Planning a Trip to Hawaii: DOs and DON’Ts

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Planning a trip to Hawaii is something many people dream of. With its stunning beaches, dramatic volcanic landscapes, and lush green hills, it’s one of the most beautiful places we’ve visited but also the most expensive.

While we do think the islands are worth the high price, to make the most of your stay, it’s essential to plan in advance.

These tips will help you plan the perfect trip to Hawaii.


This post was originally published in June 2019 and last updated in January 2021. 

Hawaii Travel Restrictions 2021

As of October 15, 2020, a pre-travel testing programme began in Hawaii. Visitors from the mainland US will be able to avoid the mandatory 10-day quarantine by providing proof of a negative COVID-19 test taken within 72 hours of the final leg of departure. The test must be taken with a trusted testing partner

All travellers to Hawaii will have their temperature taken on arrival and will need to fill in a Safe Travels travel and health form at least 24 hours prior to departure (this can be done online with an upload of your negative test). 

I also highly recommend downloading the AlohaSafe contact tracing app before arriving in Hawaii (this is now mandatory for Maui). 

Note that wearing a mask is mandatory in Hawaii in indoor public places and outdoors when social distancing isn’t possible. Please travel responsibly. 

The situation is constantly changing so see the Hawaii Covid 19 website for the latest updates and requirements. I also recommend checking the county website for the island you are visiting (see below).

Different islands have their own rules in addition to the pre-travel test:


As of January 19, 2021 it is now mandatory to download the contact tracing app, AlohaSafe, before you arrive in Maui. If you don’t do so, you’ll have to quarantine for 10 days. This doesn’t apply to under 18s and if you don’t have a phone, at least one person in your party must download the app. 

Maui is also asking visitors to take a voluntary second test 72 hours after arrival and you can preregister here. I strongly encourage you to do so to help keep the island safe. The test is free and you’ll receive your results within an hour.

Big Island (Hawaii)

The Big Island requires a second test to be taken at the airport on arrival for 25% of visitors (chosen at random). The test is free and results will be available in 15-20 minutes.

If the test is negative, you are free to travel the island. See the County of Hawaii website for details. 


Kauai opted out of the pre-travel testing programme on December 2, 2020, but as of January 5, 2021 has partially reinstated it with new rules. There are three options:

  1. Inter-Island Travel

You can avoid the 10-day quarantine by first travelling to a different island in Hawaii (Oahu, Maui or the Big Island).

After you’ve been in Hawaii for more than 3 days (but within 72 hours of arriving on Kauai), take a COVID test with an approved partner. Upload the negative test to the Safe Travels website before travelling to Kauai. 

2. Resort Bubble

If you want to travel directly to Kauai from the mainland US, you can shorten your quarantine period to just 3 days by booking a stay in one of the approved Enhanced Movement Quarantine (EMQ) or “resort bubble” hotels. Currently there are six approved resorts.

In these hotels you are free to enjoy the resort’s facilities (including pools and restaurants) and do not have to stay in your room. You can not leave the resort, though, and your movements will be monitored with a wrist bracelet (check with the hotel for the cost of these but $80-100 seems typical). 

You’ll still need to register and take a pre-travel test as above, and in addition, after 3 days on Kauai you’ll take a post-travel test (at your own cost). If the test is negative, you’ll be released from quarantine and free to explore the island. 

3. 10-Day Quarantine

The final option is a 10-day quarantine in any hotel (not vacation rental) but you will not be allowed to leave your room. 

See the County of Kauai COVID page for more details. 

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Best Island to Visit in Hawaii

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

Hanalei Bay in Kauai

Choosing the best island to visit is one of the most challenging parts of planning a trip to Hawaii. They are all diverse with lots to offer, so it just depends what you are looking for.

Most visitors to Hawaii visit one of these four islands:

  • Oahu – The most visited and developed island is home to the large city of Honolulu and the famous and very crowded Waikiki Beach. You can surf huge waves on the North Shore and visit the museum and memorials at Pearl Harbour. You’ll find the most shopping, dining, and nightlife options here. It’s the easiest island to get around by public transport.
  • Maui – The second most visited island has beautiful beaches, world-class whale watching, and the Road to Hana drive where you can see waterfalls, bamboo forest, and red and black sand beaches. You can also watch the sun rise above a volcanic crater and visit wineries and lavender farms in Upcountry. There’s a wide range of resorts, dining, shopping, and activities as well as natural attractions.
  • Big Island – The largest island is the youngest, so it’s not as green as the other islands and has more lava landscapes. If you want to see an active volcano, this is the island to visit. The landscapes are incredibly diverse from beautiful white sand beaches to snow-capped mountains.
  • Kauai – Known as The Garden Isle, Kauai is the most lush and green of the islands. The jagged green cliffs of the stunning Napali Coast are the big draw, but there are also lovely beaches, waterfalls, and multi-coloured canyons. A helicopter ride over the island is spectacular, and there are plenty of hiking trails. Kauai has become popular, but it isn’t as developed as Maui or Oahu.
Kauai's Napali Coast from a helicopter

Kauai’s Napali Coast

If you are looking to get off-the-beaten-track, you could consider visiting one of these smaller, much less visited islands:

  • Molokai – Known as The Friendly Isle, on Molokai you’ll find a slow pace of life and more native Hawaiians, but less choice of accommodation and activities. It’s also home to the leper colony of Kalaupapa, which I became fascinated with after reading a couple of these Hawaii books.
  • Lanai – For many years Lanai was a pineapple plantation and it’s now home to a few luxury resorts. If you want to enjoy the secluded beaches without the high price tag, the ferry from Lahaina on Maui only takes an hour so you could visit on a day trip.

The character of each island also depends on which part you visit. All the islands have a rainy side where the scenery is lush and green and a dry side where you’ll usually get more sun. They are both worth visiting, which is why we decided to split our island stays between two or three locations.

We had 3.5 weeks in Hawaii and chose to divide our time between Kauai and Maui, with one night in Honolulu before our flight to Japan. We loved them both, and there’s so much to do on each island that we’re glad we didn’t try to add in an extra island.

We plan to visit the Big Island and maybe Molokai on our next trip, although we’d also happily return to Kauai and Maui.

For more details on our trip, see our Maui itinerary and the best things to do on Kauai.

Our friends Tom and Jenny have visited the Big Island many times and share their favourite things to do

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

The black sand beach at Waianapanapa State Park, Maui

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Before You Arrive in Hawaii


  • Save up – Hawaii is expensive and you’ll enjoy it more if you aren’t worrying about every penny. We spent $267 per person per day (travelling as a couple) including everything except flights from the mainland US. You could spend less by travelling in the off season, choosing non-beachfront accommodation, and skipping pricey tours. You could also spend a lot more by staying in luxury resorts and eating out for every meal.
  • Visit in the winter to see humpback whales – We were astounded by how many we saw in Maui in February. January to March are the best months, but you might see a few from November to May. Winter weather can be cooler and rainier, but we still had mostly sunny days and the ocean is swimmable year round.
  • Visit in the off season to save money – In the spring (April and May) and autumn (September to mid-November), the islands are less crowded, prices are lower, and the weather is generally good. It can be very rainy on Kauai in April though. 
  • Book your accommodation far in advance – Especially if you are travelling in the high season, want an ocean view, or are travelling to places like Hana or Upcountry on Maui where accommodation is limited. We searched for options on Booking, Airbnb, and VRBO.
  • Consider a condo rather than a resort – For families, stays of a week or more, and for those on a budget, renting a condo with a kitchen is a great way to save money. There are many to choose from and some have resort facilities like pools and beachfront locations. We stayed in condos for most of our stay and Kiahuna Plantation on Poipu Beach in Kauai was one of our favourites.
Kiahuna Beach in Kauai

Kiahuna Beach

  • Camp if you are on a tight budget – It’s not for everyone, but if you don’t mind roughing it, camping is the cheapest way to experience Hawaii. There are some beautiful campsites at beaches and state parks, although you usually need to get permits in advance. See this guide to camping in Hawaii for more tips.
  • Search on Kiwi for the best flight deals – The cheapest rates will be from Los Angeles or other West Coast cities. Southwest now flies to Hawaii at low rates. You can also get affordable flights from Asia (especially Japan) to Honolulu.
  • Fly in and out of different islands – Maximise your time on the islands by flying into one island (such as Kauai) and out of another (such as Maui). I was surprised by how many affordable direct flights there are from the US mainland to places other than Honolulu.
  • Rent a car – It’s the best (and often only) way to get around. At busy times they can run out, so book far in advance. We used Rental Cars to find the best deal and just booked the cheapest economy car.
  • Consider splitting your time between two or three locations on each island – If you want to do a lot of exploring, this will help avoid long drives to attractions. We did this on Kauai and Maui and it worked out well.
Kaihalulu or Red Sand Beach in Hana is a highlight of a Maui itinerary

Red Sand Beach in Hana

  • Book Haleakala sunrise in advance – If you want to see Maui’s most popular sunrise, you must book up to 7 days in advance. If you miss out, try again two days before when more tickets are released.
  • Bring reusable shopping bags – Plastic bags are banned on the islands.
  • Pack a sweater – While most of the time you’ll only need summer clothing and beachwear, it can get chilly on morning boat trips or if you go to higher elevations (like Upcountry in Maui or Waimea Canyon on Kauai) especially in the winter. Sunrise at Haleakala is literally freezing and you’ll appreciate as many layers as possible.
  • Bring spices – If you are self-catering, you’ll save money by bringing a small amount of spices with you. We bought some at the bulk-buy section of a supermarket on the mainland.
  • Pack hiking sandals – We wore these all the time and they were perfect for beaches and hiking. Many beaches have rough access trails so you’ll appreciate something more than flip-flops. We both love Teva sandals which are very comfortable for hiking (and most models are waterproof). For men, the Teva Hurricanes are a good option and I have the Teva Verra sandals.
  • Learn a few Hawaiian words – Even if it’s just Aloha (hello and goodbye but also love and compassion) and Mahalo (thank you). I picked up vocabulary by reading the astounding novel Shark Dialogues by Kiana Davenport (which I highly recommend every visitor reads).


  • Plan to visit more than one island per week – You’ll spend too much of your precious vacation time travelling and there’s so much to do on each island.
  • Forget hidden fees – The listed price for hotels and resorts is rarely what you’ll actually pay. You’ll have to add tax and often a resort fee, cleaning fee (for condos), and parking charge. Check the final total price when comparing accommodation options.
  • Visit during holidays – Try to avoid the busiest times of year, especially Christmas and New Year when crowds and prices soar. Thanksgiving week is another busy time. If you must visit then, book far in advance.
  • Stay on the beach (maybe) – If you are on a tight budget you’ll save by staying a short walk or drive from the beach. Airbnb is a good place to look for budget accommodation. That said, we splurged on beachfront accommodation and loved it.
Sunset at Kiahuna Plantation in Poipu, Kauai

Sunset at Kiahuna

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In Hawaii


  • Read novels set in Hawaii – Learn more about Hawaii’s fascinating culture and turbulent history by reading one of these books about Hawaii while you relax on the beach.
  • Schedule your most important activities early – Weather can change and cancel activities like boat trips and helicopter rides, so make sure you’ll have time to reschedule.
Waterfalls in Kauai from a helicopter

Waterfalls in Kauai from a helicopter

  • Use reef-safe sunscreen – Hawaii has banned the sale of sunscreen that uses coral-harming chemicals. You can pick some up from Longs Drugs, which we found surprisingly affordable.
  • Sign up to the Snorkel Report on Maui – You’ll get an email every morning with tips on the best beaches to visit that day. They also rent inexpensive snorkelling and beach gear.
  • Check the Hawaii Beach Safety website – To find out which beaches are safe for swimming or best for surfing. The Kauai Explorer Surf Report is also useful. 
  • Go whale watching – It was one of our favourite experiences in Hawaii. We chose a small boat trip with Makai Adventures from Lahaina in Maui and loved it so much we went twice.
  • Hike – All the islands have beautiful trails from easy coastal walks to challenging multi-day treks. It’s a great free way to enjoy the beauty of the islands.
Simon hiking through a bamboo grove on the Pipiwai Trail near Hana, Maui

Hiking the Pipiwai Trail in Maui

  • Rent a Tommy Bahama beach chair and umbrella – Our condos came with these, but you can rent them on the islands inexpensively. They have backpack straps for easy carrying and make beach hopping much more comfortable.
  • Visit a farmer’s market – The fresh produce is usually cheaper and better quality than the supermarkets and there are lots of tasty treats and foodie souvenirs to enjoy.
  • Cool off with shave ice – This delicious icy treat is so much better than we expected. Add a scoop of macadamia ice-cream on the bottom for maximum tastiness.
Shave Ice in Hanalei, Kaui
  • Enjoy a Mai Tai on the beach – Touristy yes, but it’s a classic Hawaii experience and these tasty rum cocktails come in cool Tiki glasses.
  • Make a reservation for Haena State Park in Kauai – Beautiful Ke’e Beach on the North Shore now requires a reservation (up to 14 days in advance) and visitor numbers are limited.
  • Drive the Road to Hana on Maui – Most people do this in one day, but we loved spending a few nights in Hana to explore without the crowds.
Sea stacks at Wai‘anapanapa State Park near Hana in Maui

Wai‘anapanapa State Park is a Maui highlight

  • Eat all the banana bread – Especially in the Hana area, homemade banana bread sold at farm stalls is so good.
  • Indulge in chocolate-covered macadamia nuts – We were addicted to the ones by Moana Loa.
  • Let local drivers pass you – They know the winding roads better than you and drive at a faster pace, so pull over and let them pass.
  • See Kauai from above – Our doors-off helicopter trip on Kauai was mind-blowing.
Waimea Canyon on a doors off helicopter Kauai tour with Jack Harter in Hawaii


  • Eat in restaurants for every meal – Restaurants are expensive and by self-catering in our condo we saved a huge amount of money. Even if you don’t have a kitchen, you can pick up a pre-made picnic lunch from a supermarket and enjoy it on the beach. Some of our tastiest meals were from food trucks which are far cheaper than restaurants. Hana in Maui and Hanalei in Kauai had the best selection of trucks.
  • Underestimate the ocean – Conditions can be dangerous and change quickly and drownings do happen. If you’re not sure it’s safe, don’t swim.
  • Turn your back on the ocean – Huge waves can come out of nowhere when you are swimming or even walking along the shore.
  • Fight a rip current –  If you get caught in a current, keep calm, float, and wave for help. Go with the current and conserve your energy.
  • Touch sea turtles or monk seals – You are likely to come across wildlife on the beaches, but it’s illegal to get too close or touch them.
Monk seals on Poipu Beach on Kauai, Hawaii

Monk seals and humans share Poipu Beach on Kauai

  • Trespass – Please respect private property. While all beaches are open to the public, they don’t all have public access routes.
  • Litter – Don’t leave anything behind on beaches or hiking trails.
  • Steal any rocks or sand.
  • Touch or step on coral.
  • Leave valuables in your car – And keep any luggage hidden out of sight in the trunk. 
  • Laugh at the hula – It’s not just a dance for tourists, but a serious part of local culture.
  • Refuse a lei (flower garland) – It’s a symbol of affection and Aloha so wear it with gratitude and don’t take it off in front of the person who gave it to you.
  • Wear shoes into someone’s house.
  • Rush – Don’t feel the pressure to do everything. Make sure you allow time just to relax by the pool or on the beach. Slow down and enjoy these beautiful islands.

I hope this post helps you with how to plan a trip to Hawaii. Let me know if you have any questions below. You can also read these other Hawaii posts:

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5 Comments (4 pingbacks)

  1. Thank you for the tips to “Bring reusable shopping bags” and “Schedule your most important activities early”. Very good points to keep in mind.

    I love that Hawaii has so many places that offer to rent (folding) beach chairs! I find that option sorely missing from the islands in the Caribbean. In fact, I ended up buying an inexpensive beach chair from Wal-mart when we were in Puerto Rico this past winter.

    Reply ↓

    • Yes, that’s definitely the cheapest way to experience Hawaii. It’s not our thing, although we saw the campsite at Waianapanapa State Park on Maui and you can’t beat the location!

      Reply ↓

  2. I’ve lived on Kauai for over 40 years. While I agree with nearly everything you say in this excellent article, there was one glaring error that any Kauai resident could confirm. Although visiting off season is, indeed, (somewhat) cheaper and certainly less crowded, the weather in April on Kauai (and generally March) is far from excellent. Many, many visitors to Kauai have had their vacations ruined by our relentless April rains (in fact, much of the north shore is still closed from catastrophic rains over a year ago, and a couple of years before that it rained for nearly 40 straight days (okay, maybe not, but any local will swear by it…). April is by far the worst possible month to visit Kauai and it does your readers a digs-service to urge them to do so.

    Reply ↓

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