours, services, airlines, accommodation, etc

🏝 Step 1: Which Hawaiian Island(s) to Visit?

The first decision you will have to make is one that first-time Hawaii travelers often don’t even realize; which of the Hawaiian islands are you planning on traveling to?

There are four major Hawaiian islands, listed in order of most-to-least popular based on annual tourism: O’ahu, Maui, Big Island, and Kauai.

Each island is very different. Kauai, for example, beckons nature lovers, hiking enthusiasts, and adventure junkies. Oahu, meanwhile, is the Disneyland of Hawaii. It is for people who enjoy curated vacations with resorts and attractions catered to tourists.

Before you can begin planning your trip to Hawaii, you first need to decide which island, or islands, is the right one for you. Begin with the quick guide information below and keep reading for more resources that may prove helpful in making your final decision:

🌴 Quick Guide to Each Island

View from the scenic Makapu'u Point on Oahu.
Oahu is the most iconic Hawaiian islands.

Oahu: The Miami of Hawaii

Incredible white sand beaches with the best nightlife and the largest city in Hawaii. Oahu is mostly about resorts and tourist attractions, drawing people who are more about a fun, curated vacation than exploration. It is by far the most visited island in Hawaii.

Bright greens and yellow in front of blue water paint a picture of tropical Kauai in this photo from Hanalei Bay in Hawaii.
Kauai is best for outdoor adventure.

Kauai: The Denver of Hawaii

Upscale accommodation and romantic restaurants exist, but the island is most known for its incredible natural beauty. Kauai is best for the hikers, adventure seekers, and nature lovers who see Hawaii as a place to explore rather than somewhere to relax.

A surfer is silhouetted at sunset on Maui.
Maui is best for diverse interests.

Maui: The Los Angeles of Hawaii

Beautiful beaches with lots of high-end visitors, but also appealing to people who like to explore by car. Maui is a mix of upscale vacation, self-drive tourism, and chill-on-the-beach enthusiasts. This is the second-most popular island for tourists.

A young female in a swimsuit walks the stunning shoreline of Waipio Black Sand Beach on Big Island north shore, also known as Poiolu Valley Beach.
Big Island is best for slow travel.

Big Island: The Seattle of Hawaii

Slow pace with the friendliest people and a lot of natural beauty to explore, but more effort is required. The Big Island is best for people who value space, seclusion, and budget over manufactured and lavish experiences.

🍍 Step 2: Hawaii Travel Restrictions in 2023

Turquoise waters and white sand beach surrounded by black lava rock as sen by airplane when traveling to Hawaii
The Big Island adventure begins before you even land!

Hawaiβ€˜i is welcoming travelers again! There are no longer any Covid-19 requirements nor mask mandates in place for the flights nor on the islands themselves.

However, there are some pre-travel requirements for international travelers visiting Hawaiβ€˜i.

Domestic Travel to Hawaii

There are no current domestic restrictions for domestic flights to Hawaii. Additionally, the REAL ID enforcement date has been pushed back to May 7, 2025 due to the recent pandemic.

International Travel to Hawaii

For those traveling from international destinations with direct flights to Hawaii, you will only need to follow federal international requirements. There are no additional State of Hawaiβ€˜i requirements.

There is no longer any negative Covid testing requirements for international travel, with the exception of people who have been in China, Macau, or Hong Kong within the past 10 days.
(Accurate as of Jan 16, 2023)

Requirements are constantly changing so ensure you check the CDC website or within your airline for current guidelines.

πŸ›« Step 3: Book Your Flights

Arrival Flights: Flights to Hawaii

If you have decided on an island for your Hawaiian vacation, it’s time to begin looking for flights!

We strongly recommend booking your arrival flight as a non-stop to Hawaii (if possible).

The reason this is so important is that issues often arise when connecting flights are involved. Something unforeseen can cause ripple effects that impact every reservation and booking you’ve pre-arranged.

If, for example, your first flight arrives late, you may miss your connecting flight and be stuck waiting for the next available, which could be days! Or maybe you’re there on time but the connecting flight gets canceled. Now you’re stuck somewhere random overnight and have to scramble to re-arrange your entire itinerary while figuring out on the fly how to get to Hawaii!

A plane is seen departing from Hawaii, silhouetted by beautiful golden light.

Departure Flights: Flights From Hawaii

The return flight is not typically as important to book non-stop as the arrival flight. While delays getting home are frustrating, most will not suffer the severe knock-on effects of missing days on the front end of their vacation.

If budget is a priority, you can potentially find a cheaper flight with an extra stopover on the return trip.

Of course, this is highly dependent on what obligations await you at home.

How to Find Cheap Flights

Skyscanner flight search for flights to and from Hawaii
An example of a flexible flight search with “Cheapest Month” selected.

If you have flexibility in your dates, use SkyScanner to find the cheapest flights possible using the flexible departure feature.

This software makes flexible searches extremely easy and looks for the best possible deals for you across all airlines!

Simply type in your departure city in the “From” field and enter the island you wish to travel to in “To” field. Then, search for the cheapest ticket within the month you are planning a trip to Hawaii or even the cheapest ticket available within the calendar year you are seeking!

πŸ›¬ Step 4: Island Hopping / Inter-island Flights

A photo showing the same girl swimming in a waterfall on Kauai, then playing on a beach on Oahu to demonstrate the appeal of island hopping when planning a trip to Hawaii.

Once you have landed on Hawaii, inter-island travel is an affordable way to explore of the Rainbow State. Commercial flights are available from each of the four major islands starting at just $45 each (accurate as of Jan 2023), with the exception being flights between Kauai and Big Island (which are more pricey).

Hawaiian Airlines is the primary service provider for inter-island flights, but Mokulele Airlines also provides small-plane options for Oahu, Maui, Big Island, and the sister islands of Molokai and Lanai.

If you are thinking of island hopping, there are two extremely useful resources we implore you to open in a new browser.

The first is the complete guide to island hopping in Hawaii which explains prices, options, and best practices.

The second is our Hawaii itineraries ultimate guide which provides itineraries for 5, 7, 10, and 14+ day visits spanning multiple islands. Just find the duration of stay you are planning and follow these guides to help you navigate the when and how.

FIND OUT MORE:
COMPLETE GUIDE TO HAWAII ISLAND HOPPING
-and-
ULTIMATE HAWAII ITINERARY GUIDE: ALL ISLANDS & TRIP LENGTHS

πŸ› Step 5: Decide Where to Stay

Once you have flights booked, you need to decide where you are going to call home for your Hawaii holiday. This is a crucial decision to get right and one you should spend time on.

Each island has its main tourist hot spot(s). These are where you will find the most accommodation options for various budgets and type, from hotels, resorts, and condos to VRBOs. These locations become popular because they are inevitably near some of the best beaches, restaurants, and services on the island.

Choosing to stay in the hot spots will make your life easy. Tours and car services will offer pick up and drop off from these locations, and necessary amenities will be nearby. The downside is the crowds.

The best places to stay in Hawaii on each island are:

🀿 Step 6-7: Plan your Itinerary & Book Tours

A collage of photos from the 4 major Hawaiian islands of Oahu, Maui, Kauai, and Big Island showing the many amazing things to do on each island for people planning a trip to Hawaii.

With flights and hotels booked, now comes the fun part; deciding what you will see and do, and how you will spend your days on Hawaii!

Crafting the perfect Hawaii itinerary is a very personal thing. Some people visit Hawaii to relax, some to explore, and some just to say they’ve been.

Only you can decide the right pace for you, and only you know what interests you!

In addition, the length of stay on Hawaii has a tremendous impact on how many islands you should try and squeeze in.

We have created a dozen different guides to crafting your version of the perfect Hawaii itinerary. These account for all islands, trip types, and lengths. Browse the titles below and simply queue up the one that most closely resembles your upcoming vacation:

Note that all of the best tours, activities, and things to do on each island will be covered in the itineraries above. These will also explain all pertinent information for planning a trip including where to stay, getting around, etc.

πŸš— Step 8: How to Get Around Hawaii

Consider renting a jeep when planning a trip to Big Island as a great  and stylish way to get the island.

All of the Hawaiian islands have tremendous infrastructure and wide roads that are easily driven. Accordingly, renting a car or Jeep is the best way to get around in Hawaii. They are surprisingly affordable, starting as low as $30/ day on any island.

While public transportation is available, it should not be relied on for a couple of reasons. The first is that “island time” is a real thing, meaning schedules are only loosely followed in Hawaii.

Second, this is going to be the trip of a lifetime and you will not want to waste time waiting for buses. Finally, the services are very limited which may make it impossible to get to some of the places you want to go.

If driving is not an option, the best option is to book tours with pick-up and drop-off services provided. This may require you to coordinate your accommodation with the tours you want to book, limiting you to the most popular resorts and areas.

It is also worth noting that rideshare apps like Uber and Lyft and both available on Hawaii.

🧳 Step 9: Packing Lists & Tips

Printable Hawaii Packing List for planning a trip to Hawaii.

The last thing you need to do when planning a trip to Hawaii is pack your bags. And yet, this simple task may be the most stressful for some!

Having a printed checklist that includes all of the essential items to bring can be a huge source of relief. Beyond that though, first-time travelers to Hawaii may not have thought of all the things they need to bring or have even been aware some existed.

To make your life easy, load our ULTIMATE HAWAII PACKING LIST in another browser. This provides a printable checklist and goes through the Top 25 items you probably wouldn’t have thought of. These are things like reef-safe sunscreen (legally required in Hawaii) and compact waterproof bags to protect your electronics on boat tours from the highly corrosive saltwater spray.

If you have never been to Hawaii before and/or do not travel often, the guide below will be your best friend.

Find a PRINTABLE CHECKLIST and COMPLETE GUIDE to packing for Big Island:
ULTIMATE HAWAII PACKING LIST

β˜€οΈ Top 10 Hawaii Travel Tips: Quick Guide

In addition to the 10 easy steps for planning already presented, below are the Top 10 Hawaii travel tips for first time visitors:

  1. Try to book non-stop flights to begin your Hawaii vacation. This will minimize impact to reservations and bookings if there are issues with connecting flights. Honolulu Airport (HNL) in Oahu has the most non-stop flights available.
  2. Book tours far ahead of time. The most popular Hawaii activities often sell out weeks or even months in advance.
  3. Bring only reef-safe sunscreen. All other sunscreens are illegal in Hawaii.
  4. Be sure to bring hard-bottom beach shoes; many of Hawaii’s beaches are littered with lava rock, sharp kiawe thorns, and even some glass and debris.
  5. Book your accommodation with care! Most islands have a wet side and dry side, and the best deal may be the worst location.
  6. Get a Costco card! Costco has the cheapest gas on Hawaii by far and it will pay for itself within 1-2 fill-ups. Not to mention great prices on food and drinks, of course.
  7. Bring your own snorkel and mask unless you only plan on snorkeling with tours. The cost of daily snorkel rentals are often more than the cost of buying one!
  8. May and September are the best months to visit Hawaii as they are within the dry season, but fall outside the peak tourist season, meaning more availability and lower prices.
  9. Bring your National Park Pass if you have one. Most islands have at least one national park site that requires paid entry unless you have the park’s pass.
  10. Do your homework first. Don’t rush into a trip to Hawaii without getting a good idea of the budget requirements, knowing which island will be best for you, etc.

πŸ€™πŸ½ Hawaiian Words, Customs & Culture to Observe

There are a few customs that are good to know before you begin planning your Hawaiian holiday.

All too many tourists forget that while this is a vacation destination to them, it is home to the locals. As such, it is important to treat people on the island as if you are guests in their home.

Performers dance to tell a traditional Hawaiian story at a sunset luau.

Beyond typical manners, here are a few Hawaiian customs to note:

  • Tipping: Locals survive on tourism! In the US, 18-20% has become standard, 15% minimum.
  • Aloha: This word means a lot in Hawaiian, including both “hello” and “goodbye”, but also “love” and “peace”.
  • Mahalo: The Hawaiian word for “thank you”.
  • Island Time: The Hawaiian culture is a “lei-d” back culture (pun alert!) Expect a slower pace and less concern with punctuality on Hawaii than on the mainland.
  • Attire: Outside of a few luxury clubs or restaurants, casual attire is the expectation. Flip-flops (known as slippers in Hawaii) can be worn to any restaurant or outing.
  • Shaka: The “shaka” is the hand signal using the thumb and pinky with a side-to-side motion that is often translated to “hang loose” on the mainland. In actuality, it is closer to “aloha” and/or “mahalo” in Hawaii. It can be hello, goodbye, thank you, or anything really with positive intention. Think of it a bit like a polite wave or a thumbs up.

πŸ“† When to Visit Hawaii

Two outrigger canoes float through the water during a golden sunset on the Hawaiian island of Oahu.

There is truly no bad time for planning a visit to Hawaii. Even in the wet months, weather systems tend to blow in and out, rather than settling on top of the islands. This means you will likely get sunshine no matter when you visit as long as you choose the right location on each island.

Additionally, the winter months are a great time for whale watching as migrating humpback whales grace the shores of the Hawaiian Islands.

With that said, the best time to visit Hawaii is in May and September, followed by April and October. These are the months that fall outside of peak tourist season, but within the dry season. Each consideration is explained in more detail below.

🌀 Weather in Hawaii

A landscape photo showing fast moving clouds over mountain and tropical greenery from the Ho’omaluhia Botanical Garden on Oahu.

The geography of each Hawaiian island creates a unique climate and weather patterns specific to that island. For example, most islands have a wet and dry side which is typically the result of mountain ranges that block and cool wind, creating clouds and weather.

Although each island varies, generally the south and west shores are sunnier and drier, whereas the northeast regions of the islands receive more frequent rainfall.

Also, Hawaii is located in a tropical zone that only has two seasons, both of which are warm: wet season and dry season. The wet season is from November-March and the dry season is from April-October. However, this does not mean that there will be clouds and precipitation all day, every day, but rather that more rain systems will blow through during these months.

πŸ– Peak Season in Hawaii

A busy Kihei beach shows why it may be best to avoid peak season when planning a trip to Hawaii.

The peak travel season is from June-August, so avoiding these months is recommended if possible. While the weather will be more reliably dry and sunny, availability will be scarce and prices will be higher, plus you will have larger crowds to contend with.

Aiming for winter and shoulder seasons means more availability for tours and accommodation, smaller crowds, and typically cheaper air and hotel fares.

πŸ“– More Hawaii Travel Guides

A couple hanging out in paradise amongst an array of tropical palm trees.

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If you have found this guide useful in planning your trip to Hawai in 2023, we have plenty more that may be beneficial to your visit!

Browse some of our most popular Hawaii travel guides below:

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