How To Spend a Weekend in New York City

Start spreading the news
I’m leaving today
I want to be a part of it
New York, New York

-Frank Sinatra

Are you planning a weekend in New York City? Whether you’ve been before or this will be your first time, you can’t go wrong with an NYC weekend trip!

No matter how many times I hear Sinatra’s “(Theme From) New York, New York” it still brings a smile to my face (and the urge to form a kickline). It immediately conjures images of the lights, the traffic, and the people.

Having now lived in New York for almost a decade, sometimes the grandeur fades, the traffic gets annoying, and you stay in your apartment so as not to see another person. This is why I LOVE when friends or family come to visit. I get to see the city through their eyes and am reminded of what an amazing city it truly is.

But where to begin if you only have a weekend in New York?

I really struggled writing this itinerary, simply because there is just so much to see. There are some touristy things you simply have to do, but of course the further you get from those touristy things, the more of an authentic New York experience you’ll have.

A long weekend in New York just barely scratches the surface, but hopefully, this itinerary helps to squeeze in as much as possible! Here’s how to spend a three-day weekend in New York City…

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Getting There

If you are flying into NYC, you’ll most likely be flying into JFK Airport or LaGuardia Airport. Both have public transportation options to get you into the city. Alternatively, you could take a taxi or ride-share service, but they will be more expensive.

If you are driving into the city, you will want to

Getting Around

This weekend in New York itinerary is predominately walking-based. While the subway is an option, staying above ground as much as you can allows you to see more of the city.

If the Manhattan grid system seems daunting, I have a handy-dandy guide to getting around NYC!

Where to Stay

If this will be your first time in New York City, I’d suggest staying pretty centrally located. While you might not want to stay directly in Times Square, staying in midtown Manhattan will give you the most transportation options. Plus many of the more popular sites will be within walking distance!

Try searching for hotels in the Hell’s Kitchen or Midtown West neighborhoods.

How to Spend a Weekend in NYC

Day 1

Dinner and a Show

Assuming you arrive in New York on a Friday afternoon, you have enough time to check in and get settled in your hotel before getting ready to hit the town.

You may have had a day of traveling and are probably hungry, so grab dinner in the Theater District. Make a reservation, if you can, as Friday nights are very busy.

There’s a whole street (w. 46th) called Restaurant Row, and you could pick any one of the restaurants there. They know that most of their guests have evening shows to catch, so service is fast, but not rushed. I personally tend to fill up on Italian at Trattoria Trecolori, Becco, or Carmine’s.

Give yourself enough time to get to the theater, as most people around you will be doing the same!

You can’t visit New York for the first time and not see a Broadway show. Seeing a Broadway show is one of the best things to do in New York; there is nothing quite like it. Even if theater isn’t your “thing”, you should still have the experience. You don’t have to see a musical- there are regular plays and magic shows as well.

Ways to score cheaper Broadway tickets:

• The Today Tix App: You can book your tickets before you even arrive in the city. If you know which show you want to see, Today Tix offers discounted tickets from one month in advance to day-of. Depending on the show, your tickets will either be held at the box office, or hand-delivered to you outside the theater by one of their representatives.
• Ticket Lotteries: Several shows, including “Hamilton”, “Wicked”, and “The Lion King” offer digital lotteries for a limited number of discounted tickets. Enter online with your email address. Winners are announced via email either the day before or day-of. (Sadly I’ve lost count of how many times I’ve entered the “Hamilton” lottery and haven’t won, but my friends have!)
• TKTS Booth: If you don’t really care which show you see, head to the TKTS booth in the middle of Times Square when you first arrive in the city. TKTS offers discounted day-of tickets.

Etiquette Tip: Turn your phone off during the show. If you are texting during a show it is distracting to everyone else around you…including the actors! (You don’t want Patti LuPone snatching your phone away, ‘cause she will.) You can check your texts at intermission.

Times Square

After the performance, wander over to the middle of Times Square, because it really doesn’t get more “New York” than that. There is something magical about just standing in the middle and soaking in the lights, the billboards, and the hum of the city.

It’s a great place for photos, as it’s almost bright enough to be daylight. (If an Elmo walks up to you for a photo, just say “no thanks”.)

Also maybe swing by Junior’s Restaurant for a slice of cheesecake.

Day Two

Bagels for Breakfast

If your hotel doesn’t do breakfast, grab some bagels and coffee on your way to your first stop of the day. Whenever I ask friends who have moved out of the city what they miss most about New York, “good bagels” is always one of the top three answers.

This weekend in New York itinerary includes a lot of walking, so you’ll want to fuel up! New York bagels are full of carbs to energize you through your busy day. (Plus they’re a cheaper option than a full breakfast!)

Top of the Rock

Start your day of sightseeing by visiting the Top of the Rock. The viewing decks at Rockefeller Center are my favorite observation decks in New York because they offer views of the Empire State Building on one side and Central Park on the other.

The elevator ride takes less than a minute and brings you to the 67th floor. From there you can explore the 69th and 70th floors as well.

Although sunset is the prettiest time to visit, it also costs more. I recommend visiting when the Top of the Rock opens in the morning to avoid the crowds. (You might even get a whole deck to yourself!)

Grand Central

Grand Central Station is actually one of my favorite buildings in the city (with the Chrysler Building as a close second). Standing in the main concourse feels like stepping back in time. Make sure to look up at the starry ceiling and try to find your zodiac!

Also check out the whispering gallery on the lower level, near the Oyster Bar. If you stand in the corner of the tiled intersection of archways and whisper something, a friend (or stranger) will be able to hear you clearly from the opposite corner!

Uptown

Take the uptown 6 train from Grand Central to E. 86th Street. If you’re getting hungry, head to Levain Bakery on (84th and 3rd Ave.) for some of the best cookies in the city. Who says you can’t have dessert before lunch?

The Metropolitan Museum of Art

You don’t have to know anything about art to enjoy The Met. Even the building that houses all the art is a work of art in itself. It would take you days to see everything (that’s why your ticket is good for three consecutive days), so I suggest grabbing a map and just picking a section or two.

Grab a small bite, or a drink, at The Met Roof Garden Bar! Take an elevator up to the fourth floor, then walk up one more flight for some lovely views of Central Park. The roof is open to anyone with a regular admission ticket, so even if you just go up for the view, it’s worth checking out!

Upper East Side Eats

If you didn’t grab food at the museum, try lunching at Emmy Squared Upper East Side, The Penrose, or even try some street food from a cart along Central Park East. I promise most New Yorkers enjoy street food, such as a hot dog, a lamb gyro, or chicken over rice (make sure to get the white sauce, yum).

Central Park

Central Park is my favorite place in the whole city. I am not exaggerating. You see it in countless movies and shows, and it’s one of the places that really lives up to its photos and footage. It’s a beautiful oasis in the concrete jungle. If you do one thing during your weekend in New York, make it Central Park!

If you enter the park immediately behind The Met and start walking west across the park, you’ll hit the Great Lawn. Walk a bit south from there and you’ll find Belvedere Castle overlooking the Shakespeare Garden and the turtle pond.

Alternatively, you can walk south down 5th Ave. after leaving the Met and enter Central Park at 76th Street. Walking west from here you’ll come across The Lake, the Bow Bridge, Bethesda Terrace, and Strawberry Fields.

Upper West Side

When you exit the park on the west side, keep an eye out for The Dakota, the beautiful building whose entrance was the tragic location of John Lennon’s assassination.

Grab some dinner on the Upper West Side. Some favorites there include Jacob’s Pickles, The Mermaid Inn, RedFarm, and Amsterdam Ale House.

Then if you still have room for dessert, you have another chance to try Levain Bakery, get a cupcake from Magnolia Bakery, or stop at Cafe Lalo and pretend Tom Hanks is gazing at you through the window a la You’ve Got Mail.

(If you love rom-coms, I have a whole guide to rom-com locations in NYC!)

Lincoln Center

Mosey down to Lincoln Center, home of the Metropolitan Opera and New York City Ballet. Grab some photos in front of the famous fountain. Then grab a drink at The Empire Rooftop and gaze out at all you saw today!

Day 3

Get out of the city

Now that you’ve seen uptown, it’s time to explore downtown. Start your day bright and early by heading away from the city! Some of the best views of Manhattan actually require leaving it.

Option A: Take the Staten Island Ferry

If you have an extra day, I’d recommend taking option A, and then spending a day in Brooklyn!

The Staten Island Ferry is free and you do not need a ticket! Riding the ferry offers beautiful views of downtown and the Statue of Liberty, similar to the view immigrants may have seen coming into Ellis Island.

To reach the ferry terminal take the downtown 1 train to South Ferry or the downtown R train to Whitehall Street. Take the ferry to Staten Island and back, but be aware you have to get off and re-board. A round trip takes about an hour.

If you only have this last day of your weekend in New York, I recommend Option B: Walk the Brooklyn Bridge

Walking the Brooklyn Bridge is another one of my favorite things to do when friends come to visit. If you are ambitious/an early riser (I am not, if I can help it), start walking around sunrise. Not only will you watch the morning light hit the city, but it will also be the least crowded time of day. The bridge sees more than 10,000 pedestrians a day.

Walking from the Brooklyn side to Manhattan will a) save you time and b) give you more impressive views. Take a Brooklyn-bound A or C train to High Street/Brooklyn Bridge and take the High Street exit out of the subway. (Follow signs for Cadman Plaza West.)

There’s a pedestrian walkway entrance under the bridge. Plan about an hour to cross the bridge. It’s a little over 1.5 miles walkway to walkway, but you’ll want to stop for photos and may have to get around other people.

Etiquette Tip: Keep to the right, but on the left side. Follow the painted markings on the ground. If you’re going to pass someone in front of you, make sure there isn’t a bike coming at you from the opposite lane.

South Street Seaport

Once you have either taken the ferry or walked the bridge, swing through the South Street Seaport, and grab a snack. It’s one of the oldest parts of the city, and walking down the cobblestone streets will make you feel like you’re walking through the past.

Financial District

Cut across the Financial District, walking West on Wall Street (yep, that Wall Street). Say hi to the Fearless Girl statue on Broad Street, outside the New York Stock Exchange. See Alexander Hamilton’s final resting place at Trinity Church and then head north.

The Oculus and World Trade Center

For another architectural marvel, step inside The Oculus– the hub, train station, and mall that is now part of the World Trade Center. Designed by Santiago Calatrava, the skylight that runs along the vaulted ceiling lines up with the autumnal equinox, in honor of September 11th.

9/11 Memorial

Pay your respects to all those who lost their lives on (and after) the attacks on September 11th, 2001. The pools are a beautiful place to take a quiet moment and read the names of those lost.

Be sure to look for the Survivor Tree– a tree that was found severely damaged at Ground Zero. After nine years of rehabilitation it was returned to the site and now serves as a symbol of resilience and new growth. Much like the Freedom Tower, towering 1,776 feet above you.

Washington Square Park

Keep walking uptown, passing through Soho and Noho on your way, until you hit Washington Square Park. You’ve now entered NYU territory, and thus should be able to find some cheap eats.

If you haven’t had any New York pizza yet, now is the time! (My personal favorite place for a $1 slice is a hole-in-the-wall on 6th Ave. and 8th Street.)

Grab some lunch, give your feet a break, and eat in Washington Square Park. There is usually always live music of some kind, lots of dogs, and the giant fountain in the middle.

Flatiron Building and Eataly

Get that iconic shot outside the unique Flatiron Building! Then head into nearby Eataly- a market full of specialty products, cooking classes, and different counters at which to eat.

If it’s about happy hour time, take the elevator to the very top floor of Eataly and get a drink at SERRA by Birreria. This rooftop bar’s menu and decor change depending on the season, even in winter!

The Highline

Keep walking west on 23rd Street until you reach The Highline. What used to be elevated train tracks is now green space and a walkway full of flowers and sculptures. Wander South along the Highline for fun views of the city (and even glimpses into the apartment buildings that sit right next to it).

Meatpacking District and Chelsea

The Meatpacking District is nothing like what it sounds like. It’s now one of the trendiest spots in the city, full of high-end shops and restaurants.

I’d recommend getting dinner in Chelsea. There are so many good restaurants, such as Cookshop, Foragers Table, and Jun-Men Ramen. You could also grab dinner within Chelsea Market– a food hall/shopping mall. Inside you can find Los Tacos No. 1, Miznon, or LOS MARISCOS.

The City that Never Sleeps

Chances are you’ve walked a lot today and are probably exhausted. But if you have it in you to do one more thing during your weekend in New York, there’s nothing like seeing the city lights from above. Have one last drink or dessert at a rooftop bar like 230 Fifth Rooftop Bar or Refinery Rooftop.

Honorable Mentions

If you have a bit more time, also check out these other places to visit in New York!

• The Met Cloisters and Fort Tryon Park: Your Met ticket is good for three consecutive days, so head uptown to Inwood to see medieval art in a rebuilt monastery, and walk along the Hudson River. It won’t even feel like you’re in Manhattan anymore!
• Ellis Island and Statue of Liberty: If you are a history or genealogy buff, the museum on Ellis Island is definitely worth checking out. Read and listen to immigrant stories and walk around the actual building that was their gateway to America. Buy a ticket at Battery Park (only from the ticket window or book online, not from people walking around with signs) and the ferry will take you to both the Statue of Liberty and Ellis Island.
• Long Island City and Gantry State Plaza Park: Take the East River Ferry or the 7 train one stop into Queens, and enjoy more stunning views of Manhattan as you stroll along the boardwalk in LIC.

I hope you enjoy a long weekend in New York! There’s a lot to see, and hopefully, this itinerary helps you plan and maximize your time. If you miss something the first time, New York will always be here waiting for you!

What are your favorite things to do in New York? Let me know in the comments!

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