Chief Editor of TravelPirates
I spent a few years working as a professional musician at night and in a coffee shop during the day, spent a few years teaching Spanish and English, and traveled whenever I could. I was born in Atlanta, raised in the Washington, D.C. area, lived for three years in New York City, two years in Richmond, Virginia, one year in Madrid, and another six months or so between Buenos Aires and Lima. In 2017, I decided to make the permanent move to Berlin and have never felt more at home.
How many countries have you visited?
More than 50.
Truthfully I’ve had life-changing experiences in more than one place while traveling, but the San Telmo neighborhood of Buenos Aires might be the single place that brought me the fondest memories to look back on. I also really loved Cabo Polonio in Uruguay for its rugged individualism. Guess it’s a tie.
1. Do your research and have patience — if you want to save money, you’ll usually need to put more time into planning. Though practice makes perfect, and once you get hang of the main methods and hacks, it won’t time so much time.
2. Be flexible in some way. If your job is flexible with vacation time, then go for the cheapest dates you can find. If not, perhaps settle for cheaper flights with a long layover and go out and explore the city. I like to approach planning with a lot of different options that might work and then narrow down from there.
3. Stop checking baggage, get status, or rely on travel credit cards — just don’t ever pay baggage fees (unless the American Express airline credit is covering them). Even when it’s possible to check baggage without a fee, unless you’re bringing a musical instrument or sports equipment, you probably don’t need to be weighed down by more than a large backpack/smaller suitcase for a trip of less than a month. Wear your heavy jacket onto the plane and stuff the pockets full if you’re going low-cost carrier.
With North American travelers in mind, I’d probably say the Canary Islands, specifically Tenerife. It can be super cheap to get to, and once there it’s also super cheap and really has something for everyone.
As a musician and music lover, I don’t have a single answer to this question. I associate different music with different places, ideas, or experiences. I heard John Coltrane’s album “My Favorite Things” this morning and instantly found myself in the mood to get on one of the cheap American flights to New York City to go hang out in Upper Manhattan. Luckily the moment ended, and I was able to finish up the deal I was working on!
I love the feeling of spontaneity, but as a borderline control freak, I tend towards more detailed planning. A part of me always hopes that something doesn’t go quite as planned, though — it’s just more interesting that way!
That depends a lot on the time frame, but I’d settle for a few weeks somewhere coastal towards the Southern part of Argentine Patagonia in November or December. Or, if allowed, I’d do an around-the-world trip with a stop in Patagonia!
Again, it’s hard to choose just one, but the 36-hour train ride that I took from Buenos Aires to Córdoba is memorable to me and definitely unique in the sense that most visitors to Argentina don’t even know the train exists. Somewhere between the haziness that comes with exhaustion, the constant mosquito ambushes from the open train windows, and the philosophical conversations that I found myself in with fellow train riders, I felt a sense of freedom that I hadn’t felt before.
For the destination, it depends on that person’s interests, but I would recommend a place that the traveler already has a connection to — things like interest or ability in a language, historical knowledge of the place, friends with connections to the place, interest in the local cuisine, or anything like that — being a nation comprised almost entirely of immigrants, it’s not hard to find a connection via your own roots. As for the kind of trip, I would highly recommend staying away from only staying at all-inclusive resorts or taking full tours, not that I’m against that kind of thing. It’s just that, to me, the investment in planning and exploring gives you the chance to develop yourself and really enjoy life in a way that more luxury travel simply could never provide. This is especially true for someone traveling out of the US for the first time! If you go back home talking about the food at the resort, it’d be a good idea to try again.
Take a (long) walk and stop somewhere for a coffee, a beer, or a meal.
Completely sealable coffee mugs.
Getting to the airport early, regardless of how many dope lounges I have access to.
Outside of living long-term in countries other than the US, I spent about six months slowly traveling from Uruguay to Peru.
I’ve taken lots of day trips, so ruling those and stopovers out, my shortest trip must have been a little under 24 hours in Dublin.
Well, I always feel like a pirate while booking transportation for my trips. While traveling in Morocco, I’d say I felt pretty pirate-like. I traveled around using the train system and found rooftops to stay on when I got to each new city — it barely cost me anything at all, and I saw a lot!