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Travel Success Tales: Last-minute anniversary trip to Maui for $11/person

It’s now close to three years since I started earning miles and points via credit card sign-up bonus. I don’t consider myself an expert by any means, I’m just another guy who found a way to supplement his desire to travel around the world for nearly free. I’ve made many mistakes along the way, but I’ve also had my fair share of success stories. They were successful enough that I was featured by two premier travel bloggers:

The Points Guy – Making Family Vacations Affordable

Million Mile Secrets – Success! Under $600 for Family Flights to Maui and Europe!IMG_0340.jpg

What makes it worthwhile about blogging my own travel success stories is when someone approaches me, asks me questions about ways to travel using m18090724_10103073948713995_1451081833_oiles and points, and then be instrumental in helping them accomplish their travel plans. This was the reason I decided to include a new section in my blog, Travel Success Tales.

To kick off my series of  Travel Success Tales, I’d like to share a story from DaddyTravels reader, Bryan. He is one of my neighbors in my community. Bryan came across my site when I shared my travel blog on our neighborhood’s Facebook page. He and his wife, Emily, recently came back from Maui, and here’s how they booked their last-minute vacation using points earned from credit cards.

When did you start earning miles and points from credit cards?

I first got into the points game back when the Chase Freedom promotions were giving 5% cash back on everything. It was probably my 2nd credit card back when I was in college. Back then though I wasn’t very smart about how I used them. For example, I would cash out every time I earned a $50 credit. Thinking back to that now, those points could’ve been used in a much “smarter” way. It wasn’t until I saw a lot of people (including DaddyTravels) blogging about how to get the most mileage out of your points that I started to get interested in it, but I’ve never really spent the time to understand how to do it.  Over the years, we’ve collected points across various credit cards through the Chase Ultimate Rewards program and points I had accumulated from flying for work on a few different carriers. We had been stockpiling them for quite a while knowing we wanted to do something with them, but not how to get the most out of them.

What prompted you to go on vacation?

My wife and I were celebrating our 3rd year anniversary this past April, and I was in charge of planning a trip. We wanted to go on a tropical vacation, somewhere that would be warm, and had lots of nice beaches to relax on.

What was your goal on this trip?

Despite numerous attempts, I somehow found myself two weeks out from our anniversary with no plans in place yet, so I guess you could say that the goal of my trip quickly became to go on a trip!


Did you run in to any obstacles or challenges in planning your trip?

Usually my wife plans our trips (she’s good at finding great deals and typically has a good idea about where to go), but right now she’s on the last stretch of her graduate program while working full time, so it was time for me to step up to the plate. The most challenging part of planning our trip was probably the fact that I was the one doing it!

How did you overcome those challenges?

As the two week window started closing in on me, I remembered that my neighbor was a travel blogger. I remember thinking to myself, “Bryan you need to ask for help”. I sent Jason a message via Facebook Messenger, and before I knew it we were chatting about a list of places we wanted to go.

How did you book your trip? What points program did you use?

We used the British Airlines site to book an award flight, and after transferring some points from Chase Ultimate Rewards to our British Airlines Avios account (which only took a few minutes), we were on our way to booking the last two seats on the plane to Maui! We used a total of 50,000 Chase Ultimate Rewards points and all we had to pay out of pocket was $11.20 each, a total of $22.40.


How about for your accommodations? Where did you stay?

For our accommodations, we were lucky to find a condo in Kaanapali that happened to have five nights of vacancy on VRBO that the owner was looking to fill. This probably was the one time booking “last minute” played in our favor because it was fairly discounted given we were just about two weeks out.



What were your lessons learned in planning your Maui vacation?

I think I suffered a lot from “analysis paralysis” in the past. The thought of trying to “figure it all out” just seemed overwhelming and the thought of “wasting” our points led me to not even using them at all! For some reason, I felt it would be a lot more complicated than it really ended up being, and I thought using points to travel was something only a few people who spent all day researching and doing all sorts of fancy tricks could pull off. So at the end of the day, I guess you could say I learned that sometimes we can psych ourselves out from doing something. Reminds me of that saying, “you miss 100% of the shots you don’t take”. At the end of the day they’re just points, and there are more important things in life, like sharing memories with family and friends.


Any last thoughts regarding using points/miles to travel?
Using points to travel is a great way to create memories without breaking the bank and it’s not as a confusing or hard as it yohelpful.jpgu might think! With blogs like DaddyTravelsNow, it makes it really easy and what sets his blog apart is that it isn’t just information on a website but there is a person behind it who is very responsive and helpful for first-timers like myself. In fact, we’re working on another trip right now to celebrate Emily’s upcoming graduation, looking forward to sharing about our experience after that trip!

First of all, I’d like to thank Bryan for trusting me to help him and Emily book their last-minute anniversary vacation to Maui. Just a quick backstory as to how Bryan and I first met. He posted a free espresso machine that he was giving away for free on our neighborhood’s Facebook page, I quickly replied, and picked up the machine later that day. Who knew that in some shape or form, I’d be helping him book a trip to Maui? To think, it all started with coffee.

Another thing that hit me during this interview was the importance of the “it’s never too late to book” concept. I can still remember when Bryan sent me a private message on Facebook. I was tired from volunteering all-day at my kids’ track meet. I was about to take a nap. But when I saw his message come through, it woke me up since I love working on little challenges when it comes to traveling for nearly free. I think he and I exchanged messages for a couple of hours, and he immediately took action, he listened to my tips, and he grabbed the available reward flights with British Airways and just like that, he was able to book two roundtrip tickets to Maui.  

Bryan and Emily’s trip, although it was last minute, took place on one of the semi-high seasons for Hawaii. They went to Maui towards the end of March through early April. This was during the height of Spring Break. One round trip ticket to Maui from LA could range from $500-$700 each (or up to $1,400 for two). However, since there were available award seats with British Airways, Bryan and Emily did not pay anything close to $1,400, instead, they only paid $22 out of pocket.

To Bryan and Emily, I look forward to working with you and plan your next vacation. We will make sure find ways to help you maximize your miles and points. Congratulations again to both of you on your 3rd wedding anniversary. Cheers!

To those inquiring minds, Bryan and Emily used their Chase Ultimate Rewards, these are rewards that you can get from signing up for cards such as the Chase Sapphire Reserve, and Chase Sapphire Preferred. Both cards offer a sign-up bonus of 50,000 Chase Ultimate Rewards, and when used wisely, the 50,000 points could be used towards two roundtrip tickets to Hawaii or anywhere in the US, or if you earn a bit more points, it could also help you get to Europe or just about anywhere in the world. img_2291-2These two cards are DaddyTravels‘ favorite credit cards and I wrote a whole blog entry as to why these two cards should be part of your portfolio of points earning credit cards.

My other favorite credit cards with special promotions:

Another card for FREE hotel stays is the Marriott Rewards
Lastly, for more FREE hotel stays, the American Express Hilton Honors card where you can earn 80,000 bonus points – great for Hilton brand hotels worldwide. hilton-hhonors

If you have your own success story to share, if you’ve learned something from me and my strategies, please let me know, I would love to hear about how you maximized your miles and points in your travels. Send me an email at




17 thoughts on “Travel Success Tales: Last-minute anniversary trip to Maui for $11/person

  1. I love earning miles. I became a huge fan when I started seeing my rewards work and took a free trip with them. With a family of six I need all the help I can get and I love seeing people help others use reward programs.

    1. Awesome! We’ve been traveling arond the world with them for nearly FREE. It would not have been possible without these miles and points. I, too, have a party of 6, we have 4 kids. We’re happy to say that we’ve all been all over Europe, Hawaii, NYC, Canada, Australia….and soon, Asia. Any questions, let me know 🙂

  2. Sometimes it is so tough being Canadian. We don’t have the same credit cards or perks, but I still have been totally inspired by this post to go out and find what we DO have. PS: My husband and I travelled to Europe in Biz Class using points from Amex. Heaven!

    1. Thanks, Carol. I have family in Vancouver, and they, too, want to find the same credit card deals that we’re getting here in the US. You might want to try and follow Canada Points Guy on Facebook….he might be able to lead you to the right path. But if the path leads you a credit card that’s based here in the US, please feel free to check with me.

  3. Great idea for a series! And it’s true, it’s never too late. My hubby just decided this past Monday to go to Kauai and now we’re leaving Sunday – hooray!

  4. my husband loves to travel but after having a few kids it gets hard. thank you for helping us find a way to do it better. i look forward to more posts like this. thank you.

    1. Thanks for the feedback. If you take a look at my other posts, you’ll see that we have FOUR kids…so it is very expensive to travel with 2 adults and 4 kids. But I have to tell you, in 3 years, I have not had to shop around for airfare. We’ve been flying for nearly free…$11 each to Hawaii…..$125 each all over Europe….and we’d stay at 4-5 star hotels in Europe and everywhere in the world for FREE. We just got back from NYC and Canada, our hotel stays would’ve been over $5000 – we got them all for FREE (for 9-10 nights) Any questions, let me know 🙂

    1. Awesome!!! Let me know if you have any questions. Bottomline, it’s all about getting right credit card, and I would start with the credit cards I listed in my blog entry.

  5. Wow, what a great deal! I’ve had flyer miles in the past, but it just seemed to take too long to build up. I may have to look into getting it again!

    1. Hi thank you. If you build your frequent flyer miles by “flying”, then yes, it will take a while to build. Nowadays, you don’t need to be flying a lot to build miles. You can simply apply for credit cards that offer bonus points (that can converted to miles). For instance, this card that I highly suggest could easily get your 2 roundtrip tickets to Hawaii or anywhere in the US….or even anywhere in the world. Any questions, please let me know

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Editorial Disclosure: Opinions expressed here are author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.
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