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Hawaii First Time: How to Plan Your Trip

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So, you’ve made the decision to book your first vacation to Hawaii! You’re probably wondering how or where to start your planning. You’ve come to right place for advice: Follow my tips and your holiday will be an escape instead of ending up like a Griswold family vacation!

In this post, we will cover the ins and outs of planning your perfect tropical getaway to the beautiful state of Hawaii, from finding a great deal on airfare to the islands most beautiful beaches. Planning the details of your vacation can make your vacation one you remember.

Surfing was born in Hawaii and is deeply intertwined with its history and culture.

Decide Where to Go

Do some research on some islands you’d want to want to visit. See which islands have the ideal attractions you’d want to visit on your vacation. It may be tempting to try to visit as many islands as you can on your vacation, but if you choose this route, you will be spending a lot of your time traveling and checking in and out of hotels.

A much better way to make use of your vacation time is to pick one island and visiting the attractions that it offers. Also, try to choose a flight directly to the island. If you take a connecting flight, you will add a lot of unnecessary travel time to your trip.

No matter which island you choose, you will find beautiful beaches and plenty to do. You can usually find some outstanding package deals that include airfare and hotel costs but we will cover this more in-depth later. Maui has been said to be the best island to visit in Hawaii. Visiting beaches are one of the awesome activities as well, so plan your vacation with factors like these in mind.

Kauai is nicknamed “the Garden Isle” thanks to the tropical rainforest covering much of its surface. Credit: Thomas Marban via Unsplash

Decide What to Do

If you ask someone which Hawaiian island is the best to visit, you’ll probably get a different answer every time. With eight main islands to choose from, you have a wide variety of options.

One thing about Hawaii most people don’t realize is that all the islands are different. Each island has its culture for you to explore. When I visited Hawaii, I went to the isle of Oahu. Oahu offers a wider variety of activities than any of the other islands. Oahu features the most shopping, dining, and historical attractions. I chose Oahu myself because I wanted to visit Pearl Harbor and the USS Arizona Memorials.

Oahu isn’t all tourist attractions, though. The island also offers a wealth of natural beauty and some of Hawaii best beaches for swimming. These beaches include Waikiki Beach, which gets over 4 million visitors a year and is one of the best places in the world to learn how to surf. Oahu also has Hanauma Bay Nature Preserve, which is a marine sanctuary that lies between two dormant volcanoes, making it a fantastic place to snorkel and view the local tropical and marine life.

As you can see, this is just one example of what to do on the island with the most diverse activities; there are eight islands in total, each with their attractions, biodiversity, and local cultures. Make your vacations adventures and explore the tropical island of your choice.

USS Arizona Memorial at Pearl Harbor, site of the WWII 1941 bombing attack. Located west of Honolulu, Oahu island. Credit: Victor-ny via Wikimedia

Decide When to Go

Hawaii’s winter season starts in November and lasts until the end of March. Some people say it entirely depends on the summer the year before it, but it’s best to prepare for inclement weather.

Rain in Hawaii doesn’t mean you will experience a torrential downpour; most rainfalls are just a light drizzle depending on which island you’re visiting. For example, the island of Kona only gets about five to eight inches of rain a year, while the Isle of Hilo gets about 180 inches.

Hawaii's temperatures can drop to lows of 60° fahrenheit (15° celsius) during the winter months and reach highs of 90° fahrenheit (32° celsius) in the summer months. If you visit Mauna Kea on the island of Hawaii or the Haleakala Crater on the isle of Maui, temperatures can drop down to lows of 25° (-4° celsius) daily.

So if you’re looking to avoid the cooler winter months, avoid Hawaii from November until March. If you want to experience Hawaii at its warmest, busiest time, visit May through October. Just take the hurricane season into account. The hurricane season lasts from June to November, but don’t worry too much, the weather is always beautiful.

Photo by lygmeister via pixabay

Pick Your Hotel

Choosing the right accommodations is key to having a successful vacation. No matter what your budget is, Hawaii has countless places for you to stay, from beach bungalows to luxury resorts. Kauai and Maui have dozens of bed and breakfasts if you’re on a budget. Most bed and breakfasts are cottages, and the owner stays in the main house.

Depending on your budget, luxury vacation rentals in Hawaii can vary from resorts to rental homes. Hawaii is full of beautiful resorts and hotels. Put together your budget and pick the perfect lodging for visiting Hawaii for the first time.

Keep an eye out for airfare and hotel lodging packages. Most of the time, travel packages will include airfare for your family and yourself and your hotel or resort reservations. It’s rare to find travel packages that include lodging in bed and breakfast, but it doesn’t hurt to look.

Photo by lygmeister via pixabay

Although it seems like it’s a lot of work to plan your Hawaii vacation getaway, half of the planning is figuring out when you’re going and which island you’ll be visiting. To reduce wasted time, stick to one island, so make sure the island you chose has all the attractions and events you’d like to attend while on vacation. Enjoy the process and plan your dream Hawaiian getaway!

 If this article was useful, you can thank us without paying a dime by using these links to make your plans. Some of these companies will pay us a referral fee, at no extra cost to you.


  • Hawaii has many useful trip planning resources on their official website, Go Hawaii
  • Lodging– For sleeping options, we recommend HotelsCombined. They compile deals from all over the web, including Booking, Expedia, Agoda, and more.
  • TransportationThis website shows how to get anywhere by plane, train, bus, ferry and car.

Want a unique experience?


  • Google Maps offers an aerial view of the area around Hawaii. Zoom, scroll around and explore!


We recommend Lonely Planet guides:

  • [easyazon_link identifier=”1743216750″ locale=”US” tag=”awsi09-20″]Lonely Planet Hawaii[/easyazon_link]

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Caroline Bird

Written by Caroline Bird

Caroline Bird is a freelance writer. She is currently based in Asia. Caroline is delighted to work with many aspiring small business owners.

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11 thoughts on “Hawaii First Time: How to Plan Your Trip

  1. On our adventure to every state capitol in America, we are saving Hawaii for last. It poses a problem though, that I never thought of. Each island is separate and it isn’t easy to hop between them. I think we will end up visiting the capitol first, then taking a plane to the big island to see the volcano’s. Originally I thought you could just hop on a cheap ferry or something, but apparently the only way is to either charter a boat or fly.

    1. We like your idea of beginning in Honolulu. There’s a third option too, if your budget allows – take one of the Hawaii cruises that stop at various islands. You would only need to unpack once, plus all your transportation, lodging and most food would be included.

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