How to Pick the Best Hawaiian Island For Your First Trip

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Looking for the best island to visit in Hawaii for first timers?  Don’t stress.  The good news is that you truly can’t go wrong!  Each of Hawaii’s islands is incredible in its own right, so there’s no need to worry that you might not choose the best Hawaiian island for your first trip.  If you’re visiting Hawaii for the first time, this guide will help you decide which island is the best place to stay.

And if you need more help preparing for your trip, check out my ultimate Hawaii packing list!

With that said, finding the best island to visit in Hawaii as a first-time visitor can have a big impact on your trip.  I’m fortunate to have spent time on most of Hawaii’s main tourist islands, so I’ve put together this guide to help make your decision about where to stay in Hawaii just a little easier!

Before you Visit Hawaii for the First Time…

Important Packing tip for Hawaii: You absolutely need to bring this type of sunscreen to Hawaii. It’s eco-friendly, and safe for Hawaii’s fragile underwater ecosystem and marine life.

 

How to Choose The Best Island to Visit in Hawaii for First Timers

Deciding which Hawaiian island to stay on for your first visit can be a difficult choice.  It’s hard to know what to expect on each island, and what the pros and cons are for each island in Hawaii.

Here’s a few points to consider when you’re trying to decide the best island for your first visit to Hawaii:

1. Choose The Best Hawaiian Island For Your First Trip Based on Flight Schedules

If you’re like me and you hate having a connecting flight, you could consider choosing a Hawaiian island for your first trip based on the availability of direct flights from your home airport.

Maui and Oahu are very popular islands, and thus are more likely to have direct flight connections, but it’s worth checking out your options ahead of time.  The best Hawaiian Island for you to stay on might be the one that’s easiest to get to!

Even if you’re coming from the West coast of the US, you’re in for a long flight to Hawaii.  For my best tips about flying stress-free, check out this post.

2. Pick A Hawaiian Island for Your First Time Based on Your Desired Activity Level

Are you the type of traveler who wants to just relax by the pool?  Or are you interested in exploration and adventure?

Since there’s such a variety of things to do in Hawaii, the best Hawaiian island to visit for your first time may depend on your desired level of activity during your trip.

The Best Hawaiian Island to Vacation for Relaxation

If you’re looking to stay close to your hotel or condo and just hit the beach or pool, I’d recommend Maui or Lanai.

There are several places to stay in Maui where accommodation is walking distance to shops and restaurants, and on Lanai, there’s just fewer things to do in general.  On both of these islands, relaxation is king, making them great Hawaiian islands to pick for your first visit.

The Best Hawaiian Islands to Visit for Adventure

On the other hand, if your idea of a great first visit to Hawaii is filled with waterfall hikes, kayaking, and volcanoes, you might really enjoy Kauai or the Big Island.  Both of these islands offer incredible opportunities to explore Hawaii in an adventurous way.

No matter which Hawaiian island you choose, you’ll definitely want to check out my tips for first time visitors to Hawaii.  I’ve got everything you need to know in one handy post!

3. Best Hawaiian Island to Stay on May Depend on The Duration of Your Trip

If you have at least a week in Hawaii, you’ll have time to really explore the island that you choose.  For a longer trip to Hawaii, I’d recommend staying on Kauai or the Big Island.

How Long Should I Go to Hawaii for the First Time?

If you’re wondering how long you should go to Hawaii for on your first trip, I would recommend at least 5 days.  A week would be even better!

Having at least 5 days for your first trip to Hawaii will allow you to mix in sightseeing with relaxation.  You’ll be able to move at a relaxed pace, but still see plenty of sights on the island you choose.

So – which Hawaiian Island is best for your first trip?

The Best Islands for a Longer Trip to Hawaii are Kauai or the Big Island

Kauai and the Big Island have so many different things to see, do, and explore, that you’ll have no shortage of things to do during your time in Hawaii, and you’ll still have time leftover to relax and enjoy the beach.

To see all of the best sights on Kauai and the Big Island, you will need to drive for a few hours, so it makes sense to visit these islands for your first trip to Hawaii if it is a week or longer.  For that reason, Kauai or the Big Island are the best places to visit for first-timers to Hawaii that have a week or more.

I put together the perfect itinerary for one week in Kauai – check it out for more details!

The Best Islands for a Short Trip to Hawaii

On the other hand, if your first trip to Hawaii is a shorter trip of four or five days, I’d recommend staying somewhere that doesn’t require you to move around much in order to see the best that island has to offer.

For trips to Hawaii lasting four or five days, I would recommend visiting O’ahu, Maui or Lanai.  These Hawaiian Islands are smaller in size, and for that reason, are much easier to get around.

Pro Travel Tip: These days, travel can be more uncertain than ever. Check for any COVID-related restrictions at your destination, and never travel without travel insurance! I recommend SafetyWing, because they have flexible + affordable insurance plans, and also cover COVID-related impacts on your trip (not all companies do)!

4. If You’re Visiting Hawaii For the First Time, Choose an Island Based on Access to Restaurants, Activities and Nightlife

During your first trip to Hawaii, do you want to be within easy access or walking distance to restaurants, activities and nightlife?  If so, staying in Ka’napali or Wailea on Maui, or near Waikiki on Oahu would probably be the best places to go for your first trip to Hawaii.

On the other hand, if you want to get away from it all, the island of Lanai is a bit sleepier.  On the Big Island, places are a bit more spread out, so you’re likely to have a little more peace and quiet.

These are good things to keep in mind when deciding which Hawaiian island will be best for your first trip.

5. Pick The Best Hawaiian Island Based on Your Preferred Accommodation Style

Are you looking for world-class resorts in Hawaii with a price tag to match?  Or do you prefer a more modest hotel, or maybe even renting a condo or an apartment?

While each Hawaiian island has a range of accommodation, some islands are better than others for certain categories, so the best island to visit in Hawaii for your first trip might depend on where you’d like to stay.

Maui and the Big Island are the Best Hawaiian Islands for High End Resorts

The best island to visit in Hawaii for first timers who want a top-end resort with amenities to match might be Maui or the Big Island.  If this sounds like you, check out one of the Four Seasons properties on Maui, Lanai, or the Big Island.

Hotels don’t come much more chic than these resorts.  Each of these hotels have stunning rooms with facilities and amenities to match.

How to Choose the Best Island to Visit in Hawaii for First Timers – An Island by Island Guide

I hope that thinking about the factors above help you choose which island to visit for your first trip to Hawaii.  If you’re still wondering which Hawaiian island to pick, here’s a few thoughts on each one, along with my recommendations according to the kind of trip you’re considering.

Staying in Maui For First Time Visitors

Here’s the lowdown on the kinds of travelers that are likely to enjoy Maui the most out of any of the Hawaiian islands for their first trip.

Maui is the best Hawaiian island to choose for honeymooners or families with small children

In Maui, there are plenty of places to stay where you don’t need a car to access restaurants and great beaches.  If you want to just take a sunset stroll to dinner, or you don’t feel like packing up the kids in the car, staying in Ka’anapali or near Lahaina will give you plenty of options for activities and restaurants within walking distance.

The Best Places to stay in Maui – My Top Picks

The island of Maui has plenty of choices for high end accommodations if you want to splurge.  My top choices for hotels for honeymooners in Maui are the Montage and the Andaz.  They’re both stunning and perfect choices for the trip of a lifetime.

If those aren’t in your budget, the Sheraton has a near-perfect setting at the end of Ka’anapali beach and is a spectacular honeymoon choice.

If you want a place to stay in Maui that’s family-friendly, check out the Westin Ocean Villas.  They’re located close to a gorgeous beach, and they even have a free shuttle into Lahaina.

Choosing Kauai For First Time Visitors

Who should stay in Kauai for their first visit to Hawaii?

Kauai is the best island choice for adventure lovers visiting Hawaii for the first time

Kauai is the best island to visit in Hawaii for first timers who love adventure.  Kauai’s scenery is stunning, and its natural beauty is a draw for visitors to the island.

But to really see everything that Kauai has to offer, you’ll need to get out of your beach chair and explore.   In fact, the best of Kauai’s scenery, the Na Pali coast, can only be seen by boat or helicopter, or via a very long hike, making it the best island to choose if you’re willing to explore during your trip to Hawaii.

How to Visit Kauai as a First Timer

If you choose Kauai for your first visit to Hawaii, I promise you won’t be disappointed!  For more info on how many days to spend in Kauai, I’ve put together a guide especially for first-time visitors to Kauai.  You’ll also love my list of the best places to eat in Kauai.

Where to Stay in Kauai – My Top Picks

If you decide to choose Kauai for your first trip to Hawaii, I’d recommend dividing your time between the North and South coasts of the island.

Personally, I think the best places to stay in Kauai are the property facing the Bali Hai in Princeville, which will open later in 2022: the 1 Hotel Hanalei Bay.  I can’t wait!

In Poipu, I would recommend the Sheraton in Poipu.  Both resorts are gorgeous and perfectly-located.

Staying on Hawaii’s Big Island for First Time Visitors

When is it best to choose the Big Island for your first time in Hawaii?

Hawaii’s Big Island is a Great Choice for Families with Older Children

The Big Island of Hawaii is a perfect choice for families, especially those with older children or teens.  I usually recommend the Big Island to families who are visiting Hawaii because of the huge variety of things to do.

There’s plenty to keep older kids busy and entertained – including volcanos and even diving with manta rays at night.

Seeing Many of the Big Island’s Best Sights Requires Driving

The reason I usually recommend the Big Island to families with older children is that driving to some of the activities can require a long-ish drive.  This can put a dent in nap schedules for little ones, so you may not get the most out of the Big Island if you have little kids.

It’s easy to underestimate how long it might take to get from one place to another on the Big Island, so just keep that in mind as you plan your trip.

If you’re looking for more ideas on how to spend your time on Hawaii’s Big Island, check out the Big Island itinerary I put together.

Where to Stay on The Big Island – My Top Picks

If you choose Hawaii’s Big Island for your first trip, I recommend staying on the Kohala coast.  It’s the sunniest part of the island, and it’s close to plenty of restaurants, beautiful beaches and things to do.  For all-out luxury, you can’t go wrong with the Mauna Lani, and families with kids will love the pool at the Hilton Waikoloa.

Is Lanai the Best Island in Hawaii for First Time Visitors?

The island of Lanai might be the best island to visit in Hawaii for first timers that want to just relax and get away from it all.  Lanai has less going on than any of the other islands, so it’s a great choice if you’re just ready to crash and enjoy the island’s natural beauty.

Choose Lanai for Your First Trip to Hawaii if You want to Get Away from it All

Since it’s one of the less frequently visited islands (relatively, anyway), there’s also fewer crowds which can be a draw in and of itself.

Where to Stay on Lanai if you’re visiting for the first time – My Top Picks

If you choose the island of Lanai for your first trip to Hawaii, you should know that there’s a more limited range of places to stay, but still plenty of variety.

For a high end honeymoon, the Four Seasons on Lanai recently re-opened after a multi-million dollar renovation, so it’s practically brand spankin’ new.

If you’re looking for something less extravagant on Lanai, your best bet might be Airbnb or VRBO.

Is O’ahu The Best Hawaiian Island For First Time Visitors?

The island of Oahu is a fabulous choice for first time visitors to Hawaii, especially if you’re traveling with little ones. It’s also a great choice if you want a more urban feel to your trip, and if you want access to more nightlife during your time in Hawaii.  If you’re looking for high-end shopping, Oahu is the place to be.

O’ahu has the most direct flights, making it a great choice if you’re visiting Hawaii for the first time.

O’ahu is also the easiest Hawaiian to get to, as many international flights arrive in Honolulu before connecting to other islands.  Even if you’re traveling to Hawaii from the US mainland, you’re likely to be routed through Honolulu.

Where to Stay on O’ahu – My Top Picks

Trying to decide where to stay on O’ahu for your first trip?  If you love Disney, you can’t go wrong with the Aulani resort.  For a grown up retreat, try the Royal Hawaiian or the Moana Surfrider.

Should You Stay on More Than One Hawaiian Island During Your First Trip?

Can’t decide where to stay in Hawaii for your first visit?  You could always explore two islands during your time in Hawaii, but I only recommend doing this if you have 10 days or more.  Otherwise, you’ll end up spending at least a half a day traveling, and it’s time better spent with a mai tai!

Hopefully your first visit to Hawaii won’t be your last!

And don’t forget – this might be your first visit to Hawaii, but hopefully it’s not your last.  You’re likely to fall in love with these magical islands.

I’m willing to bet that you’ll be back for another trip, so you can always plan to explore a different island the next time around!

There You Have it – How to Choose The Best Island to Visit in Hawaii for First Timers!

I hope that this guide helped you decide which island is best for your first time in Hawaii.  Need help packing for your first trip to Hawaii?  Check out my Hawaii packing list, and my favorite beauty products to pack for beach trips.

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