Notes from Traveling Millennials: On the Road with Bud and Eva Simpson

This is a travel hacking case study. (Read others or nominate yourself.)

When you’re young, it feels easy to appease your inner wanderlust by saying, “I’ll travel later in life.” Twenty-somethings Bud and Eva Simpson decided they didn’t want to live this way—and have spent the last year helping young adults learn to travel smart.

Tell us about yourselves.  

We’re Bud & Eva and we just married in March 2014. For us, the perfect moment is waking up to adventure on a crisp morning, sipping a cup of black coffee in a thick mug and asking, “Where will we go today? Who will we meet today, and what is their story?

We’ve discovered that at the heart of these questions lies the essence of fulfilling travel. And it’s what we’ve chosen to dedicate our lives to find and share with others. So to do just that, we became travel bloggers and started Shoestring Explorers – a travel blog for ‘twenty-somethings’ on a budget.

Why did you want to focus on twenty-somethings?

From the beginning we knew we wanted to flip the traditional model of travel blogging on its head. Where the traditional blog might focus on the blogger, we wanted to focus solely on the reader. “What’s keeping the young professional ‘twenty-something’ from making travel a priority and how can they overcome it?”

We are convinced that by understanding the obstacles that Millennials face, we can identify and test travel strategies that help them realize their dream of frequent and fulfilling travel.


What inspired you to leave home and travel?

Travel was just always kind of there, and the urge to travel became stronger over time, especially once we started doing it together. It’s funny how so many people say they love the thought of travel, but they never make the commitment to actually do it, and put it off until “later.”

But we realized early on that “later” doesn’t always work out. People age, get sick, have kids, take on tons of responsibilities. And let’s be honest, you never know when today is your last day. Ultimately, that thought is what pushed us out the door.

Can you tell us a story from your time on the road?

We fell in love with ‘getting lost’ in the summer of 2011. With no guidebook or even a map, just our backpacks and a smile, we backpacked across Western Europe. We took our time popping into sleepy ‘one-pub’ towns in the English countryside, worked a farm in a pastoral village in Bretagne, stumbled upon monastery-turned hostels in Nice with nightclubs overlooking the Mediterranean, tasted Chianti poured by the vintner herself, and spent entire afternoons mesmerized by the craftsmanship of artisans handcrafting fine leather handbags, belts, and shoes.

It remains one of our favorite trips, because we literally had nothing—there was nothing glamorous about it from an outsider’s point of view. But it was wonderful for us because we learned how little we needed to be happy.

There was one night in Avignon where we literally debated whether or not we should sleep under a bridge—which pretty much tells you how novice we were. We were stuck in a city we’d never been before, our phones were dead, and we couldn’t speak more than a few words of French.

The sun began to set as we ambled through the streets of Calais looking for a place to stay. “Un hotel? Un hostel? Je ne comprends pas… Non, non we are l’Americain.” Every place was either booked or way out of our price range.

Our only two options for lodging were the train station, or under a lovely bridge a few blocks east. In our last act of desperation we reached out to a local barkeep at a charming, rundown wine shop and told him we were looking for a room. “Of course! I will call Phillipe—he’ll give you the best room he has! Tell him Gerard sent you!”

We thanked Gerard, bought a bottle of wine, a block of cheese and trekked over cobblestone streets to the most beautiful little boutique hotel. Turns out we had the honeymoon suite waiting for us, for a fraction of the price! Moral of the story? It can pay off to connect with locals. We can’t guarantee the same results, but its definitely worth a shot.

No amount of books or blogs can prepare you for the real thing. Travel is all too intriguing, beautiful and unexpected. You’ve got to hop in and just go for it.


How do you save for your trips?

We use a little technique that we developed called the “Splurge Savings Approach,” wherein we 1) open a savings account, 2) direct deposit small amounts into the account each paycheck, and 3) supplement the fund with additional sources of income, like baby-sitting money and tax returns. So we effectively have a constant travel fund that grows while we sleep. And it’s great because it gives us the freedom to travel whenever we want without breaking the bank.

We use our “Splurge Savings” every time we travel and we accumulate enough money for one international flight every 30-45 days. Now that we use this technique, money is never an obstacle that keeps us from traveling. For most ‘twenty-somethings’ including us, cost is the #1 obstacle for frequent and fulfilling travel. But by committing to a system that does the work for us, paying for travel is a breeze.

Do you use travel hacking techniques?

When coupled with miles bonuses earned from credit cards, the “Splurge Savings” really does become a wad of cash that we can use for splurging on the things we love like fine wine, nice restaurants, bottle service and first class upgrades. Because who doesn’t love those things?

Also, we’re both members of the Travel Hacking Cartel and have opened a number of credit cards while building our miles balances. We came up with a word-for-word script that we could use to cash in on great sign-up bonuses with cards we already had. We tested it on our cards, and after a few times we started getting some positive results.

With about a 50% success rate, we were getting $400 in travel with a 5-minute phone call, just by being good customers who threatened to leave. Those are crazy-awesome odds, and you really have nothing to lose.


The great debate: aisle or window?

Eva and I always fight over the window seat. (We always imagine the pilot saying, “Don’t make me turn this plane around, kids!”)

Best travel tips. Go:

1. Keep a travel journal; write in it daily.

You don’t have to write a five-page journal entry, use bullet points if you’d like. The important thing is that you keep a record of where you went, what you did and who you met along the way. This is one of our favorite ways to relive our travels again—it’s almost like reading a book!

2. Throw away the guidebook and meet the ‘serendipitous traveler’ in you!

Let the locals be your guide. Strike up conversations; find out where people go to explore and unwind.

3. Bring your travels home with you.

Whenever you return from a trip, find fun and creative ways to share your travel experiences with friends and family. Imagine you just got back from the Chianti region of Italy; host a wine-tasting party featuring some of your favorite wines and local cuisine. Your friends will love you for it and it’s a great way to inspire others to seek fulfilling travel as well.

Where are you headed next?

We’re headed to Portland, Oregon this December. We’re writing a segment for the blog on West Coast travel by train and we’re taking the Coast Starlight from Portland to Los Angeles (and of course, stopping for some wine along the way)

Follow Bud and Eva’s journey on their site, Shoestring Explorers, or via Twitter @shoestringexp.  

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