Travel for Cheap: A How To Guide

How to Travel for Cheap

I am often caught up in conversation on how I travel for cheap so I thought I might write it down for you.

Flexibility: This is simply the most important part of traveling on the cheap. I usually travel “to the fare” as opposed to traveling for the destination. I shop the flights or the hotels more than I shop the destinations. I have my bucket list handy when I get ad emails or read about a deal, just in case.


The second most important thing is to put yourself in a position where “cheap travel” can come to you. In this case that means you have to subscribe to the newsletters and email blasts from a lot of providers. It’s not a bad idea to have a separate email account for this that you check once a day.


Check the Ads: Yes, I actually subscribe to and read all of the emails I get from the providers of my choice because the airlines and hotels frequently have “flash sales”. I put up with all the garbage they send to snag a deal here and there. To answer your question yes, they are worth it from time to time. However, MAKE SURE YOU READ THE FINE PRINT. A lot of the flash sales require booking at certain times and then traveling at specific dates, which are usually months down the road.


Timing is everything: Hit them where they aren’t. Fly when everyone else isn’t. Summer vacation will take your wallet and practice Judo on it. It costs nearly double to fly during summer vacation or Thanksgiving or other typical travel holidays. You’re much better off traveling during off peak times.


Combine flexibility with sales and magic can happen.


If the right deal comes up to a place I’m interested in seeing, I jump on it. Maybe it isn’t the top of my list, maybe it’s not the best time of year, but if I can see 3 places on the lower end of my bucket list for the price of one of the middle ones you bet your bottom dollar I’m going to do it. Half the time a flash sale will pop up to a place I have zero interest in and I still try to do it. Often times these are the best trips. EVERYWHERE has something interesting to see and do. A few years ago we were visiting a friend of mine in Atlanta and he decided that we should drive to Tennessee. We had absolutely zero desire to go but we reluctantly tagged along. As it turns out Chattanooga is an awesome little city with a place called Ruby Falls. Ruby Falls is a cavern with a 145 foot waterfall in it a thousand feet underground. You would be amazed what you will find when aren’t looking.


I found a wife this way. I certainly wasn’t looking for a wife but BAM, one landed in my lap. Not one to squander a good opportunity I made sure to get good value out of this opportunity by having, not one but two, wonderful children! My point here is you just never know so take advantage of each and every opportunity that presents itself. If you do this one simple thing you will never look back at your life and say, “Jeez I wish I had done that”. Empirically most people regret the things that they didn’t do.


Speaking of taking advantage of each and every opportunity… If my wife’s work sends her somewhere for a conference it just became a family vacation. Just. Like. That. It doesn’t matter where that place is or what time of year. Her flight is covered and so is most of the hotel room. That cuts costs by 25-40% or more! To extend this benefit out we find what’s nearby and we take an extra week. Typically this ends up with a one-way rental and leaving from a different airport. If she gets sent to Washington DC for a conference I take the kids to the Smithsonian’s and the White House and whatever while she’s in the conference. When she is done we can head over to Baltimore, or drive up to Philly, or New York or Boston. The key for us doing this is picking the city with the lowest total rate of stay and finding the interesting stuff to see and do.


Just for fun I also like to check fares to places “along the way” of my journeys. For instance, if I’m flying to Europe from LA why not see if there are any interesting places in between. Sometimes it’s nice to break up the flight; sometimes it’s cheaper, sometimes for a few Benjamin’s more you can get in a few days in NYC.


Iceland right now is having a big tourism push. If you’re flying to Europe, stop in Iceland because why the hell not. WOW airlines is offering dirt-cheap fares and if you stay one night in Iceland they will hook you up with a free guide for a one day tour! They call this their “Travel Buddy” program. This is a fantastic way to see a new place and introduce yourself to a culture you might never have even thought of.


There are so many places to see and so many deals to be had that I figure I can travel most anywhere eventually if I wait for the right fare. I check my preferred sites first thing in the morning and then I check them again in the afternoon. I check my dedicated Ad email once before bed. I’m what you might call a “committed traveler”. That is to say I really go out of my way for the best deal.


One of these days I’ll do a write-up on all the sites but for now I’ll drop this one.


My current favorite site for flight deals and tracking miles is The Points Guy.


This is a great site for reviews and if you follow it regularly you’ll come with flash sales. It will also teach you how to use your “reward” miles to the greatest effect. Miles and credit card bonuses are absolutely essential to cheap travel. Which brings me to my next point.


Have Good Credit: Seriously, this is incredibly helpful. I have a combo of American Express Platinum and Citi Prestige cards. These two cards have done incredible things for my travel. These two cards require a great credit score. For instance, I have been in the middle of booking a flight and all the travel agents have run out of seats on the cheap flights I wanted. I called up American Express Travel and you know what, they got me booked on those flights no problem. Often times, Amex Travel is CHEAPER than any travel site or booking directly. I have lost my card and they have OVERNIGHTED a card to me at my destination. I forgot my foreign currency on my desk once. I naturally realized this just before hopping on a plane to Japan. Amex setup a cash drop for me and linked my Amex to my bank account as a debit card on the spot standing in line for a flight. These guys are something special for travel. Additionally, you get access to the Fine Hotels and Resorts program. Every so often you can get a good deal here, though it is rare.


The Citi Prestige card gives me a 4th night free at any hotel I choose. This perk is currently unlimited. If I’m gone for two weeks I get 3 free nights in whatever hotels. Additionally each of these cards get you gold status at different hotel chains which equates to free breakfast at the Hilton or free upgrades and generally better treatment at other chains.


Each of these cards offers a credit on the airline of your choice. The Amex offers $200 and the Citi Prestige offers $250. The difference here is that the Citi Prestige card allows that money to be used towards the purchase of a ticket while Amex Platinum allows that to be used for bag fees, incidentals and change fees. True story, I had to move a flight by a day after booking and United billed me 200 dollars a head to change it. Amex covered $200 of the change fee. It still hurt, but not as badly.


I put all my expenses on these two cards, literally everything. I use these points to reduce costs of flying, or hotels, or car rentals or whatever. You can get A LOT more information from The Points Guy.


Travel for Cheap Preparation for the Kids: I discuss the travel opportunities with my children’s teachers on Day 1. I make it known that I travel during “Off Peak” times to save money and that travel is one of the best, if not the best, form of education money can buy. Most of the teachers are receptive to this idea especially when I bring back “artifacts” and pictures for them to use in class. Additionally we have the children keep a journal. They write down what they did every day and have a historical record of what they learned. Naturally the teachers want to have them present this and thus far they have included it into the curriculum. Be careful though, this is on a person-by-person basis and the school systems require that a certain number of days are not exceeded. Don’t push your luck 😉


Travel for Cheap Pet Prep: My neighbors are awesome. I really did luck out with the neighbors I have who are willing to take care of our pets while we are away. I try to spread out my harassment of friends and family so as to not take advantage of people’s kindness. However, having your pets at home instead of at a kennel can save a small fortune. Be friendly! You may not be as lucky as I am to have great neighbors but you’ll never know if you don’t get out there and meet them. I know a lot of curmudgeons who just can’t see past the end of their own noses. Treat people well, help them when they need it and forgive their misgivings. Just being a decent person can save you a fortune.


Know your Hubs: Flying in and out of an airlines Hub is often times less expensive then trying to fly say United out of Deltas hub in Atlanta. If you know your hubs can tailor your flights to your locations. Also, sometimes it’s cheaper to fly in and out of different airports or a nearby airport instead of the main airport.


Use Google Flights: “Google flights” is a fantastic resource for finding flights and it shows you the flight costs by day so you can very easily adjust your travel plans. Once you have found your flight, shop around. Don’t forget to check the provider’s actual site. A lot of times if you book through a travel agent, say Expedia, you can get a 24 hour cancellation policy. This is helpful if you find a GREAT deal, book immediately and then your significant other has a great big steaming problem with it.


Airline Rewards: These are in the process of being devalued right now which is terrible but they can still be worthwhile. These programs can still offer upgrades to better cabins or allow you to take higher earning points cards and transfer those points for “free” flights. Keep tabs on your status and keep tabs on the rewards by airline a lot of them will expire without warning. Special circumstances such as having one of their branded credit cards, or making sure to earn points somehow someway within the year.


Hotel Status and Rewards: We are big fans of both Hilton and Starwood rewards programs. We stay in cheap Hilton’s at the airports kind of a lot. Even though we are not paying much for the room we have gold status with the hotel chain thanks to credit card perks. What this means is that we get free breakfast for the family every morning of our stay. This perk adds up! Just keep in mind that you MUST book through the Hilton website to get this perk.


Minimize the fees: There is literally a fee for everything when traveling. These fees add up in a hurry when you’re talking about airlines. The biggest of these is the baggage fee. Bag fees are easy to vanquish, however. You can use status or certain credit card to eliminate these fees but I recommend that you Travel Light with carry-ons only. Read the fine print to avoid special surprises. For instance, if you have status with Hilton and you get free breakfast make sure to purchase your hotel directly through Hilton or they will shaft you right out of that free breakfast. Thanks Hilton!


Long story short be flexible, be prepared, put yourself in a position to succeed and plan ahead for cheap traveling success. If you have the points you have been earning all year and you come across a flash sale because you were looking for it in the right place you can snag cheap flights and or hotels you can work out the details later. Put yourself in a position to succeed and sooner or later you will!


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