Booking a Last-minute Trip to Kauai for 4 Adults 7 Days Prior to Departure with Miles & Points

It is often debatable whether collecting miles and points is even worth our time and effort, given the existence of 2% cash back credit cards. TravelWhimsy and I just returned from a whirlwind long-weekend trip to Kaua’i, HI, with our moms. The entire trip was conceived and booked on a whim – 7 days prior to departure, to be exact. A last-minute trip like ours seems to indicate that miles and points could trump cash back, and we will let you be the judge.

Kauai's Napali Coast from the Kalalau Trail
Kauai’s Northern Coastline Viewed from the First Half-Mile on the Kalalau Trail


TravelWhimsy and I had booked a trip to Fort Myers, FL, with our Southwest Companion Pass back in July 2012 for this January long weekend. My mother arrived in mid-January, earlier than originally planned, so we thought it would be nice to take her along for her upcoming birthday. However, last-minute airfares on our originally booked flights were prohibitively expensive, despite the fact that TravelWhimsy’s mom had just become a newly minted Companion Pass holder and added my mom as her companion.

While researching possible alternative destinations closer to home, I discovered that round-trip tickets from Las Vegas to Los Angeles on Southwest were only going for 5,500 points, which meant that all four of us could go to Southern California for a grand total of 11,000 Southwest points. But if you know me well, this would not be the end of the story.

I remembered flipping through a recent issue of the AAA magazine and noticing a picture of “the Grand Canyon of Kauai.” Instinct led me to looking at AA award flights between Los Angeles and Kauai/Maui (we had been to Oahu before). Both destinations had wide-open award space for every single day of the long weekend.

A quick decision favoring Kauai over Maui was made, simply because Kauai seemed less touristy. All of this happened exactly one week before our departure date.

No Time-off Required

We got back to work before 10am, a couple of hours late on Tuesday. Here is a quick overview of the flights we took.

(1) Saturday: Las Vegas (LAS) – Los Angeles (LAX) on Southwest (7am – 8am)
(2) Saturday: Los Angeles (LAX) – Lihue, HI (LIH) on American (9am – 1pm)
(3) Monday: Lihue, HI (LIH) – Los Angeles (LAX) on American (11pm – 6am)
(4) Tuesday: Los Angeles (LAX) – Las Vegas (LAS) on Southwest (8am-9am)

Flights for 4 Adults – 100,000 BA Avios Points (+$20 in taxes) & 11,000 Southwest Points (+$20 in taxes)

Most US airlines charge 30-45,000 miles for a round-trip ticket between US mainland and Hawaii, but you could use 25,000 BA Avios points to fly AA’s non-stop flights between LAX and a few Hawaiian islands. Taxes are $5 per round trip. The last-minute fares for our flights were going for $2,400 per person. The same trip would have cost 35,000 AA miles (+$75-per-ticket close-in ticketing fee).

After easily cancelling our original tickets to Fort Myers without any penalty, we booked the LAS-LAX tickets with Southwest points. If we had waited one more day, the ticket cost would have almost tripled.

Hotels – Grand Hyatt Kauai (22,000 Hyatt Points) & St. Regis Princeville ($31.25 Valet Parking)

Cheaper hotel options were going for $250 a night (plus extra-person charges ranging from $25-100 per person). The beauty of using points for hotel stays is that you generally don’t have to worry about extra-person charges. In our case, neither Hyatt nor Starwood allows online award reservations for more than 2 guests per room, but you can always call reservations to have the number of guests modified manually.

Both the Grand Hyatt and the St. Regis were going for $600+ per night.

In early December 2012, TravelWhimsy was targeted for the Starwood Bonus Beginnings free night promotion – a $100-all-in one-night stay got us a free-weekend-night award redeemable at any Starwood Category 1-6 hotel valid through February 28, 2014. We had no idea that we would be using that free night so soon. The St. Regis Princeville Resort has an unbeatable location on the North Shore of the Garden Island and offers an expansively spectacular view of the Hanalei Bay area. The reservations agent was surprised that our free weekend night was bookable for a Sunday night. All we had to worry about was the $31.25 mandatory valet parking charge and miscellaneous gratuity. This category-6 hotel normally costs 20,000 Starpoints, and has a 7-day cancellation policy.

The Grand Hyatt Kauai (on the South Shore in Poipu) was sold out for both Saturday and Sunday nights, but I was hoping that award space would open up as the 72-hour cancellation deadline approached. Meanwhile, the Westin Princeville was available for 4,800 Starpoints + $90 but specifically required $150 for two extra guests. Fortunately, Hyatt came through and I was able to book a free night with 22,000 Hyatt points for Saturday. Paid reservations also require a $25/day resort fee that covers free parking, but award bookings, for some reason, waive the resort fees. Many rooms at the Grand Hyatt come with one King and one Queen. Again, the property is beautiful and the service impeccable.

Rental Car

Most rental car companies were asking for $400+ all-in for 3 days, and Hertz (with a free-weekend-day AAA coupon) was giving me a quote of $220 all-in. I quickly checked Budget again – USAA brought the rates down to about $180 but AAdvantage surprisingly came through with an all-in rate of $138 (plus double AA miles). We were given a full-size Nissan Altima.

TravelWhimsy also found a site dedicated to rental cars in Hawaii, but we were unable to find a better rate. Million Mile Secrets is doing a series on rental cars, and you should check out this latest post on using Chase Ultimate Rewards or Citi Thank You portals for cheap rental car options.

Key Takeaways

  • Total points used for this trip for 4 adults – 133,000.
  • Total out-of-pocket expenses (excluding food) – $240 ($40 taxes, $31 parking, $138 rental car, $31 gas).
  • If we’d had to pay cash for this trip, it would have easily cost $5,000 or more (subjective and conservative value of $1,000 airfare per person + $1,000 for 2 hotel nights).
  • If your lifestyle allows last-minute trips, take them with your hard-earned miles and points. Both the trip itself and the planning for it could be fun and exhilarating. We saw the entire island in 2.5 days and put 250 miles on the rental car.
  • Flexible points, such as Chase Ultimate Rewards (UR) and American Express Membership Rewards (MR), are invaluable. In our case, UR points can be transferred to BA Avios, Southwest, Hyatt at a 1:1 ratio; MR points can be transferred to BA Avios at a 1:1 ratio and SPG at a 3:1 ratio (30%-50% transfer bonuses are often offered by MR for some of the transfer partners).


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  • Ginger

    Wow, surprised to learn how much money you’ve saved. Smart travel!

  • I usually use frequent flier miles to travel overseas.  I usually fly business or first class. I think you get the most value for your mile swhen you fly overseas although it is harder to get a flight at certain times.

    • It all comes down to personal interest and preference, Krantcents. Miles & points make travel more affordable for many who normally wouldn’t pay retail prices for it.

  • andrewleen

    Why not use Hertz points you grabbed from last year’s Amex promotion?

    • andrewleen, I didn’t buy any Hertz points, but do plan to use the points we have for our trip to Australia/Tasmania later this year.

      • andrewleen

        Sounds good! When you use Hertz points to rent in Australia, do you plan to buy insurance from Hertz? I remember Amex Premium Car Rental does not cover rental in Australia. Other credit card insurance will not cover you when using points.

        • I haven’t researched car rentals in Australia yet, but plan to use my Chase Presidential Plus card for primary coverage. I suspect that liability insurance will still be required and there might also be taxes/fees to be charged to the card. Hopefully, I don’t have to worry about activating the benefit. Fingers crossed. Do you have any free Hertz rentals experiences tp share with us?

  • David

    I like that you mentioned issues with booking rooms for > 2 people. This is never an issue with other bloggers, but a huge deal for my last 2 trips. In Asia, I found that it is property specific, and not chain specific, but Hyatt is more lenient. In Seoul, I had to pay the 3rd person charge at the Westin Chosun Seoul, but it was worth it due to Club access. 

  • Great post prominently showing what is possible in this hobby. And loved the way you outlined your thinking behind each move. You are in;-)

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  • Thanks for sharing, andrewleen. I will report back if I find anything useful to share.

  • americantaitai

    So awesome!  I’m going to have to PM you for your recommendations for Kauai as Mr. ATT and I are going in March!  Amazing that you were able to plan and book your getaway just a week prior to departure!

  • Well done, Jimmy. 🙂

    Looking forward to reading about the trip on Prana’s blog.

    • Thanks, Debbie, for reading and commenting! Not sure when Prana will be in the mood to write about the trip :D…

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