Long Weekend in NYC: Four Perfect Days in New York
Being a former New Yorker, any chance to take a long weekend in New York City is always a treat. There’s something completely different about experiencing NYC as a tourist than living there as a resident. For one, the city is your oyster.
But even a long weekend in NYC is a startlingly short amount of time to cram all of my favorite activities into.
Though I sure as heck try on every visit. Here’s how you can emulate my many trips to New York City as a tourist.
Where to stay on a long weekend in NYC
Staying at a rental in Midtown or in an iconic hotel like the Plaza alongside Central Park means you’ll be a stone’s throw from some of New York City’s best attractions. And while this itinerary doesn’t necessarily encompass every tourist stop in town, it’s a good primer for a first timer in NYC, especially if you’re not really sure how to focus your time.
If you’re more into big hotels, there are plenty of those to go around, too. And if you’d rather get more of a local’s feel while still being central and accessible to the subway, I’d recommend staying in Downtown NYC, at a vacation rental in SoHo , the East Village or the West Village .
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Day 1 in New York City
We arrived early morning via Amtrak from Boston , hopped a yellow cab from Penn Station, then dropped our luggage off in Midtown at the Plaza Hotel. While we waited, we wandered through the subterranean Plaza Food Hall and snacked on treats from its many vendors, then took a stroll through Central Park.
One of the Plaza’s greatest assets is its location: Its 58 th Street entrance literally opens out onto Central Park. Walking around Central Park with the first hints of a full blown spring peeking from the branches and ground is a great way to orient yourself and also to get a bit of a respite from the frenetic energy of a city eight-million-people strong that never rests.
When we finally got the call that our room was ready late afternoon, we were lingering nearby in the park and made a beeline for the check-in desk not wanting to miss a moment in our palatial suite.
After some downtime in our room, we headed all the way to the bottom level to Todd English Food Hall, which is basically my wildest dreams all under one roof: nine different food stations— Ocean Grill & Oyster Bar, Noodle & Dumpling Bar, Pasta Bar, Sushi Bar, The Grill, Taqueria, Pizza, Cheese & Charcuterie, Wine Bar and Patisserie—so at the end of the day, I didn’t have to choose.
Despite the station model, you still have a dedicated server, which makes the experience even better as you don’t have to go from counter to counter ordering separately. We had a little bit of everything, from pierogis to a California roll, a fig and prosciutto flatbread to tuna tartare wonton tacos and cocktails.
After dinner, we retreated to the Rose Club above the lobby and had a round of Manhattans (apropos) and listened to some live jazz before we turned in for the night.
Day 2 in New York City
Before leaving for the day, we lounged around the Plaza, then headed downstairs to the hotel’s Palm Court for afternoon tea.
High tea is an affair at every Fairmont property—by the way, did you know the Plaza is owned by Fairmont Hotels & Resorts? Yeah, I didn’t either until this trip!—and an event I don’t take lightly.
We ordered the whole shebang: the New Yorker Tea for SVV, and the Champagne Tea for me. What I really wanted to order was the Children’s Eloise Tea, but maybe next time with my niece in tow.
After tea, it was off to an observatory tower. New York City is known for its soaring views, and there’s no shortage of places to get a bird’s eye glimpse of Manhattan. Here are a few of the more famous ones:
Top of the Rock at Rockefeller Center
Empire State Building
One World Observatory at World Trade Center
The Edge at Hudson Yards
SUMMIT One Vanderbilt
Pro tip: If you’re hitting up a lot of museums and tourist attractions during your weekend in NYC, look into a New York CityPASS , which will give you discounts on pre-paid admission at many of the city’s top sites.
It’s all personal preference on observation deck yu choose, but my personal favorite is the Summit. I mean, would you check out these views?
Related Article: Is the SUMMIT Worth It? A View from Midtown NYC’s Tallest Tower
After our trip to the top, we headed down to the Financial District where we took our time exploring Wall Street and the new World Trade Center, which was rebuilt after the September 11 bombings and now features a memorial at the site of the original twin towers.
Nearby is the striking white Oculus, a 9/11 memorial and functional train station designed by Santiago Calatrava, a world-famous Spanish architect known for his structural forms that resemble organic, bleached organisms. If you do one thing in downtown NYC, go inside the Oculus, a $4 billion that took a decade and a half to come to fruition.
We also visited the 9/11 Memorial & Museum , though we didn’t venture inside, choosing instead to people watch and remember; I challenge you to find a more poignant spot than this very site, which invokes such varied emotions from its visitors. For those who have more time to spare, I’d definitely recommend incorporating the museum into your NYC plans.
By late afternoon, we were getting thirsty and a quick Yelp search told me we were but blocks away from Clinton Hall Beer Garden. I’d never heard of this place, but apparently I was the only one as it was absolutely brimming with finance workers and other young folks fresh off of Wall Street.
They also sell Walter White’s Crystal Methadonuts, which are injectable balls of goodness served with Nutella, raspberry and salted caramel filling.
That night, we took the train out to Bushwick in Brooklyn to see friends and grab dinner at Roberta’s . It’s a bit of a commute if you’re staying at the Plaza—or anywhere else in Manhattan, for that matter—but this is one of those hipster destination restaurants that’s totally worth the trip over the bridge, and you must order off-menu and have the Bee Sting pie. You can thank me later.
Day 3 in New York City
When we awoke on Saturday morning, we took the subway to Union Square then walked over to Dough , which sells donuts the size of our heads in flavors like Dulce de Leche, Mocha-Almond Crunch and Hibiscus. We devoured them within another excellent people-watching hub, Union Square, which is right nearby and was my very first neighborhood to live in back in 2005.
To offset the morning’s sugar, we lunched at Sweetgreen , which was music to my stomach with all its healthy quinoa bowls, then set out through the Village. The Village has long been my favorite part of Manhattan: so many charming streets and alleys tucked away amid bodegas and the crush of people. And dogs, lots and lots of dogs. If strollers are segregated to the Upper West Side, the Village is where New York’s canine population dwells.
Fitting then that we found ourselves down near Tompkins Square Park , where we paused to watch the pups play, thinking how much Ella would love all the sights (and smells) of New York City.
Then, we continued south down to the gritty corridor of the Lower East Side, where we were looking for SVV some quality T-shirts to expand his collection.
We came up empty—seriously, where are all the graphic Tee shops in NYC, pray tell?—but we did find a bar and some craft beer to boot at Top Hops , so I consider that a win.
Dinner that night was at an iconic Village spot, Café Loup , that most out-of-towners would never stumble upon organically. We noshed on authentic French cuisine in this charming bistro with old friends before catching the subway back to Brooklyn again to sleep.
Day 4 in New York City
Since we moved our base from the Plaza to Brooklyn for our final days in NYC, we spent our final morning in one of the city’s hippest boroughs and brunched at Carthage Must Be Destroyed . Though the signage was a bit off-putting—“no photos,” they instructed; “no touching any of the table centerpieces,” they said—ultimately the food was great and I’d return here in a heartbeat.
Bushwick is just 20 minutes from LaGuardia, where we fly in and out of via Southwest from Nashville, so we hopped a cab to the airport after brunch, excited that we already have our next long weekend in New York return mapped out for later this year and stoked to tackle the rest of our Manhattan to-do list then.
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