This post is a follow-up to my previous post: Don’t Make Plans

While I’m a big proponent of really going with the flow, there are a few guidelines that I like to follow to help avoid serious problems and get the most out of spontaneous travel.

Do some research

Even though I don’t advocate making strict plans, it’s still smart to do some preliminary research.

Pick a region

It would be incredibly thrilling to show up at San Francisco International Airport and figure out where in the world I was headed on the spot, but last-minute, long-haul flights can be prohibitively expensive. At least a couple weeks before you head to the airport, pick a general region, and book a long-haul flight if you’ll need one.

If your trip will last more than a couple months, I’d strongly consider getting a one-way ticket. You can sort out your return flight during your trip when you’ll have a better idea of what region you’ll be leaving from and when you’ll be leaving.

Once you’ve picked the spot you’ll be visiting, do some prep-work about the areas you will be traveling to.

Visas

At minimum, learn about visa requirements and tourist restrictions. It's good to be reasonably sure you’ll be granted entry, and to have some idea of how much time you will or can stay. A helpful starting point is visamapper.

Costs

Figure out how much you can expect to spend on your trip. The travel cost calculator is a good start, but bear in mind that most activities like tours, festivals, and partying will add to your daily expenditures.

Weather

If you are traveling in an extremely cold region or in the winter time, winging it completely can be extremely stupid. You should at least make certain you’ll be able to find accommodation if sleeping outside might freeze you solid.

Events

Pay special attention to holidays, festivals, and other peak weekends. These can sometimes make winging it difficult for a certain segment of your trip. Fully booked accommodation, congested public transport, and other related concerns can cause problems. It’s difficult to find a cheap hostel or a couch to surf in Munich during the Oktoberfest, for instance.

Get your head right

You need to develop the right mindset to be a successful freestyle traveler.

Say ‘yes’

In order to be successful while winging it, you have to be easy-going and willing to commit to unexpected experiences. This is the main reason you’re winging it in the first place, so be open-minded and flexible. Did your new friend in the hostel just invite you to join them for the next segment of their trip? Do it! Did a friendly stranger on the street invite you to a barbecue? Check it out! Obviously not all strangers are trustworthy, but use your best judgment and try to experience new things.

Rough it

If you want to freestyle and keep it cheap, being ready to rough it will dramatically improve your chance of success. Impromptu beach camping, sleeping on uncomfortable couches or floors, balancing sandwich supplies on your lap: these are all par for the course. A stoic mindset goes a long way here; most of the time the ‘worst-case scenario’ isn’t really as bad as you feared it would be.

Get lost

Wandering is not something we’re used to these days. With the advent of smartphones, GPS, and drop-pins, we’re constantly aware of our surroundings and what they have in store for us. It’s sometimes great to get a little lost! The best shops, parks, restaurants, galleries, and markets are often off the beaten path. Finding them on your own lends a glorious feeling of discovery, and on the way gives you a better window into another culture. Forget the map (or leave it in your hostel) for a day or two and see where your feet take you.

Don’t panic

When you eventually end up ‘lost’, don’t panic. Use your street smarts, stay alert, and avoid areas that make you feel unsafe. People will be able to help you find your way, even if you don’t speak their language. Just take your hostel address with you, or write down the names of major nearby streets. At worst, you can usually grab a taxi.

On the go

Even if you aren’t planning the whole trip in advance, you’ll often find yourself mapping possible routes in your mind for the day or two ahead.

Beware of night arrivals

Arriving at night, or even in the late evening, can be a stretch if you’re in an unfamiliar place and don’t even have directions to a hostel. I’ve done this a few times with varying levels of success. Most of the time, I still managed to find decent accommodation through affordable hostels or helpful strangers. However, I’ve also slept on the beach, improvised a campsite, or found a pricier room in a hotel.

On a related note, it’s often useful to book overnight travel arrangements, so you arrive in the morning and don’t have to spend an additional night in a hostel/hotel. You sacrifice comfort but gain time and money, an easy trade for a Hard Trekker.

Communicating

You will find English speakers in most places, but it’s also worthwhile to learn some key phrases in your destination country’s language. The locals will appreciate the effort.

If language barriers will be a particularly big problem, you can prepare a list of set phrases and have them translated on paper before you head into areas where languages you speak won’t be at all present.

Phrases like “Where is a cheap hotel?” or “Toilet?” are obviously useful. You can usually ask for translations from an English speaker you find in country, or you can get help from strangers in online forums. Beware google translate, it can easily lead you astray.

Getting around

A quick google search in an internet cafe, or talking with locals, can be a great (if challenging) way to orient yourself in a new place.

Being able to walk everywhere easily when you first arrive is one of the main benefits of packing light. Walking is free, and it’s a great way to experience your new environment. If there is a lot of ground to cover, metro or light rail stations usually have maps right on the stops, and the locals can help you manage the bus systems. Of course, taxis serve as a helpful last resort, and in many regions, are not very cost prohibitive.

Finding accommodation

It can’t hurt to look up or book a hostel a night or two in advance. If you’re trying to couchsurf, you should work on making requests a few days before you arrive. There is much more to say about accommodation, but that will be the subject of another post.

Wrap Up

Not making plans doesn’t mean being totally unprepared. Winging it comes with ups and downs, but once you get a taste, you’ll enjoy what it adds to the mix.

I’m sure some readers have great tips to add for freestyle trekking. Hook us up in the comments!