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

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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:

Ahhhh...

Ahhhh…

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:

  • JFK-SFO-OGG
  • HNL-LAX-JFK
  • Total cost: 80,000 Chase Ultimate Reawards points (40,000 each)

MAUI (4 DAYS):

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.

HAWAII (BIG ISLAND – 3 DAYS):

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

OAHU (3 DAYS):

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 Dallas.

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Editorial Note: Opinions expressed here are author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The opinions of the commenters are not necessarily the opinions of this site.

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