Memorial Day Weekend in New York: The Perfect Long Weekend Itinerary
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The Big Apple. The city that never sleeps. The place where dreams come true…New York City!
If you’re anything like me, you’ve spent most of your teenage years watching movies and TV shows set in the landscape of the concrete jungle.
I watched as the cast of Friends fell in and out of love in Manhattan.
I imagined my life as a friend of Carrie Bradshaw’s, “bar-hopping and bed-hopping” around the city, while wearing fabulous shoes.
I was OBSESSED with New York City before ever visiting (aren’t we all?).
And for the best reasons too. Cheap bites. Namely, NY-style pizza on every street corner? I could eat a slice everyday. Art and architectural masterpieces that inspire modern artistic thought? Mind-boggling. When I first saw the New York skyline in person, I was in awe.
One long, late May weekend in the “big apple” soon became a yearly tradition.
Ever since my first visit to the “city that never sleeps”, I’ve been finding the BEST ways to spend a PTO-friendly weekend in New York!
This NYC weekend itinerary has everything from iconic American landmarks to delicious New York bagels. Memorial Day Weekend in NYC is the perfect way to celebrate our nation’s heroes, while exploring the concrete jungle.
New York is nothing short of spectacular.
On my first visit, I checked-off all the boxes on my NYC bucket list, with the Empire State Building, Central Park, and Times Square being at the top of the list. A year later, as the weather started to warm and the holiday weekend reappeared, I didn’t hesitate to add NYC to my list of places to revisit, the next time finding NYC hidden gems and unique experiences. Twice and it’s tradition!
Visiting New York City during Memorial Day weekend is arguably the best time of year to go.
Temperatures are perfect, not too hot or cold, and the city reawakens with energy after the cold winter.
Coffee is never a bad idea…
The Met Museum…in slow motion!
Bella struts across the crosswalk in NYC.
Peace signs on the subway!
I’ve devised the perfect Memorial Day Weekend NYC itinerary to make the most of your late May long weekend!
Where to Stay in NYC
A lot of first-time visitors like to stay in the “hustle and bustle” of New York City, and the Times Square area is the place to be*! I stayed in The Moxy NYC Times Square, a boutique Marriott hotel just blocks away from the city lights. This location felt like I was truly immersed in NYC, with souvenir shops and 99 cent pizza on every corner. For travelers looking for a more upscale hotel in the heart of Times Square, I HIGHLY recommend Times Square EDITION hotel for a luxury stay above the city lights.
*If you prefer something quieter, yet still close to the city action, South Midtown is the perfect place to stay!
Located a short subway ride (or walk) away from the Empire State Building and other popular spots, South Midtown is quieter than the bustling, touristy areas around Times Square. Trendy cafes line the streets, and in NYC, everyone walks around with an iced coffee of some sort in their hands. South Midtown is the perfect place for travelers looking to stay near the tourist activities, but enjoy a “buffer zone” away from the chaos.
One of Manhattan’s most affluent neighborhoods, the Upper East Side is full of posh accommodations, trendy cafes, and noteworthy restaurants. A bit farther away from the touristy part of town, the Upper East Side is a worthy place to visit, even if you don’t plan on staying there. Travelers searching for a bougie, upscale New York experience will enjoy staying in the Upper East Side!
New York City’s trendiest areas, SoHo and the West Village are the lively, fashionable parts of the city. Shopaholics will love this area for its boutique stores, designer shops, and trendy restaurants!
Travel Tip!
Guests ofThe Moxy Hotel Times Square can enjoy a $30 credit to Café D’Avignon, just outside the doors to the hotel.
Memorial Day Weekend in NYC: A PTO-Friendly Weekend Itinerary
Arrival Day
Your arrival in New York City calls for a celebratory slice of NY-style pizza!
It’s ooey. It’s gooey. It’s mouth-wateringly delicious. Time and time again I return to Carnegie Pizza, located just outside of Times Square. Your NYC itinerary would be incomplete without NY-style pizza and vibrant billboards! While you’re there, marvel at the monumental billboards and dazzling lights of the busiest part of New York City.
NOTE
Beware of pickpockets and scammers! Anyone offering a service, a rose, a photo-op, or anything “too good to be true” wants to take your money. No response is a perfectly fine way to say “NO!”.
Check into your hotel and relax before FOUR full days of exploration! This NYC Memorial Day Weekend itinerary has it all!
Day 1
An Immersive Art Experience, a Local Market and NY-style Pizza
Rise and shine, bright and early, and head over to Summit One Vanderbilt, a multisensory, transformative, immersive art experience on the top of the 91st floor of One Vanderbilt.
From over 1,400 feet high, you can enjoy 360° views of the spectacular New York skyline and take amazing photos throughout the experience. The hall of mirrors makes for a mind-blowing illusion (seeing double?), and the “bubble room”, a room of inflatable silver balls overlooking Central Park will make you feel like a kid again. Summit One Vanderbilt is one activity you MUST add to your New York itinerary!
GET my ticket to Summit One Vanderbilt ⬅️🏙️
*one of NYC’s BEST immersive observation decks
Summit One Vanderbilt can get incredibly busy, so it is important to get there early if you want to avoid people in the background of your photos!
I loved this experience so much, I spent FOUR hours at the observation deck!
After your incredible experience at Summit One Vanderbilt, walk to Bryant Park and explore Maker’s Market, a “pop-up” market for handmade local goods that occurs every weekend during the month of May. The local market is the perfect place to find handmade goods for a unique souvenir of the city!
Limitless lunch options make choosing a restaurant difficult, but when in doubt, pizza is never a bad choice! Located just outside of Times Square is a little pizza joint called Famous Famiglia, which gives Carnegie Pizza a run for its money! When in NYC, pizza should always be at the front of your mind…
Tired of pizza? Summit One Vanderbilt is located near 5th avenue, otherwise known as “millionaires row”, so the options for fine dining are endless!
After lunch, catch a ride on the subway, downtown to the Flatiron District, a lovely place to explore in the early afternoon.
Since you’re nearby, you might as well visit The Harry Potter Store! Disappear into the world of wizards by choosing a wand (or better yet, letting the wand choose you!) and drink butterbeer!
For dinner, I recommend Bocca Italian restaurant, which serves fresh, handmade pasta dishes and a plethora of wine!
New York nightlife is unmatched, so here’s a few amazing cocktail bars to add to your NYC itinerary for an after-dinner drink:
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Day 2
Boozy Brunch, Global Neighborhoods and Monumental Memorials
After grabbing your morning coffee for the commute, head downtown via subway to the West Village for Saturday morning brunch at & Son Steakeasy, a trendy breakfast restaurant serving, you guessed it…delicious steak and eggs!
The French toast was TO DIE FOR. In the fast paced, hustle-and-bustle of New York City, a relaxing brunch is the perfect way to find peace. Within the restaurant is a Speakeasy, so be sure to visit after hours for a cocktail or two!
SoHo and the West Village are perfectly explorable by foot, so I recommend walking to New York City’s shopping district next. As an avid tea drinker, I loved finding the perfect tea from Harney & Sons. SoHo has a plethora of charming boutique and designer stores, art galleries, and dining options, so the possibilities are endless!
Keep walking and you just might get transported to another country! Little Italy and Chinatown are two must-visit NYC areas to explore. Much like in Italy (the country), refrain from dining at restaurants where they try to lure you inside…those are tourist traps! During Memorial Day weekend, I stumbled upon the Chinese Street Food Festival, which offered small bites and unique, exotic desserts like tanghulu, in Chinatown.
Catch the subway and travel further downtown, to the World Trade Center 9/11 Memorial and Museum, one of the most impactful memorials in the United States. Standing tall over the fountains of the memorial is “the freedom tower”, formally known as One World Trade Center, which features a stunning observation deck 102 floors into the sky. This observation deck showcases the stunning NYC skyline from downtown.
The same subway line that brought you downtown to the One World Trade can be taken further to Rector Street, a short walk to The Charging Bull and Wall Street. Of course, since it’s Memorial Day Weekend, you have to do patriotic tourist activities! The Statue of Liberty is no exception!
Travel Tip!
For a FREE view of the iconic Lady, catch the Staten Island Ferry.
Guided river cruises can be lots of fun, but also very pricey, especially for families and large groups!
Wrap up your busy Saturday by taking the subway back up to lower Midtown for dinner!
Day 3
The BEST Bagels in NYC, a Walk in Central Park and Views of the NYC skyline
Since Saturday was jam packed with typical tourist activities and exploring lower Downtown, Sunday is the perfect day for a relaxing slow morning in Upper Manhattan.
Start your morning at Kossar’s, New York’s best bagel shop on the Upper East Side (seriously, I’ve eaten A LOT of bagels in New York, and NOTHING tops Kossar’s!). A trip to New York would be incomplete without a fresh bagel loaded with shmear!
On the way to Central Park, visit New York City’s Grand Bazaar, the city’s oldest curated market showcasing a collection of thrifted clothing and antique items. Here you can find vintage objects, recycled license plates, and curated secondhand clothes for a bargain.
As you walk to Central Park, you’ll find several vendors selling fresh fruit and local products, like pure New York honey! Grab some fresh fruit for an impromptu picnic in Central Park.
Every vacation should have a moderate amount of people watching, and Central Park is the perfect place to do so. I love to imagine the stories and lifestyles of the people walking around the park.
“He’s definitely a professional dog walker!”.
“I wonder if they are on their first date?”.
“Do you think she makes a living selling mangoes with tajin?”.
The possibilities are endless.
Next stop, Brooklyn! Manhattan’s close neighbor, Brooklyn, is a neighborhood with amazing views of the New York City skyline. After spending time in Upper Manhattan, catch a train or ferry to Brooklyn, and head to DUMBO Park for an amazing place to enjoy the sunset over Manhattan.
Washington Street has the most spectacular view of The Manhattan Bridge, and makes for a perfect photo opportunity. Time Out Market in Brooklyn is a scenic place to eat near DUMBO, with amazing views over the river. Additionally, I really enjoyed Mint Heights Indian restaurant in Brooklyn after watching the sunset over the city.
Day 4
Stroll Along the High Line, Scavenger Hunt at Chelsea Market, and Living on the Edge
Your last day in New York City is the perfect chance to check off all remaining activities on your NYC bucket list!
My favorite way I’ve spent Memorial Day in New York City starts with a brief walk through the Chelsea neighborhood, window shopping in the meatpacking district’s industrial outdoor shopping center.
The Chelsea Market is the perfect place to grab breakfast and explore the local market for handmade jewelry, old records, and art from local artists. After exploring Chelsea, enjoy a casual stroll along the High Line, old train tracks converted into an eco-conservation walkway through the neighborhood (did I mention that the apartments surrounding the High Line are just DREAMY?).
The end of the High Line walk will lead you to a shopping mall at the Hudson Yards, a great place to grab a bite to eat, or visit The Edge, another glass NYC observatory deck ascending high over the city.
In the spirit of honoring and remembering the heroes who fought bravely for the United States, a visit to the Intrepid Museum is the perfect activity for Memorial Day. A military and maritime museum set on a US aircraft carrier deployed during WWII, the USS Intrepid is the perfect place to learn more about 20th century technological and military accomplishments. Make sure to purchase your tickets early because this museum gets crowded during the Memorial Day Weekend in NYC!
Wrap up your Memorial Day weekend in NYC by grabbing a slice at the world famous Joe’s Pizza in Times Square!
Enjoy Memorial Day Weekend spent in NYC! I hope my four-day New York itinerary helps you plan the ultimate long weekend getaway to the “big apple”!
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