When was the city or town founded? What is the population? Are there historic landmarks that are worth visiting?
Look at the city/town map and see if there’s something that draws your attention, like a town square, a large museum or a university.
Look up the top three cafés or restaurants. Search for the top ten sights in the city or town. Check out event listings and see if there’s anything that piques your interest. Make checklists; they’re useful and fun to compile.
Try to find out where the locals congregate, eat and attend events. If you have friends who have been in that city, or maybe even live there, ask them what they would recommend you do. When I went to Buenos Aires in Argentina, I took a street-art walking tour. It was one of the best things I have ever done in a city. Not only did I see beautiful artwork because of the tour, but I also walked through residential and nonresidential areas I might not have seen otherwise, and I learned a lot of tidbits from the tour guide. It allowed me to roam around on my own later with confidence.
It doesn’t have to be an art museum. In Hamburg, you can find a spice museum because of the city’s location on the River Elbe, which is part of a trade route. Not only is the building and its surroundings picturesque, but the museum itself is very interesting, with a mix of old photos, vintage advertisements and displays with burlap sacks of spices providing the scents that accompany the experience.
Oftentimes, quirky stores, street art and historic houses can be found in older and transitional neighborhoods.
Be sure to visit unique markets and festivals. You will meet local artists and can ask them about the inspiration for their work, buy regional foods, and experience the culture of the city.
Taking public transportation in a city whenever possible provides some wonderful benefits. You can explore and get a feel for your surroundings, and it’s great for people-watching. Check out the schedules for buses, trams, light rails, trains and subway systems. Look into whether the city has a bike sharing system. One or a combination of these will usually allow you to get wherever you want to go.
If the city has a lake, or is located on a river, check to see if there is a ferry system. Being on a boat gives a totally different perspective and provides many opportunities for taking photos. Another option: trolleys and streetcars, like those in Santa Barbara and San Francisco.
Be prepared. Get whatever transit maps you’ll need and plan your routes. Some cities like New York, Washington D.C., London and Paris have extensive underground subway systems. You can pick up a map at the transit office or at main subway stations.
I love to use a phone app called Citymapper. It not only shows you the easiest way to get around in most bigger cities of the world, but it also gives you suggestions as to which public transportation is best to take, or how long walking would take, whether you should enter the beginning, middle or end of a train, and which subway exit to use. The latter has become a lifesaver for me in New York City. You can save and access the information later, even when you are without an Internet connection.
Use common sense when you are traveling in unfamiliar areas and always err on the side of your own safety.