Hawaii Planning Tips

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Winter is here in New York, so our next trip to Hawaii has been on my brain. Last year we were fortunate enough to spend three weeks traveling to Maui and the Big Island. I’d say from the minute we flew back home, we have been mentally planning our next visit! Since I so often get asked about Hawaii trips, I am sharing with you my best Hawaii Planning Tips!

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Hawaii Planning Tips


Which island(s)?

This is the question I most often get, and a question you can LABOR over for years. I am going to help you choose, by breaking it down for you very simply, with a few words about each of the four main islands:

Oahu – Pearl Harbor, Disney Aulani, urban feel (Honolulu). Lots to do, but hustle and bustle.

Maui – Beach goers, families and honeymoons. Moderate amount of nightlife.

The Big Island – Beautiful beaches, slow pace, natural sight seeing, no nightlife.

Kauai – Remote, beautiful beaches. Honeymooners, no nightlife.



Where to stay?

Once you narrow down which island(s) you need to think about accommodations. Resorts are popular, of course, but definitely consider booking a stay one of these fabulous Hawaii vacation homes.

A vacation home is a popular Hawaii accommodation because most Hawaii trips are longer, and therefore you are more likely to crave the comforts of home. For us, staying in a vacation home allowed us to have more space, cook our own food, and do our own laundry. Eating out is expensive in Hawaii, especially eating at a resort, so being able to grocery shop and make some meals at home will allow you to splurge on amazing meals out!


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Plan your flights and itinerary

Once you sort out the islands you would like you visit, you need to book your flights, both to and from home, and within the islands as well. Based on personal experience, I would recommend visiting two islands in a 2-3 week trip. Recently a friend went for about 10 days and visited all four islands. Needless to say, all of the schlepping around overshadowed the fun she had!

From New York, you can fly direct to Honolulu only. From the west coast you can fly direct into Maui, The Big Island or Kauai. On our recent trip, since we wanted to bypass Oahu,  we chose to layover in LA and proceed directly to Maui. Prices, schedules and availability might force your hand of where you want to start your Hawaiian adventure (and something to consider if you are trying to purchase a round trip ticket to and from the same island).

Travel between islands necessitates flying. On our recent trip, we moved from Maui to Kona via a 10 seater Cessna on Mokulele airlines. Using Google flights, I stumbled upon a flight that was significantly cheaper than those on Hawaiian Airlines. When we arrived at the airport to head to Kona, we found out we were on a commuter airline! This turned out to be a great way to save a little money and offered us a unique experience we will never forget!

Right now, there are two airlines that operate inter-island flights, Hawaiian (which also travels from the mainland and destinations in Asia/Australia) and Mokulele. These flights tend to be under an hour and under $70 each way. If you are a nervous flyer, I definitely recommend booking with Hawaiian, as their planes are larger and more like the commercial airlines you are used to flying.



Renting a Car

In 2005, when hubby and I first visited Hawaii, we flew into Kona (after spending a few days in Waikiki) and literally got off the plane, looked at each other and said, “I guess we should rent a car.” Unless you plan to stay only in Honolulu, you will need to rent a car to get around!

You can read my best Car Rental Tips, but I would recommend renting the smallest car that you need, if you have budget in mind. The car rental companies do not let you take the cars off paved roads, so you will not be 4×4’ing over rugged terrain. If you are interested in doing that, you can rent jeeps by the hour or day!

It is also worth noting that on the islands, traffic moves slowly. Clearly we are not talking LA at rush hour, but many main roads have only one lane, and the flow of traffic peaks around 40mph. So budget more time to drive places than you would on the mainland.


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Planning the fun stuff

After you get your flights and accommodations sorted, now its time to plan all the fun stuff! You don’t want to over plan each minute of your trip, but any big tours or luaus that you want to attend – be sure to make reservations ASAP. The best stuff will book up and you don’t want to be disappointed!

On our Hawaiian trip, a Molokini Crater snorkeling tour and a Luau were our big activities, and big expenses! I did book each of these well in advance. It’s hard to sort through all the options, but look for tours that have consistent good reviews. I used pinterest to plan our Hawaii trip – I loved reading first hand experiences from families and travelers. I also, like with all things travel, checked for online discounts and Groupons for the things I wanted to book.

Once you plan some of the big activities, you can fill in the rest of your days with trips to the various national parks, and of course the best beaches in the world! Remember, beaches in Hawaii are either free or have a minimal charge to park! I’m also pretty confident there is no such thing as a bad Hawaiian beach!


And my best Hawaii planning tip – Don’t forget to make time in your plans to stop for a shave ice! Be sure to sit back, relax, and enjoy the magic of the Hawaiian Islands!


Check out my Hawaii Pinterest board and follow all my travel boards!


Best Big Island Beaches

What to do on the Big Island

Maui Activities

Hawaii Money Saving Tips


hover over image to pin for later:

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Flying With A Baby





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  1. This makes me want to go to Hawaii again. I’d recommend the Hukilau Cafe near the Hukilau beach… they make amazing pancakes, coconut syrup and these flat cookies called pokky (?) cakes.

  2. You have done an excellent job of demystifying a trip to Hawaii. I guess my choice of island would depend on if it was a trip without kids. The idea of Kauia is very appealing.

  3. Great tips. We’ve never been to Hawaii, but my brother and another friend went on their honeymoons and I have a great friend who lives there now. I appreciate how you broke down highlights of each island as I’m sure they each have something totally unique to offer!

  4. This post had so much valuable information! Thanks for breaking apart the different islands. Even though they are all different they all seem wonderful! I don’t even know which one I would rather go to!

  5. We just spent a week on the Big Island in November for the first time and I’ve been dreaming of heading back since we stepped off the plane home. I’d agree with everything you’ve said here, and it’s exactly why we picked the Big Island, though I’m definitely torn between going back there or visiting Kauai next.

  6. These are such great tips. I completely agree that having a small house or condo is essential. It not only saves money but makes the trip feel more relaxed. I also loved your summary of the islands, straight and to the point. Thank you for sharing this great post.

  7. Those pictures are beautiful! Never been to Hawaii – I guess I can’t justify the flight (from Florida) when I live so close to the beach already. But I’d definitely love to go for the sights and food alone!! I have a close friend from who grew up in Hawaii – she tried to move there again but came back inland because it’s so expensive! Great place to visit, I’m sure!

  8. This is a great article! I love that you include a description of each island. That’s very helpful in planning. The Big Island sounds great! Hawaii is just one more destination on my ever growing list!

  9. This is EXACTLY what I needed to read! We are really hoping to book a Hawaiian vacation in 2020 (it feels so far away)! I’m going to pour over your other Hawaii links and get my budget together.

  10. This was really helpful! I really want to check out Disney Aulani especially and didn’t realize the difference between the islands. I definitely would NOT want to fly on a little plane, but I’ve heard Norweigan has a nice cruise to each island. So, maybe Aulani with the little ones and then do a cruise once they are older 🙂 That is my dream plan! Thank you! Definitely pinning for future reference!

  11. Thank you for these great tips. When I last visited Hawaii I just went to Maui. I had not thought of Island Hopping and I like the idea of taking things at a relaxed pace. There are some great tips for saving money, whilst still having a fabulous time.

  12. I can see why we need to make a detailed planning if we want to go to Hawaii. I like your post. It’s a must read before going there. It’s complete and detailed. I have a friend who lives in Honolulu and she likes to post the shave ice and of course she knows which one is the best. There’s even one that has durian flavor, the king of fruit from Southeast Asia. My favorite fruit.

  13. Hawaii is so beautiful and ranks right up there as my favorite state. Just like you, the minute I left I was planning my next trip. We were there for our anniversary – and it was the holidays- so our expenses such as rental car were a bit high. I’m hoping to go back during the off season and maybe not spend so much. Thanks for all the tips!

  14. Great article, we have been to Hawaii twice now, both times we have stayed at Oahu. It is such a beautiful place. On our last trip we spent a week at Disney Aulani and a week in Honolulu, I can’t wait to go back.

  15. Three weeks in Hawaii sound fantastic! I have only been to Oahu but loved it there. Would like to go back and visit other islands too. Ideally, I would go to all of them since each one has something unique. #WeekendWanderlust


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