Hawaii beach

Tips For a Free Hawaii Vacation Using Miles

We recently qualified for a free trip to Hawaii (well actually from Hawaii) by adding 40,000 miles to our HawaiianMiles account. When combined with existing miles, that was enough for a free trip for two. With free Hawaii vacations in mind, following are our tips for using miles and points of all kinds. Please add yours below.

To kick off the discussion, here’s how our free ticket worked:

The American Express Starwood Preferred Guest (SPG) card had an offer this summer to earn 30,000 starpoints (it actually turned out to be 40,000) with a new card. Rob got the new card and had three months to charge the required $5,000 dollars. At that point 35,000 total points (bonus plus actual spend points) showed up in his SPG account. We then transferred those points to a Hawaiian Airlines account (one of many choices), and received an additional transfer bonus from Amex of 5,000 points. Total transfer was 40,000 points which became 40,000 HawaiianMiles. Not bad for a $5,000 spend.

In addition to this opportunity with Hawaiian Airlines, the Alaska Airlines Visa card has a $99 companion fare which is valid for a round-trip ticket to Hawaii.

Tips For a Free Hawaii Vacation Using Miles

  • Pick one way or round trip. If you don’t have enough miles for a round-trip award or it isn’t available, try checking a combination of award travel one way and paid travel the other way. Or use two carriers, one in each direction.
  • Start looking one year in advance. Frequent flier availability is first released 330 days in advance. That’s a perfect time to be looking for flights, especially then traveling during peak periods.
  • Flexibility is key. Availability may be poor for the most popular flights and dates, so try to be flexible and consider alternates. If July travel isn’t possible, can you plan your Hawaii vacation for mid to late August?
  • Elite fliers to the front of the queue. If you’re an elite with an airlines, you may have access to more frequent flier inventory than those who are not.
  • Upgrades using miles. If a free ticket isn’t available, perhaps an upgrade is. It’s always worth checking as this can be a great use for miles.

What are your Hawaii tips and tricks for using Miles and Points?

8 thoughts on “Tips For a Free Hawaii Vacation Using Miles”

  1. I used a combination of cash and miles. Using the cash going to Hawaii on the cheapest fare, which left from Oakland, and then the miles to return to San Francisco. A much easier return for me as then I could just catch BART home! (San Francisco origin and return fares seem to always be more expensive)

  2. Great tips! Any idea if the companion fares are instant? Wondering if I can apply for the card and get approved then go buy 2 tickets. Also how do you know which flights qualify for companion fares? Thanks

  3. I’m new to this. I have just over 40,000 MileagePlus miles and was hoping to travel to Hawaii March 25th- 30th or 31st. I can book the flight there for 20,000 miles, but there are no economy seats available for the return flight. So, it is not likely they will make anymore available? Should I go ahead and book the flight there for the 20,000 miles, then hope for a decent one way fare back? Or should I save the miles and wait for a good sale? Thanks in advance! Just reading your posts make me so excited to go to Hawaii for the first time.

  4. Regarding the Alaska Airlines companion fair suggestion in the postI went to the Alaska airline website regarding this airline companion ticket and it says that for the companion ticket to be valid, the original ticket can’t be purchased with miles.

    “Mileage cannot be used as a form of payment for the paid ticket, however mileage credit accrual is allowed on both the paid ticket and Companion Fare”

    Is there a way around this? I am confused.

    1. Hi Ben,

      @ Ben. Yes I think it was confusing. Sorry about that. The Alaska companion ticket is another type of deal. Not miles/points. Still $99 companion fare is a pretty good deal when used to Hawaii. It is a credit card offer.

      @Mary. Good questions. Yes, the airlines continue to release that availability as they feel the need. Your dates are pretty good given that Spring Break is early in 2014. Have you looked at the cost of return flights. I’d be a little concerned about getting caught in fees to redeposit miles if you don’t have that return nailed down now, or at least know in advance what your exposure is if it doesn’t work out.

      @Mo. I don’t believe the companion fares are instant and I believe all flights qualify.

      @Jacquelyn. Thanks for sharing.

      Aloha.

  5. Question or you. Some cards charge you a transfer fee (Alaska airlines card Thursday bofa for example) did American Express one charge you to transfer the points?

    1. Good question and good point Julie.

      There was no charge. So another thing to be aware of is obviously extra charges associated with miles/points and their transfers/use. I also know that most airlines charge extra for redemptions that are in the very near future. Another point with HawaiianMiles. You can only pool miles between people if you have their BofA HawaiianMiles credit card.

      Aloha.

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