Are you planning a trip to Hawaii? Could you use some helpful Hawaii travel tips?
We hear you!
We’ve visited Maui and Kauai (and the other main Hawaiian islands) many times. And we’ve recently returned from our latest Maui trip.
We’ve written a lot about Hawaii. (See all our Hawaii posts.) But for the best way to plan a Hawaii vacation, this is your Hawaii guide! So read on…
A word of caution.
In the past, Hawaii trip planning was easy. We simply booked our flights, accommodation and car rental – and jetted off for some welcome R&R, Aloha-style.
These days, it’s a little more complicated to plan a Hawaii trip. Hawaii is so popular that advance planning is necessary to make the most of your stay.
Planning a trip to Hawaii
Still, there’s no place like the Hawaiian islands.
From its beautiful beaches and plumeria-scented air to the ever-present Aloha spirit, Hawaii is as seductive as ever.
The things you can do in Hawaii are special.
You can swim with sea turtles, snorkel with manta rays and watch sunsets paint the sky like there’s no tomorrow.
And once you have an idea of what you want to do and where to go – and know the current rules and tips for visiting – you’ll be well on your way to having your Hawaii travel plans settled!
Hawaii travel rules
Hawaii entry requirements for Americans:
There are no special entry requirements if you’re a domestic traveler flying to Hawaii from the U.S. mainland. (You no longer need to show proof of vaccination or a negative test.)
Wearing a mask indoors is optional.
Some businesses may still suggest you wear one though. Please be respectful.
International travelers to Hawaii (non U.S. citizens):
The rules for flying to Hawaii for Canadians and international visitors are the same as for flying to the U.S.
There are no special rules for Hawaii.
All international air travelers to the United States (including Hawaii) must be vaccinated against Covid-19.
Which island to visit in Hawaii?
Now for the fun stuff!
It’s time to decide which Hawaiian island should be your vacation destination.
Picking the best island to visit in Hawaii isn’t easy. Each island has its own unique charm. It depends on what you want out of your Hawaii holiday.
Here’s a quick guide to the sun, sand-and-surf, natural beauty and other goodness in the Aloha state.
Maui – the Valley Isle:
Of the main islands, Maui is a favorite for many.
Known as the “Valley Isle,” it breathes romance with its lush landscapes and romantic hotels.
Will you be celebrating an anniversary and wanting champagne breakfasts, complete with bubbly and succulent Hawaiian fruit? Or do you covet a full-on spa experience?
Maui has the accommodations to match. It is, after all, one of the top honeymoon destinations!
There are oodles of things to do in Maui for couples.
You can fall in love with humpback whales who migrate here in winter, snorkel at Molokini Crater (keep your eyes peeled for eagle rays and octopuses!), swim with sea turtles and watch the sun rise magically above the clouds crowning Haleakala.
And if you take a tour or rent a car to drive the Road to Hana, you’ll encounter some gorgeous Maui waterfalls, a bamboo forest and black sand beaches.
But as luscious as it is, Maui is also really child-friendly.
Its sensational stretches of sand are catnip for kids.
When our son was younger, we spent many a family holiday with him on this Hawaii island, splashing about in the gentle surf.
Kauai – the Garden Isle:
Less developed than Maui or Oahu, Kauai is the lushest of the islands – fitting, since it’s known as the “Garden Isle.”
Yes, there are tons of fun things to do in Kauai!
A 90-minute helicopter tour will amaze you with a bird’s eye view of stunning landscapes – you may even recognize some scenes from the King Kong hit.
We were totally gob-smacked by how ginormous the Moreton Bay Fig tree roots are.
And wait till you see all the tropical plants, sculptures, gravity-fed water features and photo opp spots from Jurassic Park! Apparently, filmmakers are as much in love with this verdant garden island as we are.
Oahu – the Gathering Place:
Known as the “Gathering Place,” Oahu is the most visited and developed of all the Hawaiian islands.
The star city, Honolulu, is a mecca for shopping, dining and nightlife.
Honolulu is also home to Waikiki Beach, where the waters are cerulean and you can spend an afternoon learning to surf or paddleboard.
Don’t miss the Honolulu Cookie Company.
They make fun pineapple-shaped tins filled with a variety of their macadamia nut, white chocolate and other tasty shortbread confections – the perfect gift for your house sitter or BFF.
But there’s so much more to Oahu than just Waikiki.
Visit the museum and memorials at Pearl Harbor. Spend a day too on Oahu’s famous North Shore and soak up the surf culture. (Try some great shaved ice!)
For a real treat, book a luau at the Polynesian Cultural Center. Each of the six villages there introduces you to the culture of Tonga, Tahiti, Samoa, Aotearoa, Fiji and Hawaii.
And good news. The island of Oahu has a strong public transit system, so you can get around easily without a rental car.
Lanai – the Pineapple Island:
A small privately-owned island off the coast of Maui, Lanai is known as the “Pineapple Island,” mostly because of its former designation as a pineapple plantation.
Today it’s a secluded getaway – an hour away from Maui by ferry – with private luxury homes and just three hotels.
Despite its small size, there’s a lot to do in Lanai.
You’ll find beautiful hiking trails, the sugar-hued Hulopoe Beach, Jack Nicklaus-designed golf courses, the Lanai Culture & Heritage Center and even a cat sanctuary if you’re missing your furry family members.
When making lodging plans, there are two Four Seasons in Lanai. Both have their own attractions.
Hawaii – the Big Island:
The state’s namesake, Hawaii (the Big Island) draws visitors to its shores for its diverse scenery and two of the world’s most active volcanoes, Kilauea and Mauna Loa.
At night in Hawaii Volcanoes National Park, Kilauea glows fiery orange while erupting. By day, you can see volcanic gas and steam billow out of the caldera.
The largest island is also the youngest, so the Big Island isn’t as green as the other islands, featuring more black lava landscapes.
In some places, it feels like you’re on the moon.
Then again, on the Hilo side, there’s lots of tropical rainforest – and waterfalls too.
The Big Island has alluring beaches too. We’re happy as clams to hang out on the half-mile stretch of white sand at Hapuna Beach.
But there are also the snow-capped mountains of Mauna Kea (stargazing, anyone?), Kona’s spectacularly clear waters (ideal for snorkeling) and lush coffee plantations.
Molokai – the Friendly Isle:
So you’ve visited the major islands and now want to get more off-the-beaten-path?
Known as the “Friendly Isle,” Molokai was where Father Damien, a Belgian priest, cared for Hawaiians with leprosy (Hansen’s Disease) who had been banished to the island.
Molokai gained fame when Alan Brennart’s fictionalized account of the leper colony at National Historical Park Kalaupapa became a bestseller.
Brennart’s book Molokai showcases the beauty and tragedy of the island.
Life is slower on Molokai, native populations are larger and it’s physically more untouched than any of the other islands. There’s not a single traffic light!
The high sea cliffs and continuous fringing reef are starkly beautiful.
Here’s a cool Hawaii fact about Molokai: You can mail a real coconut as a “postcard” from the Hoolehua Post Office.
Should you visit more than one Hawaiian island?
Now that you know a little about each island, you may be tempted to visit more than one.
If time allows, go for it!
But don’t try to cram too much into your precious vacation. You don’t want to return home more pooped than when you left.
When planning your Hawaii itinerary, give yourself at least three nights per island.
Personally, we’d suggest you devote at least five nights to each island when planning a Hawaii trip (except maybe Oahu, if you start there – see suggestions below).
For us, a Hawaii holiday isn’t a holiday if we’re sightseeing and active from morning to night. This is Hawaii – you’re supposed to do nothing but kick back in your pool chair and sip Mai Tais some of the time!
Ferries don’t run between the islands so flights are the only way to get around between islands.
Flight times are fairly short.
For example, it’s a 25-minute flight from Honolulu (on Oahu) to Kauai and 45 minutes from Honolulu to Hilo on the Big Island. Inter-island flights between Maui and Kauai take about 47+ minutes.
But you still have to factor in things like packing up, checking out of your hotel or condo, checking in at the airport, getting a car rental at your next destination, checking into your next resort and unpacking again. Phew!
Be sure you allocate enough time to enjoy each island before deciding to hop on an inter-island flight or two.
How to plan a trip to Hawaii: Booking your flights
Flying to Honolulu:
Honolulu is the state capital, and most airlines fly into Honolulu International Airport (HNL) on Oahu.
It serves both domestic and international airlines, and there are a number of direct flights from the U.S. mainland and Canada.
Flying to the islands:
We mentioned that no ferries run between the islands.
So if Oahu isn’t your final destination, you’ll need an inter-island flight.
As well, many airlines fly directly from the U.S. mainland and Canada to the different Hawaiian islands.
Most of the non-stop flights are from cities on the west coast, like San Francisco, Anchorage, L.A. and Vancouver. You can also get direct flights from Denver and Phoenix.
How to save on flights to Hawaii:
Flying to Hawaii can hit your wallet hard. But rewards cards and companion fares can save the day.
We use our Alaska Airlines credit card to get an Alaska companion fare if flying via the U.S., and our WestJet credit card if flying directly from Canada.
Companion fares basically make it a “buy one, get one almost free” scenario. So definitely look for one of these credit cards.
The cheapest fares are often had by subjecting yourself to multiple layovers (and less than comfortable seats). If coming from the east coast, that’s a long flight – and a long miserable day of travel!
Now you gain some hours flying out to Hawaii. (When it’s 6:00 pm in New York, it’s 12 noon in Hawaii.)
But going back you lose hours and flights are often overnight. Ugh!
First or business class (even premium economy) soothes some of that with lie-flat seats or more leg room, light meals and free drinks.
If you can swing it, upgrade to a seating class that gives you more room to stretch out on those long flights.
Choose where to stay in Hawaii
Once you’ve picked your island(s) and booked your flights, the next step in your Hawaii vacation planning is to figure out where to stay.
Hawaii offers oodles of options when it comes to lodgings – from budget places with kitchenettes to luxury resorts with pool butlers and opulent spas.
If you opt for a hotel, check on those loyalty programs of yours for member discounts and points availability for free stays.
Often with credit cards like the Marriott BonVoy, you get points for every purchase you make with the card, which leads to free or less expensive stays.
And they come with bonuses like drink credits at the bar for those island cocktails.
Be sure to check on blackout dates when planning your stay.
Also consider where on the island you want to stay.
Are you set on Oahu and want the buzz of Waikiki Beach? But you also want your hotel to be a quiet retreat amidst all the action?
We love the Halekulani Hotel in Waikiki.
It’s steps from shopping and dining, but cocoons you in a Zen-like atmosphere. Superb service and a pool with a gorgeous orchid mosaic round out a luxury stay here.
As for Maui, we’ve written a whole post on where to stay in Maui.
It covers the best areas on the island, different micro-climates and top accommodation options (both condos and resorts), so check it out.
Heading to Maui on your honeymoon?
You’ll find a dreamy selection of romantic hotels on Maui for couples to suit all budgets.
Some are even adults-only for maximum couple time. Others offer champagne breakfasts and spa treatments for luxe pampering.
One hotel in the Wailea area has a Porsche Roadster for gourmet picnics in secluded spots.
Popular with hikers and other adventure lovers, Kauai has stellar hotels too.
From oceanfront resorts to sweet garden cottages to beach bungalows, the island features a wide range of accommodations for enjoying the island’s quieter vibe.
Condos or places with kitchens:
For the least expensive lodging when planning a Hawaiian vacation – or maybe because you want the luxury of more space – check out condos or Vrbo (Vacation Rentals by Owner).
If planning a family trip to Hawaii or you intend on staying for a longer period of time, a condo or vacation rental is a great option to save a little money.
Some Vrbo accommodations and vacation rentals are quite swank too. They have resort-like pools and beachfront views of those stunning orange and pink sunsets.
Indeed, you may prefer a place with a kitchen and living room, not to save money, but for the flexibility it gives you. (No longer are you forced to eat every meal out at a restaurant.)
Islands like Oahu, Kauai and Maui have large inventories of vacation condos, cottages and houses with kitchens and other amenities.
You can hit the local grocery store for your food supplies and snacks, or cook some freshly caught seafood from the Honolulu Fish Auction (if on Oahu).
For our Maui trip, one place we booked was a tastefully remodeled one-bedroom condo with two bathrooms and a full kitchen (over 900 sq. ft) in The Whaler through Vrbo.
One of the best places to stay in Kaanapali, The Whaler is right on the beach and a stone’s throw from the shops and restaurants in Whalers Village.
We walked to restaurants in the area – and also cooked in and dined on our oceanview lanai.
We’ve stayed at The Whaler before and love its location, the generous size of the units and the full kitchens (the washers and dryers too).
Renting a car in Hawaii
Whatever island you decide to visit, renting a car gives you the ultimate freedom to explore.
Look into which company has the best customer service reviews and offers the best deal.
One company to check out is Discount Hawaii Car Rental.
They’ve negotiated rates with the leading car rental agencies and promise great customer service and help throughout the process. You can browse their site by car type, island or airport.
As with all contracts, be sure to read the whole document (the fine print too!) so you know what’s included (and what’s excluded) in the price quote.
With the Aloha state being such a popular destination these days, be aware that can be difficult to score a reasonably-priced rental car.
The best Hawaii tip we can offer is to reserve as soon as you know you’re going to Hawaii.
Don’t leave it to the last minute – especially if you’re planning a trip to Maui, currently the island on everyone’s radar.
Use your rewards:
Like hotels and airlines, it helps to be a member of a rewards program. You might get a free upgrade with Hertz, for example, if you have a rewards program membership.
We hear Avis is also good.
Consider a non-airport location:
If you’re flexible about the pick-up and drop-off location, you might have better luck getting a car rental.
We had no luck finding a car (at a decent price) when trying to rent with pick-up and drop-off at the Maui airport.
But we lucked out nabbing a Hertz car rental for half of our two-week Maui trip by plugging in a rental location other than the airport. (It came to about $80 USD a day.)
Check what car insurance is needed:
Your Hawaii rental car comes with mandatory basic liability insurance (with very low coverage limits).
Check your own car insurance at home and your credit card to see if rental cars are covered (and what insurance they provide) before you buy pricey, additional car rental insurance.
For Americans and Canadians, if you own a car back home, we understand that your liability car insurance typically extends to renting a car in Hawaii. Double check your policy’s coverage, though.
Also make sure the amount of your liability insurance protection back home is enough.
Our minimum liability insurance is only $200,000 in B.C. (Canada). So we have extended third-party liability insurance, which covers us anywhere in Canada and the U.S., including Hawaii.
Also, you may not need to buy extra CDW (collision damage waiver) insurance, depending on the credit card you use to book your rental. Our particular VISA credit card, for example, includes CDW insurance.
Don’t have a heart attack! Gas prices in Hawaii are steep.
If you’re a Costco member, head to their stores for the cheapest gas. You can also check the Gas Buddy app to find the cheapest gas beyond Costco.
And be sure to return the rental car with a full tank of gas. You don’t want the sticker shock that comes if the rental company has to fill up the car at the end of your rental.
How to plan a Hawaii vacation without a car
Do you need a car in Hawaii? No. Getting around Hawaii without a car is very feasible.
If you don’t rent a car, stay in a resort area where you can walk to stores, restaurants, the beach and activities.
If this is your first trip to Hawaii, be aware that Hawaii doesn’t go in for all-inclusive resorts (unlike Mexico or the Caribbean). So you want choices for dining and tours – nothing is worse than feeling stuck in your condo, hotel or resort.
If your holiday base is Waikiki in Honolulu on Oahu, you can walk to most places.
On Kauai too, if you stay in Poipu, you can walk to nearby restaurants and shops – and have beaches at your fingertips.
Some resort areas on the islands have free shuttles to help you get around.
In the Kaanapali resort on Maui, for example, you can hop on the complimentary Kaanapali Trolley. It tootles around between the hotels in the area, the Royal Kaanapali Golf Course and the Whalers shopping village.
A beachwalk (about 2½ miles long) also makes it easy to walk from Kaanapali hotels to shops and restaurants.
Uber is another option, mainly on Oahu. Uber drivers are concentrated in Waikiki – their number dwindles the further out the island you go.
Uber service is spotty on the other islands, though.
In addition to Uber, Oahu has reliable public transportation to get around the island.
Some tours offer hotel pick-up and drop-off too.
On Maui, for example, the Alii Nui includes complimentary hotel transfers for snorkeling at Molokini and Turtle Town on their deluxe catamaran tours.
When is the best time to visit Hawaii?
The better question is: When is it not a great time to visit Hawaii?
Kidding aside, Hawaii has a year-round temperate climate.
It’s the ideal vacation spot to escape the cold winter temperatures or oppressive summer heat back home.
But some times of the year are better than others.
High season in Hawaii:
High season for tourists runs roughly from the end of November to April – lots of people want to swap out snow for sun!
Summer is also very busy, as schools are out and families go on vacation.
Oahu is busy year-round.
During the winter peak season, lodging, flights and car rentals are harder to come by on Kauai, Maui and the Big Island than during other seasons.
The weather during high season is also a little cooler. While daytime temps average 85 F in the summer months, they average 78 F in winter.
Winter is also the rainy season in Hawaii.
The rain rarely lasts for long, though.
And different parts of each island have different micro-climates. If it’s raining in Hanalei Bay on Kauai’s North Shore in winter, just drive down to Poipu, where chances are the sun will be shining.
The winter months also signal surf season.
Professional surfers are lured to the northern shores of the Hawaiian islands for the big waves they can ride during this time.
Low season in Hawaii:
The bottom line is that April, May, September and October are rife with off-season, good-value deals.
You can avoid the crowds and get more bang for your holiday buck if you travel during off-peak times.
Maybe nail a luxury vacation rental or hotel room for a price not available in winter?
Mind you, if your goal is to see humpback whales, you’ll have to book between January and March for the best chance of sighting these majestic beauties.
One last thing to keep in mind when making your Hawaii travel plans is Golden Week.
Golden Week is a little-known period outside of Japan.
People in Japan have four work holidays, and Golden Week is like spring break. Hawaii (especially Oahu) is a prime vacation destination for Japanese visitors during Golden Week.
It occurs at the end of April through to early May. So this week is a busy time in Hawaii – you might want to avoid going to Oahu then.
In addition to Golden Week, mainland U.S. spring breaks can cause holiday woes as well.
Bottom line: It’s useful to check the calendar when planning a trip to Hawaii.
What to pack for Hawaii
What do you toss into your suitcase for a trip to Hawaii?
Each island is different, so your Maui packing list might differ slightly from your Lanai or Kauai packing list.
Still, there are some essentials you should take, no matter which island you’re visiting. The obvious are swimsuits, casual shorts and tank tops, and a nicer outfit if you’re planning a date night dinner.
Be sure to pack comfortable footwear.
Ladies’ beach sandals are a great choice to go with those island-inspired sundresses.
And a pair of comfortable flip-flops for men are a must when you break out your Hawaiian shirt.
If you plan to do some hiking, include a pair of lightweight hiking shoes, like Keens or Merrells.
When you plan a Hawaii trip, remember the weather is changeable and it can rain (particularly in the winter months). Something lightweight will get you through, as the showers never really last long.
Sweater, sweatshirt or light jacket:
One of the most useful Hawaii vacation tips we learned after our first December trip to Maui years ago was this: Bring something warm!
As much as rain is unpredictable, Hawaii gets predictably cool in the evenings in winter. Definitely pack the tanks and tees for the sunshine-filled days, but add something warmer for cool evenings.
Hawaii has strict rules on what sunscreen you can and can’t use. It was the first state to ban Oxybenzone-based sunblock.
Look for reef-safe sunscreen that protects the natural corals and reefs that make Hawaii beautiful.
Snorkel or dive gear:
You might want to bring your own snorkeling gear to see all the amazing underwater life teeming beneath the surface.
A waterproof GoPro is a great way to capture those underwater adventures.
And a dry bag will provide much-needed protection for your valuables, phone and electronic gizmos while on a boat or tour.
The state of Hawaii doesn’t provide any shopping bags. You can buy one from the grocery or convenience store, but the environment will thank you if you just throw a couple of reusable bags in your suitcase.
Single-use plastics are frowned on in Hawaii so a reusable water bottle is a great idea. Plus you can keep yourself hydrated in flight and around the beach once you land.
We have the Nomader collapsible water bottles – they squish down for packing (brilliant!) and they don’t leak.
If you have tours planned, or say you want to hike Diamond head, a daypack frees up your hands, and provides a good spot for your water bottle, snacks, sunscreen and other essentials.
Other Hawaii travel tips
Here are some final tips for traveling to Hawaii to help with planning your Hawaiian vacation.
Reserve in advance:
This is worth repeating… Make reservations far in advance for hotels, rental cars, restaurants and activities.
If you want to snag an oceanfront table for sunset dining at one of the best Maui restaurants (or other top island restos), reserve early.
Pick up a Hawaii guide book:
There are many great Hawaii guides out there.
Lonely Planet has a “Best Of Hawaii” guide, as well as comprehensive individual guides for each island. They’re known for digging into hidden treasures and offering insider tips and honest reviews for all budgets.
Fodor’s and Frommer’s also have excellent guides.
Learn some Hawaiian words:
Before you go, it’s fun to learn a few words from the Hawaiian language to help in basic situations.
Beyond the ono grinds (delicious foods), it’s nice to know how to say thank you (mahalo), family (ohana) or until we meet again (a hui hou).
If traveling with kids, ask for the keiki menu at restaurants. (Keiki is the Hawaiian word for children.)
And don’t forget to learn how to shake a shaka – a gesture that indicates understanding, friendship and the Aloha spirit.
Get travel insurance:
Lastly, don’t forget travel insurance when you plan your trip to Hawaii!
Travel insurance can help offset non-refundable expenses incurred if travel is delayed or canceled. It also helps out if you arrive, but your luggage doesn’t.
And while nobody wants to think about medical emergencies while on vacation, sometimes they happen. Travel medical insurance helps to cover doctor’s visits and hospital charges.
Check out World Nomads.
Their travel insurance is designed for adventurous travelers, with coverage for overseas medical expenses, evacuation, baggage loss/delay and a range of adventure sports and activities.
Now you know how to plan a Hawaiian vacation!
Whether you’re planning a trip to Maui for a romantic couples’ celebration or planning a Hawaii family vacation on Oahu or Kauai, hopefully you’ve found these Hawaiian vacation tips useful.
Now all you have to do is go – and have a fabulous time! A hui hou.
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Photo credits: 5, 6 and 21 Janice and George Mucalov, SandInMySuitcase | 2, 3, 4 David Parias