Hawaii Travel Guides

Your Hawaii Vacation Planning Checklist

Get ready for your Hawaiian adventure with this handy checklist!

So, you’ve decided the destination for your next vacation is Hawaii. Great choice! But now comes the vacation planning, and there is always a lot to organise to get ready for a trip somewhere new. We’ve put together this checklist to help you plan your perfect Hawaii vacation.

☑️ Choose which island or islands to visit

There are 6 main islands within the Hawaiian island chain which are accessible to tourists, so the first step is to pick exactly where in Hawaii you wish to visit. Oahu, followed by Maui are the most visited islands, and the biggest range of flights are available to these islands from the mainland. Each island has its own unique flavor and special sights to see so do your research into the different ones to see which would be your ideal vacation destination.

With regular and inexpensive inter-island flights, many visitors choose to hop around the islands. Check out our blog on travelling between the islands for more information on island hopping in Hawaii.

☑️ Book flights

Once you know where in Hawaii you are heading to, you can begin to book your flights. The more flexible you can be on the dates of your trip the more likely you are to get a better deal. Weekend flights are usually the most expensive so flying mid-week can be a good way to save some cash. The cheapest time of year to fly to Hawaii is typically January and February, and the most expensive is around holidays such as Christmas and Thanksgiving.

Bear in mind that going for the cheapest flight is not always the best approach when it comes to flying! Depending on where you are coming from it can be a long journey to Hawaii, so make sure you factor in comfort when purchasing your flight, so you start your vacation off the right way.

☑️ Book accommodation

When booking accommodation, have a think about which location on your chosen island is best for you. Will you stay in a tourist area with amenities close by, or do you want to go off the beaten track and stay somewhere away from the hustle and bustle?

You’ll also need to decide whether you would prefer catered or self-catering accommodation, or a mix.

There is a huge range of accommodation available so you will certainly find something to suit your taste and budget. Most accommodation falls into one of the following categories:

  • Hotel or Resort
  • Guest House or Bed and Breakfast (including Air BnB)
  • Self-catering Condominiums (condos) or villas
  • Whole Home rentals

Check out our blog on accommodation options which looks at the pros and cons of the accommodation types on offer.

☑️ Buy travel insurance

Not the most inspiring point on the checklist but important nonetheless. Check out what insurance you may have already, and if necessary buy more travel insurance for your trip. It is always wise to have travel insurance when you are booking flights. Insurance can cover things like like lost baggage, delayed flights and unexpected illness, and will give you that extra peace of mind.

☑️ Book a rental car

The best way to explore the Hawaiian islands is by car. If you are in a position to hire a car then we would certainly recommend it. There are lots of different car rental places to choose from on the islands. Book from a reputable vendor or a brand you recognise. Most car rental places are situated near the airport for easy access when you arrive, and those companies a little further away usually provide shuttle buses from the airport to their car rental lots.

☑️ Book activities

Dream up what adventures you would like to have on your Hawaii vacation and then make them happen. There are a huge amounts of activities available on the islands, from sight-seeing trips to snorkel cruises, luaus to helicopter tours. The possibilities really are endless! You can book activities when you are on island, through your resort or an activity company directly, but the best deals can be found online before you go. It is also worth noting that the most popular activities on island will book up weeks in advance, so if there is anything you are keen to do then book before you go.

Need inspiration? Browse activities by island or category.


Royal Dolphin Swim at Sea Life Park Hawaii

From: $259.99
Get to know two of the smartest and fastest dolphins at Sea Life Park Hawaii on your royal dolphin swim experience. This is truly a dream come true. Ticket price includes admission to Sea Life Park Hawaii.

Oahu Grand Circle Island Tour

From: $101.99
See O'ahu, from Hanauma Bay to the North Shore with a stop at Dole Plantation on this wonderful van tour. With narration from your knowledgable driver, relax in the comfort of an air-conditioned motor coach and take in the sight of Old Hawaiian homes, coffee farms, sugar cane fields, Pacific Ocean views and pineapple orchards on this incredible circle tour of Oahu.

Volcano Tour from Honolulu, Oahu

From: $462.04
This will be an experience of a lifetime! The recent eruptions of Kilauea Volcano in Hawaii Volcanoes National Park on the Big Island of Hawaii have captured the world's imagination. This fully narrated Volcano Adventure features a hike over the lava flow that covered the village of Kalapana and famous Kaimu black sand beach in the 1980's.

The Grand Wailea Luau

From: $107.95
The Grand Wailea Luau is hosted by the renowned Grand Wailea Resort and Spa at their beachside location on Maui’s

Legends of Ka’anapali Luau

From: $94.95
The Legends of Ka’anapali Luau is located on Maui’s West Side at the Ka’anapali Beach Hotel, in its gorgeous Tiki

Christmas Luau – Drums Of The Pacific At The Hyatt

From: $128.00
Coming to Maui during the Christmas season and looking for a fun and unforgettable way to celebrate? The Hyatt Regency Drums of the Pacific Luau might just be the way to do it! You'll enjoy a renown Polynesian revue and Christmas luau packaged into one fun and exciting evening!

☑️ Prepare and pack

Once you’ve booked your vacation you can start preparing for your trip. Check your passport isn’t about to expire and renew if necessary. Also, don’t forget to order any medication or contact lenses you might need for your trip. If you are coming from abroad, then check what plug adaptors you may need for any electrical equipment you would like to take with you. We have put together a full packing guide to Hawaii here and also a what not to pack guide so you don’t waste precious baggage space on stuff you don’t need.

Hawaii vacation planning checklist

2 thoughts on “Your Hawaii Vacation Planning Checklist

  1. Judy Wright says:

    We are waiting for our children to get their vacation time from jobs. It will be in June 2019. As soon as we know we will checking activites on Maui. They live in Texas.

    1. Jonathan says:

      It’s great to hear that you’ll be able to come out as a family! That’ll be a special time for you, we’re sure. Happy planning, and do let us know if we can help with anything. Aloha!

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