How the hell do you travel so much?!

I get that a lot. Typically, it’s immediately followed by “I wish I could do that”.

I so badly want people to know that they can! I want them to know that they’re not constrained by domestic trips, or all-inclusives, or Econolodges. There’s an incredible world out there — ridiculous vistas, mouth-watering meals, centuries of history, time-honored traditions, welcoming locals — and there may never have been an easier time to travel than today. The internet has made travel information available and regularly up to date, you can book directly online in a snap, stay connected (if you want) on the go, get around cities in an Uber, and, maybe most importantly, travel incredibly affordably. Travelers can see more of the world today without breaking the bank.

Now, I know I’m incredibly fortunate. I make a good living and work in an industry with a lot of geographic flexibility, both of which afford me opportunities many don’t have. But believe it or not, you don’t need these things to travel further, more frequently, and for far less money than one might think.

So, how do I do it?

I’m a Follower

It’s true! There are far geekier people than I out there covering travel deals like it’s their job. Ok, maybe it actually is their job. These awesome people collect community tips, scour forums (yeah, people still use those!), and use social media to identify amazing travel deals and share them with the rest of us. Here are my two favorites:

SecretFlying (@SecretFlying) curates cheap fares from departure points around the globe, uncovering some pretty impressive flights at times. How does Chicago to Bolivia for $285 RT sound?


The Flight Deal (@TheFlightDeal) with 87.5K followers they are a bit less secret. They publish travel deals throughout the day departing from NYC, BOS, PHL, DC, MIA, DFW, PHX, LAX, SFO, PDX, SEA, and ORD. Round trip deals like $549 to Hong Kong, $149 to Guadeloupe, or $498 to Rio!

These two accounts are on a very short list of accounts I allow mobile notifications from twitter and suggest you do the same.

TheFlightDeal serving up some cheap ones

Points Points Points (points points points points points)

Those who travel infrequently dismiss loyalty programs, and for good reason. Because they’re just for boring consultants, right? No, it’s because it makes far more sense to choose the cheapest or most convenient flight option rather than focus on collecting points at a brand they’ll never spend or travel enough to attain premiere status anyway.

That said, points programs can send even the most casual traveler great distances with big bonuses from credit card signups. Between just 5 cards — Chase Sapphire Preferred, the Chase Ink Plus, Chase Southwest, Mileage Plus Explorer, and Citi AAdvantage cards — travelers can rack up 230,000 points that can be used on United, American, Southwest, hotels and more. With an economy one way flight from the US to Europe costing 20–30K miles or US to India 45–60K miles, just imagine how far that can take you.

Cards typically come with an initial spending requirement that must be first met and have annual fees, most waived for the first year, so make sure you can satisfy the requirements before signing up. (And please be smart with your credit, throw the card in a drawer if you can’t control yourself) is a great resource to start playing this game…

Be Flexible

Sometimes you need to travel to New York for your friend’s wedding or New Orleans for a conference. But, when you’re just looking for a adventure, the destination and dates don’t matter nearly as much. It’s about escaping. When you’re getting some escape vibes, look no further than these tools:

Hopper— great insight on when it’s cheapest to travel to a particular destination and how good of a deal it is, relative to the typical price. Easy UX and fun UI (bunnies!) make it a joy to use too. For even more spontaneous version of Hopper, check out their GTFO app :)

Some cheap flights out of NYC from HitlistApp

Hitlist— I always get a bit of a “wow!” from people I show Hitlist. Really, the best search tool I’ve found for identifying amazing flight deals when you have wanderlust. Search >Everywhere for a list of great deals from your departure city ($346 RT NYC>OSL!) or choose one of their lists (“Ultimate Ski Destinations”) for curated destinations for the trip vibe you’re going for.

Cleverlayover— when you do travel somewhere specific, why not stop over for a hours or days in an interesting city along the way? Cleverlayover tries to combine multiple one way flights or those with long layovers to give you a bonus experience to your trip. 16 hour layover in Istanbul? I’m in!

Kayak Explore —I don’t understand why Kayak makes it so difficult to find Explore, kind of silly. But, it is a cool tool and gives you that spin-the-globe kind of feel to finding adventures.

Skip the Hotel

It may be a surprise to some that for many people ‘travel accommodations’ is solely synonymous with booking a hotel. Why isn’t everyone using Airbnb yet!? I’ve stayed at some of the most interesting, charming, well located spaces in cities around the globe using the platform. Not only does this allow me to save tons (maintain that foodie fund!) but the experience is far richer as a result. You’ll grab a beer at a bar full of locals, you’ll walk to the train past interesting street art, get a unique view no hotel could offer. And, no, being an Airbnb doesn’t mean you must share the space with others. I’ve rented entire apartments in cities for a fraction of the cost of a hotel room.

If you’re are into meeting people and trying to travel in a cash smart way, Couchsurfing is a great community to join. Request to stay on the couch/spare bedroom/ of awesomely interesting people. I’ve made many friends around the world from these stays (Hi guys!).

If you’re still feeling that hotel, HotelTonight has great deals and Rocketmiles will accelerate your point accumulation.

So, what are you waiting for?

Tomorrow I head to Cartagena, Colombia, on a business class ticket for $87 RT and 70,000 United miles. Maybe I’ll even use an Airbnb to stay in the hip neighborhood of Getsamani while I’m there.

I have to admit, I enjoy people knowing me as the guy who travels often. Having people engage with me, acknowledging that I go on some awesome travel adventures, is validation that I’m doing what I love and doing it so often that people actually take notice. Many of you have the same passion to travel as I do and I hope this helps you travel so often people start asking “how the hell do you travel so much!?” too.