I grew up on the south shore of Boston. I've been going to New York City since 1975, when I made my first trip, with my 8th grade Social Studies class. We went to see the Rockettes; were dizzy at the top of the Empire State Building and awe-struck from the top of the World Trade Center (exciting, new buildings at the time, and the tallest in the world). We pretty much gawked and squealed our way through this epic city, and no doubt, we annoyed a lot of people in our path.
In college, I visited NYC countless times with friends and my husband-- when we were still dating. We were young and poor then; we slept on a friend's floor and we did whatever was free. I return because this city turns me upside down, and challenges me in ways that I crave. Now that I live on the west coast, visiting NYC is a distinctly bigger deal, but it never gets old! If you ever have a chance to go in late November or December, to see the holiday windows, you will die a happy person. It's hard not to believe in Santa and the magic of childhood after checking out the incredible displays throughout NYC.
Any season there is something exciting to experience in New York City. However, if you're going, these are some things that might help make your visit go a little smoother.
1) You're a tourist; get out of the way. Ok, yes, it's cool to see the Empire State Building, Broadway signs, Times Square, horse-drawn carriages, New York city characters, and yes, she is wearing that; he is in his underwear... the list is endless; but, you're a guest. Most of the people around you are just trying to get to work/a date/the grocery store/someplace to meet a friend/out for a walk. They're living their lives and you're in their way, when you stop to take selfies or photos of your friends and family, or stare at things, or study your hotel map (a dead give away that you're truly clueless in NYC). So take stalk of your surroundings and get out of the way. Step to the side to get that shot or gawk.
2) Don't text while you're walking. Yes, it's true that most of the New Yorkers around you will be doing the same thing, but you're an intruder, and it pisses people off more, when you stagger along, or don't see someone in your way, because you're on your phone. You may only be trying to check the map on your phone, but that will piss people off too. IF you're going to be lost, get out of the way to do it.
3) Do get a fruit smoothie from one of the many mobile smoothie stands that are everywhere. I know, it seems like you should go to a fancy restaurant or juice store for this, but these stands really rock a fruit smoothie! I arrived on my most recent visit to NYC and turned my nose up to these small, deceptively wonderful stands too, but my niece Julia put me in line quick. And, I was converted in one sip. Best smoothie I've had in ages! Of course, take a look at the fruit first, but don't walk past thinking that a mobile stand won't measure up; you'll be missing out on one of the best smoothies and the best prices in town!
4) Do walk. Walk everywhere that you can. Ok, the subway is fun; taxis may get you there faster (at a premium price), and there are lots of buses, but there is truly NO better way to see NYC than by foot. The people of NYC are infinitely colorful and diverse; the stores are incomparable; the sites (which you are not stopping in the middle of the sidewalk to photograph) are all around you, and spectacular. Walk. Take it all in. Absorb New York City through the soles of your feet-- in your most comfortable shoes!
5) Go see Grand Central Station. Plan to sit for a while and absorb the majestic beauty of this historic place. Jacqueline Kennedy Onassis fought hard to save Grand Central Station and it is an incredible place to watch NYC live and breathe: city residents and tourists from all over, coming and going; vendors and performers, mixing on the main floor and down in the train platforms. The place is abuzz with character and beauty. Spend a little while just observing it all, from the balcony or steps above. Note: the police do not want you sitting on the stairs. Just pause from the center
6) If you're flexible, check into half price tickets for Broadway shows. This is not a good approach if you have a short time in NYC and are determined to see one of the top shows, but if you just want to see a show, and price matters, get same day tickets and save big! You may even see Hedwig, Kinky Boots, The King and I, Wicked, Lion King, etc... for half the price of the folks sitting next to you. They are available from several sources; check at the concierge desk at your hotel.
7) Take a walk through central park. Ok, so you came to one of the greatest cities in the world, for the city life. Well, it's all there in Central Park. Stop by the John Lennon memorial, Strawberry Fields; visit the zoo; stroll along one of the many paths that wind around ponds and grassy fields and shady places to sit. You're bound to see some great street performers; you may see the celebrities who live or work in NYC, but exercise, relax and take their kids to this spectacular park, and you'll definitely get a sense of an intricate part of New York City mojo.
8) Visit the 9/11 Memorial. If you're 25 or older, you likely have strong memories of September 11, 2001. This place is viscerally impactful. Visitors speak in hushed tones; survivors and family members leave notes and flowers; it's a hauntingly powerful place to visit. The history is presented in a striking way, and the even if you just walk around outside, you will leave impressed and moved.
9) Don't assume that because it's famous, it's really the best. Sure, guide books have the research; you probably will do fine if you trust the right book for the best pizza/deli/Italian/Chinese/ clubs/donuts (um, there are great donuts in New York!)/or the myriad of other things that you rely on guide books for... But, remember that lots of people buy those books, and that often means huge lines, higher prices, and not necessarily the best. There's a lot of great: pizza/deli/Italian/Chinese/donuts/clubs/ shows/galleries/etc in NYC. Ask locals. Do some extra research. This is an incredible city and you're here; do some homework and make a plan... but then be open to just letting things unfold. You never know what you might find when you "free fall."
10) Go to New York City with an open mind. Take it in. Don't assume that you've watched enough TV or seen enough movies to know the city or the people who live there. Yes, they really do talk that way. Yes, real New Yorkers have a no-nonsense way of doing most things; they don't have a lot of patience for stupidity, and they mean business-- but they are also some of the funniest, most direct, good people around. Not everyone in NYC is out to rob you, hustle you, or piss you off. They're not there for your entertainment either. They are living in one of the biggest, boldest cities in the world. You're the guest. Be polite, be open to trying some new things (step outside your box!), keep your wits about you, take it in, and enjoy your stay.
Incredible shows on Broadway and incredible shows in the subway; the Empire State Building (but move aside to get that shot); Little Italy (for dinner or dessert); Amazing holiday windows; History at Grand Central Station