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Guide to traveling efficiently based on your situation

May 11, 2017

While the writings I do are primarily focused on proving that you can see the world with a normal career, and how to spend your time abroad most effectively, traveling to these places is, admittedly, a big part of that. So, I’ll go over my best tips for finding flights for your trip based on what scenario you’re in.

People have asked about traveling with a family, on a budget, etc. I don’t know what it is like to travel with a family yet, but I know it changes things. I think the key to everything though is that flexibility and money are inversely related. The cheaper the flights the less convenient they are, buying two sets of two tickets may be cheaper than 4  on the same flight (so, maybe one adult, and one kid for one flight, the other two for the other flight, etc.). Keep these things in mind and do what you can where you can.

Another example of being flexible is when you want to go, when you want to book, and where you want to go. Below I have various sites I’ve described based on your potential situation. I  hope it helps and whatever I have missed feel free to include in the comments below, if something is better for a situation I’ve listed.


You know where you want to go, and you know when, but you have time to book…

Hopper – Download this app, put in the date and location you want, then sit back and wait. This app keeps track of flights for you, and not only lets you know if prices are good, but by how much they will fluctuate over time. This is great for trips you want to take far in advance. Say, you always go home for Christmas, or you want to visit Australia, tickets that can be relatively expensive, it will tell you the best time to book the flight.


You know when you want to go, but don’t care where…

Google Flights – There is a feature where you can choose the dates you want to travel, and it will show you the price to get anywhere in the world during that time period. It’s a good way to find cheap flights to somewhere different.

When it is time to book…

Skyscanner  – The go-to for most backpackers and travelers because, while mainstream travel sites aren’t too good at finding regional airlines, this site is great at it. It has a great range of airlines to choose from, is easy to use, and is best for when you are on a trip and decide last minute to amend your itinerary.

CheapOAir – Terrible name, but 24 hour cancellation policy. I’ve used them before and liked them, they often have the cheapest deal available.

JustFly – I just started using this, but have heard good things, and so far it seems to be on par with the two above.



Airbnb – When I am traveling with someone else, this is my choice for finding a place to stay. You can stay with other people, by yourself, downtown, suburbs, etc. Plenty of options, and great price points.

Hostelworld – Hostels are shockingly safe, a great way to meet people, and located everywhere. I stay at hostels when I am traveling alone, and usually stay in a private room, but dorm rooms are fine too, especially on a budget.

Priceline – For hotels, I love using the name your price tool. You need to be flexible and willing to book the day of, so don’t do it for festivals or big ticket events, but for casual times or dates it is a good idea. Just put in the lowest price it lets you, the area you want to stay in, and the stars you’re looking for, and boom, you’ll get a match. If you don’t get a match, then you can do it again and go up a bit higher (I’ve always gotten a match though).


Credit Cards:

(Note: One thing that you can consider is if you’re buying a new car soon. Consider signing up for 2-3 cards in the same week, then purchase the car as soon as the cards come in with multiple payments on the various cards. You can get a ton of sign up bonuses, and then either pay off the cards right away with cash, or get the car-refinanced at a bank and use the money from there to pay off the loan. (It shouldn’t take too much off your credit, and you might be able to get to get the car-refinanced before the cards hit your credit because it can take a month for them to get into the credit bureaus)

You can get more information from (the points guy), but here are my favorites to get you started. Sign up bonuses for credit cards are a great way to get travel money for things you would have bought anyways. In the past 3 years I’ve collected roughly $4,500 in sign up bonuses towards travel, and that’s without even trying. You can get pts for hotels (the Marriott Rewards card is good) and airfare.

Chase – Chase has a ton of options for every credit rating, and I believe, has the best rewards programs in the business. The standard deal is for every dollar spent you get 1 pt, and for every pt you either get 1 mile to transfer to one of eleven different carriers, or you get 1.5 cents towards travel.

I suggest having two chase cards, I prefer the Ultimate Freedom Card, which has 1.5% pts (2.25cents/pt towards travel), and the Sapphire Reserve card which carries a $450 annual fee, but you get $300 back towards travel expenses, 3x pts on dining and travel, and a ton of other great perks. So, basically, you buy travel and dining on the reserve, and everything else goes on the Ultimate Freedom.

American Express – I have never signed up for an American Express card. The minimum spend requirement to gain the bonus is high, the points aren’t as generous as Ultimate Rewards through Chase, and American Express isn’t as widely accepted as Visa. So, I’d skip. There are some great articles out there about American Express losing the  rewards war against Chase, and so you can get some good signup bonuses from them as they try to fight back, but I’d only do it for big one-time purchases.

Barclays – The Barclays card has a great sign up bonus for travel. I recently booked two flights, got $600+ reimbursed, and I just had to spend $4k in 3 months on things I would have bought anyways. Thing is, it isn’t as good as Chase Ultimate Rewards, and so I will drop the card.

Southwest – For domestic travel, you can’t beat the Southwest card. Personally, I don’t have one anymore, but I did get the signup bonus and cancelled, and plan on doing so every couple of years. The signup bonus should pay for at least 2 flights round trip, which isn’t bad at all. I don’t use it day-to-day because of my need for international travel, but if that isn’t your thing, then this is the way to go.


I’ve signed up for, and dropped the Southwest Card, Marriott Rewards, and Barclays card (twice now), which have great sign up bonuses, but the annual fee either isn’t worth it, or you want to get another sign up bonus later.

Business Cards- There are some great rewards here as well, but you have to have a business to take advantage of it. So, I’d recommend only utilizing a business for this purpose if you are careful, pay attention, and are just truly dedicated to traveling on someone else’s dime.

Things to be mindful of…

Signing up for multiple credit cards can have a negative impact on your credit score due to too many inquiries on your credit. However, if you keep some cards without annual fees, over time, this will be good because not only will your total accounts increase, but your average age of account will remain high, even if you get a new line of credit (house, car, etc.)

A lot of people are scared of opening too many accounts, but even people who open up cards for the bonuses for a living, like the guys at have credit scores over 800, and mine is getting close to that as well. So, short term it might hurt you (especially since it will take down your average credit history), but overall, it’s not a big deal. Just maybe wait to buy a house before getting more cards for the bonus.

5/24 Rule – This rule is basically that you can’t sign up for 5 credit cards within 24 months from Chase, and possibly other card providers. Be mindful of this, as you may want to be choosy about the cards you go after. Some people had maxed out their allotment before the Sapphire Reserve came out, and they missed out on $1,500 worth of travel for $4,000 of spend. (note: this follows your social security number. So, you can’t get out of it.)




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