The Free Hawaiian Vacation Part II – Hotels

If you’re just tuning in, read my Part I – Intro and Flights writeup first.

As I mentioned in my October Hobby Update, we stayed at some pretty swanky hotels on our trip to Hawaii. Remember the remote control toilet? Here’s a rundown of all the places we stayed, and how we got them for free!

Fairmont Kea Lani

The Fairmont won us over with their kissing swan towels

The Fairmont Kea Lani in Wailea, Maui was by far the nicest hotel we stayed in on our trip. We stumbled in late at night after our long flight from DC and they greeted us with mango papaya juice, a fresh orchid lei for me, and a kukui nut lei for Mr. Chedda. The four nights we stayed there were just blissful. The hotel looks like some sort of Arabian Nights fantasy. Every single room is actually a suite larger than my apartment.

Getting the Fairmont stay for free was actually really easy. In October 2015 Mr. Chedda and I each applied for a Chase Fairmont Visa Signature card, each earning two free nights at any Fairmont hotel after spending $3,000 in 3 months, with no annual fee the first year.

We stayed in a “Fairmont Garden View Suite” which overlooked a lush garden of tropical plants and goes for over $600 a night. That’s $2,400 for a 4 night stay. What?! We paid $35 a night ($140 total for 4 nights) for the resort fee. I estimate (conservatively) that if we had to choose a hotel to pay cash for in Maui, we would have stayed in one that cost at least $100 per night, or $400 total.

Running total of Money Spent: $34 + $140 = $174

Running total of Value (conservative): $1,500 + $400 = $1,900

Running total of Value (actual value): $5,000 + $2,400 = $7,400

Leftover bonus: 40k AA miles

Hyatt Regency Maui

The Hyatt Regency near Lahaina, Maui was a very nice hotel. It’s hard for me to rave about it because we went there just after staying at the most heavenly temporary abode in existence (the Fairmont), but it’s probably nicer than any other hotel I’d stayed in besides the Fairmont. The clientele was also very different—there was a lot more of yelling and a lot less of serene strolling than we saw at the Fairmont. I’d say the highlight of the Hyatt Regency was the pool, where you could swim through a waterfall into a cave grotto area with a swim up bar inside!

We stayed two nights here, and they were kind of an afterthought during our planning. We had points from our Hyatt credit card (more on that in a moment) and we were interested in staying in West Maui to see a different part of the island, so the Regency just seemed to make sense.

View of the ocean and Hyatt Regency's enormous pool complex at sunset
View of the ocean and Hyatt Regency’s enormous pool complex at sunset

At the same time we picked up our Fairmont cards, Mr. Chedda and I each got a Chase Hyatt Visa. Each one came with two free nights and 5,000 Hyatt points after we named each other authorized users and spent $1,000. Again, the annual fee was waived for the first year.

We planned to use our free nights at the new Andaz Maui in Wailea, which dedicated credit card churners were always raving about. In a twist that seemed devastating at the time, there were no award nights available at the Andaz at all during our planned vacation. There were, however, plenty of openings at the Grand Hyatt Kauai, which is where we ended up spending our free nights. I’ll get to that in a minute.

Because of this card, we ended up with about 6,000 Hyatt points each (5k from bonus and 1k from the required $1,000 spend). A night at the Hyatt Regency was 20k points, so we each needed about 14,000 points to make up the rest.

Since we each had Chase Sapphire Preferred cards from before we started planning the trip, we had a pretty big stash of Chase Ultimate Rewards (UR) points that could be transformed into Hyatt points at a 1:1 ratio. In our quest for $0 opportunity cost, though, we didn’t want to spend those points. Instead we each applied for a fee-free Chase Freedom card, for a combined bonus of 40,000 UR points. We transferred 28k of those to Hyatt and booked our two nights at the Regency. Boom! Another free hotel stay!

The basic room we stayed in at the Hyatt Regency goes for $270+ per night ($540+ for two nights) and, as before, my conservative estimate for what we would have spent in cash on a hotel in Maui is $100 per night. The hotel waived all resort fees and parking fees (I hate that these exist) since we were booking the nights with points, so our out of pocket costs were $0.

Running total of Money Spent: $34 + $140 + $0 = $174

Running total of Value (conservative): $1,500 + $400 + $200 = $2,100

Running total of Value (actual value): $5,000 + $2,400 + $540 = $7,940

Leftover bonus: 40k AA miles, 12k UR points

Grand Hyatt Kauai

Hoo boy was this a nice hotel. The Grand Hyatt was just plain beautiful, it had a restaurant that served the best scallops we’d ever tasted, and it was centrally located (or at least as central as one can get on an island with basically one main road) in Koloa, Kauai. It also had a lazy river, which was probably the highlight of the hotel for me. I lazed my way down that bad boy plenty of times.

Frugal tip: walk around the pool area here after dusk and you’ll have your pick of barely used inflatable rafts or inner tubes that people bought in the morning and left by the trash cans around the enormous pool complex by the afternoon when they got too tired of floating around in the sun.

Swanky lobby area at the Grand Hyatt Kauai. They had parrots!
Swanky lobby area at the Grand Hyatt Kauai. They had parrots!

As I mentioned above, we got Chase Hyatt cards that came with four free nights total between the two of us. We had no trouble booking our free nights from the two different accounts as one continuous stay by calling Hyatt, and there was plenty of availability at the Grand Hyatt when we booked about 7 months out (unlike the Andaz Maui).

The Standard Guest Room we stayed in costs about 450 buckaroos per night in the off season ($1,800 for our four night stay), and more during the high season. Ditto above—my conservative hotel spending estimate for if we had stayed somewhere using cash is $100 per night. I guess it’s Hyatt policy to waive all resort fees and parking fees on award nights, so we had another $0 stay!

Running total of Money Spent: $34 + $140 + $0 + $0 = $174

Running total of Value (conservative): $1,500 + $400 + $200 + $400 = $2,500

Running total of Value (actual value): $5,000 + $2,400 + $540 +$1,800= $9,740

Leftover bonus: 40k AA miles, 12k UR points

Sheraton Kauai Resort

Our final hotel stay on the islands was also in Koloa, Kauai at the Sheraton Resort. It was a pleasant stay, but the Sheraton just couldn’t compete in terms of comfort with any of the other hotels we stayed at, not even the Hyatt Regency. I would say the crowing-at-all-hours roosters are mostly to blame for this. What this hotel did have going for it were the activities offered and the fact that it was within walking distance of a lot of nice restaurants, a rare feature because Hawaii is notoriously un-walkable.

Awesome Mai Tais at Merriman's, a restaurant within walking distance of the Sheraton
Awesome lilikoi egg foam Mai Tais at Merriman’s, a restaurant within walking distance of the Sheraton

All of the hotels we stayed at offered fitness classes and other activities for “free” for guests, but I definitely liked the ones at the Sheraton best. It felt like I was at Summer camp! Every morning, there was an excellent 75 minute sunrise yoga class overlooking the beach. In the middle of the day, there were lei making lessons, local history lessons, surfing lessons, kids’ crafts, and our favorite: the ukulele lessons. We learned how to play “Somewhere Over the Rainbow”!

To stay at the Sheraton for free, we needed to accrue Starwood Preferred Guest (SPG) points. We each picked up an American Express SPG card, which has the annual fee waived for the first year. Mr. Chedda applied first, and got 30,000 bonus SPG points for his $3,000 in minimum spend.

I applied a couple months later, wanting to put a few months between this and my prior application. Unfortunately by the time I was ready to apply the bonus had decreased to 25,000 SPG points for the same amount of spending, but that’s life in the points game. You never know when bonuses will change or stop being offered. Still, we had 61,000 total SPG points by the time we had each finished the minimum spend.

One great feature of SPG points is that you can pool them between accounts. Another is that if you book four nights on points, you can get a fifth night free. We made use of these two provisions, combined our points into one big pile, proceeded to book five nights at the Sheraton for 12,000 SPG points each (60,000 total), and got an extra night for free! We spent a total of six nights there, and we had a ton of fun!

The lowest rate I can track down for the Garden Room that we stayed in is about $200. That puts a six night stay like ours at $1,200. If I’d been booking a hotel with cash, I probably would have spent at least $100 per night, or $600 total. We paid $0 out of pocket to stay there, but I got the sense that we would’ve had to pay the $31 per night resort fee if we hadn’t been some combination of a) honeymooners and/or b) SPG Gold members.

Running total of Money Spent: $34 + $140 + $0 + $0 + $0= $174

Running total of Value (conservative): $1,500 + $400 + $200 + $400 +$600 = $3,100

Running total of Value (actual value): $5,000 + $2,400 + $540 +$1,800 + $1,200 = $10,940

Leftover bonus: 40k AA miles, 12k UR points, 1k SPG points


Wondering how our total outlay so far of $174 will be explained away? Check out the Final Roundup post.

What do you think about the way we used our points? Would you have done something differently?

2 thoughts on “The Free Hawaiian Vacation Part II – Hotels”

  1. I’ve never been to Hawaii but I definitely I want to go. I also would love to stay in the places that you did. They sound amazing.

    I have heard about people that use credit card mileage but wow this is incredible. I definitely am going to be following along because I want to one day do this.

    1. I remember being so shocked when I first read about the credit card miles and points game. It’s amazing what’s out there to be had by anyone with a decent credit score and enough organizational skills to keep all the cards straight! Let me know if you have any questions and I’d be glad to help ease you into it!

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