Visiting a new city seems easy enough but there are some cities out there that can be intimidating if you haven't been there before. There are plenty of people we have encountered in our travels that have never left their small town with a population of 1,000.
Start by asking yourself these few questions:
What do I know about the city?
What was the original draw to travel there? Is there a site you've heard about or a sports event you want to see? That is a good place to start. If your favorite things to do include learning about history or eating different foods, do some research. For example, Times Square is one of the most popular sites in NYC, but there aren't many good food options (unless Applebees' is your thing) and the history isn't abundant. This location would be more geared to a theater goer or someone just wanting to see the lights. There are some cities that might not appeal to you based on what your hobbies are. Ask yourself that question, and then determine your path.
How will I get around?
It is important to research how the city commutes. Are there public transportation options? Is there parking? Are there tolls? It's good to be aware of these to cut down on stressful situations upon arrival. Boston is a great example. It is a city that relies heavily on public transportation, mainly the subway system. There is little parking and the driving can be overwhelming. In the Midwest, almost everyone drives. By embracing the local transportation methods, not only will you get out of your comfort zone, but you will get a better feel for how the city lives and that understanding will give you a better connection to the city. Google Maps is a great resource for planning your trip. You can see all bus routes, bike paths, subway schedules, etc.
What kind of experience do I want?
Probably the most useful question to ask yourself before visiting a new city. What do you want to take away from the city? Lots of people don't really think about this and get quickly overwhelmed in a place with lots to do, see and eat. However, if you really evaluate what experiences you want to have then you can properly plan your trip - do you want to eat all the well known food, see the historical sites or just get an introduction to the city and an understanding of the "vibe." As an example, if you want to go to Los Angeles and haven't been there before, you may not realize the amount of activity there is to do there. There are tons of beaches, lots of Hollywood sites and tons of good food, shopping, poolside drinks, etc. If you know up front that you want to spend the whole time at the beach, then you have to be prepared to research that aspect as there are literally hundreds of beaches and they are not created equal. If you want to see celebrities but only stay downtown then you'll be disappointed. Once you have an understanding of what you want, you can do research on best places to accomplish those goals.
Having a plan or at least an outline can help you make the most out of your time, but you want to leave yourself room to just enjoy as well. Our advice is to get out and explore the city on foot as much as possible because the best stuff always seems to come when you aren't looking for it. But more people than not prefer a plan. Start with those 3 questions and then make sure the city works with what you want to get out of it.