11 Ways to See New York That Have Nothing To Do With Times Square

11 Out-of-the-Box Ways to See New York
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Written by: Cheryl Slayton | August 24

Bright lights, big city. There’s a reason why people from Oklahoma to Miami make it a goal to see the Big Apple at least once in their lives. But, if you’re going to do it, you’ve got to do it right. Resist the urge to waste your trip to New York on Statue of Liberty tickets and 50 selfies of you and your friends in Times Square.

Here is your Ambitious Guide to the Top 11 things you must do in New York City:

1. Become a Trapeze Artist

New York has a way of making every other “big city” in the U.S. feel like the ugly red-headed stepchild. New York has better food choices, shopping selections and entertainment options than anywhere else. Why wouldn’t it be the same for adrenaline sports?

Forget the skydiving and bungee jumping you might do while on vacation in Colorado or California and take up the art of trapeze instead. Trapeze School New York offers classes in a number of skill levels and styles. If you want to feel what it’s like to fly or just pick up a new party trick to impress your friends, this is one of the best things you can do in the Big Apple.

2. Eat REAL Soul Food

Get the best soul food money can buy. I’ve eaten everywhere from Colombo Sri Lanka to Barcelona, Spain, and I can honestly tell you that the meal I had at Sylvia’s Soul Food Kitchen was one of the best meals of my life. I felt like I had stepped back in time to a Louisiana kitchen where the cornbread is cooked with love and bacon grease is the foundation of any good meal (or side, or appetizer, or beverage for that matter).

From the authentic Southern crab cakes to the corn fritters and the friend okra, this food is as southern as southern gets above the Mason-Dixon line. But whatever you get (for the love of God), get the macaroni and cheese.

To start planning your meal now, go to Sylvia Soul Food.

3. Shop Like a Local in a Real NYC Boutique

What’s the only thing worse than wearing a fanny-pack and white tennis shoes through New York City? Being the kind of tourist who comes home with a pair of American Apparel leggings and says they’ve “shopped like a New Yorker.” Ughh.

Listen, if you want to shop like a New Yorker, you have to think like a New Yorker. These people have chosen to live in one of the most expensive and overpopulated cities in the world merely for the diversity and intricacy that the city offers. They are fierce and determined shoppers, and shop owners have to cater to their demands by offering a wide supply of eclectic styles, shapes, colors and designs.

For a full list of New York’s best standalone clothing and jewelry boutiques, go to New York Racked.

4. Go Back in Time at a Speakeasy

Thank God the 1920’s are over! I don’t know where I would be without my weekly shot of Fireball (that I take solely to pay respect to Pit Bull, of course). But sometimes it’s fun to pretend we’re still living in Prohibition times, when you had to memorize a special password and follow cryptic messages and building signs to enjoy a cocktail paired with cool jazz tunes.

The good news is that The Big Apple is keeping the tradition alive with Great Gatsby era Speakeasies everywhere from the East Village to Grand Central station. So, break out your suspenders, fedoras and handlebar moustaches! But don’t forget the password, and never ever tell the fuzz you were there.

For more information on New York’s top Speakeasy bars, go to The Guardian.

5. Say Yes to Louis Vuitton (or 2$ socks)

If you find yourself in China Town shopping for a beaded necklace for your friends back home or one of those porcelain cats that waves its hand back-and-forth, you have to understand that what you see is certainly not all you get. Especially when you hear the whispered words, “Louis Vuitton,” “Gucci” or “Prada” from the local East Asian shop owner.

They’re not making a suggestion on what to buy at the local Macy’s. They’re giving you an invitation to enter the mysterious “back room”, where custom (ahem-counterfeit) bags are offered in an array of “brand-names,” colors and sizes. Now, I’m not advocating illegal activity. Or violation of copyright laws (and I’m certainly not admitting to have participated). But, just taking a peak in the back room is enough to give you a little insight into how and why so many foreigners are able to make a living in the great city that is The Big Apple.

6. Take the Damn Subway

It was 10 p.m. on New Year’s Eve. I had two hours to meet my friend at the salsa club downtown where we would dance our way to the ball drop together. But three stops later, I realized I had missed my train connection. So, I did what any adventurous (or as my mom says, “reckless”) traveler would do. I got off the train. I mean, why not explore the strange new area I had stumbled upon?

When I emerged on the bleak, dark city streets, I found an entirely new area of New York that I had never intended to go. I found a local street vendor selling the Louis Vuitton watch my mom wanted, and I hailed a cab to make it to my destination just in time — 30 minutes before the ball drop. Sure, it was a wild, hectic and even dangerous ride. But I had experienced life as a true New Yorker. And, after all, isn’t that the point?

But, just to play it safe, here’s a little cheat sheet on how to ride the NYC Subway.

7. Walk Down Times Square At 2 in the Morning

They say it’s the city that never sleeps for good reason. Now, while you don’t want to test that theory on the lower-west side where the streetlights are dim and the company gets shadier as the minutes go by, Times Square and Broadway are full of tourists 24/7. Literally. Every. Single. Hour. Of the day.

You can find Chinese tourists taking pictures of their first NY street hot dog at 3 a.m., next to that Southern couple with their fanny packs taking in some late-night shopping before their taxi ride back to the airport. Whether you’re looking for a little escape from your traveling mates or you just want to do some late-night reflecting on your trip, there is no better way to experience the “bright-lights/big-city” feeling that makes New York City so unique.

8. Go to a REAL Classic Diner

People-watching is almost a sport among the traveling kind (which I hope you are if you’re reading this post!). But if you want a really authentic experience of the city, you want to try your hand at people-listening.

New York City is an international mecca of the world’s best, weirdest and even downright terrifying people. But in the safety of a local diner, you would be amazed at the things you might overhear while enjoying your toasted marble on rye. Cup & Saucer on Canal Street is known for its extraordinary fried fish sandwich, and Pearl Diner on Pearl Street, which is the same diner Robert Pattinson ate at in the 2010 movie Remember Me, are perfect spots to try out first.

9. Watch a Small Off-Broadway Show

First of all, you simply cannot go to New York City without watching a Broadway show. I won’t allow it. Even if you have to sneak through a dark, dirty alleyway backdoor to get in, theater is one thing that makes this city great.

But when it comes to deciding between an On-Broadway show like Cats or Phantom of the Opera tand smaller On-Broadway productions like the play Branched, A Comedy with Consequences (photo above), you have to decide between 2 things: predictability and spontaneity. While On-Broadway shows never fail to disappoint, Off-Broadway shows never fail to surprise. You just might find yourself becoming part of the play or witness an epic actor meltdown that ends with everyone naked and crying onstage. For a true theater buzz, Off-Broadway is the way to go.

10. Chase Down a Local Celebrity

If you’ve followed my above advice and learned how to take the Subway and come out alive (especially if you’ve taken the trek to Harlem for a little soul food), I would say you’ve stepped it up a notch! Now, you’re ready to put your New York agility to the test.

Visit Rockefeller Center, where The Tonight Show with Jimmy Fallon is taped, and you just might catch a glimpse of a celebrity guest. Come at the right time (and at the right stairwell) and you just might catch that celebrity walking out the front door. This happened to my friends and I when Quentin Tarantino was a guest on Conan O’Brien. (We stumbled upon the director sneaking out of the 1st floor elevator and have the pictures to prove it!)

Go to NBC for the taping schedule and information on how you can get tickets to the show.

11. Be Relentless

If you’ve gotten anything from this post, it should be that New York is much more than the Statue of Liberty, Times Square, Broadway shows and street hot dogs. Of course, those things are a must-do, but there is so, so much more to get out of the city! But doing life like a “New Yorker” doesn’t mean you have to spend all your time shopping for shoes or watching another production of Cats. It can mean whatever you want it to. That’s the whole point.

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Cheryl Slayton

Cheryl has been challenging the status quo since she ditched her training wheels in 2nd Grade and hopped a fence after losing her ticket to the local fair. Eventually, she started pushing geographical boundaries (instead of legal ones) and made travel her best friend. While two-stepping her way through Texas, climbing a volcano in Antigua, Guatemala and teaching Arabian princesses in the Middle East, she made some amazingly adventurous and ragamuffin friends along the way, like a bossy Haitian, savvy South African, wild Canadian and an Indian-French-Canadian connoisseur of bags and wine. Now, she's happy to call Orlando home again (and try her best to stay on the right side of the law) as she puts pen to paper to share her stories with the Ambitious Crew. Find her on Twitter and Facebook.

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