NYC Itinerary: The Perfect 3 Day Trip

by Alex Garrow 7 min read

NYC Itinerary: The Perfect 3 Day Trip - Paradox

For first-timers, New York City can seem intimidating - a sensory overload of blinding lights and peculiar smells, with so much to do all the time. Although I was born in Manhattan, my family only lived there for a few years, so going back to visit holds the same overwhelming and exciting appeal.

Over the summer I had the opportunity to live in NYC for a month, dorming with friends near Lincoln Center. During this time we figured out the subway system, wandered aimlessly through Central Park, and taste-tested countless cups of coffee. After a summer in New York, here are some of my favorite spots for the perfect weekend in the city that never sleeps!


Stroll through ... Central Park

What better way to start off your weekend than by spending your morning in Central Park, perfect for people watching and a light breakfast. Grab a coffee and avocado toast at Le Pain Quotidien, while observing the humans of New York:runners blaring music, moms towing strollers, and tourists with cameras slung around their necks. Take your coffee to-go and walk through The Mall, a promenade famous for its leafy canopy, lined with statues and benches - you’ll be sure to see interesting vendors and eccentric street performers. The Mall then leads to the picturesque Bethesda Terrace and Fountain, which overlook the Lake.

Take advantage of the city's art collection at ... The Met or Guggenheim

Next head towards the Upper East Side, the upscale neighborhood known for its wealthy residents and world-renowned museums. Ascend the Met’s iconic steps, the art museum home to some of the world’s most astounding masterpieces and the annual Met Gala. If you’re an art or architecture fanatic, I also recommend stopping by The Guggenheim Museum - the spiraling landmark whose design is as breathtaking as its exhibits. The Guggenheim is my personal favorite, but make sure to buy tickets in advance so you don’t waste time in line!

Go Window shopping on … 5th Avenue

You don’t have to splurge to appreciate one of the world’s best shopping streets! Go window shopping on 5th avenue, home to miles of boutiques and department stores. If you’re in the city around the holidays, stores go all out on elaborate Christmas displays.

Stop for dinner in … the East Village

The East Village is New York’s unofficial Restaurant District, with plenty of options to choose from. Wander around the neighborhood and you’re sure to find something to eat. For summer rolls and pho, try Hanoi House, a casual Vietnamese restaurant. If you’re a fan of ramen, go to Momofuku Noodle Bar. My friends and I were regulars at Superiority Burger, a cost-friendly vegetarian spot serving fast-food and mouthwatering gelato.

See a show at … Broadway, Lincoln Center, Radio City Music Hall, or Madison Square Garden

NYC is famous for its top-notch entertainment. Make sure to catch a show - whether you’re into punk rock or musical theater, there’s always a concert or play at any number of popular venues! If you’re visiting NYC in the summer, Lincoln Center in the Upper West Side has free outdoor concerts and performances. At any venue, tickets sell out fast, so make sure to reserve seats in advance. Pro-tip: TKTS sells same-day tickets at reduced prices. You can buy tickets on the TKTS website, through their app or stand in line at one of their discount booths in Lincoln Center, Times Square, or South Street Seaport.

End your night with a sweet treat at … Insomnia Cookies

After a busy day, cap it off with a warm cookie or ice cream sandwich at Insomnia Cookies, open late into the night. With locations scattered around the city, their delicious cookies paired with a glass of cold milk never fail to disappoint.


Get your caffeine fix at … Cupping Room Cafe, La Colombe, or Cha Cha Matcha

For a lovely brunch in Soho, head to Cupping Room Cafe. The vintage cafe, with exposed brick and natural sky lighting, serves classic American eats such as omelets, pancakes, and of course, coffee. La Colombe is also a fan-favorite spot in Soho for coffee. Matcha is another way to get your caffeine fix, for energy throughout your day’s adventures. Cha Cha Matcha, a cutesy shop with “I Love You So Matcha!” as its slogan, specializes in the trendy green tea powder. Buy a matcha latte and take your bright green beverage to-go.

Go shopping in … Soho

Shop for designer clothes and roam through high-end art galleries in this trendy upscale neighborhood. In Soho, the streets are a runway, so look out for stylish streetwear and snap a picture for Instagram.

Trek over … the Brookline Bridge

Leave Manhattan and walk or bike over the Brooklyn Bridge. The 1-mile stretch should take around 30 minutes to cross on foot, and is well worth the stunning views. At the center of the bridge, there’s a platform to stop and take photos.

If you’re still in need of caffeine go to … Brooklyn Roasting Company

In need of a quick pick-me-up? Get a coffee at Brooklyn Roasting Company, an eco-friendly cafe with a distinct hipster aesthetic - watch out for beanies and distressed wood.

Take a picture of the Manhattan Bridge in … Dumbo

For an Instagrammable view of the Manhattan Bridge, go to Dumbo, Brooklyn. If you stand at the intersection of Water Street and Washington Street you’ll see the bridge peeking between the buildings for an iconic shot.

Experience a foodie’s heaven at ... Smorgasburg

If you’re visiting New York between April to November, make sure to stop by Smorgasburg, a lively outdoor food market open on Saturdays. Local vendors offer every cuisine and unique food group imaginable - from bubble waffles to Asian fusion burgers to drinks served in pineapples. When I was there, I enjoyed the vegetable dumplings and mango flavored shaved ice.

Appreciate street art and go thrifting in … Bushwick

Bushwick is an up and coming neighborhood in Brooklyn where you’ll find captivating street art and charming thrift shops. Visit The Bushwick Collective, an extensive outdoor gallery where graffiti is encouraged. Also check out Better Than Jam, a cool shop selling handmade clothes and accessories by emerging local designers.


Start your day in … Greenwich Village

Greenwich is abundant in adorable cafes and restaurants for breakfast or brunch. Blue Stripes Cacao Shop is a personal favorite, where coffee is served in beautiful blue glasses and anything on the menu can be drizzled in chocolate. Spend some time exploring the Village, as the neighborhood is filled with unique stores and vintage shops. You can come back at the end of the day for live music, comedy, and nightlife.

Flip through peculiar finds at … Strand Book Store

If you’re a booklover, you have to stop by the Strand Book Store. The historic landmark sells new, used, and rare books, as well as quirky gifts, perfect for souvenirs. Even if you’re not a reader, it’s fun to flip through the store’s library of unusual selections, with the store boasting more than 2 million books. They also hold in-store events, with speakers having featured celebrities like James Franco.

Walk around … Washington Square Park

Washington Square Park is in the heart of Greenwich Village and a makeshift central quad for NYU students. It’s widely recognized for its iconic marble arch and fountain, often featured in movies and television. Always bustling with artists and undergrads, the park is another great spot to take a moment to sit and people watch.

Wander through ... the High Line

In the early 2000s, the abandoned elevated railway was transformed into a public garden, and The High Line became the popular destination it is today. Along the 1.5 miles of tree-lined path, there are benches, art exhibits, overlooks and water features. Explore the serene area and find a quiet spot to take in the views. Walk from the High Line to Chelsea Market nearby.

Browse boutiques and stop for food at ... Chelsea Market

If you enjoy local art and clothing with a backstory, you’ll love Chelsea Market. Home to boutiques and flea markets, browse through vintage fashion and unique accessories, where it’s common for proceeds to support local artisans or developing countries through Fair-Trade partnerships. Then get something to eat in the high-end food hall, with popular vendors including Beyond Sushi for vegan rolls and LOS TACOS No. 1 for authentic Mexican cuisine. For dessert, try Doughnuttery which specializes in miniature doughnuts or Chelsea Creamline for their signature boozy milkshakes.

Snap a picture at … The Vessel

Reserve free tickets in advance online and climb to the top of The Vessel at Hudson Yards. The new attraction and interactive artwork is a massive spiraling staircase that allows for new perspectives of Manhattan and the Hudson River from different vantage points. Not up for multiple flights of stairs? Take the elevator to the top.

Get the full NYC experience with a trip to ... Times Square

Flashing lights, giant digital billboards, and dense crowds: Times Square is how most people picture New York City. Walk around the plazas and take pictures, shop in popular stores, stop for food at a trendy restaurant, or catch a Broadway show. Warning: No matter how much you love Big Bird or Buzz Lightyear, do not snap a picture with any costumed characters unless you’re willing to pay.

For the best view of the city head to … the Empire State Building

The Empire State Building in Midtown Manhattan is an NYC staple and popular tourist attraction. Open until 2 am, the Observation Deck provides a spectacular 360-degree view of the city from above.


Snap a picture in front of ... The Statue of Liberty

If you have an extra day in New York and are looking for the typical tourist experience, take the Staten Island ferry to Ellis Island to see the Statue of Liberty. You can get tickets to tour inside or take a cruise tour that circles the prominent monument for scenic shots.


This itinerary only covers some must-see spots and hidden gems, but New York is full of sights to see and places to visit - far too much to fit in a single weekend. Let us know what you think about our itinerary and share some of your own recommendations in the comments below!

For skincare tips, beauty hacks, and more content like this, follow us on Instagram @paradox. Find yourself on the West Coast? Check out our guide for a long weekend in LA here .

Alex Garrow
Alex Garrow

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