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How To Plan A Family Roadtrip To Hawaii

Every since I saw Drew Barrymore’s 50 First Dates, I have wanted to visit Hawaii. This was further solidified years later when watching ‘Lost’ – Hawaii seemed to have it all from mountains to jungles to perfect beaches.  Regular readers will know that we holiday in the US each summer, choosing a different state at random. It is our aim to complete all 50 states.

So we did what we normally do, spread out our big US map and eyed up how we would get from Singapore (where we are based) to our chosen state.  It was a toss up between the Montana and Hawaii.  Hawaii won as it seemed ever so slightly closer to Singapore. Although let’s face it, Hawaii truly is in the middle of the Pacific ocean.

photo of Family Burke In Hawaii

How to plan a route

Once we had decided on Hawaii, it was time to plan a route.  It is a fine balance to get everything right for a family of 4 (Jetlag & Mayhem are age 10 and 7).  You want to see as much as you possibly can but still make it relaxing. What I didn’t realise was just how ginormous Hawaii is. Hawaii is made up of over 100 islands, and only seven are inhabited.  Top draw for tourists are Hawaii aka Big Island, Maui, Oahu, Kauai and Molokai.  I had no idea of the size of Hawaii. I thought (rather stupidly) that you could hop on a car ferry between islands.  Nope, you need to take a big jet!  Well there was no way I wanted to do more than one internal flight within our two week trip, so I had to narrow it down to two islands.

Our trip was given a starting point in that all flights from Japan land in Oahu.  But which island to complement our week in Oahu?  Should we check out the amazing volcanic Big Island and see the real lava flow?  Or be inspired by my friend’s visit to Kauai, which she said was the most beautiful place on earth.  In the end, I decided on Maui as I wanted to drive the famed ‘Road To Hana’.

As with all our road trips, it takes a while for the route to register in my head.  I seek out the wisdom from friends, Tripadvisor forums, travel bloggers and travel guides.  I check the calendar to make sure there are no big events e.g. surf competitions that would disrupt travel plans.  In the end the trip became very clear.  We would spend a week on Oahu taking in Honolulu and the North Shore. Then we would do a week in Maui with the Road To Hana and end our trip with a resort stay in Kaanapali.  We would spend a last night back in Oahu before our return flight to Singapore.

X Days In Y has a handy breakdown of which islands are suitable depending on the activity/vibe you are going for.

What did I book in advance?

Traveling with kids, I leave very little to chance.  Once I had planned our route, I booked all our accommodation (ranging from hotel to airbnb).  Where possible I book a cancellable rate. I also booked popular activities that required a reservation e.g. the Kualoa ATV tour and dinner at Mama’s Fish House.

Getting around Hawaii

We flew to Hawaii via Japan on Delta (pleasantly surprised as it’s been a long time since we’ve flown with them).  As mentioned above, these flights take you to Daniel K Inouye International Airport on Oahu.  I booked our internal flights with Hawaiian Airlines. I was quite surprised by just how expensive these were.  According to this article, inter-island airfares have been expensive due to lack of competition. However with the introduction of Southwest’s inter-island routing, hopefully fares will discount in the future.

photo of Daisy on car in Hawaii

Car hire is also expensive comparative to the mainland. However there’s really no other decent way of getting around. We hired our cars through Hertz although decided against having one for the first few days to save money. We were staying in a hotel on the Waikiki strip where parking is expensive, so we just used uber for any trips where we couldn’t walk. We hired the car three days in as that was when we planned to visit Pearl Harbour, a 30 minute drive from Waikiki.

Top Tips For Visiting Hawaii

  • Hawaii is part of the USA (I know this is blindingly obvious but what this means is that visitors will require some form of visa). I had a last-minute ESTA panic so don’t forget to check what you need.
  • The food scene is amazing. Some of the best I’ve had on a US roadtrip. Devour the foodie blogs to find out the latest scoop and make reservations where necessary (pic below from Side Street Inn, Waikiki which is a MUST).
  • Hawaii is expensive. Keep your eye out for discounts on admission etc.
  • Check the weather. We were there the last two weeks of August. Weather on the whole was hot and steamy.
  • Which brings me to my next point. We seemed to be the only people in Waikiki wearing rashguards. I’m not sure if everyone else just isn’t bothered by sunburn but you should be sun safe.
  • Bring microfibre towels (I have a handy sand repellent one from Tesalate)
  • As you can imagine, the dress code is relatively relaxed. Flip flops are the norm.
  • For those looking for US outlet malls, discount stores – Waikiki is a great shopping destination.
  • Check the calendar for events/surf competitions. Unless you want to watch the competitions, you may want to avoid those times due to crowds and traffic.
  • Be mindful of tensions between native Hawaiians and foreigners. I can see how frustrating it must be for the locals in places like Hana, who experience vast numbers of visitors clogging up the one way mountain roads. If you see signs suggesting certain natural pools etc are for locals only, have some respect for that.
  • While Hawaii is safer than the mainland USA in terms of violent crime, it does have a higher rate of property crime, and rental cars remain a prime target. Don’t leave valuables in your car. Or if you must, keep them out of sight and try to keep an eye on your car.
  • If you plan to snorkel, pack water shoes and your own snorkels.
  • Whilst a luau is fun, one goes a long way (unless you enjoy shelling out vast sums of money). We had a lovely time at Maui Nui Luau at the Sheraton Maui, however it is eye-wateringly expensive.

photo of Waikiki Beach from Outrigger balcony

5 Comments
  • Scarlett Roitman

    Reply

    Well, I’ve wanted to go since the wonderful The ‘Descendants’ film, so will tuck your handy guide under my arm when I do! #farawayfiles

  • Leona

    Reply

    Great tips – our car hire on Oahu was expensive but so worth it #fearlessfamtrav

  • Clare (Suitcases and Sandcastles)

    Reply

    These are some really useful tips, Nicola. Thanks for sharing on #farawayfiles. I had no idea that there were so many islands in Hawaii either!

  • Nicky

    Reply

    We’ve never visited Hawaii but it’s very much on the list. The beaches look amazing and i’s love to see some of the volcanoes. Thanks for sharing on #fearlessfamtrav

  • Emma Raphael

    Reply

    I haven’t ever been to Hawaii but my husband won a trip there when he lived in Japan. I was so jealous!! This sounds like a great road trip! #farawayfiles

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