Six Keys to Successful Solo Travel

By: Anna Scott

One solo travel trip per year keeps a human healthy, stealthy, and wise.

Resolve for solo travel is my self-maintenance routine to “sharpen my survival skills,” “get back to the Girl Scout,” “do one thing that scares me every day.” Bold, spontaneous, and inspiring adventures gain part of their splendor by manifesting illusions of mystery and magic via intensive planning (and daydreaming). Blossoms of beautiful experiences are made more confident by commitment, as Beyoncé puts it “Pretty Hurts.”

A few of my secret ingredients for successful solo travel that go beyond the obvious nomenclature of ‘how to travel on a budget, substitutes for Mace that are TSA-okay,’ etc.

  Photo Courtesy of Anna Scott

Photo Courtesy of Anna Scott

Sit In The Fire: And on the third hour, she freaked out

Editorial images of a single person sipping coffee and gleefully looking toward the sun’s warmth are delusional gifts that melodiously push us into solitary romance, followed by,  “what can I pay attention to so that #confidence is holographically tattooed in the headspace around me.”

1. Dark pieces of self-criticism

“The Ideal Human,” a scrappy little voice planted in the crook of our shoulders, authors all the meanest things that could exclude us from belonging to community. Doubting whispers slowly creep and tend to grow into screaming hedges the longer we convene with ourselves in solitude.  ‘The voices in our heads’ are real, and most often, the little angel that is supposed to be balancing out on the opposite shoulder, is nowhere to be found. We are used to being qualified by another person (or object). Sitting in the fire of being alone is callous as the cocoon you are breaking through, and as beautiful as whatever you are patient enough to let emerge.

2. The Devil is your defender

The intrinsic need for approval historically kept us alive from abandonment and extinction, blind though to the actual danger of our modern-day circumstances. Practice managing internal shaming during solitude like you would any bully bastardizing your friend’s bravery. Step outside yourself to view the neurological naysayer as your paranoid friend. empower your core self by listening to the concerns running through your head with TLC, and then choose whether to validate your biological bodyguard’s cries or alleviate unnecessary self-retribution.

3. Planning solo travel is exhilarating

Social communities in routine work, social, and momentary solitary reprieves celebrate the pretty edges of our personalities. Facing our pitfalls, defaults, and sharp internal struggles in the midst of wild choice over our solo-selves is one of the most daunting, intense, rewarding, and sometimes miserable challenges as a human. When you are the only constant in your environment, the deepest, darkest fears and shameful aspects of our human imperfection shimmy to the surface like schools of fish pouring out of a worn hole in the net we have intricately weaved bit by bit through decades of practice. Let the dark details shimmy, celebrate their release to the surface, and you may just find a collection of rainbow scales in the belittled bellies you have been fiercely hiding in your regular life.

  Photo Courtesy of Anna Scott

Photo Courtesy of Anna Scott

Embrace Mania, Make Magic : Type-A Planning, Type-B Traveling

The Key to creating a magical, seemingly spontaneous and carefree solo travel trip, is to plan the crap out of your trip.

1. Play around with Google flights

Easy tool to try-and-check different itineraries – flexing your day/time/layovers can result in a less expensive itinerary with minimal inhibition on your over travel plans (E.g. Explore flight structures with extended layovers in another city on the way to your primary destination that may cost the same or less than a direct connection).

2. Escape Route

If you are squeezing in as much of the world as possible into six days of corporate PTO sandwiched across two weekends, booking all your flights and accommodations ahead of time can save you some bucks and also provide a sense of security since you have a paper trail of everywhere you were supposed to show up.

Whether you are a fly-by-night gypsy who would like to move every 24-36 hours, or would prefer to soak in one or two locales for more intimate amounts of time, both are great ways to get to know a culture. My speed-warp tour style is dual-purposed.  Explore multiple regions, and prevent chances to become unsafe by moving frequently. You won’t be spotted and identified as a sitting target because you are already Bye, Felicia by the time anyone notices you repeatedly.

Huge bonus: Your mom/primary contact will feel way more comfortable when you send over-planned excels and itinerary summaries of all confirmation #’s, mapped routes, hotel locations, and phone #’s etc.

  Photo Courtesy of Anna Scott

Photo Courtesy of Anna Scott

Know Your Role: One Envelope Can Save A Life

If I had a nickel for how many times I had been detained in international airports … including UK, China, Thailand … I would have more money to travel.

I have been guilty of relying too much on my blue-collar salesman swagger to get me out of poor research on individual travel statutes. I have been very lucky, and sweated through several t-shirts, escorted all the way through immigration by Heads of national immigration divisions, and admittedly had to default to the big, blonde crocodile tears of American entitlement.

1. One Envelope

Get a sturdy envelope (ideally manila with one of those bracket closers)  and a hair tie. The envelope will rip/tatter, etc. with in/out use, and the sturdy hair tie will keep tri-folded papers together in a succinct packet. Store somewhere accessible and zipped (I use the top flap of my hiker’s pack – can reach behind without taking off my pack, and keep sensitive info close to my cranium).

Before You Leave, Print Everything || When you are dealing with language barriers and confused authorities who are extremely liable for their decisions around your entrance/existence/exit in their national domain, having everything printed in one prepared packet provides an easier justification for trusting you, and also is sometimes the only way to prove your plans when computer systems ‘can’t find your record’ or you have booked different legs of the trip on different travel systems/airlines, etc.

**Take phone photo versions of all as well.

2. Topline Summary + Detailed Itinerary

Origin/destination/flight #’s/confirmation #’s/dates (in original, official formatting). Sequence all confirmation details in chronological order of your travel plans. Staple respective pieces of each itinerary leg, and only paperclip the collective itinerary legs together to easily separate and avoid additional confusion when you just need to communicate a specific destination or origin. Also print your excel with hotel/adventure receipts & confirms and phone #’s so you aren’t relying on technology.

3. On the back of each of your itinerary legs

Write the key phrases of that country’s language, so that you can easily reference while in-country/at the travel counters and have just that piece easily accessible when needed.

4. Scanned picture of your credentials

Stash separate pieces of paper for Passport, drivers’ license, and Health Care card (front and back of all three) outside of your envelope, deep in your pack or on your person. If the originals get stolen for any reason, you want these documents and extra cash in a separate place for backup identification.

Read travel advisories, international phone plans (way cheaper than you would think), international visa stipulations including their policies on traveling to/from surrounding countries (like China, you can stay for 48 hours without a visa but you must have a ‘place of stay, a confirmation of your exit plan from the country, and entry though different customs lines).


  Photo Courtesy of Anna Scott

Photo Courtesy of Anna Scott

Rule of Thirds: See The World, Meet Three People

Intimidating groups of wanderlusters and backpackers || Many have assembled crews across multi-city aggregations and you are traversing the middle of the hype getting to your bunk or room. Everyone is in the same boat, or was a few journey steps back; they will adopt you – it’s an unwritten rule. If you aren’t in the mood for the whole Road Rules posse, don’t worry – there is always someone in that boat too, and there is no shame in keeping to yourself. **See step one, sit in the fire and let the interactions come organically.

Goal of meeting three people the entire trip || Treat social travel situations like walking into any networking event, just spanned over days instead of minutes. Take the pressure off, relax into being with yourself, and accept introductions when they are “within your quota.” Group excursions are the easiest, because you are likely have several hours to assess individuals, and will end up connecting with one or two people during daylight. Making plans for dinner or the next day after getting to know the person(s) in a prolonged group setting is much more comfortable.

Global Gold Mines: Pick Bold Places, Find Old Faces

From the gut || Trust ‘first thought, best thought’ dream destinations for your solo travel, dig into Google Flights, and scour news headlines for timely emphasis’ on tourism or cheap flights due to various political or cultural factions. E.g. Brexit resulted in a slew of crazy affordable flights to Nordic countries, etc.

Landing in a friend-zone || If you have a friend living in one of your bucket list destinations, or close enough for a rendezvous in prime travel real estate – landing in a “friend-zone” is an awesome way break into solo-travel without going totally rogue. Even taking your own out-and-back excursions from a friend’s home base, provides a great way to stay connected and also a safety net if you are nervous about full-out solo-travel.

Never be afraid to reach out to long-lost friends or acquaintances || You may be amazed at how welcoming and empathetic ex-pats can be; after all, they are full-time solo travelers. Those brave souls living across the globe definitely do not have the same ease of access for visitors outside of their home country, and are likely open-minded and enthused about having visitors. Even if your schedules don’t align, reaching out will get you some local intel or recommendations, and also serve as another layer of social safety, with a “nearby” emergency contact in case any trouble arises. Plus, how hurt would you be if an old friend flew across the world to Small Town USA and didn’t let a sister know?

Anna plays a corporate gal by day, in the thrilling professional grind of entertainment & sports media. For better or for worse, she’s been known to “crack the whip with a smile,” tangled between sweet southern hospitality and the edges of a thousand burning candles of ambition. Tar Heel education and several lucky breaks led her through little lives in London, Los Angeles, and before her introduction to New York City. New York has kept her creative wit dutifully occupied for almost three years, and the gypsy soul  may have finally met her metropolitan match. Breaking into the fiery world of stage performing and solo singing, Anna is excited to now debut her writing for Six Degrees Society. In her other free time (ha-ha), you can find her either creating or knocking down bucket lists full of world travel, food, music, motorcycles, and thrill-seeking adventures. Follow her adventures @dieseldarling, or get to know Anna a bit more in her portfolio site,

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