By: 10xT Reader – Chris Sheehy

Editors Note: Some of these credit card offers have changed. Please visit 10xtravel.com/credit-cards for a list of current offers.

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!

A person walks barefoot on a sandy path surrounded by lush green bushes and trees, earning miles with each step as they head toward the bright, blue ocean under a partly cloudy sky.

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

Screenshot of a flight purchase summary showing two adult tickets from Richmond, VA, to Lihue, HI, for 90,000 miles plus $22.40. The trip includes two connections and details each flight segment and timings for your travel plans.
Computer screen shows a roundtrip flight itinerary for 2 travelers from RIC to LIH on March 5, 2018, returning March 13. Total cost is $2,237.22, including $206.82 in taxes and fees—points or miles could help offset costs for future travel.

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

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!

A person holds a can of Maui Brewing Co. beer in the foreground, while a smiling woman with glasses and a braid sits on a couch in the background, indoors with framed art on the wall—perfect for relaxing after earning miles or points.

After landing in Kauai we picked up our rental Jeep, which would have cost $600 out of pocket! We decided to use our $300 annual travel credit from the Chase Sapphire Reserve® and booked the rest through the Chase Travel portal. At the time of our trip, this gave us a fixed 1.5 cents per point value, so we used 17,000 Ultimate Rewards points to cover all but $26. Today, that has been replaced by the Points Boost feature, which offers up to 2x value on select hotels and flights booked through the portal.

A smiling man in a black shirt and red shorts sits on the hood of a white Jeep with the drivers door open, parked on a dirt lot among tropical trees and a house—capturing the spirit of adventure and miles yet to explore.
A payment summary shows 17,000 points redeemed and $326.10 billed to a Chase Sapphire Reserve card for a travel purchase. The total remaining amount is $326.10. Contact info is at the bottom.

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.

Outdoor pool with lounge chairs and colorful umbrellas, surrounded by a two-story hotel building. Palm trees and lawn are visible, with the ocean and sky in the background—perfect for earning miles or redeeming points on your next getaway.

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!

A table shows 12,000 points and $51.72 cash. Below, it says Total Points Redeemed: 12,000 and Amount Billed to Card: $51.72, with a partially redacted card number—highlighting points used alongside your purchase.
A tropical resort with a round swimming pool surrounded by lounge chairs, palm trees, and thatched umbrellas; white two-story buildings stand in the background under a partly cloudy sky, perfect for earning points or miles on your next getaway.

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.

A hotel bill summary showing nightly rates of $529 USD for four nights, with a subtotal of $2,116 USD. Additional taxes and fees bring the total per room to $2,566.97 USD—ideal for earning extra points or miles on your stay.
A hotel booking summary shows Grand Hyatt Kauai Resort and Spa reservations: one booking with 25,000 points plus $300 on 3/9/2018, and two nights redeemed with points on 3/12/2018.

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

Tropical resort scene at sunset with palm trees, a round pool, lounge chairs, lush greenery, and colorful flowers, as sunlight streams through the clouds and reflects on the water—a perfect escape for those who love to earn points and miles.
A smiling couple takes a selfie outdoors near a tropical pool at sunset. The woman shows off an engagement ring, and both appear happy and excited. Lush greenery and palm trees surround the pool, capturing a perfect moment from their points-filled getaway.
A bottle of sparkling wine and two filled champagne flutes rest on a sandy beach, with rocky cliffs and ocean waves stretching for miles in the background under a partly cloudy sky.

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.

A person with braided hair sits barefoot on a grassy hillside, gazing out over a green valley and distant mountains that stretch for miles under a cloudy sky.
A man in sunglasses and blue swim trunks stands on a grassy area by a rocky beach, with the ocean and a distant shoreline lined with palm trees and buildings, dreaming of earning more miles under the sunny, blue sky.

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.

A smiling man and woman pose for a selfie outdoors near a hotel, enjoying their travel. The woman holds a drink with a pineapple slice garnish. Green plants and the multi-story hotel building are visible in the background.
Screenshot of a Chase Sapphire Reserve Ultimate Rewards summary showing 29,454 points redeemed, with the total points redeemed listed as 29,454 miles or points.

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.

A woman with glasses sits at a restaurant table with a plate of food and a drink topped with a pickle. In the foreground, cheesy fries and guacamole are visible—perfect for relaxing and enjoying miles or points earned from recent travels.
A man in the foreground smiles widely for a selfie in an airport lounge, while another person lounges behind him, smiling and giving a thumbs-up. Drinks and a menu sit on the table, capturing the excitement of earning miles on their journey.

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