Sometimes you are destined to know little, or next to none, beyond superficial understanding about a country or city you're heading to. You might not even know straight off the bat whether the place is cheap or expensive, what to see, how to get around, what's the culture like, and so forth.
While I generally recommend not overplanning trips, especially into day-by-day, one ought to not go completely "blind" into an unknown destination. That's just a sure way to eat the wrong things, make cultural mistakes, and in general things ending up badly.
There's especially so much free valuable information out there, so that actually going anywhere without any decent understanding of that place just shows a lack of planning and plain laziness.
When you're faced with a knowledge gap before an upcoming travel destination, here's what you might do:
Guidebooks are still important for travelers. Although some might be slightly outdated, they give a good overview of how to get around and generally form ideas on what you might include on your itinerary. It sets the foundation of your planning and experience, that blogs etc. might not do to the same extent.
There's a plethora of guidebooks out there, and they do vary quite a bit. Try to find one that best suits you, and your interests and needs. Honorable mentions include Wallpaper City Guides, Time Out City Guides and Rough Guides.
Comparing Guidebook Series | Rick Steves
However, blogs can fill in a lot of gaps and further build on the foundation you've gotten from guidebooks. Generally you'll find more up-to-date information and there's a chance you can ask questions to the bloggers and their community.
Read a few blog posts for some more content and stories that will give you a sense of the destination.
And of course, peruse and subscribe to this website — perhaps an article on your upcoming destination has been, or will be, featured!
3. Ask Friends and Family for Their Advice
You might have a few friends out there who have traveled to your upcoming destination — or they might know about some others that could give you some advice. From them you might receive advice, tips and suggestions on everything from hotels and restaurants, and if you're really lucky they might connect you with people at the destination you're heading for! Imagine being so fortunate that you'll have a local host that can show you around and help you get sorted.
4. Ask the Community and Social Media
Fourth, ask the community around you. This might be slightly different depending on your own situation. I.e. do you have your own blog or some other forum etc. where you might ask some questions? What about Facebook or Twitter? I personally use those a lot and they produce heaps of messages with tips and advices, even at times some locals looking to meet up.
Generally, you might also want to check out Couchsurfing. The website exists to connect travelers and locals, and there's often a very active community in most cities.
Last, but not least, buy some books on the country or destination if you have the time. You can't really know a place if you don't know its history — and every place has its very own unique and rich history!
Besides buying books, especially if you're short on time, reading the Wikipedia article of a country can come a long way in giving you a general overview.
By following these tips you will gain a sense of the destination. Obviously your plans, route and ideas may change when you get there, and you'll never know exactly what a place is really like until you go – but now you'll have a better idea as to what you are getting yourself into.
You'll have a sense of what to expect and that makes you more comfortable about visiting, as well enriching your experience and appreciation of the destination.