How to Travel More Affordably (A Miniature Guide + Sample Itineraries)

Travel, to me, represents spiritual pilgrammage: transformational journeying.

For someone who grew up in a small town in the smallest state in America, I only learned to love travel when I realized I needed to push myself beyond my literal and figurative comfort zones. So in 2011, I began to travel across the nation to conferences and events from Austin, Texas to Seattle, Portland, Los Angeles, Atlanta, and New York.

Then I went international, beginning with Iceland in June 2013.

Since then, I’ve visited 21 countries.

As much as it is an incredible privilege, travel still remains a personal challenge for me, too.

As I’ve traveled, I’ve had my own expectations, pre-conceived ideas, assumptions, comfort, standards of living and identity entirely upturned:

Travel submits the self into states of uncertainty and unknown, which seem undesireable — to be avoided, even!

And yet, what is “uncertainty” but another way to say “freedom”?

What is less known, less certain, less sure than the burden of liberty that allows us to choose who we are, what we believe, and how we will live out the course of our lives?

As a traveler, I’ve cultivated a relationship to uncertainty that has helped me live more freely.

This is why something like travel can become so profoundly rewarding for your soul.

By challenging your thinking patterns, presumptions, habits and routines, we realize that there’s little other choice but to open ourselves up. We imagine, again. We see ourselves, and our world, anew. Our hearts, too, are shattered by simple struggles and personal vulnerability. Instead of becoming “broken,” we discover in our wounds how to allow more of our own loving capacity to out (and how to allow more love in). When we travel, we see ourselves mirrored in faces of every color and origin, and feel the call to live more courageously for one another.

Travel helps me find that, time and time again.

It can, and will, for you too.

Today, I want to encourage you to take a spiritual journey of your own.

I’ll even show you how to replicate a very similar trip to the one that I took (when I originally wrote this piece for my newsletter subscribers) to the cities of Sarajevo, Ljubljana and Zurich, on just 6 days notice in 2016.

A Miniature Guide to Traveling Affordably (and on Short Notice)

In January 2017, I spent 10 days in Cuba over my 31st birthday, which I booked on 2 weeks notice. The year prior, I threaded together a visit to Peru on just 13 days notice, and accomplished my goal of standing on Macchu Pichu for my 30th birthday.

But not all travelers can approach trips like I do, because I work for myself. Flexibility is my biggest unfair advantage.

And, my work travels with me. So, I know it’s not as easy as I can make it out to be. Booking trips around vacation days, tax season or the fiscal calendar, your children’s vacations, and so on, are all indeed logistical nightmares.

But there are still ways to save, first beginning with when and how you book your travel.

Primary Expense #1: Airfare

Traveling has never been more affordable. And, a plane ticket halfway across the world comes down to pennies per mile.

Here are more tips to keep your primary expense, airfare, as low as you can:

Search Early in the Week. It’s cheaper to book your travel on a Monday, Tuesday, or Wednesday — so it’s been said, studied, analyzed and meticulously debated. Ticket prices do fluctuate based on availability, anticipated demand and other sneaky algorithms.

Depart/Return on Weekdays. What days of the week you travel matter, too. Try to schedule your departure and return on weekdays, not weekends, if possible. Lots of folks book return flights on Sundays for convenient acclimation back into the standard work week. This may save you hundreds.

Be Aware of Holidays. It’s always a good idea to try to avoid traveling around major holidays, public school vacation weeks, and college spring breaks whenever possible. Demand won’t be as high and neither will be the price!

Wait Until You Book. Few realize that booking as far in advance as possible for your trip is not necessary. In fact, it will probably cost you more.

It’s said that the ideal window for booking the cheapest airfare for international flights is 10-12 weeks, while 6-8 weeks is usually best for domestic flights.

Airlines know that you like to feel safe, certain and sure. That’s why there’s usually a higher market demand (higher cost) when you book as early in advance as possible. As I mentioned above, ticket prices already fluctuate from what day of the week you search for your tickets, too.

Primary Expense #2: Accomodations

With airfares very affordable when you do it right, accomodations are another big expense — at least, they used to be.

Nowadays, the hospitality industry is in a state of wild disruption that really benefits us travelers. You have super cheap options when crashing with backpackers in dorms thanks to reputable hostel brands, but I recommend embracing home-sharing services like Airbnb to kiss overpriced hotel rooms (with cold corporate atmospheres) goodbye.

My favorite way to find accommodations for cheap while traveling (especially last-minute travel) is Airbnb.

More than just a “place to say,” these Airbnb families have been so hospitable and welcoming in my “home away from home,” that they’ve helped make so many of my trips so worthwhile and memorable.

Oh, and for just dollars per day. I’ve spent $90/night in New York City, $60/night in Salt Lake City, or $18/night in Havana, or $28/night in Sarajevo.

I’ve had travel-families pick me up from the airport in a foreign city I’ve never visited. I’ve had travel-families force-feed me enormous meals as if it were from the kitchen of my own grandmother. They’ve taken me into their homes. They’ve set up my cab rides and adventure tours. They’ve recommended bohemian streets, made me soup when I felt unwell, and showed me the best cafes to frequent.

I can’t believe how many amazing, hospitable, giving people there are, everywhere.

Truly, Airbnb has helped me open even more of my heart to the world — and made the world so accessible, so affordably.

Here are 2 real cost breakdowns for you.

These are the exact prices I paid on 6 days notice for my international trip to 3 new countries (Bosnia and Herzegovina, Slovenia, Switzerland) over 12 days in September 2016:

$580 – International round-trip airfare (Swiss Air)
$101 – Airbnb private room in Sarajevo (5 nights, $18/night plus fees)
$182 – Continential round-trip airfare (Sarajevo to/from Ljubljana)
$172 – Airbnb private room in Ljubjlana (4 nights, $35/night plus fees)
$143 – Airbnb private room in Zurich (1 night)

= $1178 Total

$1200 isn’t a cheap trip, but for visiting 3 new countries on 6 days notice, it’s money I happily part with.

In the case of my flight, I got lucky finding space available on flights that the airlines were interesting in selling. That’s the “flexibility” key (and advantage I have) that I mentioned earlier. I benefited from their need to reduce overall cost of the flight that was already going to happen. The airline was hoping to incentivize a few more ticket sales to maximize their overall profits for the flight. So, I bit.

Here’s what my recent 10-day adventure to Cuba, which I booked on two weeks’ notice, ran me:

$489 – International round-trip airfare (Southwest Airlines)
$74 – Airbnb private room in Havana (2 nights, $37/night plus fees)
$40 – Airbnb private room in Vinales (2 nights, $20/night plus fees)
$48 – Airbnb private room in Cienfuegos (2 nights, $24/night plus fees)
$53 – Airbnb private room in Trinidad (2 nights, $27/night plus fees)
$32 – Airbnb private room in Havana (1 night)
$75 – Buses and collectivos (shared taxis) between cities (4 trips, $18/average)

= $811 Total

Remember, I’m not a so-called “travel hacker.”

I don’t bank tens of thousands on credit cards to redeem trips that in turn appear “free” after the fact. This is just what I do to travel, and keep my short-planned journeys affordable for me.

And based on how I value my money and what I receive in return for a transformational journey into new cultures and countries, the cost of $1200 feels like a genuine steal!

Ready to try it for yourself? Okay. Let’s do it.

With the tips and advice listed above, here’s the exact process I use to book my last-minute adventures.

It’s your turn to try.

1) Choose, Kind Of. Get your destination region in mind — flexibility, again is key! If you’re going to just one place, that obviously limits your options. But if you’re traveling to a couple spots, see if arriving in one location is cheaper than the other. Be flexible.

2) Research Your Flight Options. Flights are your biggest cost, so be choosing in scouting ahead. Google Flights (or Kayak, or some related tool) is your new best friend: check a few different flight routes, nearby departure/arrival cities, average price ranges, and some date ranges ahead of time. Let this be your predictor for how much you really need to spend. Budget accordingly.

3) Track Your Flight Prices. Next, I use an app like Hopper — in addition to Google Flights price tracking — to automatically track flight prices and predict cost going up or down. I scouted flight options to Sarajevo for about a week and a half leading up to my trip before finally committing.

4) Compare Prices Before You Book. When you’re close to committing, double check see if there are any price advantages on the airline’s own website versus using a travel booking site like Kayak (or Expedia, which often includes a free 24-hour cancellation window if you make a mistake or plans change).

5) Acquire Frequent Flier Miles. Always input frequent flier mile number when you book — even if you sign up for the airline’s program right before you book. Most programs allow some form of sharing frequent flier miles between partner airlines, too. So, you might as well!

6) Get Settled In with AirBnb. When your flights are booked, click over to Airbnb and book your accommodations.

I began by booking entire homes/apartments to myself when I felt awkward about staying with families, but lately, I’ve only been staying in private rooms with the home owners present. They’ve been (in my experience, 100% of the time) incredibly kind, generous hosts with huge hospitality in them!

Contrary to what news headlines makes you believe, the whole world is not out to get you.

Remember: “Travel is never a matter of money but of courage.”

That’s what Paulo Coelho says, at least, in his semi-autobiographical novel, Aleph.

Getting out of your comfort zone and into a new corner of the world has never been easier — or, in the big picture, more affordable.

Of course, you need money to pay for a trip. And you need to retain the job that finances your trips, too — you know, the one that probably doesn’t give you much paid vacation time, like most Americans. (Most nations in Europe grant workers to upwards of 30 paid vacation days and holidays per year, while the average American only receives 10-16 days).

But if you’re really passionate and determined to take a spiritual journey, it’s courage and tenache that will carry you there.

Your dollars are few and precious. But if I’m being honest with myself, I know that there’ll never be “enough” money to make me feel absolutely emotionally comfortable enough to throw myself into the unknown and uncertainty of traveling.

But that is why we endeavor.

To travel is to seek, and surrender to, the gifts of transformation that await.

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