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Written by Justine Jenkins
A Guide To Planning Your First Trip To Hawaii

A Guide To Planning Your First Trip To Hawaii

April 4, 2022Justine Jenkins14 min readAdd comment
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So you’ve decided to plan your first trip to Hawaii? Excellent! Read on to discover our step-by-step guide and top tips to help you plan your dream trip.

Hawaii is one of – if not the most – beautiful places my husband and I have ever visited together. Our time there had such an impact on us and is the main reason why we started this travel blog that you’re on now. We’ve also often joked that we’ll retire to Hawaii one day. 

The Hawaiian islands are the personification of paradise. They’re a place where the people of the land have such a love and respect for nature, their neighbours and their surroundings, which we in turn respect and admire.

Keaukaha Beach Park near Hilo Hawaii
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There’s so much natural beauty to see in Hawaii as well as adventure and true bucket list activities – and we can’t wait for you to experience it all first-hand yourself.

RELATED: 29 Incredible Hawaii Bucket List Ideas & Things To Do

So, to help you with planning your first trip to Hawaii and quite possibly one of the most amazing trips you might ever experience, here’s what you’ll discover in this Hawaii travel guide:

  • How to plan your first trip to Hawaii step-by-step
  • Where to stay on the islands of Oahu, Maui and The Big Island
  • Important things to know before visiting Hawaii
  • Some must-know Hawaiian words and phrases

A Step-By-Step Guide To Planning Your First Trip To Hawaii

A Guide To Planning Your First Trip To Hawaii

Step 1: Determine what your budget is

I know, I know. This step comes into play for any trip you’re planning, but it’s an especially important point to remember when planning a bucket list trip such as this one.

Will you be chilling out in hostels? Getting comfortable in 3-star accommodation? Or splurging on luxury resorts?

Will you hire a car to get around? Join day tours? Or find your own way around with public transport?

Waikiki Beach Hawaii

These are all questions you need to ask yourself before planning your trip as your answers determine how long you’ll spend in Hawaii, what you’ll see and do while you’re there and whether you’ll island-hop or pick just one island to explore.

Your budget may also help you decide when to visit Hawaii as – understandably – some times of the year are more expensive than others.

Step 2: Think about when you want to visit

The peak travel season in Hawaii is usually from around mid-December through to the middle of June. 

This is because Hawaii is a fantastic winter destination for those in need of sunshine and warmer weather.

Temperatures in Hawaii in winter are usually in the mid-twenties Celsius (70-ish Fahrenheit).

And then you’ve got Spring Break in March or April where – once again – Hawaii is a prime destination.

So, if you want to save some money and see Hawaii when it’s a bit quieter then we’d recommend planning your trip for September or October.

The weather should still be warm enough for relaxing beach days and it’s also a great time for more adventurous excursions like hiking through volcanic craters and stargazing on Mauna Kea.

Hawaii Volcanic Crater flowers

Step 3: Decide which island or islands you want to visit

There’s so much natural beauty to see and tons of culture to soak up in Hawaii, but each of the islands also have their differences.

Will you spend your time on one island? Two? Three? More than that?

We’ve already written various guides to help you choose which island or islands you might want to visit on your first trip to Hawaii (linked below), but in a nutshell:

  • Oahu is easy to get to, convenient and there’s lots to see and do there
  • Maui is good for watersports and nightlife
  • Kauai is the ultimate destination for nature and outdoors lovers, but it’s a little harder to get to
  • Molokai is one of the most remote and traditional Hawaiian islands
  • Lanai is also remote and off the beaten path
  • The Big Island is full of adventures in nature and has a relaxed atmosphere (especially compared to Maui and Oahu)

Read More:

Halona Beach Cove

Step 4: Choose what you want to do

Each of the Hawaiian islands offer something different and something for everyone.

Are you an outdoors and nature lover in search of adventure? Or do you prefer to sip cocktails and chill out in the sunshine? Do you want to soak up some local culture during your trip?

To help you decide, we’ve written various articles about all the amazing tours and experiences you can enjoy while in Hawaii (linked below):

Mauna Kea Sunset

But if you’re short on time to read those, then here are the experiences and tours we think every first-time visitor to Hawaii should try:

Discover more amazing things to do in Hawaii >>

Justine at Pearl Harbor on Oahu, Hawaii

Step 5: Map out your itinerary

Once you’ve figured out which island or islands you’re heading to and what you want to see and do while you’re there, it’s a good idea to plan out your first Hawaii itinerary.

We use Google My Maps for this as you can create “layers” for each day and see how everything looks on an actual map.

At this point, you’ll want to pencil things in as you may need to make changes once you’ve actually booked everything and confirmed the dates of your flights and hotel stays. 

Hawaiian Flowers

Using a map to plan out your itinerary also helps you to visualise your trip as a whole and ensures you’re not trying to do too much on any given day. 

We usually go with the idea of having no more than two or three activities planned for each day. Of course, this dramatically reduces if you’re booking full-day or half-day tours.

To help you even further, check out our 7 day Hawaii itinerary for first time visitors, which shows you how you can spend a few days on both Oahu and The Big Island and what you can see and do during your time.

RELATED: Your Perfect 7 Days in Hawaii Itinerary

You might even want to add on a few days at the beginning or end of your trip for city breaks in places like Los Angeles or San Francisco. 

After all, you’ll probably be transiting through one of these on your way to Hawaii anyway. 

In this case, check out our 2 week West Coast USA itinerary, which shows you how to make the most of a LA city break, San Francisco city break and time spent on two Hawaiian islands. Yep – all in one trip!

Need even more help? Do you know about our itinerary planning service? We can help you create your own bespoke Hawaii itinerary! Find out more here >>

Chinaman's Hat Island Hawaii

Step 6: Choose where to stay

Once you can see where you’ll spend most of your time on the islands, you’ll better understand which sides of each island you’ll want to stay on to help you get around.

Seeing as most first-time visitors to Hawaii will head to either Oahu, The Big Island or Maui, we’ll focus our attention on these three main islands in this next section.

But feel free to get in touch with us if you’d like suggestions for the other islands as we’ll happily help you with those as well.

Where to stay on Oahu

Honolulu

On Oahu, you’ll find Honolulu (where Waikiki Beach is) as one of the most convenient places to stay. 

Not only is this ideal for getting to and from the airport, but there’s also lots to do on this side of the island. It’s also an ideal pick up point for most day tours.

In this area of Oahu, you’ll come across plenty of large chain hotels and highrises alongside some privately-owned self-catered accommodation.

RELATED: Epic 3 Day Oahu Itinerary For First Time Visitors

Rainbow in Honolulu Hawaii

Here are some hotels that come highly recommended in this area that you might want to take a look at:

Find more places to stay in Honolulu >>

North Shore

If you want to spend most of your time on Oahu relaxing on beaches, then you might want to consider the North Shore area instead. 

This area is more lowkey than Honolulu, while the type of accommodation most prevalent here is resorts, vacation rentals and holiday cottages.

Here are a couple of places you might want to check out:

Find more places to stay in the North Shore area >>

Oahu beach

Where to stay on The Big Island

Hilo

Hilo is a city on the Eastern side of The Big Island. It has its own airport and there are various things to see and do within the city itself. Check out our mini Hilo travel guide for some ideas.

Hilo is also an ideal pick up point for most tours to other parts of the island including ones to Volcanoes National Park and Mauna Kea.

As The Big Island is fairly relaxed as a whole, you’ll find an array of accommodation to choose from including larger hotels, hostels, B&Bs and self-catered vacation rentals.

Here are some suggestions:

Find more places to stay in Hilo >>

Hilo, The Big Island, Hawaii

Kailua-Kona

Kailua-Kona is a town on the Western side of the island and offers a variety of things to see and do locally including watersports activities and whale watching.

Kona also has its own airport making it easy enough to get to.

Here are some suggestions of where to stay in this area:

Find more places to stay near Kona >>

Volcanoes National Park

If you plan on hiring your own mode of transport during your time on The Big Island, then you might want to consider staying close to Volcanoes National Park. 

Volcanoes National Park is on the Southern side of the island and makes for a dream bucket list adventure.

You’ll find it easy enough to get to and from with your own transport. You’ll need to fly into Hilo, which is roughly 30 miles away.

Here are some ideas of where to stay near Volcanoes National Park:

Find more places to stay near Volcanoes National Park >>

Hawaii Volcanic Crater

Where to stay on Maui

West Maui

Lahaina, Kaanapali and Kapalua (all along the Western coast of Maui) are some of the most popular places to stay on the island. 

You’ll find plenty of hotels, resorts and B&Bs to choose from across these areas and most budgets are catered for. 

You’ll fly into Kapalua Airport and you should find it easy enough to get to any of these areas from the airport.

Here are some hotel suggestions to take a look at that are highly rated by other travellers:

Find more places to stay in West Maui >>

Wailea

Wailea on the Southern side of the island is another popular destination, but you may find it more expensive than the Western side. 

You’ll likely fly into Kahului Airport on the Northern side of the island, so you’ll also need to plan how you’ll get to and from the airport to Wailea.

Still, if beaches and luxury resorts are your kind of thing, then Wailea might be the perfect area on Maui for you. 

Here are a few hotel suggestions to check out:

Find more places to stay in Wailea >>

Sunset at Waikiki Beach

Step 7: Book everything!

So, by now, you should know:

  • What your budget is
  • When you want to travel to Hawaii
  • Which island or islands you wish to visit
  • What you want to do during your trip (especially the amazing bucket list activities!)
  • What your ideal itinerary looks like
  • Where you’re going to stay during your trip

This means there’s only one thing left to do… book everything! And then patiently wait for your trip to start.

In case it helps, we like to use the following websites for booking our trips:

  • Booking.com for its wide range of hotels, resorts and other accommodation
  • Get Your Guide for tours and activities with free cancellation should your plans change!
  • Google Flights and Skyscanner for great flight deals and to see when it’s cheapest to fly to your destination

Important Things To Know Before Visiting Hawaii

Hawaii is a place of respect. Everyone there has great respect for what’s around them – from the land they walk on to the air they breathe. 

With this in mind, here are some important things to know ahead of your trip to Hawaii to help you respect the people and their culture.

Respect your surroundings – especially Kapu (sacred sites)

The Hawaiian people have a deep found respect and love for their land (their ‘Aina). 

While there are many Kapu (sacred sites) dotted around the islands, remember that all land is sacred to people in Hawaii. 

At the very least, take your litter with you and avoid moving or touching anything in nature that doesn’t belong to you.

Hawaii's Buddhist Temple (as seen from the bridge)

Do not move or steal rocks or anything in nature

Speaking of respecting nature, do not be tempted to move or steal rocks, sand, pebbles or anything from Hawaiian land. 

Within the Hawaiian culture, Pele is the goddess of volcanoes and fire and she created the Hawaiian islands. 

The Hawaiian people believe that should you steal anything that belongs to Pele then you’ll be subjected to Pele’s Curse. 

Stealing rocks is taboo in Hawaii and highly offensive to their culture, so just don’t do it!

Keep your distance from marine life

There are several federal and state laws in Hawaii, which protect marine life. 

Animals like sea turtles (Honu), monk seals, humpback whales and more all fall under this protection. You’re required to stay a specific distance away from each of them – ranging from 10 feet for sea turtles to 100 yards for humpback whales. 

So, to be on the safe side, it’s best to keep your distance from all marine life or you could face a substantial fine.

Slow down and take the time to reflect

Island time is a real thing in Hawaii and it appears to stem from the peoples’ love and respect for one another. 

They take their time with everything, so you may find drivers giving way to each other even when the roads are busy. This is known as driving with aloha.

Service in restaurants may also be slower than what you’re used to. 

The idea is to just go with the flow, relax, take your time and enjoy the freedom that comes with slow travel and island life.

Take note of Lei etiquette

You may be offered a Lei (flower garland) during your trip and they come with some strict customs.

Lei symbolise aloha, aka love and affection, and you should always accept one to avoid offending anyone. Should you need to remove it, it’s best to do so discreetly or in private.

If you or someone you’re travelling with is pregnant, then you may find that the Lei given to them is untied. This is because a closed Lei is considered bad luck for pregnant women.

Finally, don’t throw your Lei away. Typically, you should use your Lei to bring fragrance and nature to your car or home, or return it to the earth from whence it came by hanging it from a tree or burying it.

Lei etiquette - fragrance your home

Don’t text or look at your phone when crossing the road

It’s illegal to text or look down at your phone when crossing the road in Hawaii – and there’s a hefty fine for any pedestrians caught breaking the law.

Don’t smoke around children (Keiki)

It’s also illegal to smoke around children (Keiki) including e-cigarettes. Once again, a hefty fine awaits anyone caught breaking the law.

Single-use plastic bags are banned

Single-use plastic bags are now banned in Hawaii, so you won’t be given one in grocery stores. 

Some stores may offer you a paper bag, but most won’t give you a bag at all. It’s probably best to carry your own reusable tote bag just in case.

Remove your footwear when entering homes and sacred sites

When entering someone’s home in Hawaii, you should remove your footwear. 

This stems from the Japanese culture, which has influenced some of the cultures you’ll see and experience in Hawaii today. 

Hawaii Buddhist Temple on Oahu Byodo-In Temple

You may also be asked to remove your footwear when visiting sacred sites such as the Japanese Buddhist Byodo-In Temple on the island of Oahu. 

You’ll likely see a sign asking you to remove your footwear at sites like these.

Must-Know Hawaiian Phrases

Although there are lots of Hawaiian phrases you could learn before your trip, there are two words in particular that we think everyone ought to know.

Aloha

You’ll commonly hear ‘Aloha’ when someone’s wishing you ‘Hello’ or ‘Goodbye’. 

But the meaning of it goes far beyond that within the Hawaiian culture. It also means love and affection. 

Everything should be done with aloha in mind and you should treat everyone with aloha during your trip and beyond.

RELATED: Reasons to visit (and fall in love with) Hawaii

Mahalo

Mahalo means thank you. 

But as with most Hawaiian words and phrases, it has a deeper meaning. It also means gratitude, respect, admiration and more. 

Think about what you’re most thankful for. This is your very own slice of mahalo – and just like aloha – keep it at the forefront of what you do as this will help you act with great joy and happiness in life and towards others.

Rabbit Island Hawaii

Understanding directions

You might also find it helpful to take note of how people in Hawaii give directions as they don’t normally use north, east, south or west.

Here’s what they may tell you instead:

  • Mauka – toward the mountains
  • Makai – toward the ocean
  • Ewa – west
  • Diamond Head – east

You may also hear Hawaiians use these two words when talking about which side of the island things are on:

  • Windward (or windward side) is the wet, tropical side of the island, which is usually in the north or east
  • Leeward (or leeward side) is the sunny, cooler side of the island, which is usually in the south or west

Windward and leeward are related to Hawaii’s trade winds, which – in simple terms – refers to the direction the wind is blowing in and how this affects the islands’ climates. 

I hope you’ve enjoyed this guide to planning your first trip to Hawaii and that it was helpful. Should you want to ask us any questions about your trip, please drop us a line in the comments section below and we’ll reply to you asap.

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A Guide To Planning Your First Trip To Hawaii
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