Build a Better Vacation: A Beginner’s Guide to Travel Hacking

Wait. [For the bus during two hours]

Photo by Margot Gabel on Flickr

Frodo and Sam had it right.

Get where you want to go by any means necessary.

Of course, had they just hitched a ride with the giant eagles from the beginning, maybe they’d have gotten to Mount Doom a lot sooner. And without all the fighting and near death experiences.

Sam and Frodo were the original travel hackers, using what their wits and ingenuity to get where they wanted to go. But you don’t have to fight orcs and face down the evil Sauron (have I geeked out on Lord of the Rings enough yet?) to save a few bucks and enjoy your next trip. It just takes a little planning and some elbow grease to get started hacking your vacations.

Getting Started

The word “hacker” has a bad connotation these days. We hear “hacker” and think of bad guys stealing passwords and cleaning out bank accounts, but the original computer software hackers were tinkerers who stripped down the fluffy exterior interfaces to expose the gooey interior code. Then they’d tinker until they had made something better. These guys were innovators.

Travel hacking, then, is the practice of breaking open the system to expose the gooey underbelly (oh, that’s an image, isn’t it?) so that you can travel efficiently, comfortably, and inexpensively, no matter your destination. Getting started as a travel hacker is a matter of setting goals and doing a little research.

*Note: In future posts, I’ll delve deeper into each one of these topics; for now, I’ll give you a brief overview to get you started in your new travel hacking lifestyle.


Let’s say you’ve decided on three big trips in 2014: A week in London, a week in Montana (fly fishing!), and a long weekend in San Francisco. Depending on where you live and when you want to go, those can be some pretty expensive flights. And let’s not forget food and lodging. Traditionally, you’d start looking up airline fares at an online dscount ticket broker, nearly faint from the prices, and go back to staring out the window across from your cubicle. But now that you’re a travel hacker, you have some tools to break into the system and see what magic lies inside.

Before you even look at fares, plan out your adventure. Where do you want to go? What do you want to see? What kind of lodging do you want to stay in? Will you eat out everyday or are you ok with cooking for yourself? Determine the level at which you want to travel (i.e., luxury, budget, hobo, etc.). When you figure out the travel level, it’s time to research free stuff.

Credit Cards

Credit cards get a bad rap these days, but we only have ourselves to blame. Sure you can yell at the credit card company for high interest rates and crazy late fees, but ultimately, it’s up to us to use them responsibly. And if you can use a card responsibly, why not get some free stuff out of it too? Many card companies, airlines, and hotels offer rewards cards—credit cards that give you points or miles that you can use toward full plane tickets or upgrades to business or first class seats. Most of these cards will give you a HUGE sign on bonus when you spend certain amount of money within a certain amount of time, and several have partner shopping portals that give you extra bonus points for shopping with them.


It’s difficult to predict when airfare prices will drop significantly, and the fares tend to fluctuate. There are websites that try to predict when fares might drop, but they’re unreliable at best. There are three surefire ways to find the best airfares: email, social media, and flexibility. Most airlines post super crazy awesome deals on their website, but often the first people to find out about them are the subscribers of the airline newsletter. Then social media fans find out. Then everyone else. Sign up for the newsletters of your favorite airlines, and keep an eye on your inbox and social channels.

The other best practice is to be flexible with your travel dates. If you can give yourself a few days of leeway in scheduling your trip, you will often get better prices. The search features on airline websites often give you a travel window with various prices. The lowest fares tend to be in the middle of the week, when fewer vacationers hit the air.


Again, you’ll have to decide at what level you want to travel. Hotels are obviously the most expensive option out there, but if you want the luxury of big beds, free breakfasts, and hot tubs, they’re your best bet. Hostels, the favored lodging of backpacking gap-years, are actually better options for cost conscious travelers than you think. Quality hostels are easy to come by if you do a little research ahead of time. While you may sometimes have to share a bathroom, hostels aren’t just dorm style party houses. Most hostels offer family or private rooms, common areas, and even full kitchens. You’ll have to make your own bed and clean your room, but it can be worth the effort.

Relatively new on the scene, crowdsourced lodging is an interesting alternative. Services like Airbnb and seek to match up travelers with hosts who open up their homes to weary vagabonds. Many of these services are much less expensive than hotels or hostels, and give you a local’s eye view of the area you’re in.

And of course, camping and RVs are available in many places for those of us who like our lodgings a bit more rustic. Also generally less expensive than a hotel, camping and RVs offer a nice change of pace and the freedom to go just about anywhere you want.


We all have to eat, and when we travel, you’ll want to sample the local cuisine. But for longer journeys, or to just keep your budget in check, consider cooking for yourself when you can. Hit up the local grocery store for healthy snacks and meals, or search for a local farmers market to pick up fresh, local ingredients. You never know what you’ll find, and with suggestions from the locals, you may just eat better than dining at restaurants every day. Mix it up.


Getting around can be tricky in an unfamiliar place, although GPS has made it a little less perplexing. If renting a car has you clutching your wallet close to your heart, consider some alternatives. Public transportation is available in almost all major cities in the world. Buses, light rail, trains, taxis, rickshaws, and the like will get you where you want to go, relatively cheaply. Be aware of ripoff artists who will over charge you for even the most basic of services.

Many cities and towns offer bike rentals. During most times of the year, this can be a fun (and healthy) way to see an area. The bonus is that you see much more of your destination than you would from the seat of a car or bus. Many European countries are very bike friendly, with special attention paid to road layouts and traffic patterns for cyclists.

Of course, there’s nothing quite like the Great American Road Trip. Rent a car (or take your own) and hit the open road for parts unknown. This may be a bit more expensive, but depending on your trip, it can be more memorable than any other option. I recommend that for travel in the U.S., stay off the Interstate highway system. Stick to the smaller roads that our grandparents drove in their journeys across the country. Visit the small towns and good people who you meet along the way.

This post is just the beginning of what I hope to compile into a definitive guide for the wide world of Travel Hacking. Keep an eye on future posts to learn more. If you like what you see, sign up for the PTV Newsletter, where in 2014, I’ll be talking about more personal stories and secret tips for living the lifestyle you’ve always dreamed of.

Chris Cavallari

About Chris Cavallari

Chris is a longtime digital content producer based in Maine. Since 1999, he has been an early adopter and active participant in blogging, podcasting, and social media, and has been guiding small and mid-sized businesses in leveraging video, social media, and digital publishing to the fullest. With an avid love of travel and the outdoors, Chris started in 2009 to give him a platform to showcase his outdoors and travel adventures, and to help educate others in doing the same.