How I Turned My Vacation Into A Profit Machine & Why I Would Do It Again

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Buying Gift Cards While Traveling

Recently someone posted in our Facebook group asking if others pursued their miles/points passions even while on vacation. In other words, do you continue this craziness while you are traveling or do you actually relax and enjoy yourself? While the answer to that varies for me, on a recent trip to Hawaii, I just couldn’t resist.

A Great Sale But Bad Timing

It all started earlier this year with an amazing Alaska fare sale to Hawaii from the West Coast. For less than $500 TOTAL for 3 tickets (utilizing a companion fare), my wife, daughter and I headed to Maui on the week before Mother’s Day. The flights to/from Maui (where my daughter and I were upgraded to Virgin America First Class) were from San Francisco, meaning we had to reposition. I was able to get us a cheap flight to SFO (where we spent 1 1/2 days before Hawaii), but flights back to Las Vegas were expensive so I held off.

Gift Card Season

When I booked the flights I didn’t take into account that our trip was the week before Mother’s Day. In other words, one of the best gift card buying times of the year. And there we SO MANY DEALS. I just didn’t want to miss out. Thankfully I was able to work in some of the deals into our trip.

First in San Francisco, we found a store that had a great deal only a block from our hotel. Since we had to pass it quite a few times coming/going, we made sure to stop in there and buy what we could. It was a good way to start the trip, but it didn’t end there. Of course it didn’t! 🙂

Buying Gift Cards While Traveling
Visiting the World Famous Sea Lions on Pier 39. About a 10 minute walk from our hotel past that store. 🙂

More Gift Cards in Hawaii

The same chain also had several locations on Maui and the timing worked out well for us. We actually landed late at night and stayed in a cheap(er) hotel by the airport since it didn’t make sense paying for another night at the Hyatt Regency when we would arrive so late. This allowed us to hit up 3 locations of this store in the morning before we headed out to the hotel. Score.

We ended up being in Maui for 5 days and that meant we headed to town once or twice. Lahaina (near the hotel) had one location of this store so we made sure to stop in there only when we were already headed out. (No special trips.) Then of course on the last day we hit up all 3 locations on our way back to the airport for our redeye flight home.

Buying Gift Cards While Traveling
Hyatt Regency Maui

Driving Home?

Unfortunately though flights from San Francisco to Las Vegas never really improved so I came up with an interesting idea. What if we rented a nice car in San Francisco and drove our way back home hitting up a bunch of stores along the way? Airfare was going to cost us about $500 for the three of us, but this way we could make a profit.

Buying Gift Cards While Traveling
Now that’s a savings!

To pull this off I decided it was time to use a couple of my National Free Night Certificates. Since I am Executive Elite, I can use my certificates for any car. To make sure I would get something nice, I rented a Premium SUV at the price of $321.07 per day. This netted us a nice new Cadillac Escalade for our drive home.

And so it went. We drove through the Bay Area hitting up some stores before eventually making it south where we hit up some more. Heck, as a side benefit I even got to check out the brand new Hyatt Place in Delano, CA. It is nothing special, but it may just be the most remote Hyatt Place in the U.S. 

Buying Gift Cards While Traveling
Our Escalade outside of the Hyatt Place Delano.

Was It Worth It?

If you made it this far you are either thinking that this is the dumbest thing you have ever heard or you completely understand it. What I will say is the drive home netted us over $3K in profit after factoring in expenses. It took us 1 1/2 days to get home, but those were working days anyway since the vacation was over.

We also made sure not to take too much time out of our vacation to buy gift cards and worked the buying into our schedule. Let’s face it. We were staying five days in a $1K per night suite in Maui for free because of stuff like this. I don’t feel the least bit guilty spending a few minutes buying gift cards. It is all worth it in the end.


So yeah perhaps I’m a bit crazy, but I do believe in taking advantage of opportunity when it presents itself. I can honestly say I have only done this occasionally while traveling and don’t make a habit of doing it regularly. But truth be told, when the universe gives you the ability to buy a bunch of gift cards and drive ten hours home instead of flying one hour, you take it! 🙂

What’s the craziest miles/points thing you have done while on vacation?

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. Lol a $321 car rental per day just to blow money. Even reading this blog feels like I’m supporting some drug lord in the mafia.

    • Hey Ferris. Thanks for reading or should I say reading sort of. The car rental was free using a free night cert. It clearly shows that in the picture and says that in the post. Whenever I rent at National and pay I book a midsize so I have access to the Executive Aisle. I would never pay that much.

      As for your last sentence, you’re sick. Get some help my friend.

  2. Shawn, what was your ROI? I think that is what you call it? Return on investment? Just curious. That all plays into whether a deal is worth it. Thanks. Gib

      • Thanks Shawn,
        I appreciate your posts and it is always good to learn from them. Thanks Again. Is there a link to learn more about gift card reselling? I know for a lot of you guys you have “Relationships” with sellers. How much do you have to sell to them to get those relationships? For me in the midwest, I’m really struggling to find any gift card deals to make money on let alone break even without a “relationship.”

  3. nice post bro.

    this is something that is always on my mind, but i never do it because of the potential risks. maybe i am being way too cautious. large purchases in different locations at the same store multiple times in a day outside of your address triggers many fraud alerts and puts eyes on your accounts. too many DPs suggest simple fraud alerts lead to people reviewing all your other suspicious transactions and shut downs. but i know you have many other organic spend so thats a good buffer.

    if i did this, my transactions would span multiple states and many different locations. Not sure how Citi and Chase would feel about that. And now, seems Amex is shutting people down too. but i guess its been working for you. appreciate the DP.

  4. How was Hyatt Regency Maui? I have a stay coming up in December and have booked same hotel. I am also arriving late at night and was thinking about maui beach hotel, near the airport. Did you stay there?

    Also any tips for Maui you can share?

    • Hyatt Regency is nice. We have stayed twice before and do enjoy it. Great pools and you can use the timeshare facilities next door as well.

      We did the Maui Seaside Hotel which is next door to the Beach hotel. Seaside is clean and nice and perfect for a quick stay. As for Maui, so much to do. From the Hyatt I really enjoyed the loop around the West side of Maui. Takes about half a day but it’s beautiful and not too crowded.

  5. I managed to snag 7k worth of GC at Staples to net 35000 fee free UR pts. I would gave grabbed more but since I accumlated 150k, I didnt want to max out the 200k/year limit with 6 months remaining until it reset. Assuming Staples was the deal, 60k in VGC along with BB’s 5k max monthly deposit would take a year to liquidate.

  6. For such a profitable thing to happen, you need two things
    A) A cooperative understanding parnter which I don’t have and
    B) You have to be obsessed with this hobby to the level that you are doing all that stuff even in your dreams. I do a lot of crazy stuff sometimes but I think I have not reached that level

    By the way, just out of curiosity where did you keep the cards while travelling. That must be a heck of cash which will make me so nervous.

  7. This post is not helpful, you are not revealing how you made money buying gift cards. I understand if you don’t want to reveal your secret. But if that is the case, what is the point of this post?

    • Read through all of the posts in this series. There is a lot of knowledge to gain. The skills required can be learned but for me to share with the world which deal it was would be irresponsible. With that said, over time I have shared a lot of info about how to find things and we also share the deals too. The key is to learn how to put those skills to use to pluck the deals that are most profitable. The title isn’t clickbait. It just isn’t.

  8. Sounds like a Staples deal 🙂 I bought $45,000 worth of VISA GCs and it was the last statement of card member year so my annual $50,000 limit reset a few weeks later 😀 Hoping for a repeat soon!

    • We cover a lot of profitable gift card deals on the site. The deals I took advantage of were covered the week of Mother’s Day here. I have to keep some secrets to myself though unfortunately.


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