Hawaii: 10 Days and 3 Islands for $100 a Day

The Chase Sapphire Preferred card was my first premium credit card.

Before that, my credit history was full of collections, defaults, and charge-offs. My credit score was in the low 500s.

In early 2012, I resolved to finally get my credit under control. I used my tax return (in conjunction with my full-time job at the time) to pay down my credit cards to $0. I started making big payments at the end of January.

By late February, my credit score shot up to 702! Pretty amazing – but was I ready to apply for a premium card?

My relationship helped

The ace in my back pocket was the Chase Freedom card I’d had for 10 years.

Even though I’d only paid the minimum payment for a looong time (never do that btw!), it established a positive banking relationship with Chase.

When I paid it off, it sent the signal I could be trusted with new credit (at least I hoped). I applied for the Chase Sapphire Preferred when the sign-up bonus was 50,000 Chase Ultimate Rewards points after spending $3,000 in the first 3 months.

When I hit the “Submit Application” button, I held my breath as the wheel spun on the processing screen. After a few seconds, I was approved with a $5,000 limit. I nearly screamed.

My credit was indeed much improved. The first thought was popped into my head was this:



Redeeming the points

Here’s how I used Chase Ultimate Rewards points and American Express Fine Hotels & Resorts to visit three Hawaiian islands for 10 days – for only $100/day with my significant other.

2 United flights for me and Jay in economy:

  • Total cost: 80,000 Chase Ultimate Reawards points (40,000 each)


4 nights at the Aston Maui Lu

  • 46,550 United miles (transferred from Ultimate Rewards)

I checked the price on their website before I redeemed. It would’ve been well over $1,100 if I’d paid outright. They upgraded us to an Ocean View Room upon arrival!

I got well over 2 cents per mile – maybe even 3 with the upgrade factored in. I always aim to get at LEAST .02/mile.


2 flights from OGG-ITO (Maui to Hilo)

  • $172 ($86/person)

3-day car rental at Hilo Airport

  • $167 (Booked through the Chase Travel Portal – amazing deal)

Airbnb in Pāhoa, HI

  • $70

Airbnb in Kona, HI

  • $50

Pointshound BnB in Volcano, HI

  • $100


2 flights from ITO-HNL

  • $152 ($76/person)

3-day car rental at Honolulu Airport

  • $125 (again, booked thru the Chase Travel Portal)

2 nights Airbnb Honolulu, HI

  • $140 ($70/night)
View from our suite

View from our suite

1 night at Hilton Waikiki Village

  • $376 (Our only big splurge! Admittedly, this greatly inflated our per-day spend, but we wanted one night in a nice, fancy hotel. I’m so glad we did it. It was so romantic!)

Booked thru Amex Fine Hotels & Resorts:

  • Upgrade to Ocean View Suite
  • 12 pm early check-in
  • 4pm late checkout
  • Free breakfast
  • $100 food and beverage credit
  • (Amazing value, and they treated us like little kings!)

$600 for Incidentals

  • $150 for gas to drive around the islands
  • $100 for souvenirs/t-shirts
  • $100 for groceries/sunscreen
  • $250 for nice meals/drinks

TOTAL COST of 10-day, 3-island Hawaiian Vacation: 

$1,952 or $195/day for flights, meals, lodging, and car rental or about $98/day per person!

Estimated cost if not for Ultimate Rewards and Amex upgrades: 

Easily over $6,000:

  • $2,000 for flights from NYC (though there were some good sales in January – but we needed specific dates)
  • $500 more for 7 days of car rentals (very conservative estimate)
  • $1,400 for 4-night stay at Aston Maui Lu with upgrade
  • $500 more for stay at Hilton Hawaiian Village based on upgrade (again, very conservative)

How I did it

In total, I used 86,550 United miles transferred in from Ultimate Rewards. 50,000 of those were from signup bonus. I earned the other 36,550 points through a combination of:

  • Targeted spend. I put EVERYTHING on the Chase Sapphire card. EVERYTHING.
  • The Ultimate Rewards Shopping Portal. I started buying basic necessities like toothpaste, paper towels, etc. from drugstore.com. I bought pet food for Fenwick from wag.com. The key was clicking through the UR Shopping Portal, which offered 3-10 extra points per dollar. It added up FAST.
  • Rewards Network Dining. I signed up for United, though every airline (Delta, American, Southwest) is in the program. Just Google {Airline} + rewards network.
  • Promotions. Sign up for a preferred airline’s email blasts. Sometimes there are some great deals – or even better: free miles!

Bottom line

I got the Chase Sapphire Preferred card in March, and booked the Hawaii trip in June while away on a trip to Iceland. But that’s a story for another post – you can see how quickly I got the card and then booked a trip!

With one credit card signup bonus and some concentrated focus, me and Jay were able to have a dream vacation to Hawaii for less than $100/day.

Since then, I’ve started dreaming even bigger.

This year, I hope to get to Ireland, Australia, and Alaska. AND my credit score is 716 (and continues to improve!) – all from paying super close attention to my finances. Love love love it.

Definitely got the fever!

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About Harlan

Just a dude living in Memphis, traveling, and working toward financial independence.

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