Sweet D’s Travel Hacking Tips

I’ve posted about my general travel tips, and my packing tips, but you may be thinking:

Thanks for the tips, but how do you actually do it? How do you travel two dozen times a year and afford it and actually take the vacation? How do you get upgrades all the time? I want to do that! 

The first advantage I have in doing this is that I’m childfree by choice and happy about it. I don’t have to spend money on diapers and daycare. I don’t have to take vacation days when daycare is closed or my kid is sick. I have friends with kids that travel a lot, and friends that are trapped. Be happy with your choices.


For some people, it would be totally out of their comfort zone to leave the town they’ve always lived in and go look for Komodo Dragons. For me, the converse would make me equally uncomfortable.

Keeping Points/Miles from Business Travel

I have an amazing job that I’ve wanted to do since I was four years old. I’ve worked really hard at it and have a Masters degree in Engineering and lots of years of experience. This is a privilege I have that not everyone that wants to travel for free can take advantage of, so that’s really the big “secret” that sets me apart. I’m lucky that the job I have sends me to Florida, Denver, Central California, and occasionally a few other places and I didn’t have to pay for the tickets and could build up all the miles. I keep all the points and miles I earn on business trips.

You have to pick an alliance and stick to that as much as possible. While staying within my company’s travel rules, I fly American Airlines/oneWorld alliance whenever I can, and I always try to find a Marriott. I originally went with American because my ex-father-in-law was a pilot for them and it was family loyalty. It’s what I’m used to and comfortable with now, I could status match and move if I needed to. American is a part of the oneWorld Alliance and it’s extremely extensive. I use all the points I earn to travel on their partner airlines. Same with hotels – I use Marriott. I can almost always find a way to burn my accumulated miles at some point on vacations. I’ve found that Marriott has consistently given me the best customer service and value for my money, even though they’re now the largest hotel chain in the world.

But, you also have to know what kind of traveler you are – if you’re not earning free points and miles through work like I am, and you’re only traveling once a year, this alliance rule isn’t as important for you. You could go with the cheapest option. But know that if you go with the super cheap airlines like Ryanair/Spirit/WOW, you’re going to get nickle and dimed on the back end and it won’t necessarily be as cheap as you think it’s going to be. And some of the super cheap airlines have gone bottom up lately and you could be screwed if you don’t have travel insurance.

Should you get travel insurance? I saw a quote once that said “if you can’t afford travel insurance, you can’t afford to travel.” – Really read the fine print. It’s not going to cover as much as you think it should. But I think it’s a smart idea. If you’re going to scuba dive, you absolutely have to get it, IMHO.

Sticking with one alliance & upgrades

Sticking with one alliance is also how I get upgraded so often. If you’re flying frequently, you’re probably chasing status. People on the upgrade list are ranked by their status. The more you fly, the closer you are to the top. “I’m on my honeymoon, can you put us in first class for free?” rarely works anymore. In fact, I’d be pissed if I had given the amount of loyalty I give oneWorld if someone just asked or tried some hack and got upgraded and I didn’t. I would totally status match and switch airline alliances and airlines don’t want to lose the business of their frequent fliers.

How upgrades work on American Airlines: The more you fly the more “upgrade tokens” (I made up that word) you get towards upgrading. They’re called “500 mile upgrades” because each one is worth 500 miles of having your butt in a seat up front. If I fly from LAX to Orlando (MCO), it’s 2210 miles one-way. You have to round up to find out I need to bid five 500 mile upgrades to get up front. Then AA looks at everyone that’s bid for an upgrade and moves them up front in order of their status. If you don’t get moved up, then it doesn’t cost you any of your upgrades. If you do, they take them from your account. This is true if you have Platinum status or lower. If you have Platinum Pro (which I should get in 2020) or above then you are always automatically put on the upgrade list and it never costs you any more upgrades. So the more loyalty you have to one brand, the more you earn, and the more you get in return at higher levels.

The more loyalty you have, the more they want to retain you and pay you back. Another example: I’m Marriott Titanium Premier Elite (Lifetime). I get a 75% bonus on points for my stay. If the base earn at a hotel is 1000 points, an average Joe that stays a handful of nights a year is going to walk with 1000 points. I’m going to walk with 1750. Someone that’s Gold will walk with 1250, even if we’ve all spent the same amount. I’m going to accumulate points towards my next free vacation way faster than Joe will. Plus I’m guaranteed to get upgraded if there are unbooked suites available.

I would stay in AirBNBs more often, because you can often get them cheaper than you could a Marriott – but if I’m not paying for my rooms 80% of the time, the points that I earn is like a free bank account that I can use towards future travel. AirBNBs do not have a rewards system at this time, so that’s why I don’t consider them. Plus if you’re not paying for it, why not get maid service and the safety and security of knowing you’re getting a consistent product? Do the math for the big picture – free breakfast and amenities can count against a cheaper rate. I will say – on group vacations it’s very often much easier or more affordable to skip the chain hotels.

At a certain point you might be close to status for next year but not quite make it. You can do the math and see if a Mattress Run or a Mileage Run is right for you. In 2016, I was one night away from keeping my status. I payed out of my own pocket to stay at a hotel down the street from my house because I was going to earn so much value with the bonus points in 2017 that it was worth it.

I’m going to let you in on a trick on how I get hotel nights for free when planning a group trip. Utilizing the 75% bonus on points earned is the key. I calculate how many points I would earn if I reserved all the rooms for a group at my higher rate using both my bonus and my Marriott credit card. If that’s enough for me to cover one or more nights for the group, I pass it on and then spread the savings evenly. I use the points I had previously banked (since you won’t receive the points until after check in) because I didn’t want to earn off my friends. It made it super reasonable and you get to use the Titanium perks. Marriott does have a limit of you can only earn off three rooms, and the Marriott member has to stay in one of them. I used this when we were in Cape Town and had six rooms for six nights and saved us a bunch of money.

I plan everything. I am my own travel agent. That saves me money.

Flexing time to get more vacation days

With my company I can use flex time to get extra vacation days. I have to work 80 hours every two weeks, but I don’t have to work 8 hours a day. If I work 50 hours one week, I can work 30 the next week. If I want to take a two week vacation, I split it across two pay periods:

  • Pay Period One
    • Week one: Still at work, but work 48 hours, or four 10 hour days and one 8 hour day. Leave Friday night or Saturday morning.
    • Week two: First week of vacation. I only have to log 32 hours of vacation instead of 40.
  • Trapped weekend – two bonus days I don’t have to take vacation for
  • Pay Period Two
    • Week three: Second week of vacation. Log 32 hours of vacation. Get home on Sunday.
    • Week four: Repeat the work schedule from week one.

I’ve been gone for sixteen days and took eight days of vacation. Some times I’ll work even more hours on week one or four, sometimes I work less. Sometimes I come back on Saturday so I can recover on Sunday or have a buffer day in case of flight delays.

Credit Cards

You have to play the points and miles game. Follow The Points Guy on social media and check out his blogs. He’ll teach you how to use credit card sign up bonuses to earn extra points and miles when you’re not traveling. (Consider everything carefully, he makes his money by the credit companies paying him for every reader that clicks through and gets their cards on his recommendations, but he’s helped me with what I’ve went with). You use different credit cards for different expenses, because they give different bonuses. I get 3x points for Travel on my Chase card, but 5x points on my Marriott card at Marriott properties. I use Chase for buying plane tickets and charge my hotel stays to my Marriott card. This advice only works if you pay off all your credit cards in full every month. If you are paying interest charges, then it’s cancelling out all the free travel perks that you’re earning. Use credit card shopping portals. Follow your airlines on social media to see what special contests and bonuses they’re doing. This is a hobby that you have to invest time in to make it work.

I put everything I possibly can on credit cards. Less than $2 at a coffee shop and I have cash in my wallet? Charge it. Every point counts – they do add up! I put the down payment on my new car on my credit card – hello bonus points! If I could, I would be definitely paying my mortgage and my taxes with my credit card. (There actually is a way to do that – but there’s a fee.) Do the analysis – check and see what the points/miles you’d be earning are worth, consider how badly you need them, and see if it’s more or less than the fee.

There are all sorts of Travel Facebook groups and notifications you can sign up for deals. If you’re flexible about where and when you’re going, then you can get some awesome stuff. (I get the emails from Scott’s Cheap Flights and let him do the work for me!) If you have to go to Australia to visit family when you have time off for Christmas break, you’re going to spend out your nose. But if you’re flexible and can go anywhere and don’t have many time restrictions – you can get a glitch trip that takes you all the way around the world for $177 like I did. South Africa has always been on my bucket list, but all my friends jumped on a $600 flight to Johannesburg for spring of 2018, I jumped too and had to rearrange a bunch of other plans for when I would take other trips.

Sometime later I’ll add in a section explaining the difference between and perks of using credit card points versus airline miles. Thanks to everyone that’s been reading for so long!



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