Planning a first-time trip to Hawaii

Later this year, I’ll be going to Hawaii for just over a week. In this post I outline some of the process of planning a first-time trip to Hawaii.

Planning a first -time trip to Hawaii:

Way back, before my (now almost 18 year old) daughter, Queenie, had even started primary school I planted the seed. Now, wouldn’t a mum and daughter trip somewhere nice be a much better thing to do than going to schoolies once you finish your final school exams?

For those not in-the-know about ‘schoolies’ or schoolies week (also known as leavers in Western Australia and coasties in the Australian Capital Territory), it is the Australian tradition of Year 12  graduates (the final year of schooling in Australia) having a week-long holiday following the end of their final exams in late November and early December. 

It turns into a  week-long party, fuelled by a bit of alcohol (as many of the schoolies are over the legal drinking age of 18 years by then). Think USA’s college spring break vacations, and it’s in that cultural ballpark.

Anyway, a couple of years back when Queenie was within sight of this milestone, I floated the idea of a trip to Hawaii with me instead…and she jumped at that chance. One of her friends, and her friend’s mum are also joining us, so it will be an all-girl vacation to Hawaii.

Planning a first -time trip to Hawaii:
Photo credit: Hawaii Tourism Authority (HTA)/ Tor Johnson

When to go

Our timing is locked in by the end of exams, so we’re heading over there at the end of November, which is technically the start of Hawaii’s ‘winter’. But with relatively consistent weather all year round, we’re looking forward to average daytime temperatures of around 25.6º C (78º F). That’s the kind of winter I can handle!

There’s only minor changes in temperature throughout the year in Hawaii, with two seasons: summer from May to October and winter from November to April. The busiest three times of year are December to April and June to August…and Thanksgiving week (which just happens to be EXACTLY when we’ll be there!)

For full details of all the variations in Hawaii’s weather, including specific island details, check out the Go Visit Hawaii website weather page. The Go Visit Hawaii website is an independent Hawaii travel blog with a wealth of information.

Where to go

We have just over a week on the ground in Hawaii (we leave Melbourne on Friday afternoon and arrive in Honolulu Friday lunchtime, then depart nine days later on Sunday lunchtime, to arrive back in Melbourne on Monday night – that pesky International dateline!)

Hawaii is made up of six main islands, all of which are tourist destinations in their own right –  Kauai, Oahu, Molokai, Lanai, Maui and Big Island – and each of which has distinctive features and flavour. The first step in organising an itinerary is picking which idyllic island or islands to include.

The girls were pretty keen on doing some shopping in Honolulu and hanging out at the iconic Waikiki beach, so Oahu was the first island picked, while the mums thought the Big Island sounded interesting with its volcanos, black sand beaches and frolicking whales.

I’ve been using the GoHawaii website (and its Facebook page specifically  for Australians) as a great source of essential information, itinerary suggestions, news, tips and links. Go Hawaii is the website of the Hawaiian Tourism Authority. There is an excellent feature on the website “Choose an Island” which gives a great summary of each of the islands and their highlights.

I’ve also been reading the Love Big Island website, which is specifically about the Big Island of Hawaii and shares information about activities, itineraries, beaches, restaurants etc.

Planning a first -time trip to Hawaii:
Photo credit: Hawaii Tourism Authority (HTA)/ Daeja Faris

How we’re getting there

Flights from Australia to Hawaii disembark at Honolulu International Airport, which is the main gateway to the State of Hawaii.  It’s also the home hub of Hawaiian Airlines, which offers flights between the Hawaiian Islands.

There are several airlines that offer direct flights to Hawaii from Australia. From Sydney the flight takes just under 10 hours, from Melbourne it is 10 and a half hours.

We’ve chosen to fly with Qantas, which does not offer direct Melbourne to Honolulu flights, so we’re taking a domestic Qantas flight to Sydney, then transferring to the international terminal to join the Qantas direct Sydney to Honolulu flight.

Then, we’ll fly with Hawaiian Airlines to Kona on The Big Island. All up, it will be three flights totaling just under 12 hours, plus layover times in between…but we’ll still get to our end destination on Friday afternoon ‘before’ the time we left Melbourne that same day (thank you international dateline!)

How to get about

The most common option for getting between each of the Hawaiian Islands is by plane, but there are also ferries connecting Maui with Moloka’i and Lana’i. There are three airlines offering inter-island flights: Hawaiian Airlines, Mokulele Airlines and Island Air.

Then, once you’re on an island, the choices vary from island to island, but generally it seems your main options for getting around are bus tours, car rentals and taxis. Most guides I’ve read strongly recommend renting a car to get about, which is what we’re going to do on the Big Island.

Things to keep in mind when renting a car in Hawaii are:

  • Like the rest of the USA, you drive on the right-hand side of the road, and the driver sits on the left-hand side of the vehicle (opposite to Australia).
  • For foreign (non-US, non-Canadian) drivers, most rental companies in Hawaii require a valid license and a passport from the driver’s home country. If the information on that license is not in English, you also need an International Driving Permit.
  • Cars should be reserved in advance.
Planning a first -time trip to Hawaii:
Photo credit: Hawaii Tourism Authority (HTA)/ Tor Johnson

Where to stay

In choosing our accommodation, we’ve used my usual tried and tested process – reading a few bloggers’ perspectives, and checking out websites such as and to see what is available (and at what prices), and then cross-referencing that information with Tripadvisor reviews.

We’re staying the first three nights beachside at Waikoloa Beach Marriott Resort & Spa on the Big Island, where we plan to totally relax and do as little as possible!  Then we’ll take a bit of a road trip to the other side of the Big Island, where we were keen to stay a couple of nights in the town of Volcano, so that we can get at least one full day exploring the Hawaii Volcanos National Park. For that night I hit  the AirBnb website for the first time. I have found a three-bedroom house that sleeps up to 8 people, and I was particularly attracted by the home’s outdoor jacuzzi. There will be plenty of room in the house for the four of us.

After that we fly back to Oahu, to spend the remainder of our time at Waikiki. We were a bit torn about choosing accommodation in Waikiki…as we were all super-keen to stay right on the beach. But then I found The Modern Honolulu, which is not beach-side, but marina-side (and just a short walk to the iconic beach). The Modern looked so cool and seemed to have such a great vibe, that we’ve gone with that choice. Plus the hotel is home to Morimoto Waikiki restaurant. Our experience at Morimoto in New York City was so outstanding, I’m eager to give another Morimoto a go!

Planning a first -time trip to Hawaii:
Photo credit: Hawaii Tourism Authority (HTA)/ Tor Johnson

What to see and do

Primarily, we’re looking forward to just chilling out after the pressure of end of school exams. However, we can’t go all that way and not check out some of the highlights! So a few things we’re thinking about doing are:

  1. Going to a luau
  2. Hiking around the Hawaii Volcanos National Park
  3. Visiting the Pearl Harbour Historic Sites
  4. Taking a hula class
  5. Experiencing a traditional Thanksgiving dinner
  6. Shopping on Black Friday (the busiest USA shopping day of the year)

Of course, I’ll be writing posts about all the best experiences after we return. Sign up for email updates (see the box in the sidebar) or my monthly newsletter if you don’t want to miss a single word. And, of course, I’ll probably be live-Instagramming and Facebooking the trip (wifi and/or data permitting…)!

Planning a first -time trip to Hawaii:
Photo credit: Hawaii Tourism Authority (HTA)/ Daeja Faris

How to stay connected

Which brings me to the all-important question of how to stay connected via phone and/or data while in Hawaii?

My iPhone is one of the first things into my handbag each day. And while I’m travelling I use it  as much more than just a phone – it’s a guidebook, it’s maps, it’s a travel itinerary, a bank, a camera, a post office…plus it’s my means of updating Facebook and Instagram!

However, all those uses can chew through both the battery and the data. I deal with the battery issue by carrying a portable Powerbank, and I plan ahead to have cheap access to data rather than incurring exorbitant data roaming charges.

On a previous trip to the United States, I purchased a US SIM card from Teleway for a month with unlimited data included. It was delivered to my home before we left for the US and I just swapped over my Australian SIM for the US one, and forwarded my Australian phone number to my new US one, while I was at the airport.

This time, we’re just away for ten days, so I’m going to use the option my mobile provider (Vodafone) offers of accessing my home data allowance for an extra $5 per day while travelling in the US.

Guide books

Guide books are really useful in the planning stage of any travel. There is just sooooooo much information on the Internet, that narrowing it down and making sense of it can be an overwhelming task.

I like to start off reading through a couple of trusted guidebooks, which I then use to create the framework of an itinerary. After I have all the essentials in place, the Internet is great to add the colour and spice.

For this trip the guidebooks I’m using are:

Plus for a bit of pre-trip reading just to set the mood: has a huge range of travel guide books at great prices and I usually order all the ones I need from there for delivery straight to my mailbox.

Disclosure: The links to travel guides at in this post are affiliate links, which means that if you click on them and then purchase anything from the site, I will receive a small amount of each sale. You don’t pay any more than you would normally. 

Packing and what to wear

And then of course, as we get closer to the time, packing and what to wear will be a major consideration for all of us. But I won’t need to think too hard about it, as once again the lovely Kirralee at Escape With Kids has done the thinking for me.

You may recall the fab visual packing guide she whipped up for me for our Japan trip. It was excellent as a prompt for how to organise the packing so that I didn’t take too much unnecessary stuff. And after being inspired by her great choices, I ending up buying the ‘F for Fairlie’ jumper, a pair of Walnut Shoes canvas plimsoles and a denim skirt – which all proved to be great choices for Japan.

So now she’s done another excellent one for us for Hawaii. Check out her blog post on What to Pack for Hawaii for the full run down (click the text link or the screen shot below).

Planning a first -time trip to Hawaii:


Is Hawaii on your ‘list’? Or have you already been? I’d love any tips or ideas!

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