I’ll soon get the opportunity to travel to New York and Chicago for vacation. 🌆

I worked and lived in Chicago for one year from 2009-2010 while I worked for AmeriCorps, but I have not visited since.

I have never visited New York.

Part of me is confident that I’ll remember Chicago like the back of my hand, though I wonder and am curious to see how much it has changed and in what direction. I always liked Chicago. It’s a rough city, and so different in the winter and summer, but it’s a great city to live in. It feels like a more condensed version of Los Angeles with a slightly more compact and useful transit system (and varying weather, no mountains and no ocean). But I did appreciate the lake-side waters of Lake Michigan and even swam in them, which somewhat curtailed the need for an ocean.

I look forward to seeing downtown again and I’ll try to do as much as I can, though the weather may guide what can be done in the winter.

With New York, I don’ t know what to expect. I’ve never visited, know about it just generally, so need to study some of its geography and its transit systems.

I know that I want to stay in Manhattan since I want to see some of the main parts of New York, though I’m sure I could spend a lot more time in the other suburbs, and I would also like to drive up New York state one day because I hear it has a nice countryside. But only taking a peek with a quick start in the city for now.

I spent nearly the entire night looking at hotel reviews in New York. I finally grew tired of comparing reviews from one site or the other, and then checking Yelp to see what it said there. It’s funny how one bad review makes 10 other great ones not matter.

However it looks like a decent time to visit NY with regards to cost as many of the hotels I’ve seen seem to be a lot pricier during the peak travel summer times.

Will I feel like I’m walking around Disneyland as I walk by Times Square? Or feel it authentic?

As a Californian, how will I feel surrounded by a lot more people on the street?

How am I going to feel in the subways?

Am I going to come across the legendary attitudes and aggressive personalities that we all hear about?

How will it feel to be in the most popular, most condensed and most populous city in the United States?

The thing about vacations is that they completely kill your productivity. At least for me. I start thinking about it too much, not to mention the research and booking that needs to get done for lodging and transportation.

However as for transportation, I’m not planning to rent a vehicle for these cities. With Chicago, I’m confident I can get to where I want to go through the Metro, and I know I’ll feel generally safe since it should (hopefully) feel familiar. And we all hear that you can get anywhere in the NY transit system, so didn’t even consider looking into a car.

Uber? Lyft? Metro? Taxi? We’ll see.

I wonder if I’ll feel as proud of humanity for having built such a place as I did when I visited Venice, Italy. Venice to me was a unique piece of architectural art, and in spite of how cynical it’s easy to be about humanity at times, it made me feel proud that we’ve built amazing cities and civilizations.

Will New York give me that feeling, in a more modern way? A symbol of American industrialization? Or will it disappoint like the way some people say Hollywood in Los Angeles disappoints, with trash lining the sidewalks and drunks walking by the homeless?

Not sure what to expect. So these are my rambling thoughts. A much more researched Jose should feel much more informed soon.

If you’ve visited before and have any advice on the above, please let me know!

Ultimately, it’s a blessing to take a vacation and here’s to a good and safe one. 😎✌🏼💪🏼

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