The Essential Guide To Traveling Solo


Once I entered the real world, I soon realized that synchronizing my vacation time with my good friends was practically an impossibility. As new hires, we are lucky to get even three full weeks of vacation, and even luckier if we have any say as to which three weeks those are. In late November, I was informed that I would be on vacation the week before Christmas. I immediately sent out a group text to my friends urging them to take the same week off…crickets. People with real jobs can’t drop everything to pencil in a mid-December bender. This is our new reality.

I was still determined to make the most of my week off, even if I had to go it alone. I had a living wage-level salary burning a hole through my pocket, and I needed to blow some of it in a different zip code. I waited until the last minute and booked a quick three-day trip to New York City. What follows are a few points to keep in mind for those of you that make the decision to travel solo.

1. Avoid traveling to destinations geared toward couples.

It’s pretty much inevitable that you are going to see lots of couples no matter where you go. Most people in serious relationships eventually get bored, so they travel. However, with careful planning, you can manage steer clear of the absolute coupley-est of destinations. For me, meticulous planning was not in the cards. As a result, I arrived in the Big Apple at what is apparently the most romantic time of the year to visit. Skating outdoors while holding hands and taking photos in front gigantic Christmas trees are basically what couples live for. I’ve been single long enough that this fact escaped me when I booked my trip. You can still have fun solo, just be prepared to feel slightly out of place every time you step outside into a sea of budding romance.

2. Meet people.

Just because you don’t have a soulmate to canoodle with doesn’t mean you have to be completely alone. You will likely run into at least a few other solo travelers on your trip that are ready and willing to make a new friend. If all else fails, stop by a pub or lounge and strike up the time-honored tradition of random vacation conversation. Everyone is more sociable after a beer or two. Just make sure to drink in moderation.

3. You are not on Spring Break.

As a veteran of no less than five Spring Break trips, I instinctively associate traveling with getting shitfaced. However, blacking out while completely alone in an unfamiliar city is likely a poor choice. As I found out, even getting casually tipsy on a Monday night will strike people as odd. Unless you’re in Cancun, you will probably be surrounded by a lot of people who plan to go home to their families and/or work the next day. After five or six drinks, I probably stood out like a sore thumb, without even coming close my typical level of belligerence. This is probably best summed up by the interaction I had with a bartender on my last night in New York. I stopped by a pub near my hotel to grab a quick bite and a night cap. Before settling up I offered to by a round of drinks for the bartender and I, to which she responded, “Um, I don’t know if I can. This has never happened before.” Her reluctance was probably for the best, there were still a few things I wanted to see the next morning before heading to the airport.

4. Actually make an itinerary.

Whenever I travel with my friends, the details are usually taken care of by, well, someone else. I can usually count on one person in the group to be responsible enough to actually put some forethought in to making sure we get from place to place on time and do what we came to do. As a solo traveller, you can no longer outsource this task. If you want to pack as much action as possible into your trip, you’ll have to do some heavy lifting. This heavy lifting will likely include the following: reading a map, figuring out what spots to hit, and familiarizing yourself with local transit options. You will also have to fight the temptation to oversleep. You’re on vacation, and the hotel bed is probably more comfortable than the twin size mattress in your childhood bedroom that you have recently become reacquainted with. Without anyone else to force you out of bed, accidentally sleeping until noon can happen easier than you might think, even with an exotic locale at your fingertips. Set an alarm, then set another alarm, then ask for a wakeup call.

5. Don’t be a slave to your itinerary.

One of the best things about traveling solo is that you are never stuck doing something that you don’t want to do. Want to make a last minute change of plans? Go for it. Perhaps you planned on spending 3 hours checking out an exhibit at a local museum, only to discover that 19th Century Interpretive Origami is actually boring as shit. Fuck it, leave and move on to something else. You don’t need to hang around with your one friend that is inexplicably still interested in the obscure exhibit. Being alone means that you can be as selfish as you want. Take advantage of that.

Email this to a friend


No one told me I'd have to crawl before I ball.

6 Comments You must log in to comment, or create an account
Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More