When it comes to vacations, there are two main options - one where the goal is rest and relaxation or one where the goal is to see the sights. About a month and a half ago I went on a trip with my sister to Destin, Florida and you could probably guess that our number one priority there was to enjoy time on the beach. I haven't been on a trip to a big city in a long time, so I was really excited to soak it all in. City vacations require more structure and planning than a beach trip, so I thought I would share my tips and tricks for having a successful trip!
Do have a plan for each day. Whether you want to be as detailed as an itinerary with times or just want a simple layout of your day with key places to go, a plan of some sort is a must. It will help keep you on track so that you get to see all of the major spots on your list. Also, keep in mind location of each sight. You don't want to go zig-zagging all across the city from one place to another.
Don't overfill your days. On our first day exploring, we didn't wrap up our last activity (a boat cruise on the river and lake) until after 9 PM. Part of this was because they were running behind schedule, but nonetheless, we ended up having to take the next latest train back to our hotel because we missed the one we planned to catch. We also had to grab fast food at the train station (not the most ideal situation) because everything around the area was either closed or would have taken too long. The next day we called it a wrap earlier than planned because we were still wiped from day one.
Do take advantage of public transportation. The beauty of a big city is public transportation and how quickly it can get you around town. We stayed in a suburb and took the train in each day, and then used the subway and buses once we were there. They usually offer deals, like a 24 hour unlimited pass or a pass for however many days you need, so that you don't have to keep paying a fare for each trip. It's not only cost effective but also will save you a lot of walking.
Don't try and walk (or drive) everywhere. I don't think you could pay me to drive into Chicago, let alone around downtown. The glimpse of Chicagoland driving I did experience was more than enough and made me very, very thankful for minimal Louisville traffic. And when it comes to walking, you will get tired quickly, unless maybe you're a pro athlete. You can't really appreciate how much walking it takes to get around a big city until you've done it, so trust me and my mom's Fitbit count on this one.
Do wear comfortable walking shoes. Some walking is inevitable because the subway and bus won't always let you off right where you need to be. I went with my Keds and those did pretty well for me for two days, but I could tell that if we had spent another day walking I would have been miserable. Sometimes you have to prioritize function over fashion and this is definitely one of those instances. And hey, tennis shoes can still look stylish with the right outfit!
Don't think you can get away with sandals. Just trust me, don't do it. Unless you are staying in the city itself and have the opportunity to change clothes before say, dinner, then don't do it. No matter how comfortable your favorite sandals are, you won't be thinking that so much when you have a blister on your heel (or sore feet from lack of support).
Do take a camera to capture photos. With smartphones these days, you're probably already set with this one. Of course you'll want to capture shots for Instagram (wink, wink) but if you have a real camera I suggest you bring that as well! When you're on a trip to sight-see you'll want photos to look back on from time to time.
Don't make photos your top priority. Sure, you might see that perfect shot and want to snap it, but don't forget to live in the moment too. I am a firm believer in the importance of experiences and viewing your trip through a camera lens the whole time is just not the same thing.
PS - You can read all about my beach tips here!
PPS - Y'all. I have to share a funny story from our trip up into the John Hancock building. We chose to go to the 96th floor lounge as opposed to the 94th floor observation deck, mostly because the line was shorter and you could get away with spending a little less money for the same view. As we were standing in line, waiting to be seated 96 floors up in the air, my mom and I each took a turn in the ladies' room. There were floor to ceiling windows in there and a lot of people were going just to take photos! As I was standing there looking out, a girl asked me if that was downtown out there. I stood there for a second because I honestly wasn't sure how to respond. She said she was from Cleveland, and didn't know. Now, I'm from little ole' Louisville and I knew that it was downtown. Rather than make her feel silly for asking (because I'm pretty sure she was serious), I just nodded my head and said I was pretty sure it was. My mom and I definitely had a good laugh about it afterwards!