Travel Planning to Kona, Hawaii- A Tutorial

John P.

My wife and I were planning on accompanying my brother and soon to be sister-in-law to the Big Island of Hawaii in June, and as a result I did quite a bit of planning for the trip. Being cost efficient is important to all of us, but making sure we end up with decent accommodations at a good value is possibly even more important.

I thought I would document my search methodology in case it helped others to find and book their travel online. Please note that I am very meticulous when it comes to travel planning. I’m picky about where I stay, how I get there, and want to know what I’m going to do while I’m there. I even make printouts and carry a small binder with me. Anal, I know… but it works for me.

To start with, I need to arrange air travel, accommodations, and a rental car. To complicate matters my brother intended to use air miles to get there, and I was undecided as to if I was going to do the same thing or not.

The Methodology

  • I begin all my planning with Start by looking up your destination and reading the Hotel reviews. Nothing can ruin a trip faster than a crappy place to stay. And you can not trust the marketing from any of the travel sites. Indeed, even many trusted brands can have bad locations, so TripAdvisor is the best place to get opinions (though not always perfect).
  • When it comes to getting the best deal, I approach this via two methods. First, I check the price for airline tickets and hotels separately. Then I check for air+hotel “packages”. In no instance do I ever include the rental car in a package because I have never found that to be cheapest.
  • I searched for the air, hotel and car on the following travel sites:,,,, to gauge the general range of pricing.
  • I also search for them on each of my preferred travel provider sites, namely American Airlines, Hilton and Hertz.
  • I have a special Citibank credit card which offers a benefit of free companion tickets, so I gave them a call to get the rate.
  • Optionally, it is sometimes useful to check, although I generally wouldn’t book there unless I was reasonably sure I knew what I was buying. Again, you can’t trust the marketing hype.

Here’s What I Found

After researching hotels on I was extremely glad I had done that. Initially I was pre-disposed to stay at the Sheraton because it is a Starwood property (and there are no Hilton properties) and I love their beds. However, the reviews were pretty bad and that quickly disillusioned me. I then checked out the “Other Lodging” tab and found a highly rated condo which looked good.

The ResortQuest Kona By The Sea offered large 2 bedroom, 2 bathroom units with actual ocean front views for around $300 per night. This would add up to $60 a night cheaper than two rooms at the Sheraton, plus the condo offers a full kitchen, living room and washer/dryer. That $60 per night saving would also add up to $360 vs. the Sheraton during our stay!

Next I chose the Check Rates button. I love this button… it brings up a window that allows you to check rates and availability from basically all the reservation sites out there without having to continually enter your information. I selected to search most of the sites and then went through them one at a time. It was a very good thing I did this too because all of the major reservation sites were asking $300 a night, but it turns out that had it for $250 per night and the site had a weekly rate which was only $238 per night! That little gem saved me another $320!

So the advice at TripAdvisor not only saved me from picking a hotel with a lower likelihood of satisfaction, but found me an alternative which will save nearly $700 while we’re there.

Now, before I booked the hotel, I had to go back to the flight situation to make sure we could get reasonable tickets for those days. Sometimes you have to go back and forth a little if your schedule is flexible in order to get the best deal.

Since I had such good luck with finding the hotel through TripAdvisor I decided I’d check out their flight search too. It works the same way as the hotel finder. You put in the dates, which in this case it conveniently remembered from the hotel search, and then you start selecting the search buttons to find rates on all the travel sites.

I restricted my search to on 1 stop and here is a table that demonstrates what I found:

Travel Site American US Airways United Multiple
Orbitz $861 $727 $944 $802
Travelocity $827 $745
Expedia $936 $797
Priceline $864 $805
Hotwire $946 $807
CheapTickets $861 $727 $944 $802

Finally, I called up the Citibank travel folks and found out I could book 2 round trip tickets on American Airlines with my travel companion benefit for $1,189 – taxes included. So, obviously $595 per person is far better than any of the rates on the travel sites.

At this point it’s just a matter of deciding whether to pay for the tickets or to redeem miles for them.

  • American Airlines wants 70,000 miles per ticket, so 140,000 for the pair.
  • The trip generates 7,480 miles per person, but only if you pay for the tickets.
  • Normal tickets within the continental US cost 25,000 miles per ticket.

Therefore redeeming awards miles for 2 tickets to Hawaii will cost the equivalent of 6 normal tickets (140,000+[7,480×2]=154,960 miles). If we assume that a normal ticket is going to be around $300, then the redemption to Hawaii would cost roughly $1,800 – considerably more than the $1,189 my Citi card can get me. Plus I get a number of other benefits if I actually pay for the trip on my card including additional reward points, travel accident insurance, medical evacuation coverage, and trip cancellation and delay insurance.

Now, unfortunately after all that work a little glitch came up in our plans that prevented us from actually going to Hawaii, but we’re going to San Fran and Las Vegas instead so I’ll write about them later while we’re there. Still, I thought that the methodology might be useful to people who are interested in saving as much money as possible while still finding excellent accommodations.


  1. Meg says

    Great info! One other thing I want to add, don’t forget to check Southwest flights to/from Hawaii. I was just looking up tickets and comparing prices and found it a lot cheaper to fly to OAK and then from OAK to Hawaii (purchasing separate tickets) than on sites such as farechase and travelocity. The good thing with Southwest is that if you know you are going far enough in advance, you can usually get really good deals!

  2. says

    Mahalo Steve. Excellent point and thanks for chiming in.

    A car is imperative on the big Island. In fact, don’t go if you aren’t going to get a car because you actually need to drive all over the place in order to see everything. Furthermore, I would only go for a 4WD rental because there are cool beaches that you can only get to with a Jeep or something similar.

    By the way, great blog you’ve got there. I would love to learn to scuba dive one day… especially in Hawaii! :-)


  3. says

    Good advice.

    One piece of info I think needs to be added is that a car is practically mandatory here. You figured it in, but you’d be surprised at how many people think they’re saving money or convenience by not getting a car…. likely wrong on both counts as there’s no real public transportation here and there’s a fair amount of distance between things here. Another good reference would be, it has lots of condos and apartments listed by their owners, and as you found, a condo can be a better deal than a hotel.



  4. says

    Nice tips, I always search for a gps map which i install on my mobile and use it with a small bluetooth gps, this way you’ll have the freedom of going around by yourself

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