Memorial Day Weekend in New York: The Perfect Long Weekend Itinerary
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 obsessed?). 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 a modern school of artistic thought? Mind-boggling. When I first saw the New York skyline, I was in awe!
A plethora of things to do, people to see, and fun to be had? Count me in!
My first trip to New York City was over Memorial Day weekend in 2023. I had taken Friday off to explore the streets of Manhattan, and spent the weekend skipping around midtown with Lily before I bid her farewell on what she called her “world tour”; an abbreviated trip around Europe and the Middle East. Hardly a “world tour”, but I supposed she’d work up to the remaining continents.
My first trip to New York was nothing short of spectacular! Lily and I checked-off all the boxes on our NYC bucket list, with the Empire State Building, Central Park, and Times Square being at the top of the list. And I can’t forget Lady Liberty…we saw her too! So a year later, as the weather started to warm and the holiday weekend reappeared, we didn’t hesitate to add NYC to our list of places to revist. 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. Not to mention, fleet week! The perfect way to find a husband…
Coffee is never a bad idea…
The Met Museum…in slow motion!
Bella struts across the crosswalk in NYC.
Peace signs on the subway!
So maybe you’re not looking for your Top Gun in New York City but…
I’ve devised the perfect four-day itinerary to spend Memorial Day weekend in Manhattan!
Thursday (Arrival Day!)
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 we return to Carnegie Pizza, located just outside of Times Square! 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!
Here are some notes about my favorite parts of Manhattan for finding accommodations:
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*! We stayed in The Moxy on Times Square, a boutique hotel just blocks away from the city lights. This location felt like we were truly tourists, with souvenir shops and 99 cent pizza on every corner.
*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 touristy 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 (I prefer tea, but when in New York, drink what the New Yorkers drink!). 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 (yet understand the expenses associated with it) 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 of The Moxy Hotel Times Square can enjoy a $30 credit to Café D’Avignon, just outside the doors to the hotel. Every morning we used our breakfast credit, enjoying coffee NY-style…on the go!
Friday
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.
Note: 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! We loved this experience so much, we 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. This year, a futuristic art installation connecting New York to Dublin called “The Portal” made its appearance on the Flatiron South Public Plaza. Whether or not it will be there next year, is a mystery of time and magic…
Speaking of magic, 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 drinking 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 for an after-dinner drink:
Saturday
After grabbing your morning coffee (or tea, in my case!) 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! Did we mention that 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, we 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, 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 St., 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!
Sunday
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, we’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 St. 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, we really enjoyed Mint Heights Indian restaurant in Brooklyn after watching the sunset over the city.
Monday (Departure Day!)
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 holiday weekend!
Wrap up your long weekend in the city by grabbing a slice at the world famous, Joe’s Pizza in Times Square!
Enjoy Memorial Day Weekend spent in New York City!
