How to travel alone
I love traveling alone. And, like anything, there is an art to doing it. I wouldn’t deign to say that I’ve mastered it. But I’ve reached a point from being somewhat afraid of it to absolutely loving it, and I wanted to share a few pointers I’ve picked up along the way.
You’re probably wondering why you would want to read this or why you should care. You probably have friends or a partner who likes to travel. There should be space for that, too, but there is something unique about being in a place you don’t know entirely by yourself.
I find travel brings out people’s true personalities. I often go on trips for second or third dates because I think it’s the best litmus test. How better to meet someone at their core than in a space neither of you knows and you’re free to explore together? Who are you/they when you lack known structures or creature comforts to fall back on? Who are you/they when things aren’t going your way? Who are you/they when you can be anyone? Travel forces a certain level of vulnerability, rawness, and adaptability. And in the same line of thought, travel is the best time to explore yourself. To go deeper into who you are, what you like, and so forth.
Point in case - I wrote most of this from Kyoto, where I booked a one-way trip on a whim. I desperately needed a break; I needed to do something to soothe my soul and space to explore my creativity, and thus, here we are. I had a loose - tenuous, if best - excuse to be here, but it was an intentional trip to reunite with myself. I booked my flight there and hotel for the first few days, and that’s about it. I left the rest as white space to fill in and remain open to all of the possibilities that could be. You don’t need to do something as extreme as this - you can start small with a dinner or a weekend away, but just start.
I used to travel to run away; I now travel to come home. I am unbelievably fortunate to have the means and the freedom (and lack of kids and pets) to do this. I’m sure this will shift as my life shifts, but solo travel will always be a key part of my self-care and self-nourishment routine.
So here is a smattering of my recommendations. There is no rhyme or reason to the order. I am very eccentric, particular, and structured in my own special way, so these may resonate or not for you. I will keep adding to this list as time goes on.
Limit your social media time. When traveling, I batch post and promptly put away my phone. Who cares what anyone else is doing? You’re with yourself.
Even if you’re only planning on traveling domestically, bring your passport. You never know who you might meet and where you might end up.
Timebox work if you can. Giving your mind a minute to think about something other than work can help you become more efficient and effective at your job.
When choosing a location, I prioritize places that enable me to be outdoors in nature.
I like to study a place's history before I go and learn some basic vocabulary so I can explore off-piste from typical tourist destinations. It depends a little on the place, but I’ve gotten a lot of value from The Great Courses. They have awesome and accessible video lectures and textbooks.
I primarily take photos while walking around to remind myself of the colors or patterns of places. When I’m in a new place, I often choose something to focus on — it can be a color (I focus on all instances of a certain pink when I’m in Mexico), an object (street lights in Japan), or something natural (flowers everywhere). It helps me escape from my de facto ‘task-based’ daily life to a space of pure presence and enjoyment.
I’m often totally engaged with one or two friends while I’m gone as my defacto travel journal / so someone knows exactly where I am if I suddenly don’t reply. A select few of my best friends also know where I am at all times for safety reasons. Engagement with people outside of yourself is okay as long as it’s helpful to keep you present in the moment you’re experiencing. For instance, what I’m eating that day, where I’m going, what I’m seeing, highlights, and random philosophical pondering are all fair game. I try to limit conversations that are off-topic or will distract my head. Obviously, factor in work, but do whatever you can to time-limit or batch it if you have the freedom to do so.
When I ate alone at a restaurant for the first time, I was nervous. I didn’t know who to talk to or who to look at. I brought a book with me for the first several times, but I realized that the most beautiful part of eating alone is indeed just that: being wholly at ease and enjoying every part of your meal alone without distraction. It’s meditative.
I prefer short-form fiction vs. long-form when I’m traveling alone. Think short stories, poetry, and short spiritual texts. The reasons for this are multifold. I love to read and lose myself in a book, but that’s not the point of this time for me. The goal is to enable a conversation with myself - to read a few lines, a page or two, and see where those thoughts take me. I don’t want to let another voice fill the space. I want to leave enough room for mine to emerge.
Here are a couple of my favorites to bring - I’ve read each countless times. I’ll usually bring one or two per trip. They are all short, meditative, and philosophical:
Invisible Cities: Italo Calvino
Einstein’s Dreams: Alan Lightman
The Inner Life: Thomas Kempis
Labyrinths: Jorge Borges
The House of Belonging: David Whyte
The Heart Sutra: Trans. Red Pine
The Secret of the Golden Flower: Trans. Richard Wilhelm
Book of Common Prayer
Mediations: Marcus Aurelius
Exhalation / Stories of Your Life: Ted Chiang
Change Your Life: Rainer Maria Rilke
The Prophet: Kahlil Gibran
The Periodic Table: Primo Levi
I plan only one or two things max a day (including meals). I generally like to have a sense of things that could be fun and then fully go with the flow. I get a lot of use out of Google Maps pins. I like to spend some time pre-pinning interesting things so I can choose a neighborhood and go with the flow.
Food-wise, I eat a lot, get hungry often, and hate panicking. To avoid this but not lock myself into planned meals, I bring a lot of snacks (that could be meals if I’m desperate). If a meal is a must-have, I’ll make a reservation; otherwise, I’ll just walk in. Most places can usually fit one person in at the bar, especially early or late.
I travel everywhere with green juice powder with probiotics (I have it every morning), tea bags (mix of mint or ginger for digestion and chai rooibos or turmeric to ground me), electrolyte tablets, and oatmeal packets. Depending on the destination, I’ll supplement this with dried fruits, nuts, chocolate, and power bars.
I typically bring a small candle or incense to light when I get to my destination and daily once I’m there. I find it helps to center me.
I never regret bringing earplugs. I usually have three types on me: sleep, party noise reduction, and swimming.
Travel via carry-on, ideally a combo of a backpack and roller with a day purse inside. I like to be footloose and fancy-free. I never know if I’ll need to run for a plane or train or carry a bag up a few flights of stairs.
Bring a spare bag. I like to shop, so I bring a 45L duffel bag that packs down in case I find anything interesting during my travels.
I try to avoid looking like a tourist in athleisure. I always feel better when I look good, even if no one will ever see what I’m wearing. That said, I always wear shoes I can walk 10 miles in and an outfit I could run in if I needed to. I prize comfort, packability, and things that photograph well (you can always ask someone to take your photo).
Regardless of where I am going or what I’m doing, I always bring a swimsuit, a sweater, a hat, and something that could work for a black-tie event in a pinch. I also recommend bringing great lingerie (or the male equivalent)—you never know!
I fly a lot. Business class is always preferable if you can swing it, but admittedly, I’ve mastered the art of international overnights in economy, so it’s not that bad. Mind you, I’m 5’11.5” and have very long legs. Here are my tricks. I always do a window seat to cocoon myself and not be woken up if I sleep. I prefer bulkheads or an emergency exit to have more legroom. I bring a neck pillow, weighted eye mask, compression socks, and a cashmere blanket that can double as a scarf. If the plane supplies pillows, I’ll use that to prop my head against a window; otherwise, I will use a compression bag that has clothes in it. This is counterintuitive, but I usually leave my backpack down to put my legs on it for better ergonomic support. I then put on my airplane sleep playlist, take a light sleeping pill if I feel I need it, and sleep as long as possible. I do my best to fall asleep as soon as the plane takes off (or if I can’t sleep, I try to keep my eyes closed and my body relaxed for as long as possible).
If I really can’t sleep, I listen to a Yoga Nidra meditation or a story from Calm.
I know there are all of these new apps and ways to hack jetlag. Mine is pretty simple: sleep as much as you can to eliminate sleep debt, don’t drink and avoid big meals on the plane, get a workout and shower in when you land, and then spend as much time as possible in the sun to reset (wear sunscreen and a hat please).
Creating art is one of my meditation practices. I mix up what I bring depending on the circumstance and destination. I typically have a mix of watercolors (or sumi-e ink), drawing supplies, a sketchbook, origami supplies, and embroidery supplies on me. It is all portable and easy to carry. I prefer watercolors and sketches if I’m going on a hike or sitting in a garden and want to shift my attention outwards, while I use origami and embroidery to shift my attention inwards.
I work out a fair bit in ordinary life, but I rarely do so when I’m traveling. I’d rather explore and be outside vs. be in a gym. I fit in as much walking as possible (or swimming or surfing if that’s an option). I aim for about 20,000 steps a day. I’ll occasionally add a run into this, but I like the optionality of walking - you can stop, browse, and look.
It depends a little on where I’m going, but I usually have personal safety gear on me, just in case. I don’t drink in general, but I am careful never to let my guard down fully when I’m out. Honestly, I generally avoid bars and parties when traveling alone. I'm happy to give you more pointers here if you’re interested. I take this very seriously, especially as a solo female traveler.
If I know I will be outside a city and away from a drugstore with band-aids, I will also bring an emergency kit. If I plan on an outdoor adventure, I’ll add more safety items relevant to the place and type of adventure. I adventure a lot, so I keep separate kit bags for ocean, hiking, and cold-weather adventures.
Hotel-wise, I prefer boutiques over chain hotels. There is a time and place for those - I love that you will always know what to expect from a Four Seasons - but it takes the fun out of it for me. I like the art of adventure. I generally prefer Airbnbs so I can feel more at home and feel no obligation to talk to people. I love to swim (and also love spas), so I always strongly prefer places with either. Any place that’s too “sceney” is a negative for me for these trips - I am very focused on alone time and time with myself.
I swim in the ocean daily when I’m at home in San Francisco. If I can’t find a pool or an ocean, I’ll take a cold shower or an ice bath instead. If I’m ever feeling off, I fill the sink with ice water and dunk my head.
I’ve made friends in line for coffee, for breakfast, at restaurants, waiting for a taxi-cab, sitting on the airplane, shopping, you name it. There really isn’t any art to it - ask someone to take your photo, ask for recommendations, ask for directions, compliment someone’s outfit. If I’m not vibing with someone for whatever reason, I leave (respectfully).
I often end up on sidequests with new people I’ve met but I try to time-limit these to prioritize my alone time. My general rule of thumb is a maximum of an hour or one adventure per new person. For example, if I make a friend while hiking, I’ll walk with them for an hour until I break off to do some watercolors. I always say yes to adventures that sound borderline insane or things off the beaten path. I hope this goes without saying but trust your gut if anything feels off and run away as fast as possible if so.
I try never to eat something that I can at home. I prioritize local snacks and local foods. If I’m at a restaurant, I usually never look at the menu if I can help it and just ask for their recommendation. My best meals have come from the question, “What would you eat here if it was your last meal?”. Waiters/chefs tend to make it a personal challenge, and they put in more effort if they feel like you care. If you’re worried about what they might bring you (aka you’re in Asia and don’t want to eat a live fish), I would limit the downside risk by saying you’re vegetarian.
I love getting recommendations from locals. There is more downside risk, but I typically end up on weirder and more interesting adventures.
If I go to an art museum or a gallery, I play a game my mom taught me as a kid that has helped me refine my taste, “If I could have any piece in this room, which one would I want and why?” Do it for every room you walk through.
I take advantage of every bathroom stop I see (within reason). You never know!
I always have a notebook on me. I like to write down random thoughts, document snippets of strangers’ conversations, note interesting street signs, and doodle.
Bring out your book or notebook if you don’t want to talk to someone.
Sheet facemasks are great for traveling. Since my skin gets dry on planes, I’m very diligent about my moisturizer and skincare routine when traveling.
I never buy clothes or things I could get at home or online. I love finding one-off random shops, flea markets, or antique markets. Before I buy anything, I always wait for my eye to adjust to the specific place and aesthetic—it can take anywhere from a few minutes to a few hours. If I see something I like, I get it. I try never to go back to a place once I’ve left it.
Diets and normal meal times don’t matter. Eat when you’re hungry. Don’t when you’re not. Tune into what your body wants and needs. Get dessert if it will make you happy. I caveat this with the previous point regarding making sure you have a meal plan if it’s around normal meal times; most places don’t have room service, Uber Eats, or 24/7 stores.
I love to start each day or adventure when I’m traveling by pulling an oracle or tarot card. I don’t know or care if this is the wrong or right way to go about this, but I focus my intention while shuffling the cards on the question, “What does my spirit want me to know?” and pull a card. Sometimes, I’ll draw one card. Sometimes, I’ll draw three. I also really like conversation question cards for this purpose.
I do continuous check-ins to ask myself what I want to do. I find I often fall into the trap of ‘I need to do this, I need to be here,’ and it’s helpful to take a moment to remember that I am entirely by myself and there is nowhere I need to be.