Planning A Trip to Hawaii: What I've Learned So Far

image courtesy of Visual Hunt

Ninety percent of the time my dreams are bigger than my bank account or the amount of time I have on hand. And while this can really put a damper on travel planning (Where do I go? What can I see when I don't have any money?), I think the aspect I love most about travel planning is trying to make everything work out anyway.

Planning a trip to Hawaii has been no different. Here's what I've learned so far.


When you see a flight deal for a trip to Hawaii, you don't necessarily stop to ask yourself about particulars. Typically, you just jump on it. But luckily, because it cost so many points (80,000 Delta points, to be exact), I wanted to make sure I knew what I was doing. I knew 80,000 points could get me 5,000 points or so at a time all across the US. And also knew that 80,000 points was one step closer to a free trip to Europe. So was 80,000 points to Hawaii a good deal? Was it worth (would it be worth) throwing all of my eggs into one basket rather than diversifying, spending points here, there, and everywhere?

Unfortunately, I don't have an answer for you if that's your question.

For me, the answer would initially have been no. But that's why I'm in a relationship. And, technically, these were my husband's points. His points: his decision. 😀 So, I went with it; I booked the flights.

Typically flights from GA to HI cost approx 22,500pts/trip or 45,000pts RT making this deal a 10,000pt savings.

But first I had to consider the fact that Hawaii wasn't just Honolulu.

And guess what?

Those Delta points could get us to any of the islands we wanted.

So … where did we want to go?

image courtesy of Visual Hunt


Going into Hawaii booking, I had heard of Honolulu, Maui, and the Big Island, but I had no idea what could be found at any of these places. (And technically I had heard of Lanai and the purchase of it by Oracle founder, but hearing that and knowing what is being discussed are two totally different things!)

Then I read about people booking to one island and leaving from another. Could we do that?

Turns out: yes. Yes we could. 😀

Ultimately I decided that Maui was my place. But I wanted to see Honolulu and the Pearl Harbor memorial. Not knowing then what I know now (you can take a day trip from Maui to Honolulu to visit Pearl Harbor with various tour groups), I ultimately decided to book a flight to Maui and out of Honolulu (just don't ask me what the airport names are or which island Honolulu is located on. It is all Honolulu to me!)


Next big lesson: Getting between the islands is not a piece of cake.

You have two options:
1. Fly. ✈️

Hawaiian airlines is recommended, but there are smaller airlines that make the flights too.

Or, alternatively, you can use points/cash to book bigger airlines like Delta, United, or American. Flying into/out of the main airports on Maui and the island with Honolulu (see?!) are the easiest; you may need a layover in OGG or HNL if you are flying a big airline between islands which can cost more.

2. Ferry. ⛵️

BUT! Only from Maui to Lanai or Maui to Molokai.

It leaves the dock once a day to go to these locations and I've heard that, even for people that don't normally get seasick, the boat ride back from Molokai to Maui can be miserable.

I also learned from various sources that it is best to stay on one island if you only have a short while to visit and it's your first time.


image courtesy of Visual Hunt


When I first started making accommodation plans, I didn't know the first thing about Waikiki or Diamond Head … or Hana. I spent a lot of time scouring the Go Visit Hawaii website and learning as much as I could.

Like, for example, did you know there are certain roads in Maui that your rental car insurance will not cover? … These are roads with lots of turns, cliffs, rocks that fall into the road, sometimes one lane and sometimes dirt/gravel, and occasionally there are no guard rails to keep you from going off the edge. And signage warning you of these roads does not exist! 😧

I can definitely say it's been in my best interest to learn the islands as well as I can before traveling there. It would not have been fun to accidentally find myself on one of those roads with a car problem and no rental insurance to pay for it.


This is the part of Hawaii planning that I most wanted to share with you. Mostly because Club1Hotels is offering a free membership for this year ($675 value) allowing you to book hotels for cheaper prices and still get credit (points, status) for your stay. The offer expires on 10/31, so I wanted to go ahead and mention it despite not having used the service to book a hotel yet.

So far, my experience with club1hotels is that they are hit or miss (but mostly hits). I'll give a more full review at a later date, but just two days ago I saw a hotel for $440 that was going for $275 on club1hotels. That's a $165 difference! Surely finding deals like that should convince you to at least sign up and try the service! What is there to lose? I'm only seeing money gains for the 5 minutes it took me to sign-up!

I've also been working with four different apps to nail down and solidify my travel plans and goals.

1. TripIt

I've been singing it's praises from Day 1, and now is no different. Though I would like to mention that the app doesn't seem to notice when I make changes to my travel plans, like cancelling a restaurant reservation or hotel booking … or that time when Delta changed my flight times. It does do a great job of pulling information from my email and keeping my schedule super-organized. ❤️

2. Google Trips (itunesgoogle play)

This is a new app I recently heard about that I wanted to give a try. So far, I'm not loving it. 😕 While it does input your reservation/booking information, the information is not exceptionally organized. And, when things change, it's hard to alter how the information appears (and whether or not it continues to appear) in the app. I do like that Google Trips offers suggestions for where to eat and what to do at specific locations, but it all seems to be pretty generic and not based on the specific locations you are at or what you've already reserved . (For example, it'd be awesome if they recommended other Italian restaurants, if I book one. Or other extreme sport activities, if I have a reservation for skydiving. Instead, if Good Trips sees you have a reservation for skydiving, they might recommend a photography excursion or a history museum? And that makes no sense to me!)

3. Visit A City

I had heard about the website from a travel blog, but I hadn't really used it too much. So when i was planning what to do in Maui and Honolulu, I decided to see what itineraries their website already had up. (Their website provides itineraries based on where you are going including suggestions for how long a visit will take you and the approximate time it will take to get from one location to another.) Anyway, when I didn't find any itineraries that suited me, I started building my own. And what fun it has been! As I fill in my hotel and restaurant reservations, I can look on the map they provide to see where these things are located and how far they are from my ideal attractions. This has made a big difference in how I plan, because I'm working with the areas I'm in rather than driving from one end of the island to the other not actually realizing the time that is being lost to the commute. Once again though, I won't fully be able to review this site/app until I've actually attempted using it while on vacation, but so far I'm loving it and would highly recommend at least looking at it before your next vacation!

4. OpenTable

I always use this app. In fact, I've reviewed it here before. Basically, you earn points as you make reservations at restaurants. Eventually, you will have enough points for a free meal! Plus, you can get bonus points for booking at specific restaurants at specific times (usually when they aren't busy). All in all, it seems like a win-win. The restaurants know to expect me, and I, eventually get a free meal. 😀

image courtesy of Visual Hunt


I'm not actually done planning my trip to Hawaii yet, so I am sure I will learn far more both in my time spent continuing to plan and in the actual visiting of the place. But one thing I've discovered in planning so many trips is that all of the knowledge I acquire through travel builds on itself making me a better explorer, both in finding deals and becoming more aware of the world in which we live.


While I know not everyone reading my blog is planning a trip to Hawaii, I still hope some of what I've shared in this post is relevant to you. Like, the apps I mentioned, for instance, or learning more about the location you are visiting before traveling there and finding yourself in a metaphorical pickle.

Despite the fact that you may not plan as in depth as I do when traveling (or you might? who knows?), do you often manage to learn something new when traveling (or planning travel)? Will you be checking out any of the apps mentioned in this post or perhaps the hotel website to make future travel planning ore fun/cheaper/easier?

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