Best Island to Visit in Hawaii First Time: 8 Tips to Know Before You Go

February 28, 2023

If you’re staring out your window daydreaming of palm trees, crystal clear water, and a care-free day, you’re in desperate need of a vacation to Hawaii.

Follow along to learn the best tips and tricks for planning a Hawaii vacation for the first time.

We’re willing to bet you can already feel the ocean breeze on your skin as you laze away under the hot Hawaiian sun. Hold on, daydreamer! Before you can get to the good part, there’s a bit of work to do. Aside from knowing where to go in Hawaii, first-time visitors will also need a slew of other tips for planning a trip to Hawaii for the first time.

When visiting Hawaii for the first time, visiting beautiful beaches, tropical forests, and sizzling volcanoes are essential. However, getting to all these dreamy destinations will take some traveling tact!

Use our travel tips when you head to Hawaii! Keep reading to find out where to go in Hawaii, first-time visitor tricks, and money-saving tips.

Decide If You Are Going to Island Hop

What is the best way to see Hawaii for the first time? Island hopping!

Before jetting off for your first trip to Hawaii, the first step is to decide if you will split your time between multiple islands or spend your trip on a single island. Island hopping is a great way to see the whole state. However, it can come with a price tag!

There are eight islands total in Hawaii:

The Big Island (Hawai’i), Oahu, Maui, Kauai, Lanai, Molokai, Niihau, and Kahoolawe.

The first four islands are the most popular tourist options. We’ll dive into the draws of each, but first, you have to decide if you will set up camp on one island the entire time or travel between them.

Aerial view looking over Waikiki Beach towards Diamond Head State Monument on a sunny day with bright blue water in Oahu, Hawaii, USAPros of Sticking With One Island

Transportation will be simpler to plan. Additionally, you won’t have to worry about booking any inter-island flights! You’ll also have the chance to fully immerse yourself in the island’s culture, history, and activities. Hopping between islands often means experiencing the highlights and skipping everything else. Sticking with one means you’ll get to see it all!

But above all else, hello! Simple itinerary planning. You won’t have to juggle multiple trip schedules since everything will happen in one spot! 

Cons of Sticking With One Island

While you may get to fully experience the island you’re staying on, you won’t be seeing any of the rest of the state. But hey, it’s just another excuse to come back again!

In addition, there are many, many activities to choose from throughout the state of Hawaii. If you’re stuck on one island, this will limit the offerings you have to choose from. 

Three hula dancers in bright red and yellow costumes dancing on stage at Chiefs Luau in Honolulu, Hawaii, USA

photo credit: Chief's Luau via Facebook

Pros of Island Hopping

You’ll get to see more of Hawaii! Since Each island has its own personality. You’ll get to mix and mingle among them all! Different landscapes and activities make for exciting variety.

And, if you won’t be able to return to Hawaii for a while, you’ll get a good taste of it all before you go.

Cons of Island Hopping

You’ll have to book inter-island flights. This can add up! If you’re budget-conscious, this might not be the best option. Unfortunately, you will have to miss out on some experiences on the islands due to splitting your time between them all; honestly, island hopping can sometimes make for a hectic, complicated schedule.

Hawaii for Beginners: Pick an Island

If it’s your first time going to Hawaii, you’re probably still in the dark about the unique characteristics of each island. As a result, you’re likely asking an important question: “Which one is the best island to visit in Hawaii for first-time visitors?”

The answer isn’t so simple because each island is marked by its own brand of tropical wonder. So it’s really up to you! If it’s your first time in Hawaii, here’s the scoop on each of the popular tourist islands to help you decide where to go in Hawaii.

Aerial view of the beach at Halona Blowhole in the day time with crisp blue water in Oahu, Hawaii

photo credit: Halona Blowhole via Facebook

The Big Island (Hawai’i)

The largest island in Hawaii, of course, is the island of Hawai’i (referred to as the Big Island). This is the best island to visit if you’re looking for diverse nature landscapes.

We’re talking black sand beaches mixed with active volcanoes! There’s more to discover than just stereotypical white sand beaches.

Of course, Hawaii Volcanoes National Park is an obvious stop to add to your itinerary if you opt to visit the Big Island. It’s home to the largest active volcano in the world!

Lava flowing on the Big Island Hawaii

Molten lava flowing into the Pacific Ocean on Big Island of Hawaii at sunrise


This island is geared toward tourists and is likely to be the most crowded. However, if you like the bustling atmosphere of fellow travelers, this island is for you!

Plenty of attractions to choose from (snorkeling, anyone?), fantastic shopping, and the ever-famous Waikiki Beach mean this is one happening locale. If you’re up for hanging ten, Oahu’s North Shore is the place to be for surfing paradise!

Aerial view of the Dole Plantations and their pineapple themed mazed on a. sunny day in Oahu, Hawaii, USA

photo credit: Dole Plantation via Facebook


For quiet nature respite, make your Hawaiian plans in Maui. Around 80 beaches mean more than enough shoreline to pitch an umbrella and start relaxing!

Moreover, the Road to Hana on Maui is an exquisite scenic drive. Make the journey through breathtaking vistas and heart-stopping waterfalls! Afterward, up for some whale watching? Maui is known for the humpback whales that call the surrounding ocean home.

People walking along Kaanapali Beach - Maui, Hawaii, USAKauai 

You’ll see green in Kauai, tagged “the Garden Isle.” Plenty of undeveloped land means luscious rainforest backdrops exist around every turn. This is a great place to get some hiking done!

Reward yourself with a relaxing beach sunset after a long day of hiking! Kauai isn’t as crowded as the more popular Oahu, so you have a better chance of soaking it in sans strangers.

Pro Tip: Still need to know more? Our guide to the Hawaiian Islands can help!

photo credit: Kauai Sea Tours via Facebook

First Time Family Vacation to Hawaii: Make a Budget

When visiting Hawaii for the first time, the next step is to make a budget. Unsurprisingly, trips to paradise aren’t without a hefty price tag! Never fear. Take our advice so you can visit Hawaii on a budget! 

One of the first tips you’ll need to know is that the time of year you plan your first time visiting Hawaii is a big consideration. Visiting during the off-season usually means significant savings!

The peak seasons are in summer and winter. So naturally, you’ll want to plan your trip around these times for the best chance at scoring Hawaii deals. 

Other ways to make a budget work include booking hotels and attractions at a discount! Of course, there’s no better deal than free. Check out this list of free things to do in Hawaii!

With a little insight, organization, and preparation, it is possible to experience all the Hawaiian wonder you can squeeze into a trip on a budget! Now, it’s time to start putting your plan into action. 

Happy family - father, mother, child in snorkeling mask dive underwater with tropical fishes in coral reef sea pool. Travel lifestyle, water sport adventure, swimming on summer beach holiday with kidsBook Your Hotel and Flights ASAP

Booking your flights and hotel rooms is important in preparing for your first time in Hawaii. Doing so as soon as possible will give you the best chance of getting a deal since prices are constantly fluctuating. Find a good deal and secure it as soon as you can!

Pro Tip: If you’re not quite ready to book, sign up for notifications about price changes. Should the price of the flight or hotel you have your eye on drop, you’ll know immediately! 

Regarding flights, here are a couple of tips to keep in mind. First of all, book early! Flight prices tend to increase as it gets closer to the date of the flight. Off-season flights are typically the cheapest. Additionally, flying during the middle of the week tends to save you some dough. 

Find a plethora of hotels, resorts, and condos with oceanfront views and easy beach access at a discount when you book with Tripster! Offerings on all four of the main tourist islands mean you’ll have no trouble finding a luxurious abode to relax in during your Hawaii vacation.

photo credit: Hilton Waikoloa Village via Facebook

First Visit to Hawaii: Itinerary

To make the most of your time, arrive in Hawaii with a plan. This will ensure you get to do everything you dream of doing on your trip! There are countless places to visit in Hawaii, so sorting through the options before you go will save some impromptu planning stress. 

When visiting Hawaii, first-time visitors may be tempted to plan for endless beach days with nothing to do. This has a time and place, but it can get old if lazy days comprise your entire trip. The best first time trip to Hawaii is to plan a mix of relaxing days spent resting in paradise and busy days filled with exciting activities, taste testing, and memory making!

To hit the planning sweet spot, craft a set itinerary. However, make sure you stay flexible throughout the trip. If things don’t go according to plan, roll with the punches. You never know what Hawaiian serendipity may be waiting around the corner!

Pro Tip: The best way to see Hawaii’s natural beauty? Tours! Make sure you carve some time out of your schedule for a helicopter or scuba tour.

Some activities to consider adding to your Hawaii trip itinerary include:

  • Snorkeling
  • Swimming
  • Hiking 
  • Surfing
  • Museums and landmarks
  • Luaus
  • Ziplining

Hiking trail near the ocean on in Kauai, Hawaii, USABook Activities Before You Go

So, you have a general idea of how you want to spend each day. Now, it’s time to make some reservations! Doing this ahead of time is essential to make sure you can do the activities you want to do on the days you want to do them.

Relying on a concierge service to book activities may seem convenient. However, this is often a pricier way to do so. So, make reservations online ahead of time! Again, this is the easiest, cheapest way to go. 

Tips for First Time Travel to Hawaii: What to Pack

Traveling to Hawaii for the first time means you probably aren’t sure what to pack in your suitcase. 

First-time Hawaii visitors will want to keep these tips in mind when packing:

  • Most of your clothing will need to be geared toward sultry, hot weather. However, you may also want to bring a jacket in case a windy evening on the shore gets chilly after the sun has gone down!
  • Reef-safe sunscreen is essential. Protect your skin from the scorching sun while also protecting beautiful reefs.
  • Don’t worry about packing bulky outdoor gear, like surfboards and beach chairs. These things are hard to wrangle on a plane. You’re better off finding a place to rent!

For the complete lowdown on what to pack when visiting Hawaii, check out our ultimate packing list!

close up of Kamehameha Statue adorned with lays surrounded by palm trees and building in background - The Big Island, Hawaii, USA

photo credit: HAWAII Magazine via Facebook

Best Way to Explore Hawaii: How to Get Around

Before your first time traveling to Hawaii, don’t skip over this one little detail: transportation. Amidst a swirl of attraction reservations and hotel bookings, it’s easy to forget this small but crucial aspect of planning your trip. 

Related Post: Getting Around Oahu When You Don't Know What You're Doing

There are many options to consider. We suggest you do some research to determine which one will be the best for both your island of choice and your personal budget!

Here are some ways to navigate Hawaii:

  • A rental car
  • Public transportation
  • Ride-sharing services such as Uber or Lyft

close up of coastline and blue waters at Puako Bay in Big Island Hawaii, USANow That You Know How to Save Money, What to Pack, and Where to Go in Hawaii, First-time Visit Plans will be a Breeze!

Are you planning on visiting Hawaii for the first time right now? Don’t go it alone! Tripster is here to help with more insider advice, attraction deals, and discount hotels. 

Planning a trip to Hawaii for first-timers sounds intimidating. With a little help along the way, however, it doesn’t have to be! Plan a trip to Hawaii today with ease. Dreamy rainforests, beaches, and sunsets -- here you come!

What Did We Miss?

Do you have any advice to share on where to go in Hawaii for first timers or what to know before traveling to Hawaii? Leave us a comment below!

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Written By Michaela

Michaela is a journalist who views every story she writes as an adventure, leading her to explore new places and meet new people. She is based in the Midwest ...

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