Traveling is not something you need to do with a group, or even a partner. In fact, it's often even better when done alone. It's a scary thought, but if you do it right, it's very rewarding.
Recently, I did just that. I had a very tough year, and in the valley between Thanksgiving and Christmas, when I was feeling the weight of family obligation and coordination, I decided it was high time I did something for myself. So I booked a trip! Somewhere sunny, timed for the mire of chilly February! For myself and no one else! I wanted to go somewhere warm and get some peace and quiet, free from distraction, from conversation, from anyone else's needs and desires but my own. That was reason enough for me, and you don't even really need a reason at all. There isn't a wrong way to do it, necessarily, but here are some pointers that will make flying solo even better.
Get over any fear or apprehension you may have about spending a block of time by yourself. It's challenging, but very peaceful. I think people are sometimes nervous to do things by themselves because of how it looks to others, but a little independence is a powerful thing. Also! You can be as selfish as you want to be. You don't have to wait around for anyone, and you can do exactly what you want to do, whenever you want to do it.
Plus, of course, you can go wherever you want. I knew I was looking for a) somewhere warm, to escape the frozen tundra of New York City; b) somewhere I could get to relatively quickly and without a time change; and c) somewhere remote. Very remote. I looked to Central and South America, because flights are pretty reasonable this time of year, and it's beautiful and tropical and generally pretty affordable to move around once you get there. I nixed Honduras because of the whole "Miss Honduras being kidnapped and killed thing" thing, plus there was a State Department travel advisory when I Googled it—same deal with Nicaragua. (Personally, that doesn't totally scare me, but my mother worries.)
Costa Rica was the place, then, because it's very safe, it has dozens and dozens of possible destinations when you get there, and it's naturally, ruggedly, and utterly beautiful. No need to share that beauty with anyone.
Now comes the fun part: the actual planning. But don't do too much of that. Set a basic blueprint of where you want to go, but don't marry yourself to it. I learned this when I was traveling in Brazil a few years back: I had a path all laid out, but then someone told me I couldn't miss a little beach town called Buzios. I took the rec on good faith, and it was one of the most beautiful and interesting places I've ever been. Flexibility is good!
In addition to that, don't overbook yourself. Don't try to squeeze too many cities into one trip. Pick fewer places and really get to know them. For me, in Costa Rica, that meant spending five days in Montezuma and exploring the sleepy surf hamlets throughout the peninsula.
I know the internet exists and print is dead and you're not trying to travel like your dad, but still: Buy a guidebook. You never know when you're going to end up somewhere with bad internet or no internet at all, and a book is a handy thing to have. Lonely Planet guides are generally pretty solid for just about anywhere you might want to go.
Bring: books, music, journals. Don't bring: your laptop, your iPad, your phone if you can handle that. Usually I take put my phone in airplane mode, use it like an iPod, and try my best to disconnect completely. It usually takes me a few days away from home and work to fully release and relax, and not being hyper-connected to your real life speeds up that process. Realizing you have no idea what's up on Facebook and dumb stupid idiot blogs is a very good feeling.
Cab drivers know everything. It is a universal everywhere. Want to know where to eat? Ask a cab driver. Want to know where to find weed? Ask a cab driver. This is not a theory; this is a proven fact. Every place I go, when I want to find weed, I make nice with a cab driver. If you want something harder, well, they can help with that, too. For example, Rodolfo, the driver-plus-weed-procurer I befriended in San Jose, told me about a guy he knows from Miami who comes to Costa Rica to shoot up heroin. Definitely don't do heroin, but my point is, if you want something, you can find it, and a cab driver can help.
Locals know what's up because, duh, they live there. They're going to steer you toward the good spots that aren't overly touristy. You want to eat good food, see good sights, and get an authentic experience? Talk to them. In Costa Rica, I found myself in La Fortuna, a town that only exists because people come there to see Arenal Volcano, one of the most active volcanoes in the world: A volcano creates all kind of natural attractions that people want to see, and will pay out the butt to see. But most of, say, the natural springs were accessible only through hotels, and charged up to $85 a day for access. But there was also a free hot spring, one I would have known nothing about had I not asked a cab driver. Knowing another language helps, I suppose, but just talk to people, and it's easier if you haven't brought somebody along who you have to talk to, too.
Look, not all hostels are created equal: There are some really, really shitty ones out there. But there are plenty of options for nice hostels, and in most cases, you can pay a little extra for a private room. It's not that expensive, either—depending where you're traveling, you could pay anywhere from $20-$50 for private lodgings in a hostel. The point, however, of staying in a hostel, is not just saving money: It's to meet people. In hostels, or at least in good hostels, people tend to hang out in the common area, chat, cook, drink, trade tips, and make friends. You'll find things to do where you're staying, and people to do those things with. You'll also figure out, based on the advice of people who have come before you, how to get from point A to point B, which is pretty key when you're all by yourself.
Yes, a joint, ooooooOOOOOOOOOOOOoooooohhhhhh. The best way to make friends is to travel with a joint. I'll say it again: The best way to make friends is to travel with a joint. Roll one up, stick it in your bag or shirt pocket or something, and offer it up at some point in a conversation with potential new mates. The worst that can happen is they'll turn you down. The best that could happen is ... well, who even knows, but you'll make a good friend and at least enjoy some interesting conversation. People bond through the smoking of the proverbial peace pipe. Believe me. On this past trip, I rolled dozens of joints and made dozens of friends. It's foolproof. Even if you're not using it as a friend-making mechanism, you can bask in the thrill of lighting up on a beach or in the rainforest.
Other than that, the point of traveling alone is that the world is truly your oyster, and not an oyster you have to share with anyone else. You'll do less waiting in line—less waiting on other people in general, really—and you'll spend more time chilling with yourself. That rules! It really, really rules. I read four books, I filled up half a journal. I slept, I swam, I hiked through the jungle, climbed up a volcano, and felt real quiet, the kind that's impossible to feel at home or at work or with other people. I admit I was a little nervous before I left: I had a tinge of worry that being alone for nine days would be too much, or that I'd be bored or lonely or feel generally weird. But I had none of that, and I never would've known had I not given it a shot. I also got a very nice tan.
Art by Tara Jacoby
Adequate Man is Deadspin's new self-improvement blog, dedicated to making you just good enough at everything. Suggestions for future topics are welcome below.