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 Hawaii dozens of times over the years (and written many Hawaii travel articles for U.S. and Canadian magazines and newspapers).
We’re here to help you decide which island is ideal for you, where to stay and what to see and do – and we share helpful tips on things like car rentals and the best time to visit.
Note: Prices are in USD.
First time to Hawaii
If this is your first visit to Hawaii, you’re in for a treat. But you already know that.
The thing about all these picture-perfect islands is that you’ll want to do it all.
Whale watching in winter. Snorkeling at Molokini Crater and Turtle Town on Maui. Boogie boarding on Waikiki Beach. Yes!
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.
Here are a few rental, gas and insurance tips to help you get and drive the most affordable car rental in Hawaii.
- Rental – First, you might not want to rent at the airport. That’s the most expensive place to pick up your vehicle. (On the other hand, the airport is usually the most convenient place to rent your car, so convenience may trump cost.)
- Gas – Gas is pricey, so check the Gas Buddy app to find the cheapest gas locations. Or better yet, join Costco. They have the cheapest gas around.
- Insurance – Check your own car insurance policy, as well as your credit cards. Sometimes they’ll cover everything you need, and you won’t have to buy extra insurance.
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
If you’re on a super tight budget and want to spend less than $100 USD a day, you’ll probably need to camp, stay in a hostel, go off-season, participate in only free activities and cook most of your meals.
And still, it’ll be a challenge.
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
Hawaii is your oyster if you want to go all out and splurge.
Take a helicopter ride, go island hopping, eat at all the best restaurants and more. Lucky you!
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?
We wish there was a clear-cut answer to the best Hawaiian island for first-time visitors.
But it’s an impossible choice. One we’re happy to go back to as many times as possible to figure out. So, we’re definitely on the case!
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.
- Shop in Honolulu.
- People-watch on Waikiki Beach.
- Visit Pearl Harbor. Pearl Harbor is an absolute must for every first-time visitor to Hawaii who stays on Oahu.
- Enjoy a luau at the Polynesian Cultural Center.
- Snorkel at Hanauma Bay. (It’s one of the best spots for snorkeling on the entire island.)
- Hike up Diamond Head.
- Tour the North Shore. (Maybe do a North Shore tour combined with hiking up Diamond Head? Or a full-day circle island tour that includes visiting Oahu’s beautiful North Shore beaches, like Waimea Bay?)
- See the Lulumahu Waterfall.
- Hike in Waimea Valley to the Waimea Falls.
- Learn about pineapple farming at the Dole Plantation (and ride the Pineapple Express Train).
- Go on a Lost (the TV show) tour.
- Admire some 55,000 pieces of Asian, European and American art at the Honolulu Museum of Art.
- Learn to surf.
- See the 1882 Iolani Palace, the official royal residence for Hawaii’s last reigning monarchs.
Where to stay in Oahu
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).
It’s on the far end of Waikiki Beach – close enough to shop for the best Hawaiian souvenirs but worlds away when it comes to the serenity it offers.
Vive Hotel Waikiki
This trendy boutique hotel in the heart of Honolulu offers great value.
Vive Hotel is walking distance to shops and restaurants and few minutes’ walk to the beach.
The Surfjack Hotel & Swim Club
Tucked away from the hustle and bustle of the city and a short drive to Diamond Head, The Surfjack Hotel & Swim Club has a laidback modern Aloha spirit.
Rooms and suites sport a vintage 1960s-inspired décor.
Where to eat in Oahu
You’ll be spoiled for choice when it comes to restaurants on Oahu – it’s home to some terrific chefs. These are some must-try Honolulu restaurants:
- Senia – Enjoy elevated Hawaiian food, where the chefs create magic in the kitchen.
- Helena’s Hawaiian Food – This iconic no-frills place has been serving traditional food since 1946.
- Orchids – Looking for the best brunch in Waikiki? You’ve got it, from omelets and a roast station with suckling pig to fluffy banana macadamia nut pancakes and champagne.
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.
- Chase waterfalls – like these epic waterfalls on Maui!
- Snorkel Molokini. It has the best marine life in the area. (Check out this cool super-raft snorkeling adventure that leaves from Kihei – combining Molokini with Turtle Town.)
- Hike in a bamboo forest on the Pipiwai Trail.
- Watch the sunrise at Haleakala National Park.
- Swim at Wailea Beach.
- Drive the twisty Road to Hana. (While it’s an incredibly scenic drive, it’s a long drive. To leave the driving to someone else, here’s a top-rated small-group guided tour to Hana.)
- Watch humpback whales (December to May).
- Visit the red sand Kaihalulu Beach.
- View the turtles in Paia.
- Walk the boardwalk along Kaanapali Beach.
Where to stay on Maui
The following are the major resort areas where visitors currently stay in Maui:
- Ka’anapali – For couples, honeymooners and families who want to stay on a beautiful beach, with lots of buzz and action around. (See our post on the best condos and resorts in Ka’anapali for details.)
- Kapalua – For couples who want a peaceful retreat with luxury vibes. It’s less built-up than other areas, so it’s less touristy.
- Napili – For families and couples looking for a more affordable Hawaiian vacation. It’s more rural here, and it’s all about condos instead of luxury resorts.
- Kihei – For families looking for an authentic and affordable Hawaiian vibe. It’s a good blend of locals and tourists here.
- Wailea – For luxury seekers who like mega-resorts and the possibility of celeb-spotting. (See our post on the best places to stay in Wailea.)
- Paia – For surfers and trend-spotters who love a boho-hippie vibe.
- Hana – For anyone looking to escape the crowds and be enveloped by lush hiking trails and forests. It’s a perfect location for exploring the Road to Hana, the waterfalls and the powdery-soft beach.
The town of Lahaina was ravaged by the August, 2023 wildfires, and it’s presently closed to the public.
Beautiful honeymoon hotels
Now we’ve already mentioned the island is a beacon for honeymooners.
So it’s no surprise that Maui boasts some beautiful honeymoon hotels. Three of the most romantic are:
For adults only, the boutique Hotel Wailea has 72 deluxe suites and offers complimentary transfers to its beach club.
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.
Where to eat in Maui
Maui’s restaurants and eateries? They’re winners. Don’t miss our faves:
- Mama’s Fish House – We love this breezy seafood restaurant on Maui’s north coast for fine dining! The fish is so fresh that the name of the fisherman who hooked it that morning is listed on the menu. (An advance reservation is essential!)
- Leoda’s Kitchen and Pie Shop – Don’t miss this bakery, known for its sweet and savory pies. (Our favorite is the coconut cream pie. Or maybe it’s the banana cream pie? Hmmm…) Plus, the next-door market has the most delicious types of fruit in Hawaii.
- Kinaole Grill Food Truck – This popular food truck is located in Kihei. Pick up your lunch (or dinner) of coconut shrimp or crispy mahi mahi, served with rice and salad, and eat it on the nearby beach.
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.
- Visit the botanical gardens on Kauai (the Allerton and McBryde Gardens are our favorite).
- Hit the beach! Check out the best swimming beaches in Kauai.
- Walk the Maha’ulepu Heritage Trail.
- Drive through a tree tunnel in Poipu.
- Gawk at Waimea Canyon (aka the Grand Canyon of the Pacific) – it’s a free Kauai experience that’s a must-do.
- Go on a thrilling Na Pali Coast boat or helicopter tour. (Or soar above the Na Pali Coast and Waimea Canyon on this 5-star-rated deluxe scenic flight.)
- Hike the Kalalau Trail (or even just a part of it).
- Find the best places for SUP or stand-up paddleboarding in Kauai
- Go ziplining through jungles.
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.
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.
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.
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
The following are some of our favorite places to eat on Kauai:
- Dolphin – With an indoor/outdoor setting, this fresh fish, seafood and sushi paradise is known for the best fish on the island. Which says a lot.
- Bar Acuda – Check out locally sourced tapas on the North Shore at this popular resto. (It’s consistently packed with diners.)
- Beach House Restaurant – Yes, it’s pricey. But you can’t beat this oceanfront Poipu institution for epic sunset views. (And the food is quite decent too.)
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.
- Ride ATVs to secluded beaches.
- Snorkel with sea turtles.
- Hike the Koloiki Ridge.
- Relax on Hulopoe Beach.
- View the ruins of a prehistoric Hawaiian village at Kaunolu Fishing Village.
- Explore Lanai City.
- Marvel at the red rocks at the Garden of the Gods (Keahiakawelo).
- See the rusted hulk of a World War II navy barge at Shipwreck Beach.
- Horseback ride through the forests.
- Play a round of golf at the seaside Manele Golf Course, designed by Jack Nicklaus.
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.
Where to eat in Lanai
There aren’t a lot of places to eat on this island, but these are don’t miss spots:
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.
Big Island highlights
- Explore Hawaii Volcanoes National Park. (Walk through lava tubes and more!)
- Chill on the white sands of Hapuna Beach.
- View the sunset at Mauna Kea (and stay for stargazing).
- Swim at Coconut Island in Hilo.
- Get up-close-and-personal with manta rays on a night dive or snorkel – a bucket list experience!
- Spend the day at Kaunaoa Beach (Mauna Kea Beach), a picturesque white sand beach.
- Go on a farm tour near Hilo.
- Soak up the rainforest scenery on a drive along the Hamakua Coast between Hilo and the Waipio Valley
- Check out the coffee plantations and learn all about Kona coffee.
- Hike to the 422-foot Akaka Waterfalls (a short easy hike near Hilo).
- Visit Punalu’u Beach, the most famous black sand beach on Hawaii.
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.
Open since 1965, the Mauna Kea Beach Hotel has been keeping families returning generation after generation.
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!)
Where to eat on the Big Island
For some of the best food on Hawaii’s Big Island, hit these spots:
- Merriman’s – Located in Waimea, this is the flagship restaurant for award-winning chef Peter Merriman. They use local ingredients, adding a regional flair, and have an extensive wine list.
- Da Poke Shack – Poke is the epitome of Hawaiian fare. And this place has the best on the island. In Kona, they’re open until 4:00 pm daily, but they sell out long before that time, so get there early.
- On the Rocks – For casual, toes-in-the-sand food and fun, hit this Kona resto with a beach club vibe.
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.
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!