NYC Travel Tips

Though I haven’t lived there for years now, in some sense New York will always be my home. It’s the city where I was born, where I went to college, and where I lived for most of my 20s. It’s one of the few places in the world where I instantly feel like I belong, the minute I step off the train. In New York, the chaos in my brain matches the chaos of the streets, the ever-changing sights always look familiar to me, and I can blend happily into the surroundings no matter how long I’ve been away.

So I was puzzled when I first realized that for many of my fellow Connecticutians, New York can seem intimidating, its choices overwhelming, its streets and transportation options confusing. Many don’t venture into “The City” if it’s not for work or to attend a Broadway show or sporting event, and of those who do want to explore, some feel group tours or other supervised field trips are safer and easier than independent travel.

I find this a little bit sad, to be completely honest. To my mind, wandering the streets of New York – whether aimlessly or with a personalized travel to-do list – is one of life’s greatest and simplest joys.

So, inspired by two recent day trips into Manhattan, I decided to write a little NYC how-to post, with tips on planning an itinerary, getting around, and generally having the best time possible in one of my favorite places in the world. (And yes, this is a completely Manhattan-centric post, though New York’s other boroughs are of course worth exploring as well, and many of these tips will apply there too, although not all.)

First, I should mention where I went. I had quite a random collection of to-dos on my list, but they somehow came together to create two very enjoyable days. On the first trip, I wanted to see the historic Essex Street Market before it moved and modernized, and to finally make it to the storied Economy Candy. I also wanted to check out an art installation called “Moms-and-Pops of the L.E.S.” in Seward Park, walk beneath the Instagram-famous flags of Stone Street, and get some healthy soft serve from Chloe’s Fruit. Those places were all new to me, but I had a nostalgic agenda as well. I wanted to browse at Fishs Eddy, where I spent an inordinate amount of time in my late teens, imagining my future grown-up New York life with cool mismatched tableware. (Update: this did not come to pass.) Finally, I wanted to flaneuse around the streets of the West Village, where I spent my first years of life and where evidence of a much older New York still remains.

On the second trip, most of my destinations were further uptown. I love NYC’s pocket parks but had never been to Septuagesimo Uno (incorrectly called New York’s smallest park) on the Upper West Side. While there, I ended up taking a little stroll in Central Park. I also wanted to walk across New York’s oldest bridge, the High Bridge in Washington Heights, which was reopened to the public in 2015. For my dose of nostalgia, I wandered around some of the neighborhoods where I used to live or hang out: the Upper East Side, Gramercy, and Flatiron.

Ok, on to the NYC travel tips!

-To decide where you want to go, keep a running travel to-do list of places you stumble across that sound interesting. Ideas can come from anywhere: books, magazines, scrolling through Instagram, having conversations with friends – or maybe something on my eccentric list will inspire you.

-If you want to plan a trip and don’t already have a list, ask yourself what kind of experiences you want to get out of a trip to New York. Are you drawn to certain kinds of neighborhoods, specific eras in history, or features unique to the city? Do you enjoy particular environments like parks, waterfront restaurants, or old-fashioned bars? Are you interested in certain cultures? Shopping for a hard-to-find item? Craving a weird food? New York has almost everything, so you no matter what you want, you can probably find it with a quick Google search.

-Once you have a wish list of places, use a map to see how their locations relate to one another. If your destinations are very scattered, it might make more sense to break your sightseeing up between two trips (or to stay overnight and split your activities between two days.)

-In general, it’s easiest to group East Side or West Side attractions together, because traveling uptown or downtown is usually faster than going crosstown (or, heaven forfend, diagonally across the city.) Another good bet is to stay within a few adjoining neighborhoods so you can mostly walk everywhere you want to go.

-However, there are always exceptions when it comes to navigating New York, because every part of the city is a little different. Advice that applies to the part of the city where the streets form a grid, for example, isn’t relevant in Lower Manhattan where the grid plan turns to a bowl of angular spaghetti. You may hear that crosstown buses travel slower than a small child can walk, and while that’s true in Midtown, they practically sail through Central Park, making them one of the best and easiest uptown transportation options.

-Avoid backtracking and unnecessary travel by plotting your itinerary as a sort of loop that starts and ends at Grand Central or Penn Station (or wherever you are beginning and ending your day.)

-If anything on your travel to-do list has a time constraint (e.g., you have tickets to a show or want to get lunch at a specific restaurant), then those items should take precedence, and other activities should be planned around them.

-The subway has a bad reputation due to a combination of news stories from decades ago and loud complaints from New Yorkers who depend on the system to get them around on a daily basis and are understandably frustrated with frequent delays and closures. However, for the vast majority of visitors, the subway will seem surprisingly convenient and user-friendly, and the occasional issue will be more of a funny anecdote than a trauma worthy of a Twitter rant.

-Don’t discount the usefulness of the bus for certain routes, and as long as you’re in Manhattan and it’s daytime or evening, don’t bother trying to understand the bus schedule; another bus will come along soon.

-Avoid traveling by car (whether it’s a cab, Uber/Lyft, or your own vehicle) if possible, as this is usually very slow and expensive. However, there are some occasions when you’ll want to grab a cab, like when you find yourself in one of those rare pockets of the city that don’t have convenient access to a subway station or bus stop.

-You can tell if a cab is occupied or off-duty by looking at the light on top. If you’re able to, hail a cab that’s already going in the direction you’re heading; you’ll save time and money by eliminating the need for the driver to turn around.

-Always build time into your schedule for unexpected time-sucks like long lines, delayed trains, and walks that take longer than you’d imagined. (A mistake as simple as exiting at the wrong end of a subway station can add many long blocks to your route.) Also assume that you’ll want to spend some time sitting down to rest, checking out an intriguing shop, or stopping somewhere for a cold drink. If you’re planning activities that are spread out across the city, you can add in as much as two hours per day of buffer time, just to be safe.

-That said, also think about what you’ll do if you end up with too much time on your hands. New York is full of places where you can kill time (e.g. coffee shops and parks.) But it doesn’t hurt to have two or three backup plans in mind in case you get the gift of extra time.

-To figure out where you’re heading and how to get there, take advantage of your smartphone. I use a free app imaginatively named New York Subway, which is one of dozens of similar apps; the map app on my iPhone, which can give walking directions or route you using public transit; and the maps on the MTA website.

-But don’t depend on your phone. Mine sometimes gets thoroughly confused in the densely built-up, non-grid streets near the Financial District, and apps can’t always keep up with ever-changing subway construction schedules and station closures. It really pays to have a good sense of the layout of the neighborhood you’re in, so if your phone fails you, you won’t feel stranded. Also keep in mind that for many years, people (including me) navigated New York just fine with common sense, a little pocket subway map, and the (admittedly inconsistent) signage provided at stations and bus stops and on trains.

-If you’re disoriented, remember that traffic goes west on odd-numbered streets, east on even-numbered streets, and alternates up and down on avenues. (Except, of course, on the streets and avenues with two-way traffic.)

-There is a formula for determining cross-streets; in the age of smartphones, it’s not really necessary, but I used to carry a little newspaper clipping of it in my planner! (I promise I was not born in 1893.)

-Traveling with credit cards and cash is a good idea in all situations, but especially when dealing with Metrocard machines, which sometimes get sulky and decide not to accept one or the other method of payment.

-When calculating how much money to put on your Metrocard, remember that a single ride costs $2.75 and includes a free transfer within a two-hour window between the subway and bus, between two buses, or between two subways. The last situation is less likely to occur, because you don’t need to swipe your card when switching to another train unless you exit the system in between.

-Think of a day trip to New York like a mini-expedition, and pack supplies like water, snacks, and bandaids. New York means more walking than most of us do regularly in CT (outside of a workout) and involves a lot more stairs. While you can of course buy anything you need in the city, it will be more expensive, especially if it’s purchased from a street vendor in front of a major attraction. And although some find Duane Reade an enjoyable shopping experience, you don’t want to be searching for the nearest one and wishing you’d just packed some BandAids or mints or whatever in your bag.

-If you do need to buy any emergency supplies, remember that in addition to drugstores, bodegas have everything.

-New York also means spending a surprising amount of time outside, so be prepared. This usually involves wearing comfortable shoes, dressing in layers (temperatures outdoors, indoors and in trains and train stations can vary extremely in any season), and applying sunscreen.

-Bring a large bag, like a tote or backpack. You’ll need it for your supplies, and you’ll probably also be lugging a camera and other techy things. A roomy bag comes in handy if you purchase anything small, eliminating the need to carry whatever it is around in a shopping bag all day.

-Bring an external charger for your phone. You will drain the battery, and you won’t always be able to find an outlet, and even if you could, who wants to waste time in New York sitting beside a charging phone?

-Screenshot your Amtrak eTickets in case you can’t open the email or app in Penn Station, where WiFi can be spotty. (Or print out your tickets.)

-Avoid Times Square, Rockefeller Center in wintertime, that eatery you saw on a TV show, and other tourist traps – that is, unless you have a true desire see them for yourself. These overcrowded, overrated destinations are almost always generic and look exactly like they do in pictures – even if you’ve never been, you’ve already seen them. Now go see something more interesting.

-Contrary to stereotype, the vast majority of New Yorkers are very nice and want to help you enjoy their city. (Unless you walk slowly for no reason, stop suddenly on the sidewalk, or linger in the left “lane” of an escalator. Don’t do these things.) If you’re lost or unsure how something works, don’t hesitate to ask someone.

-Not every Starbucks in New York has a restroom (though some do), but other options include McDonalds, Barnes & Noble, department stores, and certain parks.

-Don’t ignore the places in between. As you travel to each of the stops on your itinerary, don’t miss out on the little details you’re passing. Half the charm of New York (perhaps more than half) is spotting a little work of art spray-painted on a wall, noticing a tiny storefront that has survived decades of gentrification around it, or observing people going about their day in all the normal, eccentric, and fascinating ways that New York allows to flourish.


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