How to Plan a Trip to Hawaii

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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 how to plan a trip to Hawaii.

Plan a Trip to Hawaii

Hawaii Planning Tips | Hawaii Vacation Tips | Hawaiian Vacation | Maui Vacation | Maui with Kids | Hawaii with Kids | What to do in Hawaii | Hawaii inter-island flights | Hawaii Vacation Big Island | Big Island with Kids | Family Travel | Hawaii Travel Tips | Hawaii Travel Guide #Hawaii #Maui #Kona


How to Plan a Trip To Hawaii

Hawaii Planning Tips | Hawaii Vacation Tips | Hawaiian Vacation | Maui Vacation | Maui with Kids | Hawaii with Kids | What to do in Hawaii | Hawaii inter-island flights | Hawaii Vacation Big Island | Big Island with Kids | Family Travel | Hawaii Travel Tips | Hawaii Travel Guide #Hawaii #Maui #Kona

From New York, it takes longer to get to Hawaii than it does to Italy! Even from the west coast, its a long flight. So even though technically a domestic trip (no passports required, ZIKA free destination!) its a big trip and one that takes careful planning.

In Hawaii there is so much to see and do, and like a Disney trip, you won’t be able to do it all. Its important to plan and choose what is important to your family.

Probably the best thing you can do in planning your Hawaii trip is to click the banner below. I am a full-service travel agent with Paradise Travel. Our Denver based agency plans A TON of Hawaii trips and I have personally been three times (as a kid, as a couple with my then-boyfriend-now-husband, and with my own family). Our services are free, and you get all our expert planning knowledge and access to great package prices.


Which Hawaiian islands to visit?

This is the question I most often get, and a question you can LABOR over for years. Here are som key take aways about each, unique island.

Oahu – Honolulu is the capital of Oahu and the only airport you can fly direct to from the Eastt Coast. But Honolulu is very urban chic, with high rise buildings, hotels and a bustling downtown. More Miami Beach than Adventures of the South Pacific. On Oahu you can visit the historic Pearl Harbor site, and stay at Disney Aulani. I love Waikiki which has that urban, surfer feel. The North Shore of Oahu has lots to do with a more local feel and this is a surfers mecca. For more about Oahu, check out this 7 Day Oahu Itinerary.

We are hoping to get to Oahu as a family real soon. I have personally been twice, but pre-kids. I would love to stay at Aulani before my kids get too old (not sure you can ever really be too old for a tropical Disney resort, but needless to say it’s something we plan to do in the next year and a half. Thinking about staying at Aulani? Then read What to Expect When staying at Aulani and definitely reach out as I am a College of Disney Knowledge graduate and have all the Aulani training!

Maui – There is so many great things to do in Maui. We loved touring the Maui Ocean Center, the Haleakala Crater, visiting the amazing beaches, and driving the Road to Hana.

Maui is a great island for honeymooners, and families alike. Maui has lots of nature to explore, beautiful beaches for surfing and paddling, but gorgeous resorts and amazing restaurants.

The Big Island – The biggest island is named “Hawaii” but is also known as “The Big Island”. Most visitors stay on the west side, in the Kona area, but you can also stay on the east side, Hilo.

The Big Island is very black and volcanic, but there are beautiful big island beaches.  Life on the big island takes on a slow pace, with lots of natural sight seeing, and no nightlife. There are fun things to do on the Big Island, a trip to Volcano National Park being a highlight of this island! I mean where else can you see active lava flow?

Kauai – Kauai is the one major island I have not been to – yet! This island is the smallest, and most remote. Kauai is great for adventure seekers, honeymooners and those looking to really just relax! Kauai has beautiful beaches and amazing hikes.



Accommodations in Hawaii: Condo vs. Hotel vs. Resort

Once you narrow down which island(s) you want to visit, you need to think about what type of accommodation makes sense for your stay. Hotels and resorts are popular, of course, but definitely consider booking a stay in 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! Staying in a rental helped us visit Hawaii on a budget.


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However there are some amazing resorts on the Hawaiian Islands! On our 2016 trip, we stayed in Maui for 8 nights (in this one bedroom condo), the Big Island for 8 nights (in this 2-bedroom townhouse) and then moved on to 5 nights at the Waiakoloa Beach Marriott.

A split stay is a great option to balance condo amenities with resort luxury. Just remember to be sure (with all accommodations) that you are aware of any resort fees, parking fees, etc. Hawaii hotels and resorts are infamous for hefty resort fees.

Favorite Hawaii Resorts and Hotels


Hilton Hawaiian Village Waikiki Resort

The Laylow, Autograph Collection

Turtle Bay Resort

Aulani, a Disney Resort



Four Seasons Resort Maui

Andaz Maui

Westin Maui Resort and Spa

Mana Kai, Maui

Travaasa Hana


The Big Island:

Waiakoloa Beach Marriott Resort and Spa

Hilton Waiakoloa Village

Four Seasons Resort Hualalai

Sheraton Kona Resort and Spa



Kauai Marriott

Grand Hyatt Kauai

The Westin Princeville

Plan your Hawaii 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.


What to bring to Hawaii? Check out this Hawaii Packing List for Female Travelers


Renting a Car in Hawaii

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 what to do in Hawaii

After you get your flights and accommodations sorted, now its time to plan all the fun stuff to do in Hawaii! 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.

See Hawaii By Cruise Ship

Another way to see all four major islands – on Norwegian Cruise Line’s Pride of America. This ship does a seven night, round trip, weekly sailing from Honolulu.

Pride of America Itinerary

5 reasons to Cruise Hawaii

Taking this cruise allows you to see a lot in just seven days. Plus you sleep and eat on the ship, so can help keep your budget in check. We love sailing on Norwegian, the service is top and its a great vacation! Even though I’ve been to the Hawaiian Islands three times, I’d love to do the Pride one day!

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!



Family Friendly Food on Kauai



hover over image to pin for later:

Hawaii Planning Tips. Which island is right for you? Planning your trip to Hawaii #Hawaii #Maui #Oahu #HawaiiiTravel #HawaiiHacks #TravelPlanning #FamilyTravel

Hawaii Planning Tips | Hawaii Vacation Tips | Hawaiian Vacation | Maui Vacation | Maui with Kids | Hawaii with Kids | What to do in Hawaii | Hawaii inter-island flights | Hawaii Vacation Big Island | Big Island with Kids | Family Travel | Hawaii Travel Tips | Hawaii Travel Guide #Hawaii #Maui #Kona


Flying With A Baby





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70 Comments to “How to Plan a Trip to Hawaii”

  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

  16. Amazing tips, it looks like such a beautiful place. Great advice on car rental, must be much cheaper with a smaller car. I would love to go to Hawaii, in my head it will be to do the Ironman there one day. I can dream! Thanks for linking up to #familytraveltips

  17. Ada

    Aww you made me miss Hawaii! I was there 3 months ago and just like you I knew I wanna go back when I was taking off! Ive only visited Oahu and Maui but I know the other island as beautiful! I cant wait to go back and explore more! Especially when the flight between islands are so short 🙂 Mine from Oahu to Maui was 17 min! 🙂

  18. Planning is almost as much fun as the trip itself for me. I love how much useful stuff you’ve shared here, especially about deciding on which islands, travel time on the roads, and the cost of meals out. The small plane sounds amazing – I’d love it (it’s even smaller than the teeniest commuter flight I’ve taken to date) but my husband would be way less keen…

  19. Hawaii is one of our favorite destinations. We’ve always returned to Oahu simply because there is so much to do on the island. We typically return to hike to Diamond Head’s gorgeous view, and Pearl Harbour is a must for us.

    You have some great tips – thanks

  20. These are great tips for planning a trip to Hawaii! It’s high on my bucket list and I always get overwhelmed trying to figure out which island(s) to visit and where to stay.

    1. harmskills Author

      Its hard because realistically you probably can’t do everything, so you have to pick what is important! I do think the Pride cruise is a good option for those that have a short time and want to see the highlights.

  21. We love Hawaii and go every year. We have been to all four major islands but Maui is our favorite. Each island is so different. Your post does a fantastic job of explaining what to do and where to go, as it is overwhelming to decide. It is such a magical place. Great post!

  22. We have never been on a family vacation to Hawaii! I’m worried about the length of the flight and if I would feel too claustrophobic flying for that long 🙂 Anyhow, this is such a great post when it comes to planning a family vacation to Hawaii!!!


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