Basics & Planning For A Trip to Hawai'i (Maui and O'ahu)

When I started planning my trip to Hawai'i, I bought a bunch of books, spent countless hours at the local bookstores looking to see what books would be helpful for my trip, and then got to busy researching online. I don't even know how many hours I spent going through the process, but I did discover a few great sources along the way. In this post, I'm going to share a few that I think you should consider checking out for the next trip to Hawai'i you plan!


+ Go Visit Hawaii

I spent so much time looking through the Go Visit Hawaii website. There are articles for everyone, from the newest Hawai'i visitor to someone who has been multiple times. There is also a myriad of tips for people wanting to save money … or splurge. The details on this website will help you get a concrete idea of what it is you are looking at doing while in Hawai'i and if it's worth your while to include it in your itinerary. Are you a hiker? A foodie? Do you want to compare luaus? Check out Go Visit Hawai'i for all of your Hawaii planning needs! (But start a few months in advance! It will take you that long to get through all of the information on this site!)

+ Look to Hawaii

Look to Hawai'i is also a decent site for putting together a Hawai'i itinerary, but it is far less detailed and intense than Go Visit Hawai'i. This site is just a secondary source. Either start with this site and move to Go Visit Hawai'i to fill in your itinerary after you get a basic idea of what you want to do or start with Go Visit Hawai'i to come up with all of the ideas and use Look to Hawai'i to form it into a doable itinerary.

+ Rainfall by Month in Hawai'i

As part of the Go Visit Hawai'i collective, this page on the website will help you get a basic idea for the weather you can expect on each of the Hawai'i islands.

One important tidbit I learned through my research: If it's raining where you are on a Hawai'ian island, consider driving to the opposite side of the island. There is a high likeliness that it won't be raining there. Alternatively, wait five minutes. Most rain showers end quickly. If you drive away, you may miss the after-rain rainbow!

Maui Specific Sites

+ Two good sites for planning your Road to Hana road trip: Hecktik Travels and Million Mile Secrets

While these sites will help you plan your road trip, use them very loosely. And consider printing them before you leave for your road trip. The Internet is very spotty on the road to Hana and, furthermore, mile markers are few and far between. These sites will at least give you an idea of what to expect during your Road to Hana experience so you can determine if it's worthwhile for you.

It may also be wise to check out Google Maps road view to pretend "drive" yourself along Road to Hana. It will show you just how windy and narrow the road actually is so that you can decide whether or not you will need a tour guide or not.

One last Road to Hana tip: download a Road to Hana guide on your phone. Yes, they cost but they are very much worth the cost. The phone's GPS will work with the app to notify you of the best stops along the Road to Hana route. It's far easier than trying to follow along with a map, a book (like I tried to do), or keeping up with the mile markers. (They recommend setting your trip meter, but it gets confusing when you go to stop and the trip meter gets off.)

+ Back Road to Hana

Along the same lines, consider reading through and checking out the pictures from this site to be sure driving the back road to Hana is for you. We thought it was worth the risk, but it may not be for you!

(Remember: the Back Road to Hana is not covered under most rental car agreements. Carefully consider before deciding to try the road for yourself.)

* One more note: We were in an economy car rental. You do not need a jeep or offroading vehicle to take the Back Road to Hana. However, only you know your own limitations.

O'ahu Specific Sites

+ Waikiki Historic Trail

My husband and I did not follow the Waikiki historic trail while we were exploring O'ahu but what fun it would have been! If you are visiting the Waikiki area, definitely consider trying this!

+ Top 10 Must-Dos

At a loss for what to do on O'ahu? Start here. Surely one of these things is what drew you to visit O'ahu in the first place! (Pearl Harbor, much?)

+ TPG guides to O'ahu: 1, 2

TPG guides are where I usually start my travel planning. They tend to be great overviews of the location including the best hotel options, activities, and ways to save money by using points. These particular guides are a little outdated, but what online guide isn't outdated after a month or two of being online? (Sometimes a matter of days!) It's a great place to start your travel planning and see what works for you.


+ Hecktik Travels

They did a great picture post for what to expect on Molokai. Check it out if you are considering a visit to Molokai!


+ O'ahu Revealed and Maui Revealed

These were some of my favorite books on the topic of Hawai'i travel and I would definitely recommend them to any visitor going to Hawai'i, especially Maui Revealed. I read both books cover to cover but enjoyed Maui Revealed more than O'ahu Revealed. You can get the information for O'ahu Revealed in other books if you have a particular brand you like (like DK Publishing).

+ Driving and Discovering Maui and Molokai

I enjoyed this book for the pictures, but I do not recommend it for travelers. The book feels a bit outdated. And if you try to use it when driving Road to Hana, it just doesn't work. It's too hard to follow the mile markers. Get this book for the pictures not necessarily the text! (And there are a lot of great pictures in this book!)

+ Honolulu and O'ahu Day By Day and Maui Day by Day

Maybe consider Honolulu and O'ahu Day By Day if you want a pocket guide to O'ahu that's easy to travel with, but you do not need both this book and O'ahu Revealed. Pick one!

Maui Day By Day is absolutely not necessary. Buy Maui Revealed instead; it is far superior!

Other Helpful Hints For Travel Planning

While I'm going to provide more specific tips during the course of April A-Z, here are a few generic travel tips.

+ TripIt is great for keeping your itinerary plans straight. It does read your email (maybe set up a separate travel account if you are concerned with privacy issues), but it also imports all of your hotel, rental car reservations, flight confirmations, OpenTable reservations, and so much more! (Sometimes it misses some, so be sure to follow up and double check the app!) After using this app, you will never go back to the old way of travel planning.

* If you use the paid-for version, it will keep tabs on your travel points, letting you know when they are about to expire from lack of use. It will also let you know if your flight is running late.

+ I love OpenTable for collecting points anytime I want to make a restaurant reservations. The points can be exchanged for money off your restaurant experience. Who doesn't like "free money"?

* Seated is also great for trying new restaurants and getting Amazon gift cards at the same time! There are far fewer restaurants you can book with Seated, though. And they are much more strict about purchasing full meals for getting cash back. And if you cancel outside of their cancellation window, they can kick you off the app! Be careful with this one!

+ AutoSlash makes it easy to book car reservations on the cheap. And it will even notify you if the price drops! I have saved so much money using this app!

+ VisitACity makes itinerary planning super easy! While it doesn't important your plans directly like TripIt does, you can input your locations and get generic times for how long it will take for you to walk, bus/metro, or drive to your next location. And the times you get are pretty consistent with what Google directions say, so you can use VisitACity confidently in your travel planning. And if it says you are packing too much into your day, you can back it down a little. It's just great! I love it. Save your itinerary, print it from your computer, or download your itinerary via an app on your phone.

+ Packing Cubes make packing easy. I don't regret having them in any way!

So… when are we going to Hawai'i? You're planning your trip now, right? 😉


It's day three in the A-Z blog challenge! This month I'll be sharing all about my five year anniversary in Hawai'i – providing insight into the places I went, reviewing the hotels I stayed at, and telling my story. Today's letter was B for Basics and Planning For a Trip to Hawai'i!


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