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Reader Success Story: Dream Trip to Hawaii on Points/Miles

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By: 10xT Reader – Chris Sheehy

My fiancé and I took our second trip to Hawaii earlier this year. We choose the island of Kauai this time and had an incredible 9 days trading out the cold Virginia winter for 80-degree beach days.

Hawaii is one of those places that most people think is unobtainable due to the cost of flights and hotels but, fortunately, they’re wrong! Overall, this trip would have cost close to $6,500 but we only paid 99 bucks!

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There is no way we could have come close to affording this without points and miles.

Our Trip to Kauai

  • Richmond, VA to Kauai, HI
  • Kauai Shores Hotel – 1 night
  • Aston Islander on the Beach – 1 night
  • Grand Hyatt Resort and Spa – 4 nights
  • Courtyard Marriott at Coconut Beach – 2 nights
  • Kauai, HI to Richmond, VA

Credit Cards We Used For Points

One of the major ways it was easy for us to do this is that every time I would decide to get a credit card that had a good offer, my fiancé would do the same. This allowed us to double down on points which made saving points for this trip so much easier.

These are the cards we used for our trip, however not all of these cards currently have the same sign-up bonuses as when we got them:

  • Chase Sapphire Reserve: 100,000-point sign-up bonus each
  • Chase Sapphire Preferred: 50,000-point sign-up bonus each
  • Chase Ink Business Preferred: 80,000-point sign-up bonus
  • Chase United Mileageplus Explorer: 70,000-mile sign-up bonus
  • Chase Hyatt Card: 2 free nights at any Hyatt property
  • Barclay Arrival Plus: 50,000-mile sign-up bonus

Flight from Richmond, VA to Kauai

There are a million great ways to fly to Hawaii on points. You can even fly there for as little as 25,000 Chase Ultimate Rewards points if you are flexible with your travel dates!

Unfortunately, for this trip we needed to travel on specific days. We decided the best option was to fly with United. On the United award chart it costs 45,000 miles per person to fly to Hawaii. You can book the same flight for fewer miles by booking through one of United’s partners such as Singapore KrisFlyer—also an Ultimate Rewards transfer partner.

However, in this case, award space was not available to partners. Fortunately, as a United MileagePlus Explorer cardholder, I have access to additional saver level award space on United.

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Cost using points vs out of pocket cost.  I’ll take the points any day.

After booking, I had 24,000 United miles from my sign-up bonus still to use, so we decided to transfer 66,000 Chase Ultimate Rewards points to my United account to cover the rest of the cost. We paid the $22.40 in taxes and got excited about our upcoming vacation.

Day 1

We had an early flight out of Richmond, but we didn’t mind since our destination was Hawaii!  People may not like United but the benefits of priority boarding and a free checked bag from the Chase United Mileageplus card made flying United a little more tolerable for us.

Our itinerary was Richmond (RIC)-Chicago O’Hare (ORD)-Honolulu (HNL)-Kauai (LIH). Not an ideal booking with two layovers but when you fly out of a small airport like Richmond sometimes you have no choice.

After 12 hours of flying, we landed in Honolulu and had 3 hours to kill before our next flight. We knew some drinks would definitely fix the last 12 hours of sitting in economy, so we took advantage of our Priority Pass Select membership to visit the Hawaiian Airlines Plumeria Lounge for some beer and snacks!

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After landing in Kauai we picked up our rental Jeep, which would have cost $600 out of pocket! We decided to use our $300 travel credit from the Chase Sapphire Reserve and used 17,000 Ultimate Rewards points for the remainder. That covered all but $26 of the cost.

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After getting the rental car, we went to our hotel for the night. We stayed at Kauai Shores hotel at it was all we needed for our jet-lagged selves. The total for one night came to $153.44. With the Barclay Arrival Plus, we essentially “erased” this travel purchase with our Arrival miles. 15,400 miles covered the cost of the hotel and it was very easy to erase the purchase online using the credit card portal.

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Kauai Shores Hotel – Right on the beach and not bad for free!

Day 2

We could have stayed at Kauai Shores for another night since we were spending 2 nights on the East coast of Kauai but we decided to explore another hotel. We ended up booking the Aston Islander On The Beach hotel which was actually right next to the hotel we had stayed at the night before.

To book this stay, we decided to use Chase Ultimate rewards points and booked our 1 night for 12,000 points and ended up paying the remaining $50 out of pocket. We did a lot of exploring of the north shore this day so the hotel was really only a place to drink Mai Tai’s after dark and sleep!

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Aston Islander on the Beach

Days 3-6

We couldn’t wait for the next part of the trip.

I was lucky enough to have opened the Chase Hyatt credit card when the sign-up bonus was still 2 free nights at any Hyatt resort/hotel in the world. We knew one of the best places to use these two free nights was at the Grand Hyatt Resort and Spa in Poipu so we jumped on the opportunity to do so.

We also decided that 2 nights would not be enough here, so we booked two additional nights using the “points plus cash” option on Hyatt’s website. It cost us 25,000 and around $350 for two nights. I transferred 25,000 Chase Ultimate Rewards points to my World of Hyatt account and used my the 35,000 Arrival miles to cover the cash portion of the booking.

If there is one place I can recommend anyone stay at if they come to Kauai, this would be it. My fiancé and I had to pick our jaws up off the floor walking around the grounds. We also could NEVER afford to pay to stay here out of pocket. Below are the out of pocket costs vs the points we used to stay here.

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Almost $2600 for 4 nights at a hotel?! This is why I do what I do.

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The Grand Hyatt Resort and Spa.  We also got engaged this trip!  The complimentary bottle of champagne helped make for a nice celebration!

We were greeted with a complimentary bottle of champagne upon our arrival and due to the fact that our room wasn’t ready on time, we were also given $50 in credit to use at the hotel’s bars (really helped take the bite out of the cost of an almost $20 Mai Tai).

We loved staying on the south side of Kauai for the majority of our stay. We knew we were going in rainy season, so the sunny south side of the island was more our style. The Grand Hyatt was a great location to explore great beaches and insane views.

If you find that you are in Kauai and bored, you must be doing something wrong! We were sad when our last day at the Hyatt arrived, but luckily our trip was not yet over.

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Exploring the south shore

Days 7-9

We hadn’t booked any hotels for the last two days because we wanted to hold out hope that the weather on the north shore would cooperate enough to explore the beaches. Sadly, the surf was incredibly high the duration of our trip, so this was not possible.

At the last minute, we found that the Courtyard Marriott at Coconut Beach on Hotels.com had dropped from about $330 per night to $180 per night.  We used the Chase Ultimate Rewards portal to book the hotel for 29,000 points.

While not as nice as the Grand Hyatt, it was a great place to spend the last two days and was still quite nice.   As our room was not ready when we arrived, the front desk gave us an additional two free Mai Tai’s (on top of the two they had already given us) and we made our way to the pool bar to drink and watch the ocean.

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Courtyard Marriott at Coconut Beach

Return Flight Home

This was the day we were dreading as we could have stayed in Kauai for forever. We dropped our jeep off at the rental company and made our way to our gate. Our routing home was LIH-Denver (DEN)-RIC so it was a little easier than our flights to Kauai.

We arrived in Denver jet lagged and starving. While Priority Pass doesn’t have any lounge partnerships at DEN, our Priority Pass Select membership offered $28 per person credit at Timberline restaurant which was perfect for breakfast.

After we ate, I used the two free United Club passes that came with my United MileagePlus Card for access to the United Club. While nothing crazy, this was a nice place to sip a bloody mary and wait until our flight to Richmond.

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Why wait at the gate when you don’t have to?

Estimated Cost Of Trip If Booked With Cash

Flights:$2,237.92

Hotels: $3,393.91

Car Rental: $581.10

Lounges: $254

Total: $6,466.26

Our Total Cost: Points And Cash

Chase Ultimate Rewards: 149,000 points

United MileagePlus Miles: 24,000 miles

Barclay Arrival Plus Miles: 50,000 miles

Chase Hyatt Card: 2 Free nights

Total out of pocket:  $99.40

If you add up the totals on all the bonuses we received with the cards we got, you will see we still have lots of leftover points. We could have really gone crazy on this trip and stayed at nicer places and flew business class but we decided to save the points for our next trip!

It’s easy for anyone to get started. You don’t have to know all the in’s and out’s of every loyalty program or all the different uses of points. You can always start collecting now and ask questions in the 10xTravel Insider’s Facebook group as you go.

Happy Travels,

Bryce

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