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7 Financial Mistakes I Made While Traveling the World for a Year

May 04, 2019
13 min read
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The first and only time I traveled overseas during my school years, my dad and I stayed in a youth hostel next to the train station in Nice, France, and subsisted mostly on baguettes and brie that we'd eat on the steps of churches. That trip was a direct result of my parents freaking out at the price tag for a middle-school class trip to Washington, DC, and declaring that for that kind of money, our whole family of three could go to Europe instead. (My mom had to stay home at the last minute in rural New Mexico, where I grew up.)

What I couldn't know at the time was how deeply the lessons of frugality on that jaunt to France and Italy would seep into my lifelong travel philosophy. We never stepped foot in a luxury hotel or ate a fancy meal, but I will forever remember the Milan-San Remo bike race my dad and I climbed a mountain to watch, surrounded by hundreds of screaming Italians, for free.

Last year, I had the great privilege of circumnavigating the globe as the New York Times' inaugural 52 Places Traveler, tasked with reporting on, photographing, and creating digital content from each destination on the paper of record's 52 Places to Go in 2018 list. It was a yearlong journalistic assignment -- the hardest and most rewarding job I've ever had -- and I certainly didn't pay for it myself. But I did have to front a lot of costs and work from a modest budget, while sticking with the Times' strict no-freebies ethical standards. Moreover, I wanted to travel in a way that readers who were a lot like me, who worked full-time and had to stretch their dollars over limited vacation time, might be able to mimic.

You'll find plenty of great hacks on this site for how to manipulate hotel and airline points systems, and I encourage you to explore them all. My haphazard itinerary didn't allow for me to stick with loyalty programs. I did, however, learn a ton about how to be smart with my wallet in other ways. Hope you find them useful too.

(Photo by Kerri MacDonald / The New York Times)
(Photo by Kerri MacDonald / The New York Times)

1. Not Dealing Directly With Hotels and Airlines

First, a disclaimer: I'm quite aware that hostels and Airbnbs are often far cheaper than hotels. I just couldn't stay in them most of the time. Hostels didn't offer enough privacy for me to write, and I found Airbnbs too isolating as a solo female traveler. After arriving in Glasgow, Scotland, after midnight and having to retrieve the key to my Airbnb from a lockbox down a dark alley while a man lurked near me, I decided my safety was worth paying a little extra.

One of the big draws of the Citi Prestige card that I’d used to start off my trip was a fourth-night-free benefit for long hotel stays. There were hoops to jump through, though: I had to book on the phone through Citi’s concierge, which took time I didn’t have. Plus, starting September 2019, Citi is limiting the use of the fourth-night-free benefit to twice a year. I've already downgraded that card to a no-fee Citi option.

You don’t need a fancy card to get great deals on hotels, though. I found that when staying at small hotels or bed and breakfasts, I could get a significant discount from listed prices on and Expedia if I talked to owners directly. They usually gave me the raw room cost, without a markup for online commission, with savings of sometimes $50 a night. And I was able to negotiate for rooms with better views, king beds or other factors that I couldn’t control without in-person interaction.

Hotel Casa Hacienda Achamaqui, about 20 minutes outside of Chachapoyas, Peru. (Photo by Jada Yuan / New York Times)
Hotel Casa Hacienda Achamaqui, a "serene and picturesque" hotel roughly 20 minutes outside of Chachapoyas, Peru. (Photo by Jada Yuan / New York Times)

Dealing directly with hotels, as well as airlines, also made it easier to cancel or change reservations. A hotel in Thailand I had to cancel at the last minute told me they would've been happy to help if I’d booked through them, but because I’d used Expedia, I was responsible for the full amount. Airline changes, likewise, seemed to cost more and required a lot more runaround when going through a third party.

2. Extending a Stay at the Front Desk

My exception to dealing with hotels directly was when extending a stay. Hotel’s rates change night to night, and what you see on a booking site is usually an average of wildly different prices from, say, Saturday to Sunday. A few times, I’d bounce down to the front desk and extend my stay, not realizing that night’s rate was much higher than the rate I’d previously paid.

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The best way to guard against this is to book all your nights at once, locking in a decent price. But if you’re like me, with fluid plans, the next best thing is to look at the online price for your room and bring that information to the desk when you extend. The rates that clerks see in their system are often higher than what’s available online. Sometimes they can match the deal you’ve found. More often, you’ll want to make an online booking at the good rate and then arrange with the hotel to stay in the same room. Housekeeping gets a break, and you don’t have to move to a different hotel or go broke. It’s win-win.

3. Accepting an Unitemized Reservation

While booking a room in Kigali, Rwanda, through Marriott’s website, I found a rate of around $185 that seemed too good to be true. (Spoiler: It was.) I clicked to reserve, and a number popped up for the total cost of the stay that seemed high. I ignored it.

Cut to the end of lovely stay that is now forever marred in my mind. When I saw my bill, I realized that the $185 rate had not been inclusive of taxes and fees, and only applied to the first two nights of my seven-night stay. The rest were charged at around $300.

The $185 price was the only rate I’d seen on the Marriott site during booking. It wasn’t until scrolling through several pages of ads in my confirmation email that I saw the breakdown of the nightly prices. My lessons: Always demand itemization and do your own math, even when dealing with a company you think you can trust.

4. Assuming Amazon Prime Was My Friend

“You can just get it on Amazon!” friends told me when I panicked that I’d leave something important at home. I have a hard-won travel mantra: Avoid having anything shipped to you. That goes double for ordering anything off of Amazon Prime. Free two-day shipping often turned into four or six. A bunch of items I’d ordered showed up a week late to my Brooklyn apartment after I’d left, and I had to pay someone to send them back for me.

Returns were near impossible to complete while on the road. Everything would arrive in one big box, and then I’d find out that each item required a different shipping service -- UPS, USPS or FedEx -- if I wanted to send them back. Do you know how hard it is to find boxes in a city you don’t know? Let alone a shipping center that takes all three services and is open on nights and weekends? And what about packing tape? Half the time, I lost money because the return shipping wasn’t free and because of all the money I spent on Lyfts trying to get boxes to various shipping centers. I canceled my Prime membership and started buying locally and haven’t regretted it yet.

5. Buying Transportation Through Local Vendors

I had a great travel credit card, the Chase Sapphire Reserve, and still found it difficult to complete online transactions in Europe and Asia, especially when purchasing museum tickets or transportation directly from a local vendor. That's because US credit cards are chip-and-signature, while much of the rest of the world uses chip-and-PIN cards. No PIN, no transaction. Sites like Trainline, Go Euro,, and Rome2Rio were invaluable proxies that let me use my card for buying last-minute flights, trains and buses without a headache.

One caveat: Though they worked great for buying travel, all those sites were cumbersome when it came to changing my travel schedule, which happened often. The best course of action in almost all cases was to walk into a train or bus station and speak with an agent, even when online fine print said the deadline for changes had passed. It took very little time, and agents were happy to help me make new arrangements at no additional cost.

6. Using a Credit Card With a Wire-Transfer App

While in Vilnius, Lithuania, I realized I’d left my favorite jacket at airport security in Tallinn, Estonia. The only way to get it back was through a courier service, and the only way to pay the courier service was through wire transfer. And this all had to happen in the four days before I left the Baltics — courier services like DHL that delivered outside the region cost a fortune.

My bank’s transfer fees exceeded the cost (and sentimental value) of the jacket. So I did a bunch of research and stumbled upon TransferWise, an app that allowed me to wire money with negligible fees and a great exchange rate. Or so I thought.

The TransferWise fees were low, but I’d used a Citibank credit card as the payment method, and to my card’s computer brain, that transfer was a cash advance, requiring a hefty fee, plus interest -- which added up to pretty much what my bank would have charged.

I still love TransferWise and have used it for everything from booking independent tour guides to paying off speeding tickets. As soon as I linked the app to my debit card (your bank account would also work), the high fees went away, and I’ve been happy ever since.

And sadly, Citibank isn't the only credit card company that codes TransferWise transactions as cash advances or ATM visits, even though they should be coded as an online payment service, like PayPal. When I called Citibank, armed with that information, they couldn't (or wouldn't) reverse the fees they'd charged. If you're squeamish about using a debit card, TransferWise also offers a borderless account where you can load money and get personalized local bank details in over 30 countries. That means people in the UK, for instance, could send you British pounds that you could then convert to US dollars at a real exchange rate. There's even a TransferWise debit card you can use to spend money in any currency.

7. Sacrificing for Status

You’d think that after this trip, I’d get to walk onto planes right after people with small children and members of the military. The erratic nature of my travel, though, meant I was flying on a different airline for each leg. The prices were better for small airlines unaffiliated with big loyalty programs -- Air Baltic, AirAsia, Rwandair. And they were often the best, and sometimes only, way to get to all my random destination. I actually lost my Gold status on American Airlines this year.

It doesn’t bother me that much. I’ve never flown in a class higher than Economy Plus, which I think helps stave off disappointment — I can’t miss what I don’t know. I use SeatGuru to choose a spot that will maximize my legroom and try to make sure I have a window seat (better for sleep, plus I love gazing outside). Then I throw on compression socks, leggings and a wireless bra for comfort, and stick in noise-canceling earbuds, and I’m ready to sleep from takeoff to landing. Long-term travel has taught me the joys of checking a bag — it rarely gets lost, I don’t have to drag it around the airport, and everything important is in my carry-on — so the order I get on the plane doesn’t matter.

As for hotels, I knew that staying at boutique properties was going to cost me points, but honestly, I would have gone nuts staying in chains for an entire year. Some of my best days were spent writing in lovingly decorated lobbies, or chatting with owners who’d spent years pouring their life savings into building their hotels with passion and a deep desire to host people. As mentioned above, there can be financial advantages to going small: owners who are willing to negotiate rates and nongeneric restaurants with chefs who care, which will save you money and time from traveling further afield in search of food. Often in small hotels, I'd find a free minibar filled with carefully curated snacks. A gorgeous riverside lodge, The Weasku Inn, in Rogue River, Oregon, served afternoon hors d'oeuvres so delicious and plentiful I was able to skip dinner, plus it was a great way to meet other guests. My breakfast at the Parkhotel Laurin in Bolzano, Italy, was so decadent, with an incredible cheese spread and fresh orange juice, among so many other delights, that I could skip lunch.

It's certainly easier to maximize points and perks from big-brand bookings, but when you're traveling for a long time, that monotony can be draining and depressing. I was never lonelier than when staying somewhere corporate. Paying a little more on boutique hotels I'm sure saved me in psychotherapy bills later.

I may never hack the system well enough to fly business class and stay at five-star resorts, but as long as I can use the points I do have to get more tickets to see more places, I’ll be ecstatic.

All photos by the author unless otherwise noted.