How a Single Guy Vacations During the Winter

Travel solo and take the road less traveled.

Matt Branhamby Matt Branham

When the winter blows through, it’s time to begin another chapter. And what better way to start it off than with a little adventure? A trip to Disneyland with the wife and kids can be a tease of a good time, just like cramming into a car and heading for the border with a bunch of bearded bozos. So why not take a trip by yourself, for yourself, instead? Read on and learn how a single guy can vacation in the winter the right way.
single man, vacation, tourist
Go Someplace New
It’s no fun constantly going someplace you know, where the pleasures of finding cool cafes, used bookshops and unimaginable sights have already been spoiled. Treating your eyes to something that’ll make your eyelids coil back and drop your jaw to the floor is more like it. Or, just go someplace you’ve never been and always wanted to go if you’re afraid those might be permanent body disfigurements.

There’s something truly exciting about being someplace you’ve never been, even if it’s a dank motel with bullet holes in the wall; you’ll still feel a bit more alive. So don’t waste your free time and money on something that won’t surprise you in some way. Every new place has the potential to show you something new about yourself, whether you never realized how much of a mountain man you were, or that your tolerance for crowded places with slow walkers is about zero. It’s cool to travel outside of your comfort zone. If you’re a small town guy, maybe try a few days in the Big Apple and see what you think. A good destination for a trip is going someplace you’d never live, and when it’s done you’ll appreciate what you already have that much more.

Take Trains Over Planes, Walks Over Taxis
Your mode of transportation is a key part of the process, since it seems something gets lost in the translation of convenient travel. Although a plane may be the quickest, safest route, you’re more likely to miss everything along the way. Life, as you’ve no doubt been told, is about the journey, not the destination. Planes are simply there for getting you to your destination, and the only journey involved is testing your ability to not backhand a screaming child. Trains have the ability to take you places and show you a whole lot along the way.

The same goes for taxis. These modes of transportation are built for people who need to be someplace at a certain time. When you’re on a trip or vacation, time is not a factor; that’s why it’s called a vacation. Leave the little yellow taxis for the business suits who need them. Get out and walk around, stretch your legs and take some pictures. You’ll remember a lot more from your trip this way, which also leaves plenty of room for spontaneity and stumbling on hidden gems.

Pack Lightly and Rough it a Little
And while you’re getting from place to place, you’ll be glad you left your six favorite jackets at home when your shoulders start to scream and your kidneys feel like they’re being punched with every step you take. When packing, remember to take only what you need, maybe plan for a little rain or slush, but there’s no need for packing multiple items of the same thing. One good jacket, one good pair of pants, one reliable, multi-purpose pair of shoes is all you need.

If you’re a 58-year-old woman who carries a spare hip and needs a bag just for her meds, that’s one thing. But you’re a man dammit, and we’ll be a monkey’s uncle if we’re going to send you out there to whine about how heavy your load is. Pack lightly, carry a few snacks and leave the kids and diapers at home, unless you think the diapers might help.

Take the Scenic Route
This is the idea that goes hand-in-hand with your modes of transportation. There is usually, in most places, a road less traveled, and then there will always be the road with 15 Starbucks on it. With the road less traveled, there is probably more to see and fewer tourist traps to fall into if you avoid the common folk and go your own way.

Get yourself a map and find some places you want to see. You don’t have to roam the crooked alleys aimlessly either, but it’s better to find some solitude along the road to your next stop. There’s time for thinking and laughing like a weirdo to yourself. If you come home with a box of photos that look like everybody else’s trips to the same place, you didn’t do yourself any favors, did you? It’s always better to find things in certain places that speak to your personality, whether it be a dive bar with blind women, the perfect sandwich shop or a cliff you climbed with a view better than any guided tour.

Document the Hell Out of It
There will come a time when you’ve traveled the world over and seen all you thought your eyes could see, but eventually all those images in your head and memories of people you met along the way will slowly disappear like something out of a bad Will Smith movie. That’s why it’s so important to capture poignant moments along the way of where you’re going.

We’re fortunate to live in a time when technology is as convenient and lightweight as it is, but sometimes we can be consumed by it. That’s why we recommend taking a camera, like a real camera, not the one on your phone, and capturing some real photographs — ones you can collect and proudly frame later. In addition, take a pad of paper or journal and write and date some of your thoughts that coincide with the places you are and the things you’ve been witness to, however funny, odd or inspiring. Then when that day comes that they ship you off to a home because you keep answering the door naked and peeing in your favorite shoes, you’ll have these memories with you to help convince others you weren’t always a lunatic.

Travel Alone and Leave Your Phone
In addition to the idea of heavy documentation, another reason for using a real camera over your phone’s is that it wards off distraction, an easy adversary to have. Technology is nothing but filler in the off-peak hours of everyday life, keeping our minds off the important things.

If you’re too busy finding the right word for a game of Scrabble while your train passes by a field of golden fairies blowing pixie dust on horses, turning them into unicorns, well then you missed the whole point of a vacation. Seeing the world with your head in the palm of your hands and looking up through a filter is no way to go through life, let alone a vacation. Facebook will be there when you get back, we promise, but what you’re doing at the moment is far more important than anyone’s status update.

And traveling alone is just one more way to avoid distraction, take in everything completely and find a little peace of mind and body. There has to be some sort of connection with yourself, or you’ll just be a body who’s lost someplace. Everybody needs a break from everything they know, sometimes even themselves, so there’s definitely no room for guests on a single guy’s vacation.

Experience as Much New as You Can Do
That means no McDonald’s for lunch. You’re on vacation, so it’s imperative to stretch your boundaries, get weird with your decisions and maybe do something you’d normally be terrified of, whether that’s bungee jumping over a canyon or eating octopus for dinner.

There’ll be plenty of time for you to live your boring, old life when you return home to rot away, but for now, live like a wild man and do things that’ll make yourself hard to recognize in the mirror. If that means getting blonde frost tips, piercing your belly button and taking a hula dance class, then that’s exactly what you should do on this vacation. No judgments. It’s your vacation; you can choose to make it one of the best experiences of your life, or just another time you’ll forget.