The #1 question I get when I’m traveling solo is simply, “How do you do it?! What are your tips?” To preface this post, I’ve always been a really independent person, in all facets of life. By nature of my job, I work alone almost every single day. Even before I was running B&S full-time, I was the first full-time employee at my old company. I ran our NYC showroom while the rest of the team was in Rhode Island. I worked in an office by myself almost every single day for well over a year before we hired my assistant. On the personal front, I live by myself and have for quite a few years. So when you think about it, traveling alone isn’t that different from my everyday life. However, I do live in Chicago with all of my college besties. My best friend lives in my same building and we’re always together when we aren’t working. And sometimes when we are, too! So, for me, the main difference while traveling is the lack of socializing. Weekends are a lot different when I’m traveling solo versus when I’m home in Chicago, or even in my second home, NYC. And when you’re traveling somewhere where most speak a different language, it can be even more isolating.
“Is it lonely??”
While I wouldn’t call it lonely, isolating maybe? Let’s call a spade a spade, here… You’re by yourself for an extended period of time. You will see and do things that you wish your friends and family were there to experience with you, no doubt. But I try to embrace the “me time.” I’ve always been the girl that needs time to myself. Even when I’m on trips with groups of friends, I like to go off and explore on my own a bit. Get lost, both in my own thoughts and in a new-to-me city. I’ve found that soaking this up can be extremely rewarding! Most of the time, I like to wander without much of an agenda. Sure, have a light outline of a plan (areas, maybe a few coffee shops or cafes I want to find, etc.), but I just explore. You never know what you’ll find! Most of the gems that I’ve found in so many different cities were not on all of the lists that I read while researching for the trip. I simply stumbled upon them!
“How do you handle dinners?”
Dinners are, by far, the time where you will feel most “alone.” Chances are, you’ll be surrounded by groups of friends, coworkers, couples, etc. And you’ll be sitting at a table by yourself. If you tend to be a self-concious person, you might feel out of place. But these people don’t know you! Who the f*ck cares what they think, you know? In your head, you might be thinking that you look like a loner, but flip the conversation! You might come across as intriguing… Who the heck is this girl sitting by herself, chowing down on a three course meal, and guzzling wine? Or maybe that’s just me… 😉
I do have a few tips for dining solo though…
- I always try to sit outside, if possible. People watching is the best and there’s so much more to see and soak in! I always love dining alfresco, but it feels so much less stuffy when you’re dining by yourself. Sometimes that’s not an option and I usually prefer a table by the window so you can still see out. While you might default to your phone (everyone uses this as a security blanket!), I really encourage you to keep it off the table at dinner. Yes, even when you’re by yourself! Being alone with your own thoughts can be terrifying, but I’ve learned to embrace it. If you really need something to do, you can always bring a book to read, too!
- Since there are weirdos out there, I always take a cab or Uber home from dinner, especially if I’ve been drinking. You never know who could see that you’re obviously alone and follow you out of the restaurant. Better safe than sorry! This never bothers me during the day because it’s light out and lots of people around, but I swear by this rule at night.
- I haven’t abided by this rule as much in Paris because I’ve been trying to watch the sunset from a scenic point each night, but when I was in Italy, I always opted for an early dinner to make sure I could get back home before it was too dark or too late. (Cabs aren’t as much of a thing in Positano, and definitely no Uber.) You’re home early, still have time to catch up on work, go to bed early, and wake up and seize the day!
“Why do you travel alone?”
There’s quite a few reasons for this, but I would say the main reason boils down to my schedule. I have a unique situation that a lot of my friends don’t have… I can basically work from anywhere with wifi, I don’t have a set number of vacation days, and I don’t have a boss to ask permission from. I’m in my late twenties without much of anything tying me down… No husband or boyfriend, no kids or pets, and a very flexible work schedule. I want to capitalize on this unique time and experience as much as I can before I do “settle down” someday. I felt myself wanting to do things, but felt like I was waiting around for friends to be able to get the time off or for me to find a boyfriend to travel to these places with, and I was finally just like F*CK IT, I have the opportunity and I’m doing it solo. “Waiting around,” in any sense of the phrase is generally never a good thing. Seize the moment, folks!
A few other general tips that I swear by when traveling solo…
- I leave the designer duds at home in Chicago! When I’m in Chicago, my LV tote goes everywhere with me during the day. When I’m traveling solo, I swap it for a plain leather tote, like my Cuyana. My navy Gucci crossbody is one of my go-to bags, but if I wear it out here, I flip it inside out so the logo isn’t showing. A lot of times, I’ll also wear my crossbody under my jacket, just to be safer with the whole pickpocketing thing.
- I don’t wear much jewelry when I’m traveling alone. This is even more relevant after the Kim Kardashian robbery (different post for a different day), but I avoid all things flashy. Obviously I don’t have 10 mil worth of jewelry, but I’ve just found that drawing the least amount of attention to myself is key. Same goes with clothing.. I keep it simple and don’t wear anything that would turn heads. Anything that looks expensive is just going to attract the wrong crowd, you know?
- On that same note, I rarely wear makeup when I’m by myself. For starters, I’ve got no one to impress and might as well let your skin breathe. But really, I don’t want to draw attention to myself! It’s no secret that most of us look much better with a bit of makeup on and if you follow along on Snapchat, you know my #IWokeUpLikeDis self ain’t cute. When I am wearing makeup, it’s basically just concealer and mascara to avoid frightening you guys on social media.
- Speaking of social media, I never post in real time when I’m away. NEVER! I’ll usually put my phone on airplane mode and send snaps to my story. Most of the time, they will save (unless Snapchat is being glitchy) and still be there when you return to wifi, at which point you can “tap to retry” and push them all live. If you’re worried about losing the content, I always take regular photos and videos to have those as a backup, just in case. As we’ve learned in the media lately, it’s far too easy to trace someone’s steps with social media. And just to show how much people pay attention… I’ve never once said where I’ve lived in Chicago. But with general neighborhood mentions and maybe snapping my view, I met someone a few months ago that said, “Oh yeah, you live at XYZ, right?” At first I was thinking, WTF, how does she know this? But it can be way too easy to piece together the puzzle pieces sometime. Just like when I was in New York! I knew Kylie Jenner was staying next door because of the Snapchat she posted of her view. It’s a weird world we live in, people, and there are some strange birds out there. Better safe than sorry!
- When in doubt, channel your inner bitch. Sounds mean, but again, better safe than sorry. I rarely stop or even look when anyone says anything to me on the street. Get that RBF on, and keep it moving. There are exceptions, I’ll stop if a woman is asking for directions or something simple, but if I get a skeevy vibe, I just pretend like I don’t understand the person and keep walking. (Always, always, ALWAYS trust your gut reaction and listen to your intuition!) On that note, there will always be cat-calling pricks, no matter where you are. NYC prepped me for this quite well! I’ve noticed in France that it’s mostly groups of guys making fun, not really saying anything in a sexual way. Again, mentally flip them the bird and keep walking. Ain’t nobody got time for that.
Alright, so where do you start?
I’d recommend easing yourself into solo travel, just to make sure it’s for you! Chances are, you probably have to travel alone with your career from time to time. Ease yourself in by eating dinner alone at a restaurant instead of opting for room service. Or if you are traveling with friends, take a day and explore by yourself before meeting back up with your friends for dinner! Or even if you’re just in your own city and not traveling, go to a movie with you, yourself, and you. Or eat dinner somewhere by yourself! You may fear that you’ll run into someone you know, which I can understand, but honestly, who really cares. Make up an excuse if it makes you feel better! Or start with lunch, I feel like eating lunch alone is a lot more common than dinner. But bottom line, if you even have the itch to travel alone, I’d highly recommend exploring it!
Let’s keep the conversation going!
I’m sure there are some questions I missed, so please, please ask them in the comments below and I’ll make sure to respond! Or shoot me an email if you want to keep it private. I’ve gotten so many questions about this topic this summer, and I want to offer as much insight as I can! xoxo JRS
PS: I realized this week that people thought my #JetSetJRS hashtag meant “jetset juniors.” I was crying laughing! I guess I see it, but nope, those are my initials and the hashtag I use to sort through my travel content.
And as always, all of my travel recommendations for most of my favorite cities are on my Travel Guide!