Hawaii 101: Let’s Plan a Trip!

The question most often found in my inbox goes something like: “I’m trying to plan a trip to Hawaii. Will you give me some advice about where to start and also some recommendations about what we should see while we’re there?”

I love that my readers, friends, and family turn to me for advice about traveling and planning trips. It makes me so happy to help others achieve their travel dreams! And while I’m not technically a certified Hawaiian expert, 😉 I have learned a thing or two on our eight different trips to those incredible islands.

Wai'anapanapa Black Sand Beach

Welcome to a special two-part Aloha inspired series: up first, I’m sharing some tips about how to begin Planning a trip to Hawaii, and later this week I’ll share my favorite tips on getting a good deal on that trip. (You guys won’t want to miss that one!) Let’s get started, shall we?


  1. Begin by Choosing an Island

    When you think about your trip to Hawaii, what activities do you want to do while you’re there?
    Hawaii is a dreamy tropical paradise, however, each of the six main islands are drastically different from one another. I personally feel that Maui has the best beaches, Kauai is more lush and feels much more “remote,” and the Big Island has amazing diving; however that’s not to say those are the only great qualities of each island.
    Whenever I talk to people about Hawaii I’m fascinated to find out which island is their favorite (and why) because everyone has a different “favorite” island. I LOVE Kauai because it’s not as touristy and has insane scenery, but others LOVE Maui because it is a good balance between things to do and relaxation by the beach. (For the record, it’s a close race between Kauai and Maui in my book). 🙂
    I always start by asking my friend(s) the question above, and after discussing their dream trip I’m able to recommend an island or two, as well as provide suggestions on things to do and restaurants to try.
    Once you choose an island I recommend buying one of the “Blue Books.” (Maui Revealed, Kauai Revealed, etc. are incredible resources and enjoyable reads). 
    Kauai Tree Swing

  2. Price Flights and a Rental Car

    Once you’ve narrowed down your island of choice, you should start reviewing airfare and rental car prices. I start with google.com/flights to see airfare prices by month and after analyzing the results I turn to Kayak.com to set a price alert. The daily price alert from Kayak allows me to grab that awesome deal the moment airfare prices drop.
    When it comes to rental cars, I always reserve through Hotwire.com because we have scored some pretty amazing deals. Another bonus is that you can add a price alert on Hotwire to track prices for your rental car. Now all you need to do is sit back and watch those daily price alerts while you daydream about your upcoming vacation. (Just don’t forget to book when prices drop!)

  3. Think about Lodging

    Are you planning on living large in one of the many luxury resorts? Perhaps you’d prefer a condo to give you and your family a little more room to spread out? Maybe you’re hoping to reserve an entire house near the beach through VRBO or AirBNB? (If that’s the case, click here for $35 OFF your next booking). 
    Whatever your preference, now is the time to start thinking about your budget and which option will work for you. If you’re looking for specific suggestions in Maui, check out my lodging reviews here.
    Nahiku Cottage

  4. Plan your Itinerary

    Once you have booked the flights and hotel you can start reserving excursions and researching different restaurants to try. I try to tailor my advice to the person I’m helping; for example, I’m not going to suggest that my sweet grandparents go on the strenuous hike through Maui’s bamboo forest, instead I tried a more relaxing and delicious suggestion, which they thoroughly enjoyed.
    I’ve written extensively about our Hawaiian adventures, so if you’re looking for some inspiration or ideas to add to your itinerary, feel free to daydream here.
    Punaluu Beach, Big Island

While these tips are pretty general and could be used when planning any vacation, hopefully it will get you started. As always, if you ever have questions feel free to send me an email or fill out the contact form and we’ll get your next trip planned with advice and recommendations tailored just for YOU!


Have you been to Hawaii? What advice would you add? 

5 Comments

  1. January 3, 2017 / 10:19 PM

    Our favourite island is Maui, it is quieter than Oahu and as you mentioned has a good balance between beaches and sights. We tend to alternate between beach day and activity day.

    Other than flying over to Oahu for a day trip to the Arizona Memorial, etc we avoid that island. To busy, but if you want night life in the tropics that the best island.

    For car hire, we have always got excellent deals with Discount Hawaii Car Rental. They are excellent if going with family or multiple couples, as they permit extra drivers at no charge.

    • January 4, 2017 / 9:02 AM

      Aloha my friends!
      I could not agree more with your advice about O’ahu. I loved Pearl Harbor and the North Shore, but overall I feel that it is really too busy for a relaxing island getaway.
      I’ve never looked into Discount Hawaii Car Rental, I’ll have to check it out for our upcoming trip. Thank you!
      Hope you two are doing great!! Good hearing from you.

  2. January 4, 2017 / 4:17 PM

    Maikai Krystle, all great tips!! and I agree with oriana on using Discount Hawaii Car Rental, that’s what I use whenever we go home. A hui hou!

    • January 4, 2017 / 5:28 PM

      Mahalo, Auntie! I am definitely going to have to check those guys out when we go to the Big Island. 🙂 Thanks for sharing your advice. A hui hou!

Join the Conversation...