Help a Reader Travel: Hawaii Island Hopping

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Welcome to another post of helping a reader travel! As I’ve mentioned before, I have not been to every destination (unfortunately), but do get questions from friends and other blog readers on all sort of travel destination questions. Thus far, we’ve been able to help other readers travel to MauiThe Greek IslandsPacific Coast HighwayArgentina /Buenos AiresCosta RicaCape Cod & The IslandsIcelandGenevaCanadian RockiesRomeIsraelPeru / Inca Trail, StockholmChicagoParisHanoiAustinPuerto RicoBrugesSalzburgIstanbulLas Vegas, Jamaica, India/Golden Triangle, Auckland, Singapore, Moscow, The Oregon Coast, Seattle, and Portland.

So this weeks travel destination includes the Hawaiian Islands. I received the following email from reader Greg:

“My wife and I have read your reports on the various Hawaiian Islands, and the reader input on those trips (and Maui as well) but what we want to do is spend an extended period of time there island hopping- and we want to do it as close to free as possible. We are fairly new to all these tips and techniques for acquiring free travel, so are just finishing what this hobby would call a first churn. We are limited to just one of us applying for a credit card. What we would like input on are any tips readers may have in areas that we won’t be able to get for free based on their experiences. .

We realize that Hawaii isn’t the optimal use of points- but don’t care. We can stay in 3 star or above hotels, and will use miles to fly first class from PHX unless we find out it is a much, much better use of miles to drive to LAX- or somewhere else close to there (we live in North-Central AZ). A 7 hour drive would have to save us a whole lot of miles to be considered, though. A big area of concern to us is the expense of inter-island travel, and how to get around that. Thanks so much.”
Another question Greg had was what 2-3 credit cards should he apply for to get free hotels. Here are my tips:
  • Hyatt Rewards Credit Card – Can use the two free nights you get at the Grand Hyatt Kauai. This is a great hotel that I’ve personally have stayed at. You could also use the two free nights at the Hyatt Maui (although I’ve heard the one in Kauai is better). You can also get one or both of the Chase Ultimate Reward earning cards (Chase Sapphire Preferred or Chase Ink Cards) and transfer the 40,000 or 50,000 points (depending on the card you get) directly to Hyatt at a 1:1 ratio. This will get you another 2 nights free by redeeming points.
  • Citi Hilton Honors Reserve Credit Card – You will get two free nights, but only valid for weekend nights (Fri, Sat, Sun). You might be able to use these two free nights at the Grand Waila in Maui. The only caveat is that these two free nights are only valid for standard rooms so you will need to call Hilton and see if this hotel has standard rooms and if they take the two free night vouchers.
  • American Express Starwood Preferred Credit Card – I’ve heard good things about the Sheraton in Kauai which requires 12,000 points a night but is available for Cash & Points often. This will give you two free nights once you earn the 25,000 points by hitting the minimum spend. It is very close to the Hyatt Kauai. There is also a Sheraton in Kona that goes for 10,000 points a night.

The reason that I did not mention Honolulu is because you can typically find relatively cheaper hotels in Waikiki beach, so if your points are being spent elsewhere then this might be a place to find an extremely reasonably priced 3 start hotel.

If you’ve ever to the various Hawaii Islands, please help out reader Greg by commenting below.

Also, if you have any upcoming travel where you need some help, feel free to email me at to be a featured “Help a Reader Travel” Monday special. Thanks!

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. US has non-stop flights from PHX to many of the islands. That’s how I’m flying tomorrow to LIH. You will want to get Hawaiian Air cards to defray the expense of inter-island flights as it is very difficult to book HA flights using partner miles.
    Marriott has a number of hotels in Hawaii, but it will be tough to get more than 2 nights free if only one of you can apply for cards.
    I always find it cost effective to stay in vacation rentals in Hawaii because it’s easy to find them at a lower price than hotels and I save so much on restaurant bills.

  2. If you have a few thousand ff mikes with AA, United, and US Airways, you can island jump pretty cheaply. The Hawaiian cards get you 35k after $1k spend, I think each island hop is 7k points. I booked an AXON 4 at the Hilton Waikiki Beach for 125k hh points. Saved a few thousand hh points. Subscribe to HNL groupon if you are looking for fun activities.

  3. Also dont forget the st regis in princeville (kauai) – probably the nicest starwood hotel in hawaii…cash and points is a great deal considering what the nightly rate goes for.

  4. I’m HNL based, but my wife and I island hop a lot. I found pretty good award availability (depending on when you go) through united. 5k each way pp. Were going to OGG in a couple weeks for 10k pp RT. Another option is to check out the “hotel tonight” app. I found some good deals for Maui, and a staycation in HNL, and was able to get some free $$ from using coupon codes. You can find them online or send out your own for people to use (I think it was covered on here, if not, message me and I can get you started). Have fun!

  5. My wife and I both signed up for Chase Hyatt cards and used the free nights at the Hyatt on Kauai. It was a fantastic hotel. Generally speaking, Hawaii does not offer great point redemption value for hotels. This was especially true in Oahu. But the Hyatt on Kauai was an exception.

  6. you mention the Sheraton Kuaui, but not the Westin Princeville (also on Kuaui). Why is that? IT’s also 12k points per night. I typically prefer Westins, and I also like the Princeville area.

  7. UA miles is the way to go for inter-island trips. Only 5K per one way trip. But you need to book early as seats are limited. Get the UA Explorer card for 50K-60K miles each.

    Forget HA miles. They want 7500 per o/w. And using AA miles ‘can’ be worse. They charge 5000 per leg/segment. So if you fly LIH-HNL-OGG it’ll cost you 10000 AA miles. But if you fly HNL-OGG it’s only 5000.

  8. Not sure what your travel “style” is, but the Hyatt on Maui is very busy and overrated in my opinion (kids loved it though). If I were to go with just my husband again I’d stay at the Sheraton.

  9. We have been to Hawaii every year (Maui and Kauai) for the past 7 years, and here’s my 2 cents: Stay at least a week (2 is better) on each island if you can. Definitely use UA to island hop as mentioned above. Definitely get the Hyatt cards and stay at the Hyatt on Kauai. I recommend staying on the south side of Kauai if you are there during any other season but summer (june-september). During the summer months we love to stay up north in Princeville or Hanalei for at least half our trip as the weather up north is perfect (no rain) and the beaches are fantastic in summer (too wavy in other months). The Sheraton on Maui is nice – right in front of a good snorkel spot and in walking distance to some nice shops and restaurants. Also, check out vacation rentals too – there are some awesome vacation rentals in Hawaii that will run under $100 a night (check out if you don’t have enough points for a hotel. You can always try negotiating with the owner for a longer stay too ;-). For vacation rentals on Maui, check out the ones in South Kihei if you want to be near some awesome beaches. Stay north or south on Kauai – not east or west. I love vacation rentals for longer stays because you have a kitchen and can save a ton if you don’t have to eat out for every meal. Have fun!

  10. Do NOT stay in the Waikiki Beach resort area. Its entirely to crowded there on the island of Oahu. Do drive the entire island though, and explore all the beautiful beaches that are opposite from the congested, touristy Waikiki area. Enjoy!

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