21 Questions: Nomad Travel Edition

When people find out that I’ve been traveling since February 2016, most are curious about when and why I quit my job, what I miss about my old life and when I think I’ll return to the U.S. All perfectly reasonable things to ask.

But there are also people whose questions are more practical… (How far in advance do you book your flights? How much do you budget each month?) …and hilariously specific (How many pairs of shoes do you have? What are the visa requirements in Vietnam?) These people are often toying with the idea of taking a trip of their own and want to know how to make it happen. If that’s you – well then it’s your lucky day because I’m going to share all my secret travel tips, 21 Questions style.

How far in advance do you book your flights?

That depends on where I’m going. If I know I want to be in a certain place on a certain date (Christmas or to meet a friend) then I usually book a ticket at least six weeks beforehand. From what I’ve read, you don’t save any additional money by booking further in advance.

If my agenda is more open – as it was this past winter – then I book just a week or two ahead. Since it was low season, I still got decent deals. Supposedly, flights are cheaper when you purchase them on a Tuesday (something to do with how promotions were run years ago) and also fly on a Tuesday (the least busy day).

Where do you find the best deals for flights?

Again, it depends on what you’re looking for. For multi-stop journeys or around-the-world trips, AirTreks has amazing fares. I used them at the beginning of my trip last year and paid about 1/3 of what I would have if I booked my flights separately on my own.

If you’re flexible about where you’re going and/or just want to book something cheap, I like the “Everywhere” feature on Skyscanner. It lets you browse a long list of cheap tickets based on your city of origin. (To find options, click on the “destination” field on the search page and then select “everywhere.”)

For regular point A to point B travel, I use the usual travel booking sites and then cross reference their fares with the airline’s site before purchasing. One thing I’ve come to watch out for is the checked bag fee. A lot of airlines are now charging for anything other than a carry on – even on international flights. I’ve seen prices as high as $70/bag – which usually negates any savings on a cheaper ticket. I’ve found that Skyscanner also tends to have the cheaper flights than Kayak, Expedia, etc. – but they often charge extra to take a bag or reserve a seat, so they’re usually where I research, but not where I book.

Did you travel everywhere in Europe by train?

Sometimes. Traveling by train is usually cheaper than flying, but it can still be expensive and it’s often impractical time-wise. A good site to quickly compare travel options between cities by all transportation methods (plane/train/driving/bus/ferry and any combination thereof) is Rome2Rio. It doesn’t provide pricing, but it gives you a sense of what options are available and how long each takes.

Unsolicited advice: Don’t overlook buses. They’re usually about the same amount of time as the train, but cost just a fraction of a train fare or flight. For example, last summer, I went from Krakow to Budapest for $8… to fly would have been over $400 and it would have taken at least 2 hours more. And believe me when I say that European buses are really nice! They usually have WiFi, free coffee/tea, and even seatback entertainment.


How did you find a job you could do remotely?

I lucked out on this one. I resigned from my job at a U.S. company. A few months later, they offered me the opportunity to work part-time in a new role, which I could do remotely. That’s rare, so this story is of no help to anyone.

Instead I’ll tell you that some of the people I’ve met have found on the road have found their travel-friend jobs on websites that specialize in remote work opportunities. One is Virtual Vocations – and you can also check out this list.

How do you make money off your blog?

I don’t. That’s why it doesn’t look like a dump. From what I understand, making any substantial money off an ordinary blog is exceedingly difficult. For me, it’s not worth the time and effort to research.


How much do you budget each month?

None of your business. :) Kidding! I’m not sharing an exact number because a travel budget varies in the same way a normal household budget would. How much money you “need” depends on what you want to do with your time and where you want to go. I’ve been places where I lived really well and spent $1000/month (South Africa, Madagascar) – and then other places where I spent more than I did living in New York City (Israel, Australia). The thing is, it’s possible to travel anywhere cheaply – so long as you aren’t picky about your accommodation and don’t load up on extras. In New Zealand, for example, you can get a shared room in a hostel for $15/night, or you can spend six times as much on a mid-range hotel. I tried both options while I was there and, honestly, found both to be equally fine – though different.

Still. This must be way more expensive than living in one place. You must be in debt!

Is there a question there? Seriously though – I find that I spend, on average, about the same amount as I did living in New York. That includes flights, accommodation, an occasional car rental, etc. Some months are less, some are slightly more – but it’s all evened out. I actually saved the same amount last year while traveling as I did the year before when I was living in the States – which is technically saving more since I took a pay cut when I went part time.


Do you carry around a ton of cash? How do you get money?

No. I carry some cash for emergencies, but rely on the usual cashpoints to withdraw money. I also carry two debit cards for two different bank accounts and two credit cards from two different financial institutions. I also have a few checks for emergencies, as do some members of my family back home. I never carry both debit or both credit cards around at the same time or keep them in the same wallet or bag on travel days. I don’t carry travelers checks.

What’s a good travel credit card?

I really like the Capital One Venture card. It has no foreign transaction fees and the rewards system makes it easy to earn points that convert to cash-back on your monthly statement. The annual fee is high, but if you’re traveling a lot and putting loads of hotels, flights and other large purchases on your card, you’ll easily make up for it.


What kind of health insurance do you have?

I have a regular health care plan through my employer. However, those types of plans generally do not cover any kind of illness or accident once you leave the country. Even for short trips, you should always buy travelers’ insurance in case of a catastrophic event and you need to be treated in country and/or repatriated.

I use World Nomads, which is underwritten by Nationwide. It covers pretty much any kind of “extreme” activity you may want to do as a tourist – like bungee jumping or horseback riding. (Not all plans do, so check before you buy something if you plan to do anything other than walking around a city.) Thankfully, I haven’t had to use it, but they have good industry ratings.

Did you ever get sick abroad? What did you do?

Just once. I got strep throat and pink eye in the same week while I was in Israel. (I swear, it was from a snorkeling mask I used in Madagascar shortly before.) In some countries, like Israel or Morocco, the pharmacist can dispense prescription strength drugs and antibiotics over the counter – so I lucked out and didn’t have to see a doctor. If not, I would have tried to visit an urgent care clinic.


What’s cheaper – mid-range hotels or Airbnb?

Usually, a “nice” Airbnb is about the same price as a mid-range hotel. But I find you get more value for your money with an Airbnb. Plus I also like being able to prepare healthy foods (not cook!), do laundry and have unlimited WiFi. But that’s just a matter of preference.

How do you find “good” Airbnbs?

I’ve mostly had great experiences with Airbnb. Generally speaking, I book places with at least 20 good reviews that are centrally located. If you don’t know the city where you’re staying, look for apartments that are clustered together (that’s usually a popular neighborhood) or scan the reviews for mentions of restaurants and bars nearby. Also, do the obvious: look closely at the pictures and imagine what the person who lives there is like. If it’s someone who seems to match your lifestyle, then you’ll probably like the place.

I avoid anyone who seems to be using their site as more of an (illegal) hotel booking service… so if a host has hundreds of reviews, for example, they’re probably just turning over the room as often as possible. That might be a fine place to stay, but my experience is that those listings are a little run down, the hosts aren’t very responsive and it’s overall not as comfortable. Plus, they’re sometimes places that are undesirable as a “normal” apartment – like the place I stayed in London that turned out to not have a kitchen sink.

Do you use a hotel rewards program?

Not really. If I book a hotel, I usually use Hotels.com because they have decent rates and their rewards program is simple: stay ten nights, get one free (average rate of the ten nights).

For last minute bookings, I also like the app HotelTonight. They tend to have much lower rates and they make it simple to find something that fits what I want (close to the airport, right downtown, etc.).


How much luggage do you have?

Up until a month or two ago, I had just a backpack and carry-on size suitcase. I could have used something bigger, but I didn’t want to lug around anything too heavy and bulky. My secret weapon is compression bags, which I use for all my clothes. If you roll them right, they take up about 1/3 of the space of non-compressed items. I tried lots of brands, but my favorite is Eagle Creek. They’re slightly more durable and tend to shrink better. But don’t overpack them because the valves break easily.

When my carry on died this winter, I upgraded to a slightly larger bag – the Osprey Sojorn, which is a cross between a roller bag and a duffel. (I did not buy it for the price listed online, so I don’t know what that’s about.) If you don’t mind checking a bag on flights, I’d recommend something this size and style… it gives you much more leeway on how you pack your bag because it’s flexible and it’s very lightweight, but still sturdy.

How many pairs of shoes do you have?

Three. I have a pair of running shoes, a pair of casual sneakers and either a pair of semi-dressy sandals or low ankle boots, depending on the season. I wear the bulkiest pair on travel days. (I also have a pair of flat sandals, but I don’t count them because they take up practically no space.)

What do you do if you find something that you really want but can’t fit in your suitcase?

I don’t buy it.

What did you do with all your stuff back home?

I sold some; I gave a lot away; I threw out even more. I loved my apartment and all the things in it, but it didn’t make sense to keep it. By the time I would have lugged it all to storage in the Bronx and paid the monthly bill for a year, I could have bought it all over again. Interestingly enough, once my things were gone, I find that hardly miss any of it.

Barcelona! #solotravel #travel #spain #barcelona #nofilter

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What do you do for a cell phone?

Initially, I kept my U.S. cell phone plan and added an international option on top for occasional use. This was prohibitively expensive ($135/month) but I thought it was the best option in terms of consistency.

My phone dying in New Zealand turned out to be a great thing. I bought an unlocked iPhone, which was very expensive upfront, but balanced out since I was then free to use local cell carries. Now I spend about $25-35/month, and sometimes don’t even bother getting a plan if I’m in a city with public WiFi. I had just about broken even on the cost of the new phone when it was stolen. Ha.

It’s also possible to unlock a phone you own already, assuming you don’t mind doing business with a guy in a van.

How do you keep in touch with your friends and family?

The same ways I would if I were still living in New York: FaceTime and Skype for calls and video chat; WhatApp for texting. I find iMessage to be somewhat unreliable, so I tend to only use that casually. In other words, no calling cards.


How did you file your taxes?

I filed my taxes remotely through an accountant. I’ve worked with him for years, so he was comfortable preparing my return and letting me e-sign. It’s also possible to file remotely on your own and/or get an extension if you’re traveling, if you don’t want to pay a professional.

Do you need an international drivers’ license to rent a car?

I actually don’t know. I can tell you from experience, I did not need one to rent a car in New Zealand, Australia or Canada. But doing something and doing something legally are two different things. Don’t trust this bloggers for this kind of stuff – what’s wrong with you?


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A few random tips:

Onward tickets. To enter most countries, you need an onward or return ticket. In my experience (read: white, American), customs officers rarely ask to see it, but the airlines often do if I’m traveling internationally on a one-way. (This is because if an airline lets you board a plane and you’re denied entry to a country, then they are responsible for repatriating you.) You can try to travel without one so that you have the flexibility in your plans to stay as long as you please, but it’s a gamble. Forging a ticket is illegal and I would also advise against that.

Visas, etc. Americans are pretty spoiled when it comes to travel. We think we’re allowed to come and go as we please because, quite often, we are. But even if you don’t need a visa to enter a country, there are still other stipulations you need to know, like entry fees, blank page requirements in your passport, or the maximum length of your stay… some places you can do a “border run” if you want to stay longer and other places (such as the EU) you need to leave for a certain period of time before you can return. It varies and you should always triple check what all the requirements are.

Lost passport. I never lost my passport, but it was once held hostage in a West African country. I visited the U.S. embassy and they explained that an emergency/temporary document could be issued within 24 hours (or it might be 48 – check!) if need be. It didn’t, which was great. In case it ever is stolen, it’s good to carry a photocopy of all your travel documents and any entry visas/stamps. (If you’re stopped by police, they don’t just want to know who you are, but verify you entered legally.) I also keep photos of those on my phone just in case.

That’s all I can think of at the moment. If you have questions or other tips, feel free to share in the comments. Happy Travels!


  1. Where do you store your clothes you don’t need for a particular location. You seem to jump around to warm and cold weather locations?

    • Hey – so I cheat a little bit on that one. I went home in December for Christmas and switched out all my summer clothes for warmer winter ones. I try to stick to one temperate zone for each “leg” of the trip. Right now I have a sundress and a bathing suit just in case I go somewhere warm, but otherwise, I’m all winter-ish at the moment. When I’m traveling in warm areas, I take a spring jacket as well as a Patagonia-type lightweight down jacket.

  2. Hi Nova – Great Q&A!! A lot of good info. Maya is going to need a place in Santa Cruz, CA, 5/28-7/28. We are finding very limited options and expensive…even AirBnB…hoping UnivSC facebook page will come thru with something…anyway, we are reaching out to everyone we can think of in hopes that someone may know someone…you get the idea…so if you know anyone who may have a place with spare room or have any tips for us would appreciate. She needs to be able to get to Southwest Fisheries at western end of SC by either bike or public trans. Probably a long shot but you never know. Keep up the great travels. BEST Paula

    • Hey! I don’t think I know anyone in that area – but I’ll post on Facebook. Happy to help – Maya is pretty much our only chance of not ruining the planet at this point.

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