Are you planning a trip to Hawaii? Could you use some helpful Hawaii travel tips?
We hear you!
Hawaii serves up some special experiences that are hard to find beyond its shores. You can swim with sea turtles, snorkel with manta rays and watch sunsets paint the sky like there’s no tomorrow.
But for tips on how to plan a Hawaii vacation, this is your go-to guide!
Planning a trip to Hawaii
A word of advice…
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, Hawaii is so popular that you need to book everything well in advance. Just a friendly warning to plan ahead!
Which island to visit in Hawaii?
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.
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.
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 50-minute helicopter tour will amaze you with a bird’s eye view of stunning landscapes – you may even recognize some scenes from the Jurassic Park and King Kong hits.
And let’s not forget what you can do on Kauai for free. Hiking epic trails? Touring a coffee farm? Check and check.
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.
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.
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 also has alluring beaches. We’re happy as clams to hang out on the half-mile stretch of white sand at Hapuna Beach.
And wait. There’s more… You’ll find 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 when planning a Hawaii trip, don’t try to cram too much into your precious vacation. You don’t want to return home more pooped than when you left.
If you decide to go island-hopping, give yourself at least four nights per island for the main islands – Maui, Kauai, Oahu and the Big Island. (An exception is perhaps Oahu. When planning your Hawaii itinerary, you could spend just two or three nights if you start or finish there.)
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!
As for how to travel to Hawaii and between the islands, you need to know that there are no ferries. Flights are the only way to get from island to island.
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!
So when it comes to Hawaiian vacation tips that ensure a real vacation, give yourself enough time to enjoy each island – before you think about hopping to the next.
How much time do you need in Hawaii?
10 Days in Hawaii
If this will be your first time in Hawaii, a good 10-day Hawaii itinerary is to start in Oahu and stay in Honolulu for three nights. Then fly to either Maui, Kauai or the Big Island for the remaining seven nights.
2 Weeks in Hawaii
If you have two weeks in Hawaii, you could start in Honolulu and then split the remaining time between Maui and Kauai.
Returning in future
If you know you’ll be returning to Hawaii again in future, concentrate on just one island, and visit another the next time.
(“Slow travel” is the way to really dig into and appreciate a destination – plus it’s also a more responsible way to travel.)
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 Hawaiian 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. We use 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!
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.
Hotels in Hawaii
If you opt for a hotel, check out Booking.com. We like the flexible cancellation options it offers – and the rates are often better than if you book directly through the hotel’s website.
Also 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 your program for blackout dates when planning your stay.
Condos or places with kitchens
If planning a family trip to Hawaii – or maybe because you want the luxury of more space – check out condos or Vrbo (Vacation Rentals by Owner).
Islands like Oahu, Kauai and Maui have large inventories of vacation condos, cottages and houses with kitchens and other amenities.
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.)
For our latest Maui trip, for example, one place we stayed at was a tastefully remodeled, one-bedroom condo with two bathrooms and a full kitchen (over 900 sq. ft) in The Whaler (booked through Vrbo).
We especially love its location in Maui, right on the beach and close to shops and restaurants.
Which part of the island do you want to stay?
Where on Maui
We’ve written a whole post on where to stay in Maui.
It covers the best areas on the island and the island’s different micro-climates, along with top accommodation options.
If you’re going on your honeymoon, you’ll find a dreamy selection of romantic hotels on Maui for couples to suit all budgets. Some are adults-only for maximum couple time.
Where on Kauai
Popular with hikers and other adventure lovers, Kauai has stellar hotels and vacation rentals 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.
But the area you stay on Kauai matters, especially if you’re rain-averse.
Surrounded by lush rainforest, the North Shore is the most beautiful part of the island. But you have to expect a drizzle or two.
If you prefer reliably sunny weather, you’ll be happier staying on the South Shore.
Where on Oahu
As for Oahu, are you set on wanting the buzz of Waikiki Beach? But do you also want your hotel to be a quiet retreat amidst all the action?
Then say hello to 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.
Renting a car in Hawaii
Whatever island you decide to visit, renting a car gives you the ultimate freedom to explore. It’s the best way to see Hawaii.
Look into which company has the best customer service reviews and offers the best deal.
Discover Cars is an international car rental website that we’ve used to book a rental car. A price comparison website, it compares rates from various rental agencies to come up with the best deal.
Another company to check out is Discount Hawaii Car Rental.
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 it can sometimes 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 visiting in high season.
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 the last trip.
But we lucked out nabbing a Hertz car rental for half of that two-week Maui trip by plugging in a rental location other than the airport. (It came to about $80 USD a day.)
We took a taxi to and from the airport. Then when in Kaanapali, we picked up the car at the Hyatt Regency Maui Hertz location and dropped it off there too.
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 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 government insurance isn’t enough so we’ve bought extended third-party liability insurance to bump up the coverage limit.)
One more thing. You may not need to buy extra CDW (collision damage waiver) insurance, depending on the credit card you use to book your rental. Our 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 visit without a car
Do you need a car in Hawaii? No. Getting around Hawaii without a car is very feasible.
If this is your first trip to Hawaii, be aware, however, that Hawaii doesn’t go in for all-inclusive resorts (unlike Mexico or the Caribbean). So you want nearby choices for dining and tours – nothing is worse than feeling stuck in your condo, hotel or resort.
If you don’t rent a car, stay in a resort area where you can walk to stores, restaurants, the beach and activities.
If you’re staying in Waikiki, Honolulu, on Oahu, most destinations are conveniently within walking distance.
On Kauai too, if you stay in Poipu, you can walk to nearby restaurants and shops – and have beaches at your fingertips.
On Maui, a beach promenade (about 2½ miles long) makes it easy to walk from Kaanapali hotels to shops and restaurants.
The island of Oahu has a strong public transit system, so you can get around easily without a rental car.
Some resort areas on various islands have free shuttles to help you get around.
In the Kaanapali resort area on Maui, for example, you can hop on the complimentary Kaanapali Trolley. It trundles back and forth between the area hotels, the Royal Kaanapali Golf Course and the Whalers shopping village.
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.
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.
As this is a busy week in Hawaii, you might want to avoid going to Oahu during Golden Week.
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 ones 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.
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.
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.
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 vacation 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.
Popular restaurants book up early. On our last trip to Maui, we couldn’t get a table at all at Mama’s Fish House – they were booked out months in advance.
Pick up a Hawaii guide book
There are many great Hawaii guides out there.
Frommer’s has a new Frommer’s Hawaii 2024 guide.
Lonely Planet also covers the best of Hawaii in 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 also has 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 SafetyWing.
They offer travel insurance for frequent travelers, long-term adventurers and digital nomads – covering medical expenses, lost checked luggage, trip interruption and more.
Now you know how to plan a Hawaiian vacation!
Whether you’re planning a Hawaii family vacation on Oahu or a romantic getaway to Maui, we hope you now know how to plan a Hawaii trip.
All that’s left is to go and have the time of your life! A hui hou.
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Photo credits: 14 to 16, 19, 26 Janice and George Mucalov, SandInMySuitcase | 5 to 7 David Parias