A beginner’s guide to New York City: Everything you need to know for your first trip

Sep 8, 2020

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Editor’s note: As the travel industry reopens following COVID-19 shutdowns, TPG suggests you talk to your doctor, follow health officials’ guidance and research local travel restrictions before booking that next trip. We’ll be here to help you prepare, whether you’re traveling next month or next year.

Heading to New York City for the first time? It can be intimidating, thinking about the city’s size and scale, its complex transportation system and nonstop crowds. But don’t worry: We’re here to help. Below, you’ll find our guide to making sense of the city, and structuring your trip like a pro.

Here’s what you must do on your first trip to New York City.

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See a Broadway show

(Photo by alanamckinney7/Twenty20)
(Photo by alanamckinney7/Twenty20)

There are few more iconic symbols of New York City than the bright lights of Broadway.  Sure, the touring companies of big Broadway shows come to cities across the United States. But seeing a musical or a play on Broadway itself is different, and is worth your time and money. Nowhere else will you see the caliber of performances, or the polish and spectacle that you’ll find in New York City.

Visit Playbill’s web site for help choosing a show, and be sure to download the TKTS app. The famous red booth in Times Square sells discounted tickets for same-day performances, and the app can give you a heads up about what’s available, and how long you’ll wait for tickets.

And, a tip for the adventurous: When choosing a show, don’t be afraid to try something new. Choose a play or a musical that you’ve never heard of, or would not be able to see back home. You may discover the next “Hamilton.”

Related: 6 reasons to love New York, according to New Yorkers

Take to the water

(Photo by javan/Twenty20)
(Photo by javan/Twenty20)

Given the height of the skyline and the density of its structures, it’s sometimes hard to remember that Manhattan is an island and that all five of New York City’s boroughs are situated on the water.

Get a sense of the city’s dramatic scale by stepping away from it and onto a boat. There are dozens of ways to do this, from spendy private charters to cheap water taxis, but the easiest is to take a ride on the Staten Island Ferry — one of the city’s great, and truly free attractions. The view of the Statue of Liberty alone makes this trip worth it. (Remember, you won’t get the perspective afforded by distance when you visit and climb the statue, which sits more or less by itself on federally-owned Liberty Island.)

In summer, we also recommend North River Lobster Company, a “floating lobster shack” that sets sail from Manhattan’s Pier 81 from Thursday to Sunday. There’s also Grand Banks, a restaurant and oyster bar on a historic schooner. It doesn’t actually sail, but is docked in a prime spot on the Hudson River.

Related: 10 most Instagrammable spots in New York City

Get out of Manhattan

(Photo by gregory.cuesta/Twenty20)
(Photo by gregory.cuesta/Twenty20)

Too many first-time visitors to New York City focus all of their energy on its most famous borough. You should go there, of course — it’s nearly unavoidable — but save some of your time for Brooklyn, Queens and the Bronx. These “outer boroughs” are where you’ll discover excellent food, busy neighborhoods, countless small museums and galleries, live music, all of the city’s major sports stadiums and an endless parade of city life.

Our advice? Pick one or two spots and dedicate time to explore. You’ll never see all of New York City in a single visit, so prioritize wisely. We recommend:

Coney Island: Gritty and a little faded, this seaside escape is heady with nostalgia. Think: vintage amusement park rides, a wide boardwalk and stands hawking everything from hotdogs to hats.

Fort Greene: Blocks of elegant brownstones, independent shops, Michelin-starred restaurants, world-class arts organizations and one giant basketball stadium. No neighborhood in Brooklyn embodies the borough’s variety (and its many complexities and contradictions) like this one.

Long Island City: This somewhat remote waterfront neighborhood in Queens is home to heavy-hitting museums, including MoMA-affiliated PS1, the Museum of the Moving Image, and the art-filled studio of Japanese-American sculptor Isamu Noguchi.

Jackson Heights: A neighborhood of immigrants since the 1960s, this is where many families of Indian, Colombian, Bangladeshi, Tibetan and Ecuadorian origin call home. Come here to experience this incredible mix of cultures through food, markets and shops.

Williamsburg: If you want to try to understand the conversation around gentrification in New York’s boroughs, head to Williamsburg. What was an affordable, residential hamlet due east of Manhattan has become, in the last two decades, the home of luxury hotels, big-brand stores and multimillion-dollar apartments. Still, the area has somehow managed to retain some of its creative sensibility. Street art, cozy bars and live music still thrive here.

Related: Best New York City activities for families

Ride the subway

(Photo by NAO/Twenty20)
(Photo by NAO/Twenty20)

New York City’s spiderweb of subway lines might seem intimidating at first, but mastering it, often, means mastering the city itself. Plus, taxis and rideshares can get stuck in New York’s infamous traffic, adding lots of time to your journey. They also get expensive very quickly, especially if you’re traveling solo or as a duo, and they won’t give you a sense of the city the way the subway will.

Whether it’s dancers doing flips across your car for tips, or the endless fashion show of New Yorkers on their way to work, parties and dinner, the subway provides some of the best people-watching you’ll ever experience.

Download a map to your phone — the official MTA app is good for tracking service changes that could affect your trip — purchase a pass that includes multiple or unlimited rides for maximum flexibility and go. Google Maps’ directions tool is a must-use when it comes to using the subway, whether you’re visiting for a weekend or you’ve lived there for a decade.

Related: Everything you need to know about getting around New York City

But also, walk

(Photo by likeamacheen/Twenty20)
(Photo by likeamacheen/Twenty20)

The best way to really appreciate New York City is to put on your most comfortable shoes and walk its streets. Remember, exploring this destination is all about what you stumble upon — an amazing ice cream stand, a shop selling bespoke hats, a basement-level bar behind an unmarked door. You might never find any of these things if you’re darting around in subways or taxis.

Many travelers don’t come equipped for walking and are surprised by the amount of it they can do (and will want to do) once they arrive. This is why pacing yourself in the city is critical. So is staying hydrated, stopping for breaks and planning your days so that you’ll visit a group of nearby attractions all at once.

The most important thing to remember when walking in New York City? Have a back-up plan. You may walk out to a site or attraction only to find that you’re too tired to walk back. This is when a ride-hailing app or a subway card comes in handy.

And a word about those comfortable shoes for the fashion-conscious. Once upon a time, comfortable footwear was a tourist hallmark and something that would single you out in any New York City neighborhood. Now? It’s just what everyone is wearing.

See an incredible view … once

In a city known for the nonstop drive and ambition of its citizens, it’s no wonder that climbing very tall buildings — not exactly in a single bound, but close — is a popular thing to do here for visitors.

There are high-in-the-sky observatories at the Empire State Building, 30 Rockefeller Plaza, One World Trade Center and at Hudson Yards, which is now home to the tallest outdoor observation deck in the Western Hemisphere. Plus, there are countless other rooftop bars and restaurants. Our advice? Pick one.

Related: Things every teen should do in New York

Focus on things you can only do in New York

Recent years have brought hordes of chain stores and bank branches to New York City. Their appearance is the cause of much-heated debate among New Yorkers: Are they ruining the city with their sameness, or are they a natural result of the city’s ever-growing wealth?

Before you stop into Sephora in Times Square or drop into the Apple Store in Soho, take a minute to make your own decision.

Our perspective on this is simple: Why go on vacation to do things you could do at home? Take a minute to find and visit New York City’s many independent businesses and shops. The things you find there will give you stories to tell, introduce you to new artists and makers of all stripes and give you bragging rights back home.

Plan ahead for meals, and keep it varied

(Photo by dillman346/Twenty20)
(Photo by dillman346/Twenty20)

Yes, you can find a cheap slice of pizza on every other block in Manhattan, but that doesn’t mean you should have it for every meal.

If you’re craving the best of New York’s culinary scene, do your research. Many of the city’s best and best-known restaurants require advance reservations, enforce strict dress codes or have quirky policies like cash-only payment.

It’s also smart to consider when restaurants will be crowded. A general rule of thumb in New York is that the busiest dining hours are from 7 p.m. to 9 p.m., and during weekend brunch, typically from noon to 4 p.m. Avoiding those dining times can mean getting a reservation at an otherwise booked establishment, or just having a more peaceful meal.

And of course, some of the city’s best eats can’t be found in any sit-down restaurant. Whether you’re in search of perfect samosas, falafel, banh mi or roasted peanuts, street carts and stands are a great way to supplement sit-down meals.

But what about Times Square?

(Photo by boneman/Twenty20)
(Photo by boneman/Twenty20)

There’s no shortage of opinions about Times Square. It’s clogged with crowds. There’s nothing to do there. The stores are corny and corporate.

To some degree, all of those concepts ring true, especially for locals and travelers who’ve spent a lot of time in the city. But that doesn’t mean you should fully steer clear of Times Square, or that it’s a soulless wasteland or that you’re not a savvy traveler if you enjoy its chaotic energy.

This neighborhood is, after all, home to some of the best live theater in the world. Its character — bright as day at midnight, forever flashing with digital screens and advertisements — is part of New York City’s fabric.

It’s where thousands of people ring in the New Year each year, where the Beatles performed on “Ed Sullivan,” where Carole King and Neil Diamond wrote songs and where nearly 50 million people visit each year. It’s more than OK to count yourself among them.

Feature photo by datsmrjones2u/Twenty20.

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