10-Year Wedding Anniversary Trip to Vegas, L.A., and Hawaii for Nearly FREE After Just 6 Months of Miles & Points Earning!

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Welcome to the next installment of our Reader Success Series where Million Mile Secrets Readers share how they booked a trip with miles & points to get Big Travel with Small Money! This interview has been edited for content and clarity.

Katie is our newest reader success story to show folks it’s possible to travel without spending a lot of money.  If you would like to be inspired by more stories like this one, take a second to subscribe to our newsletter!

hawaii grand hyatt
View From Our Hotel Room at the Grand Hyatt Kauai

What’s your name and how long have you been involved in the miles & points hobby?

Hi, my name is Katie and I have been involved with the miles and points hobby since June of 2017!  Before I got into this hobby, I would book my trips like most other people.  I’d save up cash all year long, and use sites like Expedia to book hotel stays directly with hotels.  I had just 1 credit card that I used for all of my purchases, and I simply redeemed them for statement credits!

As someone who loves to travel and stay at upscale hotels, this was really expensive.  And although I did earn points for booking on Expedia, it felt like a really slow way to earn points!

What initially piqued my interest in the miles and points hobby was when my Dad started telling me about all the amazing places he was able to travel to because of his credit cards.  He would regularly send me articles from sites like Million Mile Secrets, although I usually lost interest as soon as I read anything about an annual fee!  That’s because it just seemed too good to be true, and I wasn’t interested in paying any fees for a credit card.

But my Dad was persistent, and when he started sending pictures on top of the articles, I started to come around.  Seeing pictures of his $1,000 per night room at the Park Hyatt Paris-Vendome, for instance, was convincing enough for me to take another look into this hobby!

What was the goal of your trip?

My husband and I wanted to celebrate our 10 year wedding anniversary by having a luxurious vacation in Kauai.  The plan was to be gone for 11 days while having Grandma and Grandpa watch our 2 boys at home.  We had planned on spending 2 days in Los Angeles, 2 days in Las Vegas, and then 7 days in Kauai.

Katie Success Story
View of Napali Coast From Our Helicopter Ride

How long did you collect miles and points for your trip?

For this trip, it didn’t take too long.  It took less than 6 months to earn the actual points for this trip.

Which points did you save to take your trip?

We used a combination of Hyatt points, Chase Ultimate Rewards points, and Southwest points.

Which cards would you recommend to open for a trip like yours?

We started with the Chase Hyatt card (no longer open to new applicants).  Currently, Chase offers The World Of Hyatt Credit Card which has a different welcome bonus and perks.

I’d also recommend either the Chase Sapphire Preferred® Card or the Chase Sapphire Reserve® cards.  Because of Chase’s rules only allowing new card members to have 1 of these cards in the Sapphire product family, both my husband and I each went for the Chase Sapphire Preferred®.

Finally, I’d recommend any of the Southwest credit cards from Chase.  Earning the welcome bonus goes a long way towards qualifying for the Southwest Companion Pass, which is a really sweet deal!  I applied for 2 Southwest cards on the same day which ended up being approved, and after earning the welcome bonus on both cards I pretty much had enough points to qualify for the Companion Pass already!

Note:   It’s no longer possible to have 2 personal Southwest cards at a time.  However, you can still open 1 business (the Southwest Rapid Rewards® Premier Business Credit Card) and 1 personal (Southwest Rapid Rewards® Plus Credit Card, Southwest Rapid Rewards® Premier Credit Card, or Southwest Rapid Rewards® Priority Credit Card) to earn most of the points required for the Southwest Companion Pass.

In total, the points I was able to earn on my cards, along with a few perks like annual free night certificates, were enough to cover 1 night at a Hyatt hotel, flights to and from Kauai, and a rental car in Hawaii!

Katie Success Story
Another Fabulous View From One of the Hikes We Went On!

How did you search and find the award flights?

For the flight to Los Angeles and the flight out of Las Vegas, I just booked tickets on the Southwest website.  I used a total of ~25,000 Southwest points for these 2 flights combined.  And because we had earned the Southwest Companion Pass, my husband basically flew with me for free!

For the flights to and from Hawaii, I transferred points from my Chase Ultimate Rewards account to United Airlines, and then booked on the United Airlines website.

Overall, the process was pretty easy.  Without points, I would have paid almost $2,500 for 2 round-trip tickets.  But instead, I paid only ~$22 total in taxes and fees by redeeming a total of 90,000 United Airlines miles.

How did you find your hotel accommodations?

For our hotel in Hawaii, I just jumped on the Hyatt website to find award nights.  Without our points, a 6-night stay would have cost over $3,800+!  Instead, we used our Chase Hyatt free night certificates for 4 nights (no longer available with the new World of Hyatt card), and then the remaining 2 nights were covered with 25,000 Chase Ultimate Rewards points which were then transferred to Hyatt, and 25,000 Hyatt points we had earned through regular spending on the Chase Hyatt credit card.

I also took a tip from another reader success story here on Million Mile Secrets and emailed the manager of the hotel in advance, kindly asking if any room upgrades would be possible because we were celebrating our wedding anniversary.  He was able to come through and the room we ended up with was amazing!

The hotel in Los Angeles was paid for out of our own pockets on the Priceline website.  We stayed at the Kimpton Hotel Wilshire for around $220 per night.

And finally, for our Las Vegas hotel, I booked a hotel directly through Bellagio for around $250 per night.

I could have paid for those hotels with points, but I wanted to save them for another trip where I could get even better value.

Katie Success Story
The View From the Grand Hyatt Kauai Hotel Lobby Looks Like a Postcard!

What was the most challenging part about planning your trip? How did you solve it?

I had never booked award flights before, so I initially tried to find the best deal I could by searching for cheap award flights.  After reading some articles, I thought I could get a good deal flying from the West Coast to Hawaii, but I couldn’t figure out the logistics of it.  It also didn’t help that the award flights I did find kept coming up as fully booked and sold out!

I eventually just gave up, found a flight on United Airlines, transferred over my Chase Ultimate Rewards points, booked it and called it a day.

Katie Success Story
One of the Views From Our Catamaran Cruise

Give us a few recommendations or tips for what to do at your destination.  Parks, restaurants, hidden gems, etc.

Kauai is absolutely gorgeous and I can’t say enough great things about the island!  Before I went, I read the book The Ultimate Kauai Guidebook – Kauai Revealed.  I’m so glad I did this, because with all the money we saved on hotels, flights, and car rentals, we were able to spend our money on other activities instead!  We took a helicopter ride, went zip lining, and took a catamaran cruise!

If you do take the cruise, I’d recommend departing from the north side of the island, because that way you’ll get to spend most of the time cruising along the Napali Coast.

The Tidepools Restaurant at the Grand Hyatt Kauai was also phenomenal and a perfect way to have spent our anniversary night.  We also went to the Luau at the Grand Hyatt Kauai which had great food and unlimited drinks!  It’s offered 2 times per week and I’d highly recommend it.

Lastly, there was a great hiking trail that started near the hotel, that will lead you to a cliff overlooking the ocean.  It’s an easy hike and you’ll get breathtaking views!

Katie Success Story
Another Awesome View From Our Catamaran Cruise

What did you learn about yourself on the trip?

I learned how much I truly enjoy traveling and seeing the world.  I also think miles and points is just such a great hobby and I can’t stop talking about it to friends and coworkers.  I think I’ve turned into my Dad!  It’s incredible being able to have these amazing experiences, at great vacation spots, all at a killer deal thanks to miles and points!

Katie Success Story
Views From Our Hike

What would you say to folks looking to plan a similar trip?  Or to those who haven’t taken a miles & points trip yet!

Kauai is an amazing place that everyone should experience!  A number of movies have even been filmed on the island, many of which my husband and I have been trying to watch ever since our trip has ended!

If you haven’t gotten into the miles and points hobby yet, I’d highly recommend it.  Start slow and go at your own pace!  If it’s any encouragement, I’ve only just begun myself, and yet I’ve had a wonderful time learning all of the fun ways to earn and redeem points!

Want to Share Your Story?

If you’d like to be considered for our reader success story series, please send us a note!  We would love to hear about how you travel with miles and points!  And if you want to get more stories like this one delivered straight to your inbox, please sign-up for our email list!

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Million Mile Secrets is a contributor to Million Mile Secrets, he covers topics on points and miles, credit cards, airlines, hotels, and general travel.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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2 years ago

What’s missing from this story is how did the writer spend $14000 approximately in manufactured spend to trigger the spending?

I know so many card churners who apply for cards and then spend on extra things to meet the minimum spend. The writer is probably worse off and has less cash on hand in the pursuit to get the binus points. It makes the free travel quite an expensive ordeal.

Pls provide additional details on what you spent on. Otherwise the key point is missing.

Reply to  Max
2 years ago

Hi Max! Wow- I really did spend a lot! You got me worried so I pulled up my old credit card statements to refresh my memory as I know I definitely didn’t spend money on anything that I normally wouldn’t have just to get the bonuses. Sorry for the long response ahead, but here are the details…
We put all spending on our cards. Whenever I get a new card I switch all of my utility/cell/cable bills to that card. Outside of our normal everyday spending, here are the other items that helped us hit the spending requirements.
The biggest was approx 5500 in medical bills (unfortunately). If I didn’t have that then I wouldn’t have applied for these cards so close together and it would have taken longer to get all of these points. I actually split up one large medical bill onto 3 different cards. One tip is to not pay for medical bills directly from your HSA account. Put it on your credit card and reimburse yourself.
We had 2 weekend trips so totaling those up (2 flights, 3 hotel nights) we spend approx. 1500. I didn’t have any points to use for these since I was new to the hobby. Both of my kids birthdays are in the summer so 2 parties was maybe 500. We had a week vacation at the beach which was already paid for but we had extra expenses that week for food/fun which was maybe 800. We spent 1600 on a home sauna- this was a big purchase for us and something we wanted for years and had already saved for. We just timed the purchase. Same with a few other things- I thought about future purchases I knew I would make and just made them early. Example was I did some early Christmas shopping and also bought a few NBA tickets earlier than I normally would have for a few games I wanted to go to. This is all spending I would have normally done, I just timed it and spent it earlier. Also, when reviewing my credit card statements, I clearly have a problem eating out and spend more than I should at restaurants. Looks like I need to start cooking!!!

Tammy Mauk
Reply to  Katie
2 years ago

Just trying to learn something…..So I can actually do this? Use my credit card to pay medical bills, then how do I pay myself with an HSA?

Reply to  Tammy Mauk
2 years ago

Hi Tammy, From personal experience, anytime I get a medical bill there seems to be an option to pay the bill online with a credit card or I call and make a credit card payment over the phone. Always make sure you aren’t being charged a fee for paying with a credit card. In regards to reimbursing yourself from your HSA, it really depends on where you hold your HSA account and what their procedures are. Personally, my HSA is with an online bank and I can electronically submit receipts/bills and get reimbursed. If you have checks with your HSA account, you could write yourself a check for the amount (make sure you reimburse yourself the same year) and keep all receipts/ bills/ explanation of benefits for your records in case you ever get audited. With that being said- consult a licensed tax advisor
On a side note, just in case someone isn’t aware, not just anyone can open an HSA- you have to have a HDHP that qualifies- consult a tax advisor.

Reply to  Katie
2 years ago

There you go. There is a lot of discretionary spending that you could have avoided. My point is that there is always another side of the bonus point game that people don’t realize.

Curious how your medical bill was 5500. Most employer based insurance plans have an annual out of pocket max that is 2500 or 3000. Was this bill over several years?

Either way, spending 500 on birthdays and on hot tubs and vacations when you have so much in medical bills seems outrageous..unless you are very wealthy. Wealthy people have cash and not points. Just saying. Thanks for the detail response and cut down on eating out. This game is created by credit card companies and you got sucked into it. When in doubt, they want you to spend more to meet the minimum spend for bonus points.

J. Morris
Reply to  Max
2 years ago

Seriously, go back under your bridge. Life is about living, not judging others about how they choose to spend their money and live their lives. I applaud them for their trip!

Reply to  Max
2 years ago

Hi Max, For the comments around my health insurance, my employer only offers high deductible health plans and my employer and myself both contribute to my health savings account. My family annual deductible is high at 7k. The medical bills were unfortunately over 3 months. I won’t get into that detail. I had the money to cover the medical bills in my health savings account but paid with my credit card and then reimbursed myself.

Reply to  Katie
2 years ago

Thanks. Wish you a wonderful marriage and life ahead. Nice post on the blog. Keep churning.

2 years ago

Happy anniversary. Sounds awesome. Why did you transfer points from chase portal to United verse just booking direct in the chase portal? Same thing with Hyatt points? Don’t you get more value on chase portal than transferring to hotel and airlines?

Reply to  Nick
2 years ago

Hi Nick! In these cases, I ended up getting a better deal transferring my points to Hyatt and United instead of booking directly through Chase’s portal. For example, at the time of my stay one night at the Grand Hyatt Kauai was approx. $590 when you include tax and resort fee. The room was 25,000 Hyatt points. Therefore, I got a value of approx. $2.36 per point (590/25,000) which is a higher point redemption than I would have gotten with Chase (which for me was $1.25 with my Chase Sapphire Preferred card). Same thing with my United flights, although I’m sure there was a way to get these flights using less points but I am not experienced at booking reward flights yet.

2 years ago

I totally agree on the cash hotel nights instead of points in some instances. I look for the AAA card rate since booking with 3rd party sites more than likely will not give you points.