In the second half of 2021, I went on a four-month trip across the US. This page began advice I would send to my past self, before slowly expanding based on additional travel experiences.
If you’re roadtripping, some of this will be useful, but some will not. I have generally traveled without consistent access to a car. Also, some of this will not be as useful for international travel, though plenty is relevant no matter where you are.
Timing and Destination
Timing is key. For me, the right amount of time on the road was about two months. That’s how long I did it in 2015; in 2021 I traveled for five months and it was a little long, although, I did catch a brief “second wind” at about the 3 month mark.
Although I have enjoyed traveling during the off-season (NZ in 2015, ADK in 2021, MI and MN in 2021), it is the off-season for a reason. I have found that my favorite time travel is when the temperature is between 55 and 80°F. Use WeatherSpark to explore average temperatures when planning your travel.
Make sure that wherever you go excites you! And don’t be afraid to change your mind about your plans.
Finding a Place
Here was my hierarchy of accommodations when I’m working:
- With a friend (usually no longer than a week, often just ~3 days)
- Airbnb (you don’t need a whole apartment, most of the time, if you’re solo - just a private room that has a desk)
- Hostel (or motel/hotel)
If I’m not working, and we’re not in the middle of a pandemic, couchsurfing sites like Couchers and Trustroots are an excellent option. But it seems like they haven’t fully fired back up, yet, as of early 2022.
Another option I haven’t tried but think would work is looking for short-term sublets on the Listings Project.
Housesitting is also an option, but I haven’t tried it yet, in part because it is difficult without a car and because I’m allergic to cats. But if you are extremely flexible, it can be really great.
Lastly, if you are roadtripping or hitching, motels are of course an option, along with camping on public lands.
Being centrally located is useful when you go to a new city, if you can afford it. While downtown might not be the “coolest” neighborhood, it is often the most networked, with access to all (or at least, most) of the others. Another key plus is being within walking distance of a grocery store, or at least a convenience store. (On the other hand, staying by the beach on the Venice Lido was great.)
If you do not have a car (like me) you will want to make sure that your accommodation is within the zone of car/bike/scooter-share programs, for easier movement.
Staying close to the city center typically provides more flexibility (in terms of access to other neighborhoods) and access to public transportation and ride-sharing/car-hailing services.
Planes are typically the easiest, but I recommend trains (US/Canada), buses (Flixbus or Greyhound), and boats if you can swing it. Explore your options using Rome2Rio and Google Maps - changing up your travel method can be fun. And keep in mind that using a train or bus rather than a boat lowers your impact on the planet. (More tips on each method of travel below.)
This sort of travel is no joke. Make sure you are ready to carry your backpack for significant distances, whether that be up a mountain or from one end of an airport to the other. I recommend going on walks with your pack during the weeks leading up to your trip, and slowly increasing the weight.
Picking a Bag
There’s a lot of guidance around this on the Internet, but here are the reasons I picked a Cotopaxi Allpa 42L:
- Laptop pocket
- Zipper pckets help with organization, lots of pockets
- Opens suitcase-style for easy access to everything
UPDATE: I later dropped the Cotopaxi because it hurt my back, returning to my trust 40L Osprey backpack that’s taken me all over the world. Suitcase style is overrated because you end up having to take everything out anyway a lot of the time, and opening it up that way takes a lot of space. Keeping the stuff you need at the top of a normal backpack compartment is more efficient.
Packing & Gear Tips
Packing light is all about the mindset. Pack as light as you can get yourself to, especially when it comes to clothing. Most places have laundry available. (I brought laundry detergent and a folding bag I could use to do my own laundry, but I never actually needed it.) When I traveled in 2021, I wore everything for at least two days, and ended up doing laundry around every 9 days.
Pack clothes based on each location’s historical weather - plus a degree or two to account for global warming. When considering what to bring, layering is key. Think about how items can serve multiple roles - like a button-down shirt that can work at both a nice restaurant and a club, or a pair of shorts that doubles as swim trunks.
When you aren’t sure about something, remove it from your packing list. Don’t bring things that you “might” need. Certainly, when you are traveling the US or other European-style countries, there is no need to pack anything you aren’t going to use regularly, since you can buy anything you need. Cheap, replaceable things can be purchased or replaced easily.1 On a couple occasions when I needed something, or a restock, I had it shipped to my next stop.
The #1 thing to keep in mind is that unless you are backpacking through the Mongolian Steppe, the rest of the world is remarkably westernized, even the more remote parts. Most countries, especially cities have stores where we can buy things. Not every problem that we have to solve in our daily lives requires that we carry the solution with us at all times. For every problem you think you will encounter, analyze how much of a problem it is. If every day you dry your hair using a hairdryer, ask yourself: will where I’m going have hairdryers? If not, will I struggle if I can’t dry my hair every day? If the answers are “no, yes,” then by all means bring a hairdryer, but chances are, if you’re being honest, it’s not an actual problem. On the flip side, if the problem is “I am diabetic,” carrying your insulin is probably a good idea.
– [deleted] on Reddit (note: I replaced some ethnocentric language)
Here are some more specific packing tips:
- Bring just one bag, but pack a couple smaller (packable) bags inside for carrying food and other things. In 2021, I brought a packable tote and a packable backpack, and in trips since I have brought just the packable backpack.
- Don’t bring an umbrella - just wear clothing that won’t be ruined in the rain, have a good rain shell, and bring a pack cover (my pack had one included) - EDIT, 2023: unless you are going to a professional conference someplace, say England, for a whole week. But you can always buy one if you need
- Use packing cubes to keep things organized. And the ranger roll is a useful technique for larger times, like a rain jacket or blanket
- Get cable wraps for all of your cables and keep them in a little pouch
- Avoid liquids - I packed solid shampoo and body wash
Example Packing List
This was my 2021 packing list. Hopefully I didn’t forget anything.
- 5 synthetic or merino wool t-shirts
- 7 pairs of synthetic underwear (probably 1 more than I actually needed)
- 6 pairs synthetic or wool ankle socks (probably 1 more than I actually needed)
- 1 pair tech pants, medium weight
- black denim jacket (heavy, annoying, but an adaptable piece that can work in more formal environments)
- rain shell
- lightweight merino sweatshirt
- baseball cap (for days when I can’t shower)
- merino wool baselayer leggings and longsleeve undershirt for colder environs
- 1 pair log wool socks
- 1 pair shorts
- 1 button-up synthetic patterned shirt (for when more formal look is needed)
- packing cubes
- small compression laundry sack
- flip flops (for hostel showers)
- sleep mask
- lock for hostel lockers
- portable water flosser
- rotary electric shaver
- microfiber travel towel
- nail clippers
- solid shampoo and body wash, in Matador soap baggies
- travel ibuprofen, dramamine, and allergy medicine
- a few band-aids
- small sunscreen
- anything else you might need for your health, and for safe sex
- phone dashboard mount (for rental cars - EDIT: so many cars have CarPlay that I don’t bring this anymore)
- laptop and charger (I got a small, more portable charger partway through)
- bluetooth mouse
- bluetooth noise-cancelling earbuds (useful both for music/pods and as ear plugs)
- Apple wired headphones and headphone to lightning adaptor
- USB C, microUSB, lightning
- USB C hub (with HDMI)
- power block
- wallet w/ vaccine card (remember those? back in 2021 it was still essential…), credit cards
- playing cards (I played solitaire in a bar one time)
- backup cash
Things I brought but didn’t use:
- ear plugs (not needed with my bluetooth earbuds…EDIT: used in 2023)
- portable clothesline
- Soak no-rinse laundry detergent
- small Field Notes notebook - I just used my phone
- reusable sandwich bags
- a small roll of electrical tape
Things I would have brought if I was on the train more often:
- warm packable blanket
- combination luggage lock
Travel & Mobility
I always get there with plenty of time to set myself up and use the airport internet for a little while. Be ready to take off your shoes and take out electronic devices. Bring snacks to avoid airport prices. Fill up your water bottle after going through security. But you already know the drill.
In my romanticized version of digital nomadism, the train Internet is amazing, and you have plenty of space to work. In truth, the internet coverage tends to be pretty spotty. I often opted to use my mobile hotspot. Unfortunately, this isn’t enough to dependably attend a 60-minute meeting, since trains tend to take you through remote areas of the country.
My experience with train travel has varied drastically, and I don’t think I’ve done enough of it to draw broad conclusions. I had a good experience on business class trip once, but that might have been a fluke. In general, passengers have been quiet, and I’ve made some friends in the diner car, but they can also be the thing that keeps you up if they get drunk and won’t shut up XD
Sleeping on trains can be a challenge, especially if you are cheap and go for a coach seat. I’m a little too tall for them, so it’s a struggle to get comfortable. In addition, it tends to be chilly in the night, so make sure to have a blanket, or at least a couple jackets to cover yourself with. Earplugs or isolating earphones are also essential, since the train engine will be blaring its horn constantly throughout the night.
Keep in mind that long-distance trains often get held up by freight trains, since the shipping companies are the ones that actually own the railroad. Never plan anything for the day you are scheduled to arrive. In the US, use Amtrak’s train tracker to get info on departure and arrival times, and save yourself some stress.
Sometimes, you just need a car. It’s cheaper if you return it to the same place.
Boats & Ferries
No tips here - but they’re fun.
(Hashtag) Van Life
I stayed in a van for a week in late September in California, heading up the West Coast a bit before heading east to Yosemite. My van was fairly barebones, so I think my experience could have been different if I had customized my own. Overall, though, I felt that it was somewhat overrated. It is not as cool as the influencers make it seem. RV-life, but smaller.
I parked in: up a hill overlooking the Bay, on the beach at a state park, the back of a rural church parking lot, and a (comparatively bougie - running water!) RV park.
I’m definitely not a pro, but here are a few tips I picked up:
- Try to find a place to park when it is light out
- Use iOverlander (also Campendium, Hipcamp) to find a place. Or stay on Bureau of Land Management land
- I bought a phone mount to help me drive/navigate solo
- Buy a few gallons of water when you head off into the wilderness
- Look up how to deal with your waste properly (gray water, toilet paper, little shovel, etc.)
Public transport is awesome. I always default to it. Nowadays, most cities have an app you can use to buy a ticket in advance.
I’m a longtime fan of Citymapper for using public transport in NYC. I found that, unfortunately, Google Maps was a bit better in many of the US cities I visited.
The “Sharing” Economy
I used just about every transportation app out there to get around without a car. I don’t feel a need to endorse any of them - it was a marriage of convenience. But here’s the list, in case you need it:
- Bikeshare: CitiBike
- Ride-share: Uber, Lyft, Coop Ride, Curb
- Car-share: Gig, Turo, Zipcar (and Hertz et al.)
- Scooter: Uber, Lyft, Bird, Lime, Veo, Spin (yes, I used all of these)
- Bus: Flixbus, Greyhound
- Train: Amtrak
I’ve hitched before, but in US it is not popular, especially within cities and during the pandemic.
Life on the Road
In addition to the travel methods, accommodations, and my pack, here are the things I needed to constantly think about on the road in the US:
- Bathroom access
- Internet access (with a reasonably quiet place to take meetings and a power source)
Obviously, all of these - except, perhaps, public restrooms - are readily available in the US. But they can be quite expensive over time, especially if you do not plan ahead.
Keeping a steady supply of water is essential for long-term travel. Bring two water bottles (my second is a folding Platypus I use as a backup). Fill up, top up, whenever you can. Especially if you are trying the #vanlife thing. And make sure to wash the water bottle every so often.
Bathrooms were actually often the toughest, when you are transitioning from one place to another or exploring a city on foot. My best advice is to always use the bathroom before leaving a store or restaurant where you bought something. Worst-case scenario, if you share your desperation with a staff-person, they might be able to make an exception and let you in.
The variety of foods you have access to is one of the best things about traveling. So many amazing restaurants, wherever you go! (My favorite Google search is “vegan food” - or use Happy Cow.) But it can get expensive. So go to the grocery store!
Depending on how fast you are moving, cooking at your host’s place, or at an Airbnb, may not be a very good option. I ended up buying olive oil at every Airbnb I stayed at and just leaving it there if I was getting on a train.
I enjoy making food for my hosts, like a big Sunday breakfast or some pesto pasta with mushroom and onion. It’s a great way to say thank you and pitch in. Sometimes I’ll also buy them a bottle of (natural) wine.
Something I could have done better was bringing reusable bags/wraps for taking food away from restaurants, when I had refridgeration available.
Some folks are excellent dumpster divers. I have yet to do that, myself.
When you’re in a new place, and working full-time, you also need internet and a quiet place (and electricity) to work dependably, on-demand. After a while, being on the road won’t be a good enough excuse for being late to meetings or having a poor connection. Thus, I found that when I needed a good connection, and when I didn’t have it through my accommodation, I would choose corporate businesses like Starbucks and WeWork over local ones, simply because I could be 100% sure they would work.
The back-up for internet is always a mobile hotspot. In my case, I could tether my laptop to my phone. This was especially useful when I was living in a van for a week, and when I was traveling by plane.
You’ll want to keep your laptop and phone charged as much as possible. I kept a power block with me and fully charged as much as possible. In a couple cases, I used my laptop as a glorified power block so I could use my phone to navigate in the wilderness of eastern California.
For international travel, I recommend using an e-sim service like Airalo or Monty. I go with whatever is cheapest.
When you first arrive at your accommodations, explore the whole building, open every door, look through all the areas of your room, check under the bed, and dig through all of the kitchen cabinets. Any interesting ingredients or tools? Anything missing? Let your home inspire you, and make sure you have what you need.
You need to keep a tight schedule when you are traveling.
For me, Calendly was essential (although I may be switching to an open source alternative soon). I blocked off travel/transition days in my calendar and was able to change time zones easily. Make sure to keep track of time zones as you move around, updating your phone, computer, Google Calendar, and Calendly time zones every time you cross a boundary. And don’t forget about daylight savings time.2
Make sure to think about digital security. I used a VPN (ProtonVPN) whenever I connected to public wifi, like that of a coffeeshop.
If you have to miss a check-in, try using Loom to record your thoughts or updates.
When you are in a new place, keep your head up - literally. Look around, have active eyes. You might just notice something special. We’re always surrounded by unique moments, humdrum and otherwise.
When I get to a new place, I always look for vegan restaurants, dance clubs, farmer’s markets, and used/rare bookstores. I also search to see if there are any notable local foods or products, and which neighborhoods are the most “hip.” You’ll have your own interests, of course. I also look at:
For some activities, you’ll need to plan ahead. During COVID, many museums are requiring that you buy tickets online in advance. But when you plan, make sure to leave space for unplanned stuff and talking to local folks.
Entertainment & Personal Growth
When I left on my four-month trip around the US, with a full-time remote job, I totally overestimated what I was going to be able to do. I calculated my time using the following:
7 * 24 = 168 total hours per week
7 * 7 = 49 hours of sleep/week
8 * 5 = 40 hour work week
168 - 49 - 40 = 79 hours remaining
What I did not account for was the time-consuming grind of the travel itself - of looking for a restroom, eating out, waiting for your flight, waiting at a bus stop. And when you are traveling, you usually want to see friends, try restaurants, and go and have a good time. Or at least I did. So the little goals I set for myself, like learning another language, simply did not happen.
Even with all that, however, you won’t be traveling, working, and exploring 24/7. Sometimes you need to sit back for a day and relax. My e-reader was key for this, as were my bluetooth earbuds.
Documentation & Sharing
I ended up deciding not to take my Olympus camera simply because of the added weight. I left social media in 2020, but I still wanted to document as much of the experience as I could in particular to help me remember things years from now. It will also allow me to share (a resonable number of) photos in my personal newsletter.
I also enjoyed sending postcards to friends partway through the trip.
Although I wasn’t buying souvenirs - pack space comes at a premium- sometimes stuff gathers. When it was scannable (like receipts), I use the Dropbox app to scan it, or I took a photo of it. And if it was truly special, I made space for it.
I ended up replacing my headphones, an Apple headphone adapter, and batteries for my electric shaver. I also purchased additional layers as the weather got colder. ↩︎
Be careful when booking travel in Arizona or other areas that don’t observe DST. One time I missed my bus because my ticket was incorrect. I had ordered it before DST “sprung forward” and Greyhound’s website was not configured properly. ↩︎