Long-term Travel: The What, Why + How Behind Taking Extended Trips

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How many times have you dreamed of quitting your job, selling all your stuff + traveling the world?

I know - I used to read blog posts like this at work, slinking lower into my desk chair while simultaneously clicking out of all my other tabs (Google Flights, Airbnb, you know - the regular). I had a craving to escape my “normal” life.

And, it wasn’t just me. It seems likes the ultimate goal for our generation is to be completely free - free of debt, of commitments, of stability. We crave the ability to do anything that’s a little bit different. Anything that allows us to feel energized or fulfilled or simply …alive.

Oftentimes - well, more than any other generation - in order to fill those aches we turn to travel.

Travel doesn’t always need to mean we’re escaping something though. In my experience, traveling the world has completely expanded my view of what’s possible in my life. It’s left me feeling inspired + full + part of something bigger than me.

I don’t need to convince you all about the importance of exploring the world. But, since I returned home from a 2+ month trip this February I’ve received a ton of questions from you all about the what, why + how behind my trip (or any extended trip for that matter).

Some of the questions I got from you all were:

How did you save up to go on this trip? What types of things were you doing for work? How did you organize all your stops? Why did you choose the places you did? What was your favorite place? How were you not scared?!

This post is an attempt to answer all those questions…and more. In the past few years, I’ve traveled to 30+ countries, visited countless cities and collected hundreds of experiences. I can’t wait to share all this knowledge with you, because these trips have been with a variety of budgets, groups sizes (solo travel all the way!), number of vacation days and locations.

While it’s important to take all of this advice as one person’s thoughts based on their life experiences - use this read as a catalyst to book that trip you’ve been thinking about. To get out into the world + collect those experiences.

So, let’s get to it!


What does it mean to go on an “extended trip”? And why would you?

I just had a friend tell me: “The worst type of vacation to go on is 5 days long.”

And, I can’t help but agree. While a long-weekend trip is exciting in that you get to play hooky from work for a day or two, a typical “vacation” is kind of stressful. It takes long enough to get your mind off the work-gym-sleep grind. And then, when you finally do allow it to release, you somehow find yourself back at work.

For those of us who live in the U.S. - we aren’t blessed with many vacation opportunities (actually the least in the developed world). Even if we’re lucky enough to work for one of those cool, flexible, millennial companies that give you unlimited vacation days, studies actually show people take less vacation days than if they’re mandated.

Not to mention the fact that in the United States, we’re conditioned to believe that the only acceptable form of “success” is working really hard, buying a house & taking one vacation per year.

So, all in all - taking long trips seems unacceptable, difficult and maybe even impossible (even if the point is supposed to be fun).

Since I graduated from college, I’ve adopted the mentality of viewing travel as an investment in myself. In my growth, my happiness, my ability to become comfortable with the uncomfortable. I believe all those qualities are a requirement for living a fulfilling life - and lessons that I can’t learn while sitting in a classroom or behind a couple of computer screens at work.

So, I’ve had to buck the tradition and go off the beaten path.

Now, traveling for long periods of time doesn’t have to mean quitting your job and selling all your stuff (though many people do that when taking long trips). In my experience, I took long trips in a variety of ways: Before starting my first job, in between jobs, saving up all my vacation days, and leaving the traditional workforce altogether to run my own company.

The bottom line is - people will always have opinions. But no matter what stage you’re at in life, taking long(er) trips can be done. And, these experiences can actually change our personalities for the better.

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The logistics behind taking a long trip

This is the overwhelming part - how do you save, plan and decide on your travels - especially when you want to explore for a while?

Even for an extreme Type A planner like me, this part can be really simple - though it takes experience and a little bit of letting go. I remember when I took my first solo trip for 4 months backpacking around Australia and New Zealand I had a Moleskin notebook full of every, single place I was going to visit down to the day. That’s over 120 days of planned travel.

Needless to say, there were plenty of cross-outs in that notebook!

After many years of experience and lessons learned while traveling, this past extended trip was organized much differently. My biggest takeaway: Plan the bare minimum - enough to get by but not enough to be overwhelmed.

This is a hard thing to do for us overachievers / obsessive list-makers. It’s still something difficult for me to do, after much focus and gathered experiences. But, for this trip specifically - Dupi and I made a compromise: Let’s plan the first half of our trip before departure (e.g. research and book our flights, tours, places to stay, things to do) - and leave the rest of it to chance. Just kidding! Our goal was to plan the rest as we went.

There are plenty of people who book a one way flight and have absolutely no idea where they’ll end up. That’s awesome and I give total kudos to those humans. But, for those of us who enjoy spontaneity and stability in some forms - this was the perfect middle ground. It’s really nice to have the flexibility to shift and change things around as needed, but also not miss out on cool Airbnb’s or experiences because they’re sold out.

A couple of my favorite logistical tools for long travel are:

  • Google Flights - track your flight prices over time to see when is best to book

  • Airbnb - save your “favorite places” in a shared folder to book at a later time

  • Facebook groups like Girls Love Travel - getting feedback + ideas on what to do in certain places!

Now, comes the most important question you’ve all asked about: money. One of the most common questions I received while on this trip (and about long trips in general) is: How do you save enough to take a trip like this?

It’s a great question and to be honest - one I didn’t really give much thought about. You see - as I mentioned before I view travel as an investment in myself. In my happiness and fulfillment. So, just as you might invest in new clothes for a job or a training course to advance your knowledge - an extended trip might have the same mindset.

Though, there were a few specific things we did on this trip that helped save money:

  • Decreased our ongoing expenses: Dupi and I were able to rent our apartment so we didn’t need to worry about paying rent during this time. Making an active choice to reduce other costs while traveling (by either getting out of a lease or renting out your spot) is a wise choice.

  • Got smart about credit card points: This wasn’t something that I thought I was an “expert” in - but after lots of research Dupi and I have learned to use our credit cards to our advantage (more on this in an upcoming post!). We have the Chase Sapphire Reserve card - and used points for the majority of our flights and some expenses.

  • Continued remote work: During this trip, I was lucky enough to continue working from anywhere in the world. I am a coach (with some badass clients), brand strategy consultant and partner to some really cool freakin’ brands. I know this isn’t something that’s available to everyone, but there may be some creative ways to continue earning money while spending a long time abroad. A really great remote-work website for well-paid consulting jobs is called Catalant; check it out!


Without going into too many details, it ended up costing Dupi and I roughly the same amount that we would have spent on living expenses and rent in San Francisco on our entire two month trip (flights + experiences included!).

I know that these types of trips are not in everyone’s budget or realm of possibility (right now at least). But, the purpose of sharing these details is to show you that there are many creative ways to go about this type of travel - even if you’re not ready to quit your job and sell all your possessions!


My last thoughts: Do it if you can

While any type of travel can be exhausting, draining and potentially even scary - it’s important for all of us to get out of our comfort zones every-so-often.

Of course, not every single moment of our 2+ month trip was perfect or exciting or glamorous (we had our fair share of sleeping in airports!). But, there are no words to describe the rejuvenating, grounded-but-inspired feeling you get when seeing a place you love for the first (or tenth) time.

So, if you’re thinking about taking any form of travel - whether that’s taking a long drive or purchasing your ticket for that big trip - take this as your sign. I’ll leave you with one quote that completely changed my life, and I refer to every single time I need some inspiration to do the damn thing:

“You are still young, free.. Do yourself a favor. Before it's too late, without thinking too much about it first, pack a pillow and a blanket and see as much of the world as you can. You will not regret it. One day it will be too late.”

Katina Mountanos