The Ultimate Guide to 5 Days in New York City

Five days will feel like five minutes, or five years, depending on what you do on a trip to New York City. Hitting up these major areas and sites of interest will at least ensure you’ve spent your time well in the Big Apple, no matter how fast-paced the locals walk past you on the sidewalk.

Day 1

Start at the bottom of the city. It’s one of the oldest parts, so it’s perfect for snagging an impromptu history lesson. Walk around Battery Park, then head up to the South Street Seaport, where NYC commerce was put on the map. Grab some good eats at El Luchador or Fresh Salt, or any of the cool offerings at Smorgasburg.

Walk through Wall Street to see where business-types put the country’s finances in order, then pause for reflection at the 9/11 Memorial and Museum, a somber and beautiful reminder of New York’s strength and solidarity.

End with a trip to the Statue of Liberty and Ellis Island, where you’ll discover what keeps people coming back to New York over and over again. Climb to the Crown of Lady Liberty to get a stunning view of Manhattan and all that surrounds it, then walk through the Ellis Island’s American Immigrant Wall of Honor, where over 700,000 names are inscribed. Book your tickets in advance, as Statue Cruises sells out quickly.

Day 2

It’s time to see NYC’s vibrant melting pot for yourself. Chinatown makes for a perfect first stop, as it’s busiest in the morning when all the shops are done receiving their deliveries and open for the day. Pick up some custom chopsticks at Yùnhóng Chopsticks, or for real bargains, see what you can score at the Chinatown 25 Cents Store. Grab some cheap, but good dumplings at Vanessa’s Dumpling House, a mere appetizer for the eats that are to come.

Wander north into Little Italy. It has shrunk in size since the glory days of mafiosos and Godfathers, but it still has a wide selection of Italian restaurants to choose from. Grab a plate of chicken parm and pasta the size of your face at Parm. For authentic Italian sweets, grab some rainbow cookies or a large cannoli at Ferrara’s bakery.

You’ll end up in NoLita soon enough, where you can continue your round-the-world adventure at Condor, a shop that specializes in bringing treasures from across the globe to customers who can’t travel there themselves.

Day 3

It’s time to explore the famous “Villages” of New York. The Village has grown from one of NYC’s most eclectic parts of town to one of its poshest. Once a haven for rising artists and immigrants alike, you’re more likely to spot a celebrity sipping coffee at Third Rail Coffee, or a trust-fund hipster taking selfies at the intersection of Broadway and Lafayette Streets. Walking from the West Village to the East Village, and beyond, is small proof of how New York’s neighborhoods can change with every block.

Grab some macarons at the Boise Tea Parlor, then stop to admire the Stonewall Inn, now a national monument commemorating New York’s place in LGBT history. Walk through Washington Square Park, one of the best places to people watch.

St. Mark’s Place in the East Village will bring out the freaky side in you, thanks to its tattoo parlors and vintage shops like Search and Destroy. End the night at McSorley’s Ale House, one of the oldest bars in the city, or Sake Bar Decibel, an underground speakeasy-style Japanese bar with awesome food and even better cocktails.

Day 4

People might think you’re crazy for going above 96th Street, but that’s only because they’ve never given this part of the city a real chance. After you taste the nachos at the Amsterdam Tavern, or some chicken stuffing at Manna’s, you’ll be grateful the joke’s on them.

Get to know the city’s rich, diverse population with a visit to the Studio Museum in Harlem or the Schomburg Center for Research in Black Culture. Grab a bite to eat, or explore the West African shops in “Little Senegal” along 116th Street.

Go even further north and see what the Inwood neighborhood has to offer. You’ll find everything from colorful Dominican and Puerto Rican markets in Washington Heights, to the super quiet neighborhoods of Inwood. Inwood Hill Park provides the last remaining slice of New York City’s original, natural forest, or check out the Cloisters to feel like you’ve traveled back to medieval times.

Day 5

It may seem cliche, but really no trip to New York is complete without spending a little time in the super touristy spots. You can easily get Times Square out of the way by walking through the pedestrian zone (between 45th and 47th streets, along 7th Avenue). Score discount Broadway show tickets at the TKTS Booth, or fight the crowds at any number of brightly-lit souvenir shops. Madame Tussaud’s is a fun spot for selfies with celebrities, as long as you’re okay with them being made of wax.

Head north into Central Park and explore what the green space has to offer. With over 843 acres to explore, it’ll be a lot. You can check out the more obvious sites, like the Central Park Zoo, the Great Lawn, and Bethesda Terrace, but make some time to see the lesser-known areas of The Loch, the Conservatory Gardens, and the newly-opened Hallett Nature Sanctuary.

Find your way to Rockefeller Center, where you can take a tour of NBC Studios, or go all the way to the Top of the Rock for a full-city view. Or if you don’t want to go that high, grab a celebratory cocktail at the Top of the Standard Hotel, which offers an unobstructed view of the Empire State Building.

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