Secondary only to the question of where to go is when to go.

After all, few sights are more cringe-worthy and embarrassing than that of an American family of four strolling the streets of Paris for two weeks in August, wondering where all the kissing couples and bakers in berets could possibly be.

(Answer: they’re on vacation, from twit tourists.)

The question of when is, in reality, two-pronged:
What time of year should you go?
How long should you go for?

Both are important for not only enjoying your travel, but looking cool while doing it. Ask any seasoned globetrotter and they’ll tell you: timing really is everything.

First, let’s tackle what time of year to go.

Luckily, there’s an easy golden rule: True hipsters travel when the lamest tourists are most likely to not be around. The benefits are three-fold (at least): you avoid other Americans, everything will be less crowded and likely cheaper and you’ll get to spend more time learning a new culture, collecting stories to regale your friends with and less time being chased around by tourist trappers (like Gypsies).

Obviously, this will depend solely on where you’re going, but is generally referred to in the travel industry as “off season;” that’s when airlines and hotels are usually charging less since less people are going to wherever. For places like Europe and Asia, that’s in the late fall through winter into early spring. Reverse that for austral destinations like South America, Australia and much of Oceania. Given the heavy emphasis on eco-tourism in Africa, peak seasons there are generally dictated by the movements of animals tourists are seeking out.

Traditional travelers will often warn about going one place or another off season, touting situations like limited hours at restaurants and museums or claims that markets aren’t jammed packed with vendors. Treat these idiots with the same aloof annoyance typically reserved for die-hard Dave Matthews fans; their lack of adventurousness and know-how is wholly unacceptable.

The truth is you haven’t experienced a destination until it’s in its off-season, when officials and residents aren’t doing their best to put on a good face. So maybe it’ll be harder to find time to sneak into Madame Tussaud’s (which you really shouldn’t be going to anyway, if you have any decency about you) or it’ll be a little colder than you like when you’re out for a stroll. What’s important, though, is that you’ll be seeing where you’re going when life is most likely to be different from what you’re used to, and that’s what makes traveling so worthwhile in the first place.

And for every one thing you think you might be missing by traveling off season, you’ll probably see or experience two better things never found in a tour book in its place.

Here are some examples of great timing:

At the ever-impressive Iguazu Falls, which straddle the Argentine/Brazilian border, local tribesmen and women peddle native woodcrafts at the national parks on each side of the border (great conversation pieces for fair trade latte nights and other social gatherings with friends) and sell for a third what they do in the summer. There’s also fewer of these natives to annoy you into buying crap you don’t want.
In a wintry (read: not scorching) Venice, most of the annoying and completely unauthentic street performers (I’m talking to you, blackface mime squad) beat it back to Romania (along with many of their pickpocket pals), leaving the beautiful San Marco Square – and all of its intricate architecture – a peaceful place to explore. Also a plus: hotels and restaurants are vastly cheaper, and the canals don’t smell like shit (as much).
Colonia del Sacramento, Uruguay, a popular daytrip destination with the Buenos Aires bourgeoisie, is a nightmarishly crowded beach town during a summer weekend but a relaxing retreat during a wintertime weekday. Even then, there’s room for sweet surprises. I once assumed I’d be reading a book on the beach there, only to find out that this one winter day, August 25, happened to be the one day a year the local racetrack held a major horse derby. Price: admission roughly $1.20 each, huge asado lunch served trackside around 50 cents more. BONUS: The coveted “I was the only American there” story to boast about on Facebook and Twitter … and my iPhone got signal the whole time.

Don’t underestimate the power of the “I was the only American there” situation or experience. It’s something you can brag about forever, and the pictures you’ll get are usually Facebook worthy, if only because you’ll be able to make smug comments on your wall about them, as well as show them off on your iPhone at art gallery openings or sushi bar mixers.

The mere possibility and indeed, the significantly increased likelihood, of adding such stories to your repertoire by traveling off-season should alone make it an absolute must. Plus, going off-season makes it easier to pretend you were actually scraping together pennies to go and “find yourself” abroad when you are, in actuality, still firmly planted on the proverbial family teat. That off-price allure is super cool and so much better than admitting you needed both a visa and daddy’s Visa to get you everywhere you wanted to be.

Remember, perception is everything. (That’s why Urban Outfitters can sell so many “vintage” t-shirts for $30 and $40 a pop.)

The second question, how long you should go for, mostly depends on your financial resources, but ingenuity and connections – established both before and during a trip – can play a big role as well.

Again, there’s a golden rule for traveling cool: Three days, or three years? That’s it. Nothing in between.

Jetting off for a long weekend in (insert destination of choice here) gives people the illusion that you know what you’re doing so well that you don’t even need time to acclimate yourself to a new culture. This flippant attitude is also great for dropping stories about a “quick weekend” in Europe or wherever and showing you’ve really got a handle on how to move quickly about the globe. It also is great at breeding jealousy among those who didn’t get to go (always a plus) or too afraid to leave home for such a short period of time.

Of course, going abroad for such a short period of time has its downfalls. For one, you’ll be lacking sleep at some point, and it’s harder to justify the cost of expensive trans-oceanic airline tickets for such short periods of time. But if you follow our first rule – always travel in the off-season – that’ll be less of a concern. Second, you’re likely going to be confined to one city or region, which is fine. Remember, there are crappy places to be in every country, not just here in America (though it’s way more hip to bitch about America’s Midwest than say, a boring country drive in Iceland).

Going away for years, of course, has it’s own plusses and minuses. There’s the allure of really seeing the world with no pressures to get back home at any certain period of time. Whether you have that luxury is really up to your wallet and your own ingenuity.

Remember: when you’re traveling in a foreign land, friendliness and cunning wit can take you much farther than a dollar. Your ability to make friends abroad can help stretch a eurocent into a euro. New friends can be sources of housing and meals, not to mention interesting guides to some of the more insidery aspects of a foreign culture.

And while your spirit will be freer than ever on a years-long journey around the globe, there’s a lot of pitfalls you’ll need to watch out for. Besides arrangements like securing your life at home for an eventual return (see our chapter: The Return to Sender), you’ll also need to consider the logistics of traveling across unfamiliar borders and making sure paperwork is in order for some of the more out of the way places.

One simple tip: make sure you know where your home embassies are abroad. While they’re limited in what they can do should you get in trouble (see our chapter: Staying Safe), embassies can be invaluable resources to travelers with questions about visas and other travel documents, as well as being a key point of contact for family members and friends from home who might need to summon you home in an emergency.

Whichever route you take, forget the one or two week vacation. It’s too traditional and you look too square. Either take the 36 hours in wherever route popularized in the Sunday travel section of The New York Times or quit your routine of listening to music before anyone else and blend in all over for years at a time.

You won’t regret either option.