Plan a Hawaiian Vacation Using Miles and Points – Part 1 (Overview)

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I commonly hear about Hawaii in terms of an aspirational vacation destination for families. It’s still in the US so there are no cell phone, currency, or passport issues for US citizens. However, it is a paradise that is a world away from the type of life that most of us live on a day to day basis. But, getting to and staying in Hawaii can be quite pricey for a family, so it is no surprise that so many families want to get there using miles and points. I have written some about getting to and staying in Hawaii on miles and points, but I haven’t devoted a set of posts to Hawaii. Time to rectify that with a short series on getting to Hawaii from the US mainland, staying in Hawaii at hotels, and island hopping.


Consider Cash, Not Miles and Points:

I have been to Hawaii twice myself, with three more trips booked in 2013. Don’t judge – fares were amazing and I went a little overboard. ๐Ÿ˜‰ So, I do have some experience in Hawaii, but I will be looking to those of you who are Aloha Experts to chime in as well. In fact, my first recommendation in terms of getting to Hawaii on miles and points is to consider not using miles and points. It is not all that uncommon that rates will be in the $300 – $450 range per person to Hawaii from cities all over the US.

The West Coast especially sees fares in the $300 range, but even places like Texas and New York get in on the $350 – $400 action from time to time. One of the best pieces of advice in the travel world is to “chase the fare, not the destination” and that is true with Hawaii. I booked several trips this year because the fare was so good, and who doesn’t love a trip to Hawaii. Of course, it is never guaranteed that a good fare will pop up for when you want to go, but it never hurts to keep an eye on fares for your favorite destinations like Hawaii. If a fare you like pops up then grab it quickly. I think I stumbled on my low Hawaii fares by keeping an eye on the Mileage Run forum of Flyertalk and following @theflightdeal and @airfarewatchdog.

Naturally even at $400 a pop, that adds up quickly when buying for a whole family, but you will cut out the problem of availability that comes from using miles and points. You also earn a fare number of elite qualifying miles when flying from the mainland to Hawaii, so that can be a factor if qualifying for elite status matters to you.

Decide if a Hotel is Really the Right Choice:

I deal primarily in the world of miles and points, so in this series I will focus on lodging options that can be booked with points. However, there are many options in Hawaii outside of the traditional hotel room. Especially if you have a larger family, staying in a two or three bedroom unit available via a site like or might be a much better deal than paying for a one-room resort hotel. I saw some beautiful ocean-view three bedroom condos available on Maui in the $450 – $600 range per night. I also saw some slightly more modest two-bedroom condos closer to $200 per night. I am sure there are even better deals than that, but even $450 – $600 per night isn’t that terrible of a deal for a condo that can comfortably sleep 8 as opposed to a hotel room that might be $300 – $400 and really only comfortably sleep 2. Of course you can save on meal costs by being in condo-type lodging as well.

All of my Hawaii trips this year are either by myself, just with my husband, or just with my daughter, so a hotel room will be the best option for us on all of those stays, but I very much hope to head to Hawaii with a larger group of family members in the future and when that happens we will be looking beyond hotel rooms for those type of stays.


Be Realistic:

There are some miles and points deals to Hawaii that are (much) better than others, but it is still going to take a relatively healthy stash of miles and points to get a whole family to Hawaii and back. Even more if you want to stay at hotels on points. It is absolutely doable, but it will take a little bit of time to amass enough miles and points. Also, multiple award seats on the more desirable flights can become scarce during the peak travel seasons. So, start early and be realistic. Unless you are very aggressive and pretty lucky, don’t expect to start now from 0 (March ’13) and get your family of four to the Aloha State entirely on miles and points by this summer. Expect to start now and shoot for maybe next summer. It’ll be here before you know it anyway.

Start Researching:

There are several islands in Hawaii, and even once you pick an island you like there are very distinct parts of the individual islands, so start researching where you want to visit. The more you know about where you want to go, the easier it will be to know which miles and points programs to focus on. Of course you can island hop to more than one island while you are there, so I will cover the most cost effective way to move around between the islands. It will also help to know in advance how long you want to stay in Hawaii. I’m crazy and go there for much shorter trips than is really advisable. I think close to a full week is the minimum length that most families want when they head all the way to Hawaii, but of course the longer you are there the more dollars and points are required.

Consider the off-season:

When starting to think about your dream miles and points trip to Hawaii, think about what times of year you would be interested in visiting as this will impact the cost of the trip in terms of dollars or points. If you are tied to a school schedule you will likely be visiting during the peak demand periods, but if you are free from that schedule then consider if visiting during a lower demand period would work for your schedule. If flying in coach works for you, then traveling in the off-peak season can even save you airlines miles. For example, American Airlines charges just 35,000 miles round trip to Hawaii from the US mainland, Canada, or the Caribbean from Jan. 12 – Mar. 13 and Aug. 22 – Dec. 15, as opposed to the regular 45,000 miles required. As an added bonus, some of the off-season months (like September and October) actually offer some of the best weather.

Coming up very soon are posts on what I consider to be the good stuff… getting to Hawaii from the US mainland on miles, staying in Hawaii at hotels on points, and the best deals for island hopping.

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  1. Great tips! I’m a fanatical points person, but even I agree that sometimes VRBO is a better option (especially for family travel). We were able to get a beachfront 3BR condo in Maui for <$400/night for a week-long family trip this past Thanksgiving (vs. ~$350/night PER ROOM at many of the big hotel chain options).

  2. MP, this is off subject but you normally have a good prospective. What are your thoughts on Priority Club Rewards becomimg IHG Rewards Club in July? Do we benefit or lose? Thanks —-

  3. Food, Wine, Miles, I think that can be a very good option for families when traveling. The trade-off of course is it requires real cash from your pocket, but what you get in return makes it worth it for some trips.
    Romsdeals, good job and enjoy!
    Rich, a post on that is almost done and going out in the next few minutes. I don’t think we lose anything, but I also don’t think much is gained by actually having elite status (other than internet). With what has been announced so far they mainly just made it easier to attain/maintain elite status.

  4. I agree with your VRBO comments. When traveling with a group or my family, I have found VRBO can offer incredible savings. Having a kitchen and being able to make even 50% of your meals in can save many hundreds of dollars for a group of people or family of 4 over even a long weekend.

  5. I’ll be reading your posts on this as I just booked tickets with points for DH and I for next February to Kauai and the Big Island. We live in the midwest and never seem to get those great discounted flights to Hawaii. And I found it funny that February was off peak. February for us means the middle of winter and who wouldn’t want to be in Hawaii then? I’ll be booking hotels with points as well. Curious is you have any tips on how to get cheap car rentals. I can’t believe the prices and we’ll probably end up using some Ulimate rewards points for this as well.

  6. One of the gems of using Avios points is the AA non-stops out of LAX to LIH, OGG or HNL for only 25k r/t. Or 50k to fly up front. Albeit, many people may need a repositioning flight, but at this rate it’s worth it!

  7. Glad to see this set of points as you gave me some pointers earlier this year on strategies on getting to Hawaii! Now we are all booked for an 8 day stay in Waikiki!! Oh and we’ll be traveling with our two year old too? make sure you include some tips for long flights with the little people. Keep up the great work!

  8. I think you’re going too far with $350-$450 from “cities all over the US”. Alaska has sparked a fare war on the west coast, and Hawaiian has lowered prices from NYC. You can get occassional deals from direct cities/hubs. but rock bottom fares are difficult from mid-to-small towns (IME, based on Tripadvisor forums posters). At LAX (with no Alaska) you’re lucky to get sub $400, and only in the low seasons.

    Are you going to cover rental cars? I wrote an FAQ for Maui, but it applies to all islands. Needs to be updated for the credit card portal engines. I’ll do that at lunch.

  9. And great call on VRBO/condos. A full fridge and kitchen are so valuable with kids. Eating out with a toddler every meal gets stressful. We find its best to do the bulk of a stay in a condo then end with 2 or 3 days at a resort. Also try HomeAway, and Craigslist last minute as the owners (of properties on VRBO) try to fill in any gaps for discounted rates.

  10. Would love to see ideas on using points/miles for business/first class from the east coast to Hawaii. I just got the Amex premier gold and was wondering which airline to transfer in order to accomplish this. Thanks!

  11. Dan, totally agree.
    Shelly, I will cover car rentals some as well. I agree Feb is a great time to get out of the MidWest!
    Brad, that is a real sweet spot with Avios for sure.
    Daniel, congrats! I will cover the flight with kids and enjoy your trip!
    Tim, you are right not all cities see those great fares, but we have sure seen them from a large number of places all over the US off and on within the last six months. Will check and and share your car rental tips/link for sure – thanks!
    Margo, will present some different options.

  12. A great option for folks in the western US is the Alaska Airlines credit card that offers the $99 companion ticket. Avios can also be used on AA to get to any of the islands from LAX (HNL, LIH, OGG, and KOA).

  13. We have gone to Hawaii each of the last four years and are there right now. Fares are always $700+ from our hometown so we use miles. Thankfully I finally figured out that we can link our Hawaii trip up with a trip to London (where my husband’s family is so we have to go there yearly) and it makes our Hawaii trip nearly free! We travel with our son who will be 4 next week and my parents so we usually stay in a condo on Maui, but we have used points or free nights to stay at a few hotels (our favorite by far being the Grand Hyatt Kauai). We have always just flown economy, but tried first class on United this trip and I will never waste points doing that again. Business class to London was so worth it, but to Hawaii it was horrible – we didn’t have personal tvs, no foot rests, no more leg room than an economy plus exit row and the food tasted like international economy food so it was awful (except for the ice cream sundae which is always good). Perhaps it is worth it for a non-stop flight from the east coast, but for our Chicago to San Francisco to Maui flights it was not. We have always used because they have the best prices usually, especially as you can add 1 or 2 drivers for no additional charge which we usually need. I have also gotten very good deals on Priceline by naming my own price when we didn’t need to add drivers.

  14. My take is that you have to be realistic on availability – and take the “plan ahead” awards as they come, especially for peak periods and if you lack flexibility. When looking for multiple tickets, I start 11 months out, take what comes up on my planned days/flights, and supplement when fares fall below a certain threshold. But there is risk in not getting a group on same flight, so one may end up in a mix of coach, first/biz, and paid tix (with or without upgrades).

  15. I’m in Honolulu right now and would describe it as Las Vegas next to the water. There are no casinos but lots of shopping and restaurants. It is not as tropical as other islands or cities.

  16. If you are on the West Coast, fares are great (I just flew a $283 RT fare two weeks ago from OAK), but they are still quite high from a lot of places, especially in the summer. My parents couldn’t get anything under $1100 last summer from their small town in the Deep South. Of course, there were no mileage tickets to be had either, so Hawaii may just be pricey from certain markets!

    Best website if you are serious about Hawaii is “Beat of Hawaii.” They regularly post about fare sales from various cities so you can jump on a deal.

  17. I have been taking my 3 daughters to Hawaii for two weeks every other year since the youngest was 3! Each time we either rented through VRBO or I did exhange through RCI using my timeshare (we actually exchanged into an ocean view unit at the Hilton Hawaiian Village!). We had a lot of space in the two bedroom condo, and having a full kitchen and washer/dryer was so convinient! This summer we are heading to Kauai and I found a very nice condo for $190 a night with 8th night free! Can’t beat that price! As far as fare goes, I used our points with US Bank visa and booked 3 tickets at 30k points each and bought 2 tickets at less than $500, during the end of June and first week July and hitting both Kauai and Maui! I must say I was surprised to find out that each award ticket only cost 30k points!!

  18. I would add taking a cruise on Norwegian Pride of America as an option. Although about the cheapest cruise is around $1100 each, that includes 7 nights and meals plus you get to see 5 of the Islands. Although NCL isn’t the best cruise line it certainly is more economical than it sounds if you figure $200 a night minimum lodging plus meals (say $100 a day at least) for that same amount of time would cost at least $2100.

  19. I fly to Hawaii 4-6 times per year from the west coast for work for years now. I would consider anything under $400 to be a very decent fare. Anything under or around!$350 is really good. The lowest I’ve ever seen was about $330 on Hawaiian SJC-OGG. I don’t know where you are finding $300 fares.

  20. I can tell that your daughter isn’t in school yet. Let’s wait and see how your travels are going to go when your daughter is in school and you can’t just travel anytime a good fare presents itself.

    The reality for most of us with school age children is that great deals do not exist. I live in AUS, and I have been monitoring fares on UA from 11 months out for this summer and I have yet to see them drop below $1100 on a reasonable routing. For most mortals, that means redeeming is the way to go.

    On the hotel front, I generally don’t believe in redeeming in Hawaii because many of the best hotels are not part of the chains that have mainstream programs.

    Lastly, I have done VRBO a few times, but I decided years ago that if I wanted to cook, clean, do laundry and shop for my kids on vacation, I can do it way cheaper at home in Austin. I have stayed in hotels ever since. Really, a vacation is supposed to be a break from all the stuff you do at home…if you do it all on vacation, what’s the point? I’d rather spend the money and relax than save it and be stressed out.

    And if you do Hawaii right, it can be dirt cheap even without using miles for hotels. But that is something that only those will understand who have been to Hawaii many many times.

  21. “Unless you are very aggressive and pretty lucky, donโ€™t expect to start now from 0 (March โ€™13) and get your family of four to the Aloha State entirely on miles and points by this summer.” I’m living proof that it is possible if you have the required # of miles/points in the bank with the right airlines/hotels. You just must be flexible with your plans. I just booked a 3-week July 2013 trip on March 25 from the Midwest to Maui with return from Kona. We’ll spend 10 days on each island. AA, UA, and HI all had some dates available for 4 tickets at the economy “saver” level. This was pretty consistent over the last few weeks and I had been looking for the right combo that would work with my hotel and timeshare points (plus my wife’s ridiculous requirement that we not go to Oahu because we’d already been there! Which is a serious constraint because HNL flights are often more available). Ultimately I ended up doing the award booking with AA through their web site. I had 400K Hilton points that I wanted to burn before the devaluation. Hilton Hawaiian Village on Oahu and Hilton Waikoloa Village on the Big Island had full availability. Availability in Maui/Ka’anapali with our Starwood timeshare points (StarOptions) was a bit more tricky, but we managed to find a week that worked. Over the last couple of weeks, the trip cumulatively took maybe 8-12 hours to research and book, but it will definitely be worth it.

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