The Gritty Guide to Surviving A New York City Trip

New York City is stunning, hectic, glamorous, dirty and overwhelming all at the same time. It’s known as a place only for the very rich or the very poor.. and you only need to spend a day in the metropolitan area to see that this is true.

There’s an energy in the city that simply can’t be duplicated. From the hustlers on the subways pop-locking and pole-dancing for tips… to the Armani suit donning, upper-crust rushing to Wall Street… there’s an heir about NYC that is just as polarizing as the vast contrast between the rich & poor. Before you tackle the city that never sleeps, know what to expect, how to survive and how to be treated like a real New Yorker.

Know How to Dress

This may sound superficial, but how you dress while in NYC is everything. It doesn’t matter if New Yorkers can afford to wear Gucci from head to toe, or have to dig through second-hand shops… everyone has their own style & the avenues are runways. Your fashion choices in NYC could be the difference between you getting scammed or getting treated like a real New Yorker.

– Avoid any clothing that says New York on it like the plague (this does not include NY sports teams). If you absolutely can’t live without a t-shirt that says “NYPD” “New York Fire Department” “I ❤️ New York” or any other touristy garb, save it until you get home. These shirts might as well be a target on our chest. They let every New Yorker know that you’re not one of them. Thus exposing you to more opportunities to be taken advantage of in this no-holds-barred kind of city.

– Ladies… subways, trains & sidewalks are packed at any and every hour of the day. Wear a cross-body bag for all of your purse essentials. When in a crowded area, move your bag to the front so no one can snatch any of your belongings. Remember, NYC is a REAL city. People are hungry and pickpocketing is not a rarity.This New York City survival guide is for any newcomer to the city who wants to experience this sprawling metropolis like a real New Yorker.



-Comfortable, yet fashionable shoes are going to be your everything. Unless you’ve got the money to pay a taxi driver $30 to move you 1 mile, you will be taking the city-on by foot and train. You must have comfortable footwear.

-Muted tones of clothing will always make you look like a real New Yorker. Mix & match shades of gray, black, army green, navy and taupe. Keep it understated, don’t do too much.

-Layer, layer, layer and then layer some more. When those winds start whipping around the skyscrapers it can become very cold.

-Attitude adds just as much to your style as anything else. Walk around with confidence, like you know where you’re going. Put away the Lonely Planet NYC travel guide, the maps… & the look of uncertainty.

Shop Prince & the Pear’s NYC Fashion Picks

Understand New York City by Borough

You’ve seen it a million times over in movies and TV. The over-the-top pride that gleams from New Yorkers who claim that the best pizza comes from da Bronx… the most fashionable come from Brooklyn & so on & so on. To make the most of your NYC trip, you have to understand the stark differences between the varying boroughs that make up NYC.

Manhattan: Manhattan is usually the first borough that comes to mind when thinking of this sprawling city. Home to some of the country’s most famous sites and attractions, Manhattan can simply not be missed. Walking around Manhattan you’ll find the Empire State Building, Central Park, Broadway, Times Square, the 9/11 Memorial and Radio City Music Hall…to name a few.

Brooklyn:  Want to feel like you are walking, living and breathing in an Urban Outfitter’s ad? Head to Brooklyn. From the trendy restaurants that line the streets of Williamsburg, world-class sporting events at Barclays center… or a gorgeous walk across the Brooklyn Bridge, this borough is for the hip traveler who knows how to find hidden gems. As NYC’s most populous borough, you’ll also find that prices are considerably cheaper than those in Manhattan. The Bronx: In our books.. The Bronx is most importantly known as the birthplace of hip-hop. If that isn’t enough to make you want to discover this neighborhood, the New York Yankees, Bronx Zoo or the NY Botanical Garden just might.

Queens: Farther away from it all, Queens is a must for foodies with a flair for international cuisine or sports fanatics who’d be most inclined to watch a Mets baseball game. Ranked as the borough with the friendliest people and the most affordable housing, Queens might be an optimal place for you to rent an Airbnb and transit into the city for all your sightseeing needs.

Staten Island: Staten Island often goes missed by tourists in the Big Apple. But with a free ferry ride that is just as much as an attraction as it is transportation, there’s no reason you shouldn’t venture to NYC’s 5th borough. Staten Island is historic, cultural and family-oriented.

New York City Survival Guide: Know What to Avoid

-Tourist traps and NYC are basically synonymous with one another.

-Everyone should experience a walk through Times Square at some point, but make sure that you’re only taking a walk. Eating in Times Square is a major tourist trap. You’re going to find mediocre, overpriced NY fare… or the average Applebee’s, Olive Garden or Bubba Gump.

-Avoid anyone who walks towards you with a map of NYC offering to take you on a double-decker bus tour. You’re going to enjoy the city so much more if you go on your own excursion.

-Any sort of street carnival in Little Italy. A lot of the guys who run these booths are hustlers. Though the thought of winning a new iPad seems enticing, politely continue on your way.

-Shopping on Canal Street. Searching for bootleg bags, shoes & belts on Canal Street is a quintessential NYC adventure. However, you might want to consider the repercussions for the people who are producing these products.

Know Where to Eat

Trending Neighborhoods for Foodies

  • The Meatpacking District
  • Williamsburg
  • Greenwich Village
  • Harlem
  • MacDougal Street
  • Bleecker Street

“In New York… everybody is dealing with the same $H*# .. everybody is on the subway, elbow-to-elbow.” -Louis C.K.

This New York City survival guide is for any newcomer to the city who wants to experience this sprawling metropolis like a real New Yorker.

[DISCLAIMER: THIS BLOG POST CONTAINS AFFILIATE LINKS. WE MAY EARN A SMALL COMMISSION TO FUND OUR TRAVELS IF YOU USE THESE LINKS. YOU WILL NOT BE CHARGED EXTRA, AND WE’LL GET TO SHARE MORE STORIES… AND OF COURSE, ALL OPINIONS ARE OUR OWN!]

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