How To Get Lots of Hilton Honors Points for a Dream Vacation!

There is no doubt about it. If you’re looking to stay at a premium Hilton property, it’s gonna cost you a lot of Hilton Honors points. They have one of the most inflated reward charts out there. Hyatt’s top properties will cost you 30,000 Hyatt points per night. Hilton’s top properties can cost as many as 95,000 points per night. That’s the highest cost per night of any of the mainstream hotel loyalty programs. But, I must say, for properties like the Conrad Maldives, for us, it’s worth that cost. We would never have gone to the Maldives without Hilton points and for that opportunity, we’re grateful, regardless of how many points we spent.


So, you want to go to the Maldives or a similar property too? You look up your dates and realize that it’s going to cost you a whopping 380,000 points for a five night stay (95,000 points per night plus your fifth night free). Whoa. That’s a lot of points. Luckily for you, there are as many as 6 or 7 credit cards out there that are at your disposal to start accumulating these points. Obviously, signing up for several credit cards is a pretty long process, so plan ahead!

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Let’s start with the easy ones. Hilton is affiliated with four separate credit cards. Two of them are Visas and two are American Express cards. You can find them listed together here. Right now, their sign up bonuses are not stellar. The best one of the bunch is the Hilton Reserve Visa card which gives you two free weekend nights at any Hilton in the world after meeting the spending requirement (weekends are defined as Friday, Saturday, or Sunday night).

There is also an American Express giving you 60,000 Hilton Honors points, a Visa with a bonus of 40,000 points, and another American Express with a bonus of 40,000 points upon meeting the spending requirements. Adding these four cards up, you would have enough points for about 3.5 nights at a top property. Not bad, actually, since there are other Hilton properties that don’t cost as much. For example, our upcoming stay at the Hilton in Cairns is only be 40,000 points per night so those four cards would give us 5.5 nights there. But, alas, if it’s a top property you’re after, you need ton of points.

Luckily, there are a couple of lesser known cards out there with the ability to convert their sign up bonuses to Hilton Honors points. While the transfer rate is not as good as it once was (each used to offer 2 Hilton points for 1 mile), they are still pretty good at 1.5 Hilton point for each mile. Virgin Atlantic currently has a increased sign up bonus on their Bank of America issued Visa card. Upon spending $12,000 in the first 6 months of card membership and after adding an authorized user to that card, you receive 75,000 Virgin Atlantic miles (that is a lot of spending, but there are ways to achieve this goal).

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These miles aren’t that valuable to me because Virgin Atlantic’s frequent flyer program isn’t very lucrative. And they add fuel surcharges to their awards so it’s a program I’ve passed on. But, their miles transfer to Hilton Honors points. So, the 87,000 miles bonus (75,000 plus the 12,000 you get for spending on the card to unlock that bonus) becomes 130,500 Hilton Honors points. This card alone gets you one third of the way to a 5 night stay at top Hilton property.

There is also an increased bonus available through December 31 from Hawaiian Airlines. Their Barclay’s issued card gives you 50,000 Hawaiian Airlines miles upon spending $1000 on the card in the first three months after opening the card. And again, Hawaiian Airlines miles aren’t valuable to me as miles because their frequent flyer program doesn’t have many great offers. But, these miles also transfer to Hilton Honors points at a 1 mile to 1.5 point ratio giving me 76,500 miles after meeting the spending on the card. In order to find this offer, you need to log into your Hawaiian Airlines frequent flyer account. If you don’t have one, you can open one here.

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Both of these credit cards effectively offer higher Hilton bonuses than the Hilton affiliated credit cards (aside from the Reserve with two free nights, that is). So, through a combination of several of these credit cards, you can get a week at a top property with a little effort. While I won’t get into the details here, certain American Express Hilton credit card holders have access to AXON awards which give you discounted Hilton Honors point pricing for four night stays at Hilton properties. Category 10 properties will cost 300,000 points for a four night stay versus the 380,000 that it should cost at these properties.

So, if you combine a 4 night stay with the two free nights you get from the Hilton Reserve card, you’d have a 6 night vacation after signing up for the Virgin Atlantic, Hawaiian Airlines, Hilton Reserve, Hilton Surpass, and Hilton Visa credit cards. Five credit cards for a six night stay is a lot. But you quite literally would be in paradise so it might be worth it for a special occasion. And keep in mind that a spouse could sign up for the Reserve card in their name to take the number that one person would have to sign up for down to four.

This is almost exactly what we did when we stayed in the Maldives a few years ago. We are hoping to make it back there soon, but there are lots of other properties that may suit your plans better. Some great examples include the Conrad Tokyo, the Hilton Moorea in Tahiti, The Grand Wailea (Waldof Astoria Resort) in Maui, or the Conrad Koh Samui in Thailand.


While accumulating that many points for a free vacation in paradise isn’t easy, it is achievable as long as you plan well in advance.

Have you ever signed up for lots of credit cards in preparation for a dream vacation?

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One Comment

  1. hi Jennifer,
    I just read your interview by Darius and Emily. I am impressed by your approach to flying with miles via owning credit cards. I intend to follow your blog to learn more about the art of signing up for credit cards and using miles for travel. I am looking for a “mentor” and enhance my skills in this area. Being a senior, each trip will be my “last” one since there are so many dream spots in the world to experience. I am signing up for your blog because I am impressed by your open approach, willingness to share your knowledge, and potentially I might be using your expertise for booking award. We have a 50th anniversary coming and I am gearing up for that trip ( Singapore Airlines business or first class with miles). Your children are very privileged to be exposed to other cultures early. Have a good day.

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