How to DO and DO NOT on Your Hawaii Vacation Plan (2023)

2023-01-15 12:10:39 - Drany Macley Drany Macley, the senior editor of, brings extensive journalism background and over eight years of experience in travel writing and editing to the site, offering practical insights and first-hand knowledge through articles on innovative hotels, backed by a BA in Journalism from Ithaca College.

Kauai's North Shore viewed from a helicopter Kaumakani Coast on Kauai

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Traveling to Hawaii is on the bucket list of many. It is one of the most beautiful, but also the most expensive, places we have ever been to, with its stunning beaches, dramatic volcanic landscapes, and lush green hills.

We agree that a trip to the islands is well worth the splurge, but we cannot stress enough the importance of careful advance preparation.

In this article, we will provide you with our best Hawaii travel advice in order to help you organize the perfect Hawaiian vacation.

Whether it's your first time or fifth, we'll walk you through the ins and outs of planning the perfect Hawaiian vacation, including how many days you should spend there, which island to visit, where to stay, what to do, and what you need to book


As of March 2022, however, all entry requirements to Hawaii have been lifted, and the Safe Travels program is no longer in effect.

No longer do US citizens traveling within the United States to Hawaii need to fill out a form or show proof of vaccination or a negative test.

Although wearing a mask is no longer necessary, it may be necessary in certain professions. Be courteous, thank you.

Due to high demand, I advise booking lodgings, transportation, meals, and attractions well in advance. When flying, plan ahead of time because of the lengthy security checkpoint lines.

Tourists from Abroad who Visit Hawaii

Proof of vaccination is still required for entry into the United States for all foreign nationals.

In order to enter the United States after June 2022, a Covid exam is no longer required of most foreign nationals.

A negative test taken within two days of departure is required for all visitors over the age of two from China, Hong Kong, and Macau entering the United States after January 2023.

With healthcare costs already so high, it's more important than ever to have travel insurance before coming to the United States.

We have found SafetyWing to be an excellent budget policy. It is accessible anywhere in the world, includes protection against COVID-19, and is a great deal for families with two kids under the age of 10 because they go free.

Heymondo, which insured our recent trip to the United States, is another excellent choice if you need cancellation cover.

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Duration of Vacation in Hawaii

On average, visitors spend 7 days in the Aloha State. I'd say that's the bare minimum for an island hopping vacation, but ten to fourteen days is ideal.

Some people do make the trip to Hawaii for 4-5 days, but it's a long way from the continental United States (or anywhere else). ) for a short trip, and the first few days will be spent adjusting to the new time zone. However, any amount of time in Hawaii is preferable to none at all.

I would suggest picking just one island to explore if you only have a week to spend in Hawaii. Find your perfect Hawaiian island by reading the descriptions below.

If you only have 10 days to explore Hawaii, I'd suggest spending the first three on Oahu before moving on to Maui or Kauai.

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One of Hawaii's Finest Islands

One of the most difficult aspects of organizing a vacation to Hawaii is deciding which island to visit. They're all unique and provide various benefits; picking one depends on your specific needs.

The majority of tourists flock to one of these four islands while in Hawaii.


View of Diamond Head and Honolulu from a helicopter tour of Oahu, Hawaii The view from the helicopter of Diamond Head and Honolulu on Oahu.

Oahu has more tourists and businesses than any other Hawaiian island. It is the location of the bustling metropolis of Honolulu, where most tourists stay in the midst of the constant hustle and bustle of Waikiki Beach.

If you want to combine city and beach life, Oahu is the best island because it has the greatest variety of shopping, dining, and nightlife.

It's also the easiest place to get around without a rental car, though I still suggest getting one. Staying in Waikiki puts you within easy walking distance of the sand, as well as a plethora of restaurants, bars, and other attractions.

Tours, Uber, and the Trolley Bus will transport you to nearby landmarks like the Pearl Harbour Memorial.

In the winter, surfers flock to Oahu's North Shore, where the atmosphere is more laid-back and the waves are bigger.

Honolulu International Airport has the most flights to and from the continental United States and international destinations, making Oahu an easy addition to Hawaii vacations.

Here are some of our favorite things to do on the island of Oahu:

  • Stunning island scenery can be seen from a helicopter ride. From Honolulu, we advise taking the Rainbow Helicopters' door-off tour for one hour.
  • Hanauma Bay snorkeling
  • A day of unwinding on the beaches of the Windward Coast, particularly Wainalo and Kailua.

For more information, please refer to our 7-day Oahu itinerary.

Our favorite Hawaii hotel has been Turtle Bay Resort on the North Shore of Oahu. Incredible views of the ocean, secluded beaches (some of which even have turtles), and other dreamy amenities make this place hard to leave. to do, and fashionable accommodations It's a long way from Waikiki, Hawaii.


The black sand beach at Waianapanapa State Park, one of the best road to Hana stops on the island of Maui in Hawaii Waianapanapa State Park on Maui, home to its famous black sand beach

The island of Maui is the second most popular vacation spot in the world.

Beautiful beaches, excellent whale watching, and the waterfalls, bamboo forest, and black sand beaches of the Road to Hana drive make this Hawaiian island a must-see.

Upcountry is where you go to see the sunrise over a volcano, tour vineyards, and lavender farms.

Resorts, restaurants, stores, and activities abound, and there are plenty of sights to see.

Some of our favorite things to do on Maui include:

  • We recommend spending the night in Hana (at the wonderful Hana Kai Condos) to avoid the daytime crowds at Waianapanapa and other tourist hotspots.
  • Seeing whales in Lahaina On our small-group boat tour with Makai Adventures, we saw an astonishing number of humpback whales.
  • Taking it easy on West Maui's beaches (with occasional turtle sightings) )

For more information, view our sample itinerary for Maui.

Kahana Reef, on the western coast of Maui, has reasonably priced condos right on the water. From our lanai, we viewed whales, turtles, and a breathtaking sunset.

Big Island

Hapuna Beach on the Big Island of Hawaii Big Island's Hapuna Beach

Since volcanic activity is more recent on the Big Island (officially called Hawaii), its landscape is more arid and lava-dominated than on the other islands of the Hawaiian chain.

This is the island to go to if you want to see a volcano that is still actively erupting.

It's the biggest island and it has everything from sandy beaches to snowy mountains.

Some of our favorite things to do on Hawaii's Big Island include:

  • Snorkeling with manta rays after dark While on a manta ray trip with Sea Quest, we got incredibly close to these magnificent and enormous creatures.
  • Trip to Kealakekua Bay and Two Step for Snorkeling
  • Hiking the Kilauea Iki Trail in Hawaii Volcanoes National Park is like venturing into a molten crater.

For more information on what to do on the Big Island, check out our handy guide.

It is recommended that you split your time between the western and eastern parts of the Big Island. This quiet cabin in the forest was our favorite part of the Volcano area. This area of Hawaii is vastly dissimilar to the rest of the state.


Kauai's Napali Coast from a helicopter Napali Coast on the Island of Kauai

Kauai has earned the nickname "The Garden Isle" because of how verdant it is compared to the other Hawaiian islands.

While Kauai's popularity has grown, the island still lacks the infrastructure of neighboring Maui and Oahu.

The Napali Coast is famous for its breathtaking green cliffs, but visitors will also find beautiful beaches, waterfalls, hiking trails, and canyons of varying hues.

Some of our favorite things to do on Kauai are:

  • Take in the beauty of Kauai from above on a doors-off helicopter ride.
  • We went whale watching, dolphin spotting, and turtle gazing as we sailed along the Napali Coast, and the massive sea cliffs are breathtaking.
  • Poipu Beach's turtle and seal watching

For more, check out our article detailing the top attractions on the island of Kauai.

Our condo at the Kiahuna Plantation on Kauai's gorgeous Poipu Beach was the highlight of our trip.

Hanalei Bay beach, Kauai, one of the best places to stay in Kauai Beautiful Kauai's Hanalei Bay

Hawai'i and the other Hawaiian Islands are often overlooked by tourists.

It is possible to get off the beaten path by visiting one of these smaller, less frequented islands:

  • The island of Molokai, affectionately referred to as "The Friendly Isle," is home to a slower pace of life, more native Hawaiians, but fewer tourist amenities. The leper colony of Kalaupapa, which I read about in a few of these Hawaii books and found fascinating, is located there as well.
  • Lanai – Lanai was a pineapple plantation for many years, and now it is home to a few high-end resorts. The ferry from Lahaina on Maui takes only an hour, so you can visit for the day if you want to enjoy the secluded beaches without the high price tag.

Exactly Which Part of the Island

The parts of an island you explore determine its unique personality.

Each island has a wet side where the vegetation is lush and green and a dry side where there is typically more sunshine.

That's why we usually divide our time on the island between two or three different towns, as they're all fantastic.

The Places We Saw in Hawaii

We had 3 We spent 5 weeks in Hawaii, mostly on Kauai and Maui with one night in Honolulu before leaving.

We're relieved we didn't try to squeeze in a third island, because there's plenty to do on the two we have.

On our second three-week trip to Hawaii, we split our time evenly between Oahu (where we stayed for a week but could have stayed longer) and the Big Island.

Though we adore all four of Hawaii's major islands, Kauai is our favorite.

Preceding Materials

Traveling to Hawaii? Read This Before You Go!

  • You'll have a better time in Hawaii if you're not constantly stressing over money, so save up first. Spending as a couple, we averaged $267 per day (per person, per day). This included everything but international flights. Avoiding high-priced tourist attractions and traveling during off-peak times can help you save money on your vacation. Staying in five-star hotels and eating every meal away from the hotel would significantly increase your budget.
  • If you want to see humpback whales, you should go to Maui in the winter. We were shocked by how many we saw in February. While the best time to see them is from January to March, you may also see some from the months of November through May. Even though it was cooler and rained more in the winter, we still had plenty of sunny days, and the ocean is warm enough to swim in all year.
  • The islands are less crowded, prices are lower, and the weather is typically good during the spring and fall (April and May) and the winter (September and November). Even so, April on Kauai can be a wet month. We preferred snorkeling in October, when the water was warmer and clearer, to February.
Kailua Beach in Oahu, Hawaii The Oahu beach of Kailua-Kina's
  • When visiting popular tourist destinations like Hana and Upcountry on Maui, where lodging options are scarce, it is essential to make advance hotel reservations. Booking is great for booking hotels, and Vrbo is great for finding vacation rentals.
  • If you're traveling with a large group or staying for a week or more, but on a tight budget, you might want to look into renting a condo instead of a hotel room. Some of the many options even have resort features like pools and beachfront locations. Kiahuna Plantation on Kauai's Poipu Beach is one of our favorite places to stay in a condo. Condos can be easily found through Vrbo.
  • If you want to have the traditional Hawaiian resort experience but can't afford it for the entire trip, consider dividing your stay between a condo and a resort. We did this on the island of Oahu, first in a Waikiki condo while we explored the south, and then at the beautiful Turtle Bay Resort on the island's North Shore.
Kiahuna Beach in Kauai Beach of Kiahuna Visiting Hawaii in a condo rental was the most convenient option for us.
  • If you are on a tight budget and don't mind roughing it a bit, camping is the cheapest way to enjoy Hawaii. There are some stunning places to camp in beaches and state parks, but permits are usually required in advance. You can find more information about camping in Hawaii by consulting this guide.
  • To get to Hawaii, you will need to use a plane, so look for cheap flights on sites like Kiwi or Skyscanner. Los Angeles and other West Coast cities in the USA will offer the lowest fares. Now, you can fly to Hawaii for cheap with Southwest. Cheap flights to Honolulu are also available from Canada and Japan.
  • Take advantage of your time in Hawaii by flying in and out of two different islands, rather than just one (like Kauai and Maui). I was astonished to find so many reasonably priced nonstop flights from the US mainland to destinations other than Honolulu.
  • If you want to get the most out of your time in Hawaii, renting a car is your best bet, as some areas of the islands are inaccessible by public transportation. Car rental spots can fill up quickly during high demand periods. We search for the lowest price and book the most affordable economy car available.
  • Interisland flights are the only way to get from one island to another (with the exception of Maui and Lanai). Almost all of them are provided by Hawaiian Airlines and are both quick (20-50 minutes) and cheap.
  • If you plan on doing a lot of sightseeing on each island, it may be wise to divide your time between two or three distinct areas. This plan has been implemented successfully across all four major islands.
Sunrise at Haleakalā National Park crater visitor centre Haleakal National Park at Dawn
  • Make your reservations early for the Haleakala sunrise if you want to see the most visited sunrise on Maui. If you don't get tickets the first time, you can try again two days beforehand.
  • Reserve a spot at a state park — visitors from outside of Hawaii must make reservations and pay an entrance and parking fee at select state parks. Haena State Park on Kauai, Waianapanapa State Park on the Road to Hana in Maui, and Diamond Head on Oahu are just a few examples. Reservation times are made available 30 days in advance. Get your reservations in as soon as you can because they do sell out.
  • Bring a sweater, even if you plan on spending most of your time outdoors; early morning boat rides and excursions to higher altitudes (such as Upcountry on Maui or Waimea Canyon on Kauai) can be quite chilly, especially during the winter months. At both Haleakala on Maui and Mauna Kea on the Big Island, temperatures drop below freezing, so bring plenty of warm clothing. What to bring to Hawaii is covered in detail at the end of this post.  
  • Even if it's just "Aloha" (which means "hello" and "goodbye" but also "love" and "compassion") and "Mahalo," "thank you," you should try to learn a few words in Hawaiian. Kiana Davenport's incredible novel Shark Dialogues helped me expand my lexicon, and I strongly advise that every visitor give it a read.
  • Make reservations ahead of time for the restaurants you really want to eat at (this includes resorts), as they tend to get very busy, very quickly. It's fine to make reservations two weeks in advance, but popular spots like Duke's on Waikiki Beach are often full a full year in advance. In Hawaii, it's easier to get later reservations because most people eat early (around 6:00 p.m.).
  • While most restaurants will allow you to add a tip to your credit card bill, it's customary to pay tour guides, valets, and resort staff in cash. Learn American tipping customs if you are not an American. Twenty percent was left at restaurants and bars with wait staff, ten to twenty dollars per person was left for tour guides and drivers, five dollars was left for valet parking attendants when we returned the car, and two to three dollars was left per day for hotel housekeeping.
  • If you want to make the most of your time in Hawaii, you should split your time between several islands rather than staying on just one. While travel times between islands are relatively quick, airport security lines can be lengthy (especially when departing from Honolulu) and flight delays are not unheard of.
  • Don't believe the advertised price of a hotel or resort; it almost never is. There is usually a tax, a resort fee, a cleaning fee (for condos), and a parking charge on top of the base rate. Be sure to look at the total price when comparing hotels.
  • Plan your trip around less popular times, such as Thanksgiving, Christmas, or New Year's. This week of Thanksgiving is another hectic one. It's best to avoid the Big Island in October if you can, as that's when special events like Iron Man The time of year is notoriously difficult to visit, so if you must go, plan ahead.
  • Don't necessarily book a hotel right on the beach if you're on a tight budget; instead, look for something that's just a short walk or drive away. Yet, we frequently treat ourselves to a stay in a swanky beachfront hotel, and we never regret it.
Sunset at Kiahuna Plantation in Poipu, Kauai Kiahuna at sunset

Resuming the Main Parts

Assuming You Visit Hawaii

  • While lounging on the beach, read a novel set in Hawaii to learn more about the state's fascinating culture and turbulent history.
  • Plan ahead for the things that are most important to you; things like boat trips and helicopter rides may need to be rescheduled if the weather changes.
  • Make your reservation for Oahu's Hanauma Bay Nature Preserve two days in advance if you want to go snorkeling there. This popular beach fills up fast, so call at 7am Hawaii Standard Time on the day before your visit. Minutes are needed to fill the slots. Price of tickets is $25. Mondays and Tuesdays are the off days.
Waterfalls in Kauai from a helicopter Aerial view of Kauai's waterfalls
  • Wear reef-safe sunscreen; oxybenzone and octinoxate, two common sunscreen ingredients, have been banned in Hawaii. You should switch to a zinc oxide product, such as this SPF 30 sunscreen from Ethical Zinc. Although it is a hassle to apply, the product is surprisingly water resistant and is well worth it to preserve the reefs. Your best bets for acquiring necessary beach gear are Longs Drugs and ABC Stores.
Reef friendly tips on A-Bay Beach on the Big Island Advice for preserving the reefs at Big Island's A-Bay Beach
  • Protect your skin in the water by donning a rashguard, especially if you plan on doing any snorkeling.
Outrigger canoe in Kealakekua Bay on the Big Island Simon preps for our canoe/snorkel trip at Kealakekua Bay by donning a rashguard.
  • If you want to know which beaches on Maui are the best for snorkeling on any given day, all you have to do is subscribe to the Snorkel Report. You can also rent snorkeling and beach equipment at low prices.
  • For information on which beaches in Hawaii are suitable for swimming and which are ideal for surfing, visit the Hawaii Beach Safety website.
  • Visit a whale watching facility; it was one of our top activities in Hawaii. From Lahaina, Maui, we booked a small boat tour with Makai Adventures, and we enjoyed it so much that we went on two separate occasions! Find whale watching tours in Hawaii here, where you can see whales from many of the islands.
  • Trek — The islands offer a wide range of hikes, from short strolls along the coast to arduous multiday expeditions. It's a wonderful, cost-free opportunity to take in the islands' scenery.

Simon hiking through a bamboo grove on the Pipiwai Trail near Hana, Maui In Maui, on the Pipiwai Trail.

  • Tommy Bahama beach chairs and umbrellas are available for low rates on the islands and came with our condos. They're very convenient for using while traveling between beaches because of the backpack straps.
  • Pack your own snorkeling gear if you have room in your suitcase, or rent it once you get there. If you don't have your own, you can rent one from a place like Snorkel Bob's (like we did on the Big Island) for the duration of your trip. When we went to the beach, I enjoyed getting a glimpse of the reef.
  • Go to a farmer's market and stock up on fresh fruits and vegetables at lower prices and higher quality than at the supermarket.
  • Enjoy a refreshing shave ice; this icy dessert exceeds our high standards. If you want to take the flavor to the next level, put a dollop of macadamia nut ice cream at the bottom. On Kauai, we recommend Waikomo Shave Ice, and on the Big Island, we recommend Original Big Island Shave Ice Co.
Shave Ice in Hanalei, Kaui
  • Drinking a Mai Tai in a Tiki glass on the beach is a touristy activity, but it's a must when visiting Hawaii.
  • You should definitely try Li Hing Mui, a dried plum that has savory, salty, and sour undertones. Its origins are in China, but it has become a popular ingredient in many Hawaiian dishes. It can be purchased whole for snacking (too much for me) or as an ingredient in a variety of treats. Especially when blended with lilikoi/passionfruit and pineapple, this is my new go-to flavor for shave ice.
  • Maui's Road to Hana is a must-do, and while most visitors complete it in a day, we found that staying overnight and exploring the area was the best way to experience it.
Sea stacks at Wai‘anapanapa State Park near Hana in Maui One of Maui's best features is Wai'anapanapa State Park. Waimea Canyon on a doors off helicopter Kauai tour with Jack Harter in Hawaii
  • Eat out for every meal — Restaurants are pricey, so we saved a ton of money by preparing our own food in the condo. Picnic lunches are readily available at supermarkets, so even if you don't have a kitchen, you can still enjoy a day at the beach with friends and family. Food trucks, which are typically much less expensive than restaurants, provided us with some of the most delicious meals. The greatest number of trucks were found in the towns of Hana, Maui, and Hanalei, Kauai.
  • Don't underestimate the ocean; it has the potential to cause serious harm at any time. Don't go in the water if you have any doubts about its safety.
  • Don't face the water; large waves can appear out of nowhere while swimming or strolling along the shore.
  • Combat a rip current by remaining calm, floating, and signaling for assistance if you find yourself caught in one. Maintain a steady pace and minimize your energy expenditure.
  • It is illegal to approach or touch marine animals, such as sea turtles or monk seals, that you encounter on the beach.
  • Put food out for fish or other animals in the wild.
Monk seals on Poipu Beach on Kauai, Hawaii Poipu Beach on Kauai is frequented by both monk seals and humans.
  • Do not trespass on private property. Not all beaches are easily accessible to the public, despite being open to the public.
  • Nothing should be discarded on beaches or trails.
  • Do not park in a prohibited area, ignore "no parking" signs, or pull over to the shoulder. The issue is particularly severe on Maui's Road to Hana.
  • Take any sand or rocks you want
  • Don't accidentally damage coral by letting your fins rest on it or stepping on it while snorkeling.
  • Don't take anything of value with you, and make sure your bags are safely tucked away in the trunk. Avoid compact cars because they don't have a trunk cover, and opt instead for a midsize rental.
  • The hula is a serious part of Hawaiian culture, so feel free to poke fun at it.
  • Do not refuse a lei (flower garland) — it is a sign of love and Aloha and should be worn with appreciation and not removed in front of the giver.
  • Do not remove your shoes at the door.
  • You don't need to rush or worry about getting everything done. Be sure to schedule some downtime to unwind at a beach or pool. Take it easy and enjoy the sights of these stunning islands.

Resuming the Main Parts


You should bring light summer clothing (shorts, t-shirts, dresses), as well as several bathing suits and a beach cover-up, because the weather in Hawaii is warm all year round.  

Summer dresses and swimsuits from PrAna are my favorites.  

Casual attire is appropriate throughout your stay in Hawaii, so there's no need to bring any fancy outfits.  

In the winter, if you plan on traveling to higher altitudes or taking a boat trip, you should bring an extra set of warmer clothes. You should be good to go in a pair of jeans or leggings and a sweater or fleece.  

It can get very cold at sunrise on Maui's Haleakala or at night on the Big Island's Mauna Kea, so dress warmly and bring a packable down jacket if you have one.  


Since they are great for both walking on sand and hiking in the mountains, we spend most of our time in Hawaii wearing hiking sandals. Access trails to many beaches are rocky and uneven, so be sure to bring along a pair of shoes besides flip-flops.

Teva sandals are great for hiking and kayaking because they are so lightweight and supportive. My Teva Verra sandals are much more comfortable than Simon's Teva Fi Lites, but he still wears them.

Another dressy footwear option of mine was a pair of ballet flats. See my review of Allbirds flats for more information about the shoes I wear most often, the Tree Breezers.  

I run in the airy and lightweight Allbirds Tree Dashers.   

A Variety of Other Useful Materials

  • Protective sunscreen for coral reefs - Hawaii has banned the use of sunscreens containing oxybenzone and octinoxate.  
  • Bringing your own bags to the store is mandatory on the islands, where single-use plastic bags are prohibited.
  • Bring a small amount of spices if you plan on doing any self-catering, as this will help you save money. We got some from the mainland's warehouse-style grocery store.
  • Carry a refillable water bottle to save money and prevent unnecessary waste of single-use plastic bottles. The Vapur is our favorite water bottle because it is compact when empty and easy to carry around.  
  • A daypack that can be compressed to fit in your suitcase and then unfolded for use on hikes and excursions.  
  • You can't go wrong with a set of packing cubes, which will make it a breeze to find what you're looking for in your suitcase.  
  • Towels that dry quickly and shed sand more easily than regular bath towels are ideal for the beach.  
  • Small binoculars - Hawaii is home to an abundance of marine life, land animals, and birds. For a closer inspection, the tiny Olympus 8 x 21 RCII waterproof binoculars were the way to go.

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How Much of an Investment is Hawaii Really

A trip to Hawaii is definitely worth it, in my opinion. The beautiful scenery and laid-back atmosphere entice many of us to return despite the high prices and heavy crowds.

Please use this blog post as a guide when organizing your trip to Hawaii. In the comments, please ask any questions you have and share any Hawaii travel advice you may have.

Before We Begin

In these additional articles, we provide more helpful information about Hawaii:


  • The Ideal Itinerary for Seven Days on Oahu



Big Island

  • The Big Island's 23 Must-Do Attractions


  • If you're planning a trip to Hawaii, here are the nine books you should read first.

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