How to Plan a Trip to Hawaii: Everything You Need to Know

How to Plan a Trip to Hawaii: Everything You Need to Know

Planning a Hawaii vacation doesn't need to be overwhelming! Read on for the ultimate guide to how to plan a trip to Hawaii, from a local.
Rachel Off Duty: How to Plan a Trip to Hawaii

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Rachel Off Duty: How to Plan a Trip to Hawaii – Everything You Need to Know

COVID Travel Restrictions on Hawaii: At the time of writing, there are additional steps on how to plan a trip to Hawaii that you need to familiarize yourself with due to the ongoing pandemic. Visit Hawaii’s Covid-19 website and the Safe Travels website for the latest updates. 

Are you thinking of visiting Hawaii for the first time, and in search of some Hawaii travel tips? 

You’ve definitely come to the right place. I grew up on the island of Oahu and have visited Maui, Kaua’i, the Big Island, and Lana’i multiple times!

And, after leaving Hawaii to move to California for college, and even after traveling to see some of the world’s most famous beach destinations like Tulum and Bali, I can still say without any bias: Hawaii really is something special. 

Rachel Off Duty: Woman Hiking on Oahu
Rachel Off Duty: Woman Hiking on Oahu

When you think of Hawaii, you might picture surfers, dolphins, warm water, pineapples, and hula dancers. And Hawaii is all of those things, but it is so much more than a paradise or a vacation destination. Hawaii has incredibly complex history, beautiful culture, storied residents, and plants and animals that can’t be found anywhere else in the world.

To think of Hawaii as just a ‘paradise,’ while there’s no denying its beauty, is to do it a disservice. Because there’s so much more to know beyond the beaches and pineapples and grass skirts you see on postcards. 

But don’t worry, let me break it down for you. From Hawaii’s history, to where to go, and so much more, read on for everything you need to know about how to plan a trip to Hawaii!

First Of All, Where is Hawaii?

Rachel Off Duty: How to Plan a Trip to Hawaii

We can’t kick off a guide about how to plan a trip to Hawaii without talking about where Hawaii is! Its remoteness is part of what makes these islands so unique, after all.

Hawaii is located about 2,100 miles southwest of the United States’ west coast. It’s actually nearly smack in the middle of California and Japan in terms of distance. 2,390 miles from California and 3,850 miles from Japan!

Out in the Pacific Ocean, thousands of miles from land in either direction, the Hawaiian Islands are actually the most remote island chain in the entire world!

A Quick Hawaii Geography Lesson

Rachel Off Duty: How to Plan a Trip to Hawaii
Rachel Off Duty: Where is Hawaii?
Rachel Off Duty: How to Plan a Trip to Hawaii

The Hawaiian island archipelago includes eight major islands, as well as several minor islands, atolls, and islets. Did you know – the state of Hawaii actually counts 137 islands in the Hawaiian island chain! 

Volcanic activity formed the Hawaiian islands. In fact, the main Hawaiian islands are actually the exposed peaks of a massive underwater mountain range (the Hawaiian-Emperor Seamount Chain) that’s still evolving to this day. While the oldest and northwesternmost island, Kure Atoll, is around 28 million years old, the newest and southwesternmost island, the Big Island, is estimated to only be 400,000 years old. Just a little baby by comparison! 

While there are many more Hawaiian islands than most people realize, the travel advice you’ll need to know pertains to the main Hawaiian island chain: The Big Island, Maui, Moloka’i, Kaho’olawe, Lana’i, Oahu, Kaua’i, and Ni’ihau. 

Which Hawaiian Island Should I Visit?

For most people wondering how to plan a trip to Hawaii, this is usually the first question you’ll find yourself asking.

Of Hawaii’s eight major islands, you are able to visit six – Oahu, Maui, the Big Island, Kaua’i, Lana’i, and Moloka’i. When it comes to how to plan a trip to Hawaii, choosing which island to visit is often the hardest part for first-time visitors. Each island has incredibly unique characteristics and things to see!

Below, you’ll find a quick overview of each (including the two islands you can’t visit). These island highlights might help you decide which Hawaiian island to visit depending on the kind of experience you’re after.

Oahu

Rachel Off Duty: How to Plan a Trip to Hawaii – Oahu

Oahu – where I’m from! – is nicknamed “The Gathering Place.” Oahu is Hawaii’s most populated, most famous, and most visited island.

Though not the biggest island, Oahu is considered the ‘main’ island. The Kingdom of Hawaii was governed from Oahu after being united by King Kamehameha in the 1800s. Afterwards, Honolulu became the official capital city in 1959, when Hawaii became part of the US.

Whenever someone asks me how to plan a trip to Hawaii, I always recommend Oahu for a first visit!

Here are some things to know about visiting Oahu:  

  • Best Known For: Hawaii’s capital city of Honolulu, the hotel district of Waikiki, world-famous surfing, Pearl Harbor, and Iolani Palace.
  • Why Visit? Oahu is a great choice for first-time visitors to Hawaii because it offers a little bit of everything. From great beaches and hiking, to historical sites and cultural activities, to a culinary and bar scene that would get any foodie excited, Oahu really does hit the nail on the head when it comes to having a wide variety of things to do any kind of traveler. 
  • Good to Know: Oahu is Hawaii’s most populated island, with about 75% of the entire state population. It also received around 50% of all of Hawaii’s visitors. You can expect more traffic and more crowds here, but if that doesn’t bother you, Oahu is a wonderful island to visit! Its population size also makes Oahu the most multiracial island in Hawaii, and one of the most multicultural communities in the world.

Maui

Rachel Off Duty: Which Hawaiian Island to Visit - Maui

Maui is known as “The Valley Isle.” It has a wide valley region that sits less than 200 feet above sea level, flanked by tall mountainous regions on either side. It is the second-largest Hawaiian island with a population of just under 200,000, and was briefly home to the capital of the Hawaiian Kingdom before the location moved to Honolulu, Oahu. 

Throughout my childhood, Maui was my favorite island to visit when island-hopping with my family! 

Here are some things to know about visiting Maui:

  • Best Known For: Home to Haleakala National Park and the infamous Road to Hana road trip.
  • Why Visit? Maui is another great recommendation for Hawaii first-timers, along with Oahu, because of its balance between developed and natural areas. You won’t need to look far for a good place to eat, and there’s an abundance of hotels throughout the island. Plus, because of the island’s size and smaller population, you can easily spread out and enjoy the island away from the crowds whether you’re looking for an active or relaxed vacation.
  • Good to Know: Most people will recommend the Road to Hana – the 52-mile windy, narrow drive from Kahului to Hana town – as the thing to do on Maui. But it’s not one for the faint of heart! The Hana Highway has 620 curves and 59 bridges, making it one of the country’s most dangerous road trips. If you do decide to drive the Road to Hana, definitely exercise tons of caution and be extra respectful to local residents, businesses, and nature. Or, consider taking a guided tour (like this one) as a way of helping reduce traffic congestion!

Hawai’i (The Big Island)

Rachel Off Duty: Which Hawaiian Island to Visit - Big Island

The Big Island is actually named Hawai’i, but most people refer to it as the Big Island because it is, well, pretty dang big! In total, it would take you between 6 and 9 hours to drive around the entire island without stopping.

I love the Big Island because its geology is incredibly unique. From dried-up lava fields to endless waterfalls, the island’s scenic variety is breathtaking. 

Here are some things to know about visiting Hawai’i:

  • Best Known For: Home to Hawaii Volcanoes National Park, a wide range of colorful sand, and the occasional snowfall on Mauna Kea.
  • Why Visit? The Big Island will no doubt give you the biggest range of Hawaii’s varied landscapes, from beautiful beaches to snowy summits. There are many unique things the Big Island has to offer that simply can’t be found on any of the other islands, with the biggest draw being volcanic activity-related attractions like lava tubes, black sand beaches, and the occasional fresh lava flow from Kilauea eruptions. However, unless you go to the Big Island wanting to only see the volcanoes, I recommend dedicating at least a week to a week and a half to your visit to get a full spectrum of all this island has to offer.
  • Good to Know: Though tempting, it is believed to be major bad luck to take any sand or lava rocks from any Hawaiian island but especially this one (because as the legend goes, Hawaii’s goddess of fire Pele, is said to live on this island). Whether or not you believe it, know that the national parks in Hawaii receive countless packages each month from all over the world filled with rocks, sand, and apology letters from past visitors who’ve dealt with crazy bad luck after taking from the island. You’ve been warned!

Kaua’i

Rachel Off Duty: Which Hawaiian Island to Visit - Kaua'i

Kaua’i – “The Garden Isle” – is one of the most exquisitely beautiful of the Hawaiian islands, thanks to its lush greenery and endless waterfalls. Each time I visit Kaua’i, I am in awe that a place with scenery like this exists.

Here are some things to know about visiting Kaua’i:

  • Best Known For: The iconic NaPali coast, Waimea Canyon (Hawaii’s own version of the Grand Canyon), and mesmerizing waterfalls.
  • Why Visit? A much slower-paced, less-crowded island, Kaua’i is a great island for outdoor lovers and romantic getaways. While you won’t find as much by comparison in terms of development (the entire island is home to just around 75,000 people), you will find endless emerald green mountains, amazing sunsets, and mighty waterfalls. 
  • Good to Know: Kaua’i is a fairly small island, though massive in terms of things to do and see. When you rent a car on the island, know that despite the island’s small size, driving from place to place will still take a decent amount of time. Why? There is only one main highway – Kuhio Highway – and it only has one lane in each direction, with a top speed limit of no more than 50 mph. It doesn’t go all the way around the island either, thanks to the NaPali coast, so to get from one end to the other will take you at least two hours, give or take. Definitely check estimated drive times when planning your Kaua’i itinerary!

Moloka’i

Rachel Off Duty: Which Hawaiian Island to Visit - Moloka'iImage Credit: GoHawaii.com

Moloka’i is known as “The Friendly Isle” and also the “most Hawaiian” island due to its high native Hawaiian population. Right in the center of the main Hawaiian island chain, Moloka’i sits just eight miles or a 25-minute flight from Maui.

There are only 8,000 residents, and the island receives the fewest annual visitors of the visitable Hawaiian islands. Though, for travelers eager to get really off the beaten path and see a more rural version of Hawaii that remains relatively unchanged over the decades, Moloka’i might be for you.

Here are some things to know about visiting Moloka’i:

  • Best Known For: More rural, “unspoilt” Hawaii, the highest sea cliffs in the world, beautiful coral reefs, and the site of the historic leprosy colony, Kalaupapa.
  • Why Visit? For a much, much slower island vacation, a better chance of getting outdoor adventures all to yourself, and a more unchanged view into the lifestyle of Hawaii, Moloka’i is a fascinating visit. Best for more intrepid explorers and those who can appreciate a place even without ample vacation amenities, Moloka’i has a lot to offer for those willing to look!
  • Good to Know: Because Moloka’i is one of the least visited islands in Hawaii, you won’t be able to fly directly into the island from out of state. You’ll need to first travel to Oahu or Maui and take a quick inter-island flight to get to Moloka’i’s airport. Once here, you’ll notice other tourism infrastructure is limited, which can be an adventure in itself. There is only one true hotel (most other visitors rent homes or go camping), businesses are closed on Sundays, and there are no traffic lights on the entire island. 

Lana’i

Rachel Off Duty: Which Hawaiian Island to Visit - Lana'iImage Credit: GoHawaii.com

Known as “The Pineapple Isle” or “The Embracing Isle,” Lana’i is one of those unique examples of an island that is part of the state of Hawaii, but also privately owned by a third party (Ni’ihau, below, is another example). However, unlike Ni’ihau or even Moloka’i, Lana’i is definitely much more set up for tourism in the traditional sense. 

Here are some things to know about visiting Lana’i:

  • Best Known For: Relaxation, seclusion, and a small but incredibly luxurious selection of accommodations including the Four Seasons Sensei Lana’i, and the Hotel Lana’i.
  • Why Visit? Lana’i was once home to a plantation that produced 75% of the world’s pineapples (giving the island its nickname). Today, a visit to Lana’i is often associated with “quiet luxury,” meaning you may pay a bit of a premium to stay here (hotel rooms start at around $400/night), but in exchange you are rewarded with no crowds, no traffic, and ultimate seclusion. This is the island to go to if you’re looking for a more luxe getaway and some pampering. 
  • Good to Know: Want to visit Lana’i without staying overnight? You can easily take a ferry or a guided catamaran tour from Lahaina, Maui! 

Ni’ihau

Rachel Off Duty: Which Hawaiian Island to Visit - Ni'ihau

One of two islands in Hawaii that technically can’t be visited, Ni’ihau is known as “The Forbidden Isle.” Privately owned, the island is home to an estimated 170-ish residents who live traditional Hawaiian lifestyles and continue to use Hawaiian as their primary language. The island got its nickname after a polio epidemic in Hawaii in the mid-1900s, where you needed to have a doctor’s note and complete a two-week quarantine in order to visit. 

It’s not considered a visitable island in the traditional sense, but…

There are actually technically three ways to visit Ni’ihau (or at least get pretty close):

  1. Getting invited by a Ni’ihau resident or by the island’s owners, the Robinsons
  2. Taking a Ni’ihau Helicopters or Ni’ihau Safaris tour 
  3. Visiting the island offshore, by boat, for some spectacular snorkeling or diving (I recommend looking into the Napali Coast and Ni’ihau boat tour from Holo Holo Charters, which is the tour I did! Check availability on TripAdvisor or directly on Holo Holo Charters website).

Kaho’olawe

Rachel Off Duty: Which Hawaiian Island to Visit - Kaho'olawe

With a strange nickname of “The Target Isle,” Kaho’olawe has a fascinating and bizarre history. During WWII, the island was a training ground and bombing target for the US military. There was never a huge Hawaiian population on Kaho’olawe prior to WWII, but following its usage by the military, Kaho’olawe today remains pretty much deserted and uninhabitable, due to its small size and lack of fresh water. 

The only way to visit this island is by volunteering through the Kaho’olawe Island Reserve Commission, which offers work trips from Maui.

How Many Days Should I Spend in Hawaii?

Rachel Off Duty: Waterfall Hikes in Hawaii

Not yet decided on how many days to spend in Hawaii? Unless you plan to spend your whole trip at your hotel (which I don’t recommend!), I always suggest a minimum of 4 to 5 days for any island. Hawaii isn’t really an easy long weekend getaway because of the long 5+ hour flight from the US, so if you’re planning a trip to Hawaii, plan to dedicate at least 4 to 5 full days to your vacation. 

That said, I think 6 – 8 days is really the sweet spot to not only explore, but also to have extra time to take it easy and relax.

If you want to visit more than one island in Hawaii, I still suggest dedicating 4 to 5 days per island. So, for a two-island Hawaii vacation, you’ll probably want to plan for at least 9 or 10 days total. 

Can I Visit Multiple Hawaiian Islands Easily?

Rachel Off Duty: Choosing the Right Hawaiian Islands to Visit
Rachel Off Duty: Choosing the Right Hawaiian Islands to Visit
Rachel Off Duty: Choosing the Right Hawaiian Islands to Visit

You might be surprised by this: island-hopping in Hawaii actually isn’t that easy!

But is it possible? Yep, but it’ll take some extra planning.

Unless you’re taking a multi-island cruise, you’re going to need to book an inter-island flight to get from one island to the next. And, depending on the islands you choose, you may need to connect on Oahu or Maui. 

That means you’ll have to deal with all the same steps of air travel – the airport, TSA, checking bags, renting / returning cars – even for a short 20 to 45 minute flight. In total, that means at least three or four hours to get from one island to the next. 

Because of this, it’s usually easiest to stick with no more than one or two islands on your Hawaii trip, unless you’re staying in the state for two weeks or more.

Some islands will be easier to plan island-hopping trips from. For instance, from Oahu you can easily fly directly to all visitable islands. From Maui, you’ll also have ample direct flights and the option of taking a day trip to Lana’i by ferry or catamaran tour.

If you are planning to visit multiple islands, Hawaiian Airlines or Mokulele Airlines will most likely be your go-to carriers, as they cater specifically to inter-island service and often have the cheapest fares. Compare fares and availability for inter-island flights on Kayak to see whether a multi-island trip is right for you.

How Much Should I Budget for a Trip to Hawaii?

Rachel Off Duty: Woman With Canoe on the Big Island
Rachel Off Duty: ATVing in Jurassic Valley Oahu

When you start researching how to plan a trip to Hawaii, you’ll realize Hawaii is one of the more expensive US vacations you could take. This is due to the islands’ remoteness, high import costs, and designation as a tourism destination. 

I’d say a realistic mid-range budget per person is around $200-$325 per day

  • $100/day on accommodation*
  • $25-50/day on a rental car
  • $50-$75/day on food
  • $25-50/day on activities

*This is based on a $200/night hotel split between two people 

Factoring that in with a round-trip flight from the mainland, you’re looking at around $2,000 – $3,000 per person for a 7-day trip. 

Of course, this can easily go up if you book nicer, more luxurious accommodations, reserve private tours, dine at higher-tier restaurants, and indulge in pampering (spas, massages, etc). 

But, you can visit Hawaii on a budget as well if you hack your itinerary a bit!

How To Plan a Trip to Hawaii on a Budget:

  • Stay at more budget-friendly accommodations (like this affordable boutique hotel in Waikiki)
  • Consider staying in an affordable Oahu Airbnb
  • Go camping (or glamping in Maui)
  • Travel off-season, when the crowds are fewer and the prices start to drop
  • Support local businesses and shop at Hawaii farmers markets
  • Take public transportation (TheBus on Oahu is incredibly reliable)
  • Bring a reusable water bottle 
  • Book activities in advance to cinch better deals
  • Get a Go Oahu Pass to save money on certain sights and attractions
  • Focus on free things to do, like beaches, hiking, and window shopping
Rachel Off Duty: Woman Eating Poke at Fresh Catch Oahu

When Is the Best Time to Visit Hawaii?

Rachel Off Duty: Rainbows Off the Napali Coast in Kaua'i

Because of Hawaii’s geographic location, the islands are nice and warm all year long. There really isn’t a bad time to visit Hawaii! 

However, there are some seasonal differences that might help you decide how to plan a trip to Hawaii based on exactly what you’re looking for out of your visit.

How to Plan a Trip to Hawaii: Best Times to Visit

  • Peak Season: Peak season for Hawaii travel is always summer (May – August) and winter (December – March). These months may be pricier and a bit more crowded depending on which island you plan to visit. 
  • Low Season: Low season for Hawaii travel typically consists of all the months that aren’t peak! So, September – December, and March – May are when you may find slightly cheaper prices and smaller crowds (though on Oahu, it’ll be less noticeable because you’ll find solid tourism pretty much year-round). These are also the months that local students are back in school or university, which also helps reduce crowding at popular beaches and hikes. 
  • Humpback Whale Watching Season: Humpback whales migrate to warmer waters off the coast of Hawaii from October to May, with peak viewing opportunities usually from December to February. The verdict’s out on which Hawaiian island is best for whale watching though. Maui, Moloka’i, Lana’i, Oahu, Kaua’i, and the Big Island all offer several whale-watching opportunities both on land and by boat. 
  • Best Season for Surfing: Expert surfers (and people who want to watch expert surfers!) will enjoy Hawaii the most in the winter, from mid-November to early February. Oahu’s North Shore is the famous Hawaii surf destination, where waves can sometimes climb up to 30-50 feet in peak surf season. Generally speaking though, you can surf all year long in Hawaii and beaches like Waikiki are great for beginners. For seasoned surfers, know that the south shore has bigger swells in the summer than the north shore, and vice-versa. 
  • Wet Season: Wet season is generally November to March. You’ll get more rain, but the tradeoff is more ‘full’ waterfalls.
  • Dry Season: Dry season is April to October, but keep in mind Hawaii is a tropical state so rainfall can happen year-round. 
  • Holidays: Holidays and long weekends will always see a bit of a price jump as these are popular times to make the 5+ hour flight out to Hawaii. If you plan on visiting Hawaii for a major holiday or long weekend holiday (like Memorial Day and Labor Day), plan several months ahead to get in front of price spikes! 
  • Major Events: Some major Hawaii events to plan for, or around, include the Vans Triple Crown of Surfing, The Eddie, the Moloka’i Hoe, the Merrie Monarch Festival, the Waikiki Spam Jam, Aloha Festival, Made in Hawaii, and the Honolulu Marathon. 

Languages Spoken in Hawaii

Rachel Off Duty: Woman Doing A Shaka

Hawaii is the only state with two official languages: English and Hawaiian. As Hawaii is a US state, English is the major language you’ll use to chat, get around, and read on street signs. 

However, the English you hear in Hawaii might not always be the English you’re used to. You may also hear Pidgin, a sort of English creole formed over the past two centuries as immigrants and plantation workers came together in Hawaii and developed a unique way of communicating with one another. Today, Pidgin is a common English-based variation of communication you’ll hear, and possibly even pick up, when visiting. 

As Hawaii is incredibly multicultural, more than 25% of households also speak a language other than English at home. Philippine languages like Ilocano and Tagalog are the most common languages, as around 23% of the state is Filipino or part-Filipino. 

Sadly, the Hawaiian language nearly died when Hawaii became a part of the United States, as locals were made to learn to read, write, and speak in English. But today you can see a slow but steady revival of the language thanks to Hawaiian immersion schools throughout the islands. Lots of day-to-day sayings pull from the Hawaiian language (like giving directions using the “mauka” or “makai” sides of the island, or saying “pau hana” to refer to the end of the work day and time for happy hour), too. Despite this, today, there are only around 1,000 native Hawaiian speakers and around 8,000 with Hawaiian fluency. 

Because of the near-extinction of the Hawaiian language, it is very respectful and appreciated to attempt to use and pronounce Hawaiian words properly when they’re taught to you during your visit!

Basic Words, Phrases, and Gestures for Your Trip to Hawaii:

  • Aloha: Hello, goodbye
  • Mahalo: Thank you
  • E Komo Mai: Welcome
  • A hui hou: Until we meet again
  • Mauka: The mountain side of the road (when giving directions)
  • Makai: The ocean side of the road (when giving directions)
  • Howzit: Pidgin for “how’s it?” or “how’s it going?”
  • ‘Ono: Delicious
  • Shoots: Pidgin for “okay” or “sounds good”
  • Da Kine: Pidgin for “the one” or “that thing,” and can be positive or negative in context
  • Kama’aina: Literally means ‘child of the land,’ and in modern-day context means a local resident
  • Haole: A non-native Hawaiian or caucasian
  • ‘Aina: Land
  • Malama: To care for or protect
  • Shaka: A hand gesture that’s often used as a greeting or acknowledgment
  • Pupu: An appetizer or small plate
  • Pau Hana: Literally means “done with work” or “after work” and is often used to describe after-work fun time, or happy hour

How to Get Around in Hawaii

Rachel Off Duty: Car Rentals in Hawaii
Rachel Off Duty: Car Rentals in Hawaii

Renting a car in Hawaii is going to be the easiest way to get around when visiting any island. Oahu does have a great public bus system, but outside of Oahu and in general, renting a car will offer you the most freedom, flexibility, and spontaneity for your Hawaii vacation. 

Pretty much any car will do, but keep in mind that certain places and certain activities might require a 4WD. 

I typically visit Kayak first to compare rental car rates on the islands whenever I’m traveling around. Turo and Hui (locally owned) are also great alternatives for seeking out car rentals directly from Hawaii residents. 

On the flip side, if you’re in search of Hawaii RVs, camper vans, and the occasional rooftop tent (like the one I rented in the top left photo!), check out RVshare. This is a fun alternative if you plan on doing any national park or beach camping during your Hawaii trip!

How to Get Around in Hawaii without a Car:

  • By Bus: The bus system, called TheBus, on Oahu is a generally reliable and inexpensive way to explore the island. On Maui, you’ll have the Maui Bus. On Kauai, you can use the Kauai Bus. And last but not least, on the Big Island, you’ll be able to take the Hele-On Bus. There is no public bus system on Moloka’i or Lana’i at the time of writing this blog post. 
  • By Trolley: If you’re staying in Waikiki, the hop-on, hop-off Waikiki Trolley is a reliable way to get around Waikiki, Honolulu, and East Oahu.
  • By Rideshare: You should have access to Uber and Lyft on Oahu, Maui, Kauai, and the Big Island. Keep in mind that Oahu will have the highest volume of drivers of any island, but no matter which island you visit, remote destinations away from major cities (like beaches and hiking trails) may mean you won’t be able to find any drivers. An alternative, locally owned rideshare app called Holoholo has also recently become available and offers you the same services as Uber and Lyft if you’re looking to support local. 
  • By Bike: I would generally advise against using bikes as your main method of transportation as Hawaii roads are pretty narrow, and city centers are not as bike friendly as they could be. However, to get from a quick point A to point B, you can check out Biki on Oahu.

Food, Drinks, and Tipping in Hawaii

Rachel Off Duty: How to Plan a Trip to Hawaii – Food
Rachel Off Duty: How to Plan a Trip to Hawaii - Food
Rachel Off Duty: How to Plan a Trip to Hawaii - Food

Whether you’re planning on eating at some of Hawaii’s most high-end restaurants or looking for the best food truck or cheap plate lunch, there really is a little bit of everything no matter your taste or price range. 

On Oahu and Maui, you’ll generally find the widest variety of cuisines and highest number of restaurants.

On smaller or less crowded islands, like the Big Island and Kaua’i, you’ll have a bit less volume in terms of restaurants, but you’ll still find a solid offering of local joints, seafood, Hawaiian staples, and food trucks (bonus: Kaua’i is said to be a great choice for vegetarian and plant-based eaters).

Lana’i is known for its more expensive resort-side food offerings.

And Moloka’i, on the flip side, is known for its small, ultra-local “hole in the wall” establishments. 

If you’re into beer, wine, and / or cocktails:

How Much Should You Tip?

Regardless of the island you visit, Hawaii – just like the rest of the United States – has a tipping economy, and it’s a bit on the ‘higher’ end. 15% for good service, and 18-22% for great service, is a good rule of thumb. 

Hawaii History Fast Facts (Know Before You Go)

Rachel Off Duty: Hawaii History to Know Before You Go

Though not required, it is widely recommended that you familiarize yourself with Hawaii’s history so you can more fully understand and appreciate everything these islands had to endure, in order to become the Hawaii people are able to visit today. 

  • The islands were discovered by Polynesian voyagers more than 1,500 years ago, who found Hawaii using just the stars to guide them.
  • King Kamehameha went into battle to unite the Hawaiian islands under a Kingdom of Hawaii. Before this, the islands were actually individually governed leading to lingering nuances in people, language, and culture.
  • The sugar and pineapple plantation industries brought various cultures to the Hawaiian islands, and also caught the attention of western businesses and investment.
  • King Kamehameha proposed the Great Mahele and the Kuleana Act in the 1800s in an effort to redistribute the land. Unfortunately, as most Hawaiians weren’t familiar with the need to make land claims, this act inadvertently separated most Hawaiians from obtaining the titles to the lands they lived and worked on. Because of Hawaii’s complex and largely painful history with the concept of land ownership, the topic of vacation homes and moving to Hawaii as an outsider is a bit sensitive to many locals, especially those of Hawaiian descent. 
  • The Hawaiian monarchy was overthrown in 1893. But, you can still visit landmarks and historical residences of Hawaiian royalty today.
  • Hawaii was annexed by the US in 1898, and Hawaii later became the 50th US state in 1959.

Despite this wild history, people on Hawaii (both native and non native) generally love sharing these islands and their traditions with visitors who are respectful. Hawaii has so much more to offer than pretty beaches, so definitely take the time to learn about it  beforehand, and immerse yourself in some cultural and historical activities while you’re visiting! 

One book I found incredibly eye-opening, even as a former Hawaii resident, is Detours: A Decolonial Guide to Hawaii. I highly recommend giving this a read if you have the time (find it here on Amazon).

Hawaii Culture and Etiquette for First-Time Visitors

Rachel Off Duty: Hawaii Culture and Etiquette Tips
Rachel Off Duty: Hawaii Culture and Etiquette Tips
Rachel Off Duty: Hawaii Culture and Etiquette Tips

Because of Hawaii’s complex history, multicultural community, delicate ecosystems, etc etc etc, there are a lot of nuances to culture and etiquette for Hawaii travel.

While other destinations might easily forgive most travel faux-pas, I will say that in my observation of traveling all over the world, to be an irresponsible visitor in Hawaii (intentionally or not) is often taken much more seriously.

Why? I think it’s because Hawaii residents feel a deeply seeded unsettlement towards outsiders coming and taking from the islands, because historically that’s been a theme for centuries. But also, I think it’s because Hawaii is such a popular destination – one of the most popular in the world. So, not only does that come with growing pains, but the expectation is that you should already know some Hawaii travel tips before you come, because there’s bound to be tons of guides (like this one!) helping you out. 

Again, that’s just my observation, but as they say, “to receive aloha, you must give aloha.”

So, come prepared to show respect, be open-minded, and have fun! 

Rachel Off Duty: Hawaii Byodo-In Temple

Everyone’s opinions of tourism in Hawaii will vary, but be sure to familiarize yourself with these quick tips before you go so you’re ahead of the game.

Quick Tips for Being a Respectful Hawaii Visitor

  • Hawaiian versus Hawaii Resident: Unlike being a Californian, Utahn, Michigander, New Yorker, and so on, people in Hawaii are not by default referred to as Hawaiian. That label is reserved for those with Hawaiian blood. To be safe, the term “local” or “Hawaii resident” is more fitting for describing those that call Hawaii home. 
  • Hawaii Wildlife: I mentioned this already but it’s worth repeating! Please do not be that tourist that disrupts wildlife (especially endangered wildlife) for the ‘Gram unless you want a fast-pass to local disapproval and, if caught, a fine or jail time. 
  • Malama ‘Aina: The concept of malama ‘aina means to to care for and nurture the land so it can give back to us and to our future generations. There a lot of layers to this, but as a visitor the best way to internalize this concept is to understand that the Hawaiian islands need protecting and it’s our shared responsibility (also known as kuleana) to do so.
  • Sacred Places: Generations of Hawaiians have called these islands home, and because of this, there are lots of historic places, temples (heiau), ancient battle grounds, and royal burial sites throughout the islands. No matter where you go, keeping a mindset of malama ‘aina will prevent you from accidentally showing disrespect.
  • Reef-Safe Sunscreen: Plan to only use reef-safe sunscreen in Hawaii. If you’re unsure, buy it once you arrive.
  • Honking: Don’t do it! Well, don’t do it a lot. When driving in Hawaii, it’s actually best to avoid using your horn unless you’re about to get hit or are in an emergency. Driving is generally less “every-man-for-themselves” here than in the rest of the US. So, use your horn sparingly, allow people to merge, and throw up a shaka if someone does you a solid while you’re on the road. 
  • When to Book Ahead of Time: More touristy areas (like Waikiki, Poipu, Lahaina, Kihei, and Kona), and more popular activities like luaus, will generally require advance booking. Do a little research ahead of time and if there’s a place or activity you’re dying to try, save yourself the stress and reserve it before you arrive. 

Protecting Hawaii’s Fragile Ecosystems

Rachel Off Duty: How to Visit Hawaii Respectfully

Hawaii is home to some of the most unique plants and animals due to its unique climate and total isolation. Many of these species are endemic and can’t be found anywhere else in the world! 

Unfortunately, because of this, Hawaii is the #1 state in terms of endangered species. 

When it comes to what to know before visiting Hawaii, this is an important though often overlooked fact. Because Hawaii has so many endangered and protected species, it’s up to both locals and visitors alike to take some extra precautions: 

  • Wear reef-safe sunscreen ONLY when visiting Hawaii. While you can technically bring whatever sunscreen you want to the islands, stores in Hawaii are required to only carry reef-safe. So, be like the locals! 
  • It’s illegal to feed marine mammals.
  • By law, you need to keep a respectful distance from endangered animals, some of the most common being Hawaiian Monk Seals, Hawaiian Green Sea Turtles, Spinner Dolphins, Humpback Whales, and Nene Geese. 
  • Touching Hawaii’s wildlife, whether endangered or not, is majorly frowned upon in Hawaii due to the general understanding that Hawaii is an endangered species capital.
  • If you like to hike, brush off your hiking boots before you get to Hawaii, and after every Hawaii hike, to help prevent the spread of invasive species.
  • Stay on marked trails whenever possible.

And of course, when visiting Hawaii, don’t forget to look around and really take it all in!

You’re bound to see plants and wildlife you’ll never see anywhere else in the world, no matter which island you visit. This is honestly one of the top things that makes this island chain so special.

How to Plan a Trip to Hawaii: Your Vacation Itinerary (AKA the fun part!)

Rachel Off Duty: Planning Your First Hawaii Trip

Now that you know pretty much everything you need to know about how to plan a trip to Hawaii, it’s onto the fun stuff! Namely, choosing an island to visit and planning your Hawaii itinerary.

Check out my suggested island itineraries and things to do on Oahu, Maui, Kaua’i, and the Big Island next:

Or, to see all of my Hawaii guides in one place, just click here!

I hope these Hawaii travel planning tips help you feel more confident about how to plan a trip to Hawaii! Where in Hawaii are you thinking of traveling to? What are you most excited to do, or see? Tell me below! 

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How to Plan a Trip to Hawaii: Everything You Need to Know - Rachel Off Duty
How to Plan a Trip to Hawaii: Everything You Need to Know - Rachel Off Duty

Hey there! I’m Rachel, a travel writer and a full-time advertising / marketing expert. In 2019, I traveled more than 25 times while working 9 to 5, and since then I’ve committed myself to living a more adventurous life, even if it means bringing my laptop along for the ride.

Are you hungry to travel more, but overwhelmed with how to juggle work and play? You’ve come to the right place!

Recent Adventures:
Let's Go Places!

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