Rediscovering New York (for the First Time)

For the past several years, the word "travel" in my world has almost exclusively meant "overseas travel." In fact, the vast majority of the stamps in my passport lately are ones I received on trips to and from Italy, as I've ventured back and forth pursuing the necessary paperwork to move there. But this summer I got to do some non-family-related domestic travel for the first time in a long time, and I was reminded what a cool country I live in.

I spent a few days in Chicago in July to attend two conferences (BlogHer and TBEX), and although I did basically nothing even remotely touristy while I was there, I really enjoyed my stay. My only prior visit to Chicago had been en route back from France in 1999, when we had a long enough layover that we zipped into the city and up the Sears Tower before zipping back out to the airport and our flight home. This was, clearly, in the days before extended waits at the security line which probably would have made that 2-hour layover long enough for, well, nothing. But that's another topic for another article.

When I was planning my trip to Chicago this year, I wasn't sure what to expect in terms of costs. It's not the tourist destination that New York or Miami might be, but it's certainly a big city with lots to offer. So I was pleasantly surprised to find that airline tickets to Chicago from Portland weren't crazy expensive, even in the summer. And not only did I find a good selection of Chicago cheap hotels that I could choose from, the one I ended up in was Italy-themed (never a bad thing in my book), a mere 3-minute walk from the Magnificent Mile and way more upscale than I'm used to - while still being a bargain.

As I said, I was in Chicago for conferences, so I didn't really get out and explore much - but I really loved the feel of the city center, and walking to and from the conference sites from my hotel was a pleasure. The architecture is beautiful and varied, and I was impressed with the amount of green the city planners had incorporated into a busy city center. I know in my head that Chicago's a big city that stretches far beyond the little part I was covering daily, but somehow taking the city in bite-sized pieces like that made it feel small enough that I felt comfortable immediately (regardless of my unfamiliarity with it).

These thoughts got me thinking about my relationship with America's #1 big city, New York. It's not as positive a story. Yet.

My dad, who grew up in New York City, drilled into my head from a very young age that New York was dirty, scary, crime-filled, and a place I definitely did not want to spend any time. I really don't know what the city was like in my youth, but I have no doubts that it was pretty bad when my dad was growing up - in other words, I don't think he was trying to instill unfounded fear into his kids' minds to keep us safe. Unfortunately, however, no matter how many years have passed since he issued those warnings, I still find myself on edge most of the time when I'm in New York.

As a kid, we'd go into "the city" on a regular basis to visit relatives or for eye doctor appointments (before you ask, yes, there were plenty of perfectly fine eye doctors where we lived in Connecticut, but the New York one was a relative, and that's the way my people do things). As an adult, I've been to New York only a handful of times, and I've had really nice experiences there. So why is it that when I think about traveling I never consider going back to New York?

I think my plan of attack needs to be similar to what I did in Chicago - I need to go in without expectations, take the city in bite-sized pieces, and (above all) relax. Just like with Chicago, I know there are cheap flights to New York from Portland, and the array of cheap hotels New York has to offer is downright astounding (although I'm not so sure some of them wouldn't sour me on NYC permanently). I'm not typically a package tour kind of girl, but I might just look into what New York vacation packages include in their itineraries so I can potentially add some of those things (the ones that aren't obvious, anyway) to my to-do list. Sometimes, those vacation planners come up with nice lesser-known attractions and activities that can make a trip feel unique, which is always welcome in a heavily touristed place like New York.

Last, but certainly not least, I'd consult my now vast network of contacts who either live in or used to live in New York. I like and respect these people, and they like NYC, so there's got to be something there. Between their recommendations and the family friends I have who still live in Manhattan, I'm pretty sure I could come up with a good enough customized NY travel guide that would help me get over my childhood aversion to the city.

At the very least, I'm eager to give my theory a try.