Unlocking Hawaii With Points

Introduction:

In May 2023, my wife and I finally checked something off our bucket list: a trip to the Island of Hawaii. We spent 5 nights at the Hilton Grand Naniloa in Hilo without paying any cash out of pocket for the room! (We used points for the entire stay.)

In this post, I’ll walk you through how I booked the stay, how many points it cost, and how you can do the same (or even better) for your own Hawaiian getaway. Whether you’re just starting with points or already have some saved up, I’ll show you practical steps to make paradise more affordable.

TLDR:

• Hilton points are powerful for Hawaii. Especially with the 5th-night-free perk and waived resort fees.
• Always check the fine print before making a redemption. Parking, resort fees, and taxes can add up, but there are sometimes ways to avoid them.
• Even without using points, there are ways to reduce out-of-pocket costs when staying in expensive places such as Hawaii.

The Booking Process:

When we decided on Hawaii back in January 2023, my goal was simple: use my Hilton Honors points to cover as much of the stay as possible.

Here’s how it worked:

1. Search the Hilton site: Log into your Hilton account, search Hawaii, and select “Use Points.” Pro tip: leave dates open and use Hilton’s calendar view to spot the cheapest redemption nights.
2. Look for value: Redemption rates in Hawaii can vary wildly depending on season and location. I wanted something that fit within my ~200,000 Hilton points balance.
3. Take advantage of perks: I found availability at the Hilton Grand Naniloa in Hilo for 50,000 points per night. With Hilton’s “5th Night Free” perk on award stays, I was able to book 5 nights for exactly 200,000 points with no taxes or resort fees.

💡 Heads up: Always check for hidden extras like resort fees, valet charges, or nightly parking fees. While Hilton waives resort fees on award stays, the valet parking at our property was $15/night. I saved that cost by parking for free across the street in the evenings.

If you have Hilton Gold status or higher, there’s potential for even more value: food & beverage credits, free breakfast, and sometimes access to executive lounges stocked with snacks and drinks.

Acquiring the Points:

So how do you actually earn enough Hilton points for a stay like this? A few main ways:

1. Hilton Co-Branded Cards (US only)

• Hilton Honors Amex (no fee): 80,000 points after $2,000 spend in 6 months.
• Hilton Surpass Amex ($150 annual fee): 130,000 points after $3,000 spend, plus automatic Gold status.
• Hilton Aspire Amex ($550 annual fee): 150,000 points after $6,000 spend, automatic Diamond status, free annual night, $400 annual resort credit, and more.

In Canada, we don’t have Hilton cards, but you can still get US cards through Amex Global Transfer or by applying with a US ITIN. (To get a US ITIN, either apply by yourself online, or use a 3rd party service such as the one offered by Frugal Flyer).

2. Transfer from Amex Membership Rewards
You can transfer Amex Membership Rewards points → Hilton Honors at a 1:1 rate. While this may not the best use of Membership Rewards points as they can also be transferred to airline partners, if you have a surplus, it is an option.

3. Buy Hilton Points
A couple of times a year, Hilton sells points with a 100% bonus. For example, you can buy 160,000 points for $1,600 USD, and receive an extra 160,000 points. Paired with the 5th-night-free benefit on redemptions, you can sometimes come out ahead compared to paying cash. However, be mindful of foreign exchange fees and taxes if buying from Canada.

Alternative Booking Options:

Don’t have Hilton points? No problem. You still have options:

• Marriott Points: Marriott also has solid coverage in Hawaii and offers 5th night free on redemptions as well. The downside with Marriott is that resort fees usually aren’t waived on award stays.
• Discount Travel Deals: Sites like Travelzoo often post Hawaii vacation bundles. Example: Staying 3 nights in Wakiki for $199 per night, no resort fees and a $50 dining credit (50% in savings).
• Cashback Portals + Loyalty Programs: If you are planning to book hotels using travel portals such as Expedia, make sure to stack savings:
  1. Start with Rakuten for extra cashback (1–12% on travel websites: Expedia, Hotels.com, Booking.com, etc).
  2. Book through Hotels.com to take advantage of their “stay 10, get 1 free” program (basically 10% back).
  3. Use a travel rewards card with strong insurance coverage (Amex Gold Rewards is my go-to).

This way, even if you are not booking on points, you are still lowering out of pocket costs and getting extra value from your spending.

Conclusion:

While Hawaii is an expensive destination, it does not have to come with a massive price tag. With a bit of planning (and some points strategy), it is possible to enjoy Hawaii without draining your wallet.

Have you ever booked a vacation on points? Share your experience in the comments below, I’d love to hear them.

To see what we did and how much we spent on this entire trip, check out this post.