First Time to Hawaii? The Right Island and Other Essential Advice

Your first time to Hawaii is always magical.

Actually, even your 10th time in the Aloha state is dreamlike.

But it can be overwhelming planning a trip to Hawaii and trying to choose an island when visiting Hawaii for the first time.

Have no fear!

We’ve visited the Hawaiian islands dozens of times over the years (and written many Hawaii travel articles for U.S. and Canadian magazines and newspapers).

First time to Hawaii

If this is your first visit to Hawaii, you’re in for a treat. But you already know that.

But that’s just not possible in one trip.

So you need to know the best things to do in Hawaii to help you choose which island to go to.

Planning your first trip to Hawaii

Travel planning to these popular islands used to be easy.

We’d just book our flights, accommodation and rental car – and go! It wasn’t hard getting what we wanted. And we never thought about making advance restaurant reservations!

But with Hawaii’s growing popularity, it’s gotten trickier. (And note our Update on the Lahaina fire below.)

Doing some advance planning is now essential to avoid disappointment.

So let’s get some basic information out of the way. Certain things – sorting out a rental car, trip budgeting and figuring out the ideal length for your stay – are important no matter what island(s) you pick for your first Hawaii visit.

Renting a car in Hawaii

The best way to get around the main Hawaiian islands is by rental car.

We’ve used Discover Cars, an international car rental website, to search for the best deals on car rentals from reputable agencies.

While renting a car in Hawaii gives you the ultimate in freedom, you have to book early, as the most affordable (dare we say reasonable?) cars get snatched up quickly.

Budgeting for your first time to Hawaii

No matter which way you slice it, Hawaii is expensive.

Whether this is your first time visiting Hawaii or the 10th, Hawaii’s prices will always make you cringe.

Trying to go on the cheap isn’t that easy, but there are ways to save.

Hawaii on a budget

Mid-range Hawaii vacation

To go mid-range, prepare to spend $200 to $350 a day. Budget hotels start at $150.

You can occasionally find something mid-range starting at around $200 but don’t expect anything fancy at that price.

Food is also expensive, but you can grocery shop if you stay in a place with a kitchen. Activities also tend to be costly and start at around $85+ per day.

Luxury Hawaii trip

How long to stay in Hawaii?

If you’re wondering how many days to spend in Hawaii, know this: You can never spend too much time in Hawaii.

These days, most people spend 9 to 10 days in Hawaii. That gives you enough time to get over jet lag, explore the island you’re on and still have some time to kick back and relax.

Keep in mind that the Hawaiian islands are a long way from the U.S. mainland (or anywhere, for that matter).

A direct flight from California to Hawaii is about 5 hours and 40 minutes. From Vancouver, Canada, the flight time is about 6 hours.

From the east coast of the U.S., it’s a long flight – about 10 hours and 30 minutes or more. And Hawaii is a good 6 hours behind New York and Eastern Standard Time (EST).

So you need to allow a couple of days to get over jet lag and adjust to the time change.

10 Days in Hawaii (or more)

For a first-time Hawaii itinerary, you might want to hit two islands, say Oahu and Maui (or Oahu and Kauai).

As Honolulu on Oahu is the state capital, you’ll find more direct flights to Honolulu from more places than to the other Hawaiian islands.

This way, you could start off with the buzz and cultural attractions of Honolulu up front, then move on to a slower-paced island for more beachy and laid-back activities.

A 10-day Hawaii trip will comfortably allow for visiting two islands.

Mind you, if you have two weeks of vacation time, we’d urge you to spend 14 days in Hawaii.

You won’t regret it, especially if you plan on visiting two or more islands and doing some active adventures like hiking and snorkeling.

We live on the west coast of Canada, and all of our 20 or more trips to Hawaii over the years have been for two weeks. Only once did we go for 10 days.

And we still keep going back to Hawaii!

5 Days in Hawaii (or less)

If you live on the west coast, it’s possible to visit Hawaii for a short getaway, say 4 to 5 days.

And some time in Hawaii is better than no time at all!

For a short trip, you’ll probably want to spend most of your time by the beach and pool, sipping Mai Tais and soaking up the sultry island scenery.

What’s the best island to visit in Hawaii for first-time visitors?

Each of the major islands is unique and offers such variety, so the best Hawaii island for first-timers depends on what you’re looking for and your holiday style. Keep reading our Hawaii travel guide to help you decide for yourself.

Let’s start island hopping!

Island of Oahu

Oahu – known as the “Gathering Place” – is one of the most visited Hawaii islands and also the most developed.

As a result, the island is a fabulous mash-up of traditional and commercial, offering something for everyone.

Where to stay in Oahu

Halekulani Hotel

The name says it all. Halekulani means “house befitting heaven,” and they do their best to live up to the name.

This place is paradise (see our Halekulani Hotel review).

Island of Maui

If this is your first time in Hawaii, Maui is a very good choice.

If time is short (and you can get a direct flight), visit just Maui.

Now, some people might say Oahu is the best place to visit in Hawaii for first-timers. But Maui is our recommendation if you’d prefer a more chill island escape.

Certainly, if you have more than 7 days, you should add on the island of Oahu too.

Maui is world-renowned as a romantic island for honeymooners. But it’s more than that – it’s a fabulous place for children as well (not just for making them).

There are plenty of romantic things to do on Maui for couples, as well as kid-friendly activities for families.

Ho’oilo House

Maui’s most luxurious B&B, Ho’oilo House isn’t on the beach. But it’s quiet and luxurious. It also has a pool and offers incredible ocean views.

Hana Maui Resort

For a serene hideaway in Hana (ideally based for waterfall hikes and exploring off-the-beaten path), Hana Maui Resort is the place to bed down.

Island of Kauai

Kauai is called the Garden Isle for a reason.

Nature lovers won’t be disappointed – its verdant forests and the Grand Canyon of the Pacific (aka Waimea Canyon) alone make for two splendid highlights. And there are tons of Kauai activities that get you out and immersed in nature!

So if lush greenery is your thing, you won’t go wrong making Kauai your first Hawaiian island to visit.

And if you want to loll about on beautiful beaches, Kauai’s got you covered too.

Where to stay on Kauai

Like on Maui, many accommodations on Kauai are attractive condo-style vacation rentals with full kitchens. But you’ll also find beautiful hotels, featuring all the bells and whistles.

We’ve stayed at many of them.

The following are the best condos and resorts on Kauai.

Grand Hyatt Kauai Resort

Surrounded by lush tropical gardens with koi ponds, the Grand Hyatt Kauai Resort is a gorgeous 602-room oceanfront resort. It’s located in the Poipu area on Kauai’s South Shore – the best side of Kauai to stay for sunny weather.

Koa Kea

Another one of our top picks is Koa Kea Hotel & Resort. This upscale boutique beachfront hotel in Poipu is for adults only. Lovely!

Hanalei Colony Resort

This condo-style property offers 48 large two-bedroom suites. Laid-back vibes and full kitchens make Hanalei Colony Resort ideal for a family getaway.

Royal Sonesta Kauai Resort + Marriott’s Kauai Beach Club

With an adjacent 18-hole Jack Nicklaus golf course, this 356-room resort is perfect for golf lovers.

But families find it a great place too – it’s located on calm Kalapaki Beach. And the splendid pool with fountains is one of the largest pools in Hawaii.

Koloa Landing

This luxury resort has some of the largest condo- and villa-style accommodations on Kauai.

Unfortunately, Koloa Landing isn’t on the beach, so you’ll have to drive or take a 15-minute walk to get sand in your suitcase :-). It does have three pools, however (one is adults only).

Sheraton Kauai Resort

Location, location, location. The Sheraton Kauai Resort is on Poipu Beach, which has terrific swimming, snorkeling and body surfing. 

Waimea Plantation Cottages

The secluded Waimea Plantation Cottages is ideal for getting away from it all.

There are 61 historic cottages, ranging from 1-3 bedrooms.

This is “old Hawaii” for you.

Sip morning coffee on your lanai as birds serenade you, go for quiet walks on the black sand beach in front of the resort and revel in the totally peaceful surroundings.

Kiahuna Plantation Resort

Find privately-owned condos for rent at Kiahuna Plantation Resort on stunning manicured grounds stretching to Poipu Beach.

Since most of Kiahuna’s condos are privately owned, we advise you to read the reviews before renting directly from the owner (through Vrbo). You’ll want to ensure the condo is renovated, has a good location on the property and meets the standards you’d like.

Kiahuna is one of our favorite resorts on Kauai, and we’ve stayed here several times over the years.

Whalers Cove

In Poipu, Whalers Cove is a small, upscale oceanfront condo property. It offers large one- to three-bedroom units with full kitchens and views to die for.

Lodge at Kukui’ula

This is the Mc-Daddy collection of luxury villas.

There are 40 villas to choose from at the Lodge at Kukui’ula. It also offers three pools and an organic farm to pick your own fruit and veggies.

Stay in the four-bedroom villa, and you’ll have your own private pool to chill in.

1 Hotel Hanalei Bay

The former St. Regis Princeville Resort is now the new 1 Hotel Hanalei Bay. It’s a gorgeous luxury resort with a wellness focus and knock-out spa.

Where to eat in Kauai

Island of Lanai

Want to get off the beaten path while still getting your fill of adventure? Lanai is for you.

Think undeveloped wilderness – along with world-renowned luxury resorts.

It’s one of the smallest accessible Hawaiian islands. But there are still many things to do in Lanai.

Accommodations on Lanai are mostly of the splurge variety, however. So for a week-long vacation, Lanai isn’t the best place to go in Hawaii for first-time visitors (or anyone, really) – unless you have lots of dough.

A day trip from Maui is often the better option your first time to Hawaii.

Where to stay on Lanai

One is good. Two is better. Lanai proves that theory with two Four Seasons Hotels on the island.

So, which is the best Four Seasons Hotel on Lanai? In a world of caviar and champagne, it’s up to personal choice.

If you are there long enough, try both.

Big Island of Hawaii

Although it’s the largest island, it’s not nearly as developed or populated as Maui or Oahu.

If you’re seeking volcanoes with a side of adventure and nature, head to the Big Island.

Along with snow-capped mountains, it has no less than four active volcanoes, with Kilauea being the youngest and most active.

Fresh lava continue to flow from time to time within Kilauea’s Halemaumau Crater. You can read updates on the USGS government website here.

Where to stay on the Big Island of Hawaii

Hilton Waikoloa Village

This mega-resort is a destination in itself.

With three 9-hole golf courses, a luau three times a week, fitness classes, a spa, swimming pools, a 175-foot waterslide and a huge saltwater lagoon for swimming, snorkeling and kayaking, the Hilton Waikoloa Village is ideal for families looking for many activities.

Mauna Kea Beach Hotel

Founded by the Rockefellers, this luxury hotel is on one of the best beaches on the island (Hapuna Beach). And the spectacular views you get from the seaview rooms are worth the big upcharge in price.

Four Seasons Resort Hualalai

This is another luxe oceanfront option, with seven pools and rooms with outdoor lava rock showers.

The Four Seasons Hualalai is the perfect place for honeymooners who stay on the Big Island. (Actually, it’s perfect for anyone – it was well after our honeymoon when we stayed!)

Which island has the best beaches in Hawaii?

Hmmm, that’s a tough one.

We definitely like Hanalei Bay on Kauai. Backed by soaring emerald mountains, it’s heart-stoppingly beautiful. But with high surf in winter, it’s not the best for swimming then.

Our vote is Maui.

It gives easy access to some of the most picturesque and powder-soft swimming beaches in the world. And they are mellow and quieter than those on Oahu.

Oahu is the runner-up because it also has 227 miles of shoreline with great beaches. But world-famous Waikiki Beach and other beaches are more crowded and touristy.

Of course, there’s the North Shore on Oahu, but that’s primarily for surfing rather than swimming. Or for snorkeling, there’s Pupukea Beach (Shark’s Cove), also on the North Shore.

So Maui it is. The sandy beaches at Wailea, Kihei, Ka’anapali and Kapalua are all glorious.

Hawaii travel tips + things to know

Things to know about Hawaii

There’s more to Hawaii than romantic islands and volcanoes. And since we’ve been there more times than we can count on two hands, we know all sorts of cool Hawaiian facts.

Did you know Hawaii has a forbidden island? Hawaii is also the only U.S. state where humpback whales mate.

Here’s another fact we bet you don’t know: Hawaii has two native mammals, one of which is the Hawaiian hoary bat (the other is the Hawaiian monk seal).

Try the fruit!

Juicy pineapples, lush papayas, heavenly mangoes – oh my! You’ll drool over all the different types of Hawaiian fruits on your vacation.

Don’t miss out on a luau

You can’t go to Hawaii and not experience a luau.

And you’re in for one helluva party with a feast of traditional Hawaiian food and cocktails while being immersed in Hawaiian culture.

Fire and hula dancing, legend telling and music to fill the evening’s hours are on the menu.

You’ll find luaus on all of Hawaii’s islands (the main ones). Enjoying a luau is a must-do activity for your first-time Hawaii trip!

What to pack for a Hawaii vacation

Unless you plan to lie on a beach all day (no judgment if you do), packing for Hawaii isn’t so cut and dry.

For one, Hawaii has banned the sale of sunscreen with the coral-harming chemicals oxybenzone and octinoxate.

So you need to bring only reef-safe sunscreen (or buy it once in Hawaii).

When you’re out snorkeling, enjoying the coral reef systems, you don’t want to be slathered in sunscreen that bleaches and destroys the coral, do you?

Another thing to note: On our first Hawaii trip, we took just hot-weather clothes. Bad choice. It can get chilly in Hawaii in the evenings in the winter months.

So it’s a good idea to pack a light jacket or sweater – just in case.

Find out exactly what you need to pack for Hawaii (depending on your planned activities). You can can download our free printable packing checklist for Hawaii below.

Hawaii weather

What time of year is best for your Hawaii first-time visit?

Hawaii has tropically warm and breezy weather, with lots of sunny days and a good dose of humidity all year-round.

But there are also wet and dry seasons. Typically, you can expect some rain from December to April. But May to November is normally dry.

So the best time to go to Hawaii depends on what you’re looking for.

Winter is ideal for surfers and whale watchers. But as this is also high season, it’s more expensive.

If you’re looking to stick to a budget, the best time to visit Hawaii is the shoulder season. You can find lower prices on accommodations in April, May, September and October. 

What about the worst months to visit Hawaii?

There’s no bad month. Any time is a good time in Hawaii. It all depends on why you’re going and to which island.

Last words on booking your first vacation to Hawaii

We realize we didn’t give you a definitive answer on where to go in Hawaii for the first time. There’s just no right answer. But we hope this Hawaii vacation guide helps steer you in the right direction.

The good news is you can’t go wrong no matter where you go, and if you have to go back again to figure it out, sorry, not sorry!

We remember going to Hawaii for the first time, and we’re always happy to do it all over again!

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