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Travel Hacking Towards Better Travel: My Upcoming $8K Retail Value Trip That Isn’t “Free”

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Travel Hacking Towards Better Travel

One of the coolest things about this “game”, “hobby” or whatever you want to call it is being able to string together trips for a lot less money than they would cost otherwise. You can often stay places and get experiences you wouldn’t otherwise. I have one such trip coming up with my family that I thought would be worth sharing. Booking it combined a number of different strategies that both saved us money, but will also ensure we have an amazing experience.

Huntington Beach – 3 Nights SoCal Suite

Traveling Hacking Towards Better Travel
Hyatt Regency Huntington Beach

Earlier in the year I needed to commit some of my expiring suite upgrades and targeted this property. We have stayed here before and really enjoyed it. I sort of describe it as a Hawaii style resort in California. They have a nice pool, beautiful grounds and are right across the street from the beach. There is also a nice pier and some great shops and restaurants not far away.

  • 3 nights in a regular room for our nights would cost $1,244.14 including tax/resort fee.
  • 3 nights in a suite for our nights would cost $2,430.64 including tax/resort fee.

I decided to use points + cash along with the suite upgrade. My cost is 30,000 Gold Passport points and $511.56. I will pay with Hyatt gift cards purchased at 27% off to bring my true out of pocket cost to $373. At this hotel we will have full lounge access which will mean no need for snacks or sodas/waters and breakfast is included as well.

How to get it cheaper: I could have tried to book one or two of the nights as points only and hoped that they wouldn’t kick me out of the suite, but they have a minimum stay requirement and I had to book three nights to get the suite availability. We are still getting a great value at a great hotel.

Getting to Huntington Beach – JetBlue Points Match

Since we only live 3 1/2 hours from Huntington Beach we had originally planned to drive down there, but then the JetBlue points match came through. Since JetBlue flies from LAS-LGB and since the hotel charges quite a bit for parking anyway, we decided to fly out there and collect our JetBlue points! If we need to leave the property we can use Uber or rent a car for the day. While I won’t consider the cost of these flights or the points earned in the calculations for this trip, it is a nice side benefit and is worth mentioning.

Getting to Mexico

We are flying to Mexico on Southwest using my companion pass. The flight was $161, but I used 7,704 points + $26.58. My wife also had to pay her taxes and we had to pay a modest tax for baby Elizabeth as well. Ironically we will be connecting in SNA which is so close to where we will have been staying the previous three nights!

Mexico – Hyatt Free Nights & Suite Upgrade

Traveling Hacking Towards Better Travel
Hyatt Ziva Club Ocean Front Hot Tub. From the Hyatt website.

After Huntington Beach we fly back home to drop my son off to start school and then Jasmine, the baby and I are off to the Hyatt Ziva Puerto Vallarta. This was a last minute decision because we need to use her two free nights from the Hyatt credit card and these are the last two nights they are valid. We also have two friends who will be there at the same time so it is a win-win.

Rates for the Ziva during our stay aren’t very high, so we decided to stay an additional two nights. My wife was able to get my Diamond number added to her reservation and I booked the two additional nights with a suite upgrade. As of now we are confirmed into a $400 per night suite with a hot tub on the balcony, but I am hoping we can get into a plunge pool suite as the stay gets closer. There is also a chance we won’t get the upgraded room for the first two nights, but they have said they will try.

  • 4 nights in a regular room: $1,076
  • 4 nights in hot tub balcony suite: $1,508
  • Our cost: $538 (reduced by 27% with Hyatt GC to $393)

The hope is that we will be upgraded to the $800 per night one bedroom plunge pool suite. That is a common upgrade. The problem with using points at this price is that 20K points to save $269 is a bad value.

Going to New York

From Mexico the three of us are going to New York. This trip was planned last year when I needed to commit a couple of our expiring IHG free night certificates. Having stayed at the Intercontinental Times Square and knowing it is a good value, I locked us in for Labor Day weekend which is also Jasmine’s birthday weekend. To get to New York from Mexico we are flying Southwest again. This time it wasn’t cheap.

The one-way flight to LGA via HOU costs $408 because of the holiday weekend. Not great, but we gladly burned 24,648 points and paid the taxes. Our flight arrives fairly late into LGA so the next step was to find an airport hotel.

LGA Airport Hotel Labor Day

Apparently LaGuardia airport hotels on a holiday weekend are not pretty. I knew there was a Hyatt Place not too far away, but it was full. There was a Diamond availability rate, but I think it was a tad high!

Traveling Hacking Towards Better Travel

Next I looked at other chain hotels and discovered a Holiday Inn for 25,000 points or $344 ($398.22 including tax). We are flush with IHG points between my wife’s mattress run and writing all of those postcards, so that wasn’t a problem. In fact, we got a huge value. On a night when all of the hotels are crazy expensive, we redeemed our IHG points at a value of 1.75 cents each when factoring in the 10% rebate from the credit card!

Traveling Hacking Towards Better Travel

New York City

The Intercontinental Times Square (my review) has a great location and will be a decent place to base ourselves for two nights. The cheapest room is going for $388 per night which comes to $898.77 for two nights including tax. Our cost is $98 since we used two annual free night certificates from the IHG Rewards credit card. That is a great redemption value if I have ever seen one!

Park Hyatt Splurge

To finish our trip, we will leave the Intercontinental Times Square and move to the Park Hyatt New York. I had debated whether to spend one night or two at this property and ultimately decided on two. Since this is a category 7 Hyatt property, points + cash would be $300 + 15,000 points. I just decided to use 30,000 points per night to book a room instead.

The regular Park King room which is now sold out for the nights we will be there was going for $850 per night. That comes to $1,956.61 including tax for two nights.  I am hoping now that the hotel is sold out that we will be upgraded to a nicer room. This could of course go the other way if everyone booked into higher categories. Either way, we’ll enjoy our time at the flagship Park Hyatt and with Diamond status we’ll have free breakfast and more.

Getting Home

Jasmine and Elizabeth will fly home on a $134 nonstop flight on American Airlines that I booked with 8,375 ThankYou points. Better yet, Jasmine needs 2,100 EQMs to hit AAdvantage Gold status thanks to the BA Business Class bonanza fare and this will get her just over 2,200. With Gold status I can raid her account for last minute bookings without a close-in booking fee.

I will be heading South from New York towards Washington DC to attend the Reselling DO. Since this entire trip will be a working one for me (my real vacation doesn’t come until October), I’ll probably Hyatt Place hop for the two days until the weekend comes for the conference. More points, more stay credits, Diamond status another year and we can do this all again.

Retail Value & Final Cost

Traveling Hacking Towards Better Travel

So if you want to assign a retail value to this trip, it would go something like this:

  • Huntington Beach Suite: $2,430.64
  • Southwest Flights: $569
  • Hyatt Ziva Puerto Vallarta Suite: $1,500ish
  • Holiday Inn LGA: $398
  • IC Times Square: $899
  • Park Hyatt New York: $1,956
  • AA Flight Home: $134
  • Total Cost: $7,886.64

If you are keeping track, my out of pocket is: 25,000 IHG points, 2 IHG free night certs, 32,352 Southwest points, 8,375 ThankYou points, 2 Hyatt free night certs, 2 Hyatt suite upgrades, 90,000 Hyatt Gold Passport points and $~950. Of the cash portion, the non-Hyatt gift card amounts are either covered by BofA Travel Rewards or Citi Prestige airfare credit.


Is travel free? Perhaps not, but you can certainly get a whole lot more for a whole lot less. That is sort of the point of doing all of this isn’t it? Years ago I wouldn’t have spent a little more so I could use a suite upgrade, but today I recognize the perks in addition to the free stuff. Nothing on this trip is really extraordinary in that it isn’t uncommon or rare. It is just a lot of stuff coming together so we can travel better and for less.

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Shawn Coomer
Shawn Coomer
Shawn Coomer earns and burns millions of miles/points per year circling the globe with his family. An expert at accumulating travel rewards, he founded Miles to Memories to help others achieve their travel goals for pennies on the dollar. Shawn also runs a million dollar reselling business, knows Vegas better than most and loves to spend his time at the 12 Disney parks across the world.

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  1. Is there some calculator or guide book or a way to figure out how to do this if you’re not a full-time mileage manager? Seems so complicated and impossible to figure out. Is there a website where you can enter you in the miles you have and get help figuring out how to use them? This only seems to work if you make it a full-time endeavor. Thanks for all your info. It’s a great help

  2. […] I just got back from 18 days of travel broken up over several trips. Many of the hotels and destinations will be covered in other posts, but the trip consisted of a few days in California with my wife, son and daughter, then four days in Mexico and four days in New York City with just my wife and daughter and finally a few days in Atlantic City, Philadelphia and Washington DC by myself. I covered the award aspects in a separate post. […]

  3. […] I just got back from 18 days of travel broken up over several trips. Many of the hotels and destinations will be covered in other posts, but the trip consisted of a few days in California with my wife, son and daughter, then four days in Mexico and four days in New York City with just my wife and daughter and finally a few days in Atlantic City, Philadelphia and Washington DC by myself. I covered the award aspects in a separate post. […]

  4. Are you worried about the Hyatt GC fraud issue that people were discussing a few months back, or has that passed now? I’ve wanted to pick up some cheap Hyatt cards but that has put me off for now.

  5. Shawn,
    how can you use two free night certs at Hyatt Ziva, I tried it with two kids and it didnt allow me to. do I have to call Hyatt? or just dont declare I have kids?

    • The free night cert is only good for two people in the room. In our case the baby is free since she is under 3. You have to pay for additional people. You could pay 10,000 per person per night, but at that point might as well get another room.

  6. Travel is most definitely not free with points. There’s a ton of time involved setting these runs up. Its an awesome experience though!

  7. Great trip planning! Your trips sound very familiar but we are breaking them up and in a different order. No Hyatt Diamond for me but we just did the JetBlue run this past weekend and stayed at the Long Beach Hyatt Regency. We will use the SW companion pass for PDX to NYC in Sept. Then taking my mom to PV in January, CP for us and I’ll fly mom down from MT using my miles.

  8. A travel tip for Puerto Vallarta: Do a tour with Wildlife Connection! They’ve been in the Banderas Bay for several decades studying the local wildlife (namely: humpback whales and dolphins) and they’re science and education oriented and not at all a tourist trap like many of the other programs in the area. We swam with wild dolphins through them and it was an unforgettable experience! We spent a week in Puerto Vallarta and if you do nothing else, book with them! They’re wonderful!

  9. Congrats Shawn on the nice cobbling together of great deals and efficient point deployment. we just recently finished an essentially “free” trip to Cancun & Playa del Carmen (Zilara & Maya — even used local buses :-))….. lot of fun when it all comes together.

    As a thought for you, check the prices for those extra Hyatt PV Ziva nights via Chase Ultimate Rewards (using Chase UR points, assuming you have a stash there)….. May have learned this trick from you…. (or maybe it was Daraius) In any case, last May, I was checking the all-inclusive Ziva at Cabo San Lucas — and was startled to see it going for about 11k in Chase UR points then…. (half its Hyatt 20K/night rate — with various suite/upgrade options available too)

    Depends of course on when you’re going — and if PV would discount its rooms there during slow season….. may be quite worthwhile to check)

    Happy travel$!

    • PS: On our trip, single biggest expense ironically turned out to be those darned travel taxes, to and from Mexico…. (which yes, we also paid with much discounted SWA gift cards bought via Kroger :-)…..

      Was scoping out a return trip to Jamaica next month (to return to HI Resort there….) But …. nasty taxes to and from Jamaica are now near obscene…. over $150 per person…. (nearly double that to Mexico….) and so rethinking…. may go to PR instead.

  10. Is the hobby hard work – yes. Is all the work worth the payoff – most definitely. Have a great trip, you’ve earned it – in more ways than one!


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